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Urea levels in urine play an important parameter in diagnosing bodily conditions through liver and kidney examinations. The typical reagent for detecting urea content in urine is para-dimethylaminobenzaldehyde (pDMAB). However, it has a drawback related to the instability of color in the resulting Schiff base compound (pDMAB-urea). In this study, the synthesized vanillin compound derived from clove oil serves as the foundational material for a urea chemosensor based on the colorimetric concept. The synthesized vanillin was characterized using FTIR, GC-MS, and 1H-NMR. The formulation of the vanillin compound as a sensor was conducted by assessing the suitable solvent, determining the optimal mass of vanillin, and evaluating the acid-base conditions of the sensor formulation system both qualitatively and quantitatively. Subsequently, the most effective formulation was selected for detecting urea in urine samples. The synthesis of vanillin yielded a purity level of 95%. The optimal formulation was obtained at an optimum mass of vanilla of 0.75 g in 50 mL of 96% ethanol and 10 mL of 10% NaOH. The color change in the sample was from colorless to greenish yellow (436 nm). The vanillin obtained was applied to urine samples with the best results at a sample dilution level of 10,000×.

Epidermal growth factor receptor (EGFR) is found to be overexpressed in cancer cells as it controls angiogenesis, cell signaling, and proliferation mechanisms. Therefore, EGFR has been known as a common target for the initial screening of new anticancer agents. Either xanthone or chalcone has been evaluated as the anticancer agents, and their activity strongly depends on the type and position of the attached functional group. Therefore, molecular hybridization between xanthone and chalcone could yield novel anticancer agents through the EGFR inhibition mechanism. Herein, a series of xanthone-chalcone derivatives with hydrogen-bond-acceptor or hydrogen-bond-donor substituents at ortho, meta, and para positions was evaluated as the EGFR inhibitor. Thirty-seven xanthone-chalcones were designed and docked in the active site of EGFR. Compared to the native ligand, pristine xanthone-chalcone gave a 1.215× stronger binding energy and a 13.97× lower binding constant. Compound 3SH was found to be the most promising candidate due to its strongest binding energy (−9.71 kcal/mol) and the lowest binding constant (0.08 µM). Furthermore, molecular dynamic studies demonstrated that complex EGFR-3SH was stable for 100 ns simulation. These in silico investigations show that the xanthone-chalcone derivative is a promising novel anticancer agent to be examined through in vitro and in vivo assays.

This research involved the synthesis, antimalarial assay and molecular docking of novel nitrophenylcalix[4]-2-methylresorcinarene derivatives. Calix[4]-2-methylresorcinarene derivatives, i.e., 2N, 3N and 4N, were synthesized in a one-step reaction through the cyclo-condensation reaction between resorcinol and aldehydes, i.e., 2-nitrobenzaldehyde, 3-nitrobenzaldehyde and 4-nitrobenzaldehyde, respectively. The reaction was carried out through the reflux method with ethanol and hydrochloric acid 37% as the solvent and catalyst, respectively. The synthetic products were characterized using FTIR, 1H-NMR, 13C-NMR, and LC-MS spectrometers. Furthermore, the in vitro antimalarial assay was carried out against Plasmodium falciparum strain 3D7. The results showed that the 2N, 3N and 4N compounds were successfully synthesized in 86.4, 78.6 dan 95.7% yield, respectively. The antimalarial activity test of 2N, 3N and 4N gave IC50 values of 2.35, 1.68 and 1.79 µM, therefore, these compounds are classified as active antimalarial agents. Molecular docking performed against the PfLDH receptor showed that the 2N, 3N and 4N compounds had negative binding affinity values of -5.1, -6.1, and -6.0 kcal/mol and had specific interactions in the form of hydrogen bonds to the amino acid residues Arg109, Thr101 and Lys102 in the active site of the receptor. The molecular docking results agreed with the experimental antimalarial assay demonstrating the mechanism of action of nitrophenylcalix[4]-2-methylresorcinarenes as active antimalarial agents happened through the inhibition of the PfLDH receptor.

Malaria is an endemic disease in tropical countries, including Indonesia, with a high annual mortality rate. Because of that, serious attention shall be given to find new antimalarial agents that are highly active for medical treatment. In this work, we designed and synthesized three calix[4]resorcinarene derivatives and evaluated them as antimalarial agents through in vitro heme polymerization inhibitory assay. The calix[4]resorcinarenes were prepared from resorcinol and corresponding aldehyde derivatives in ethanol media through a cyclo-condensation reaction. The calix[4]resorcinarene products were obtained in 31.1–85.1% yield. The synthesized compounds were subjected to structure elucidation using spectroscopy techniques. The antimalarial activity of calix[4]resorcinarene with aromatic substituent (IC50 = 0.198 mg/mL) was higher than the aliphatic ones (IC50 = 0.282–0.814 mg/mL). It was found that all calix[4]resorcinarenes in this work exhibited stronger antimalarial activity than chloroquine diphosphate as the positive control (IC50 = 1.157 mg/mL). The calix[4]resorcinarenes could interact with hydrogen bonding, thus inhibiting the heme polymerization process. These findings demonstrate that calix[4]resorcinarene derivatives are potential antimalarial agents to be developed for effective medical treatment in the near future.

Abstract: The 4-hydroxychalcone compound is a flavonoid derivative that has benzene rings with unsaturated chains and a chromophore group, which can absorb UV rays and reduce the intensity of radiation exposure to the skin. This study aims to examine the effect of gelling agents on the physical properties of gel preparations, optimum formula stability, and activity of 4-hydroxychalcone gel as a sunscreen in vitro. Base optimization was carried out using Design Expert software version 10 with the simplex lattice design method and variations in gelling agent concentrations, namely carbopol, sodium carboxymethylcellulose (CMC-Na), and gelatin. The activity of 4-hydroxychalcone sunscreen gel was determined spectrophotometrically by determining the Sun Protecting Factor (SPF) value, the percentage of erythema transmission (%TE), and the percentage of pigmentation transmission (%TP). Data were analyzed statistically with SPSS software. The results showed that the optimum formula composition was obtained at a concentration of 0.67% carbopol, 2% CMC-Na, and 1.83% gelatin. The optimum formula of 0.5% 4-hydroxychalcone gel was stable during storage at room temperature and did not experience syneresis during 72 hours of storage at ± 10°C. The 0.5% 4-hydroxychalcone gel gave an SPF value of 27.37 % TE was 1.76% and % TP was 10.21%, therefore it is categorized as a sunblock.

This study aims to examine the potential of p-tert-butylkalix[4]arene derivatives, namely 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrahydroxy-calix[4]arene (TBCA), and 5,11,17,23-tetra-tert-butyl-25-monohydroxy-26,27,28-tribenzoyloxycalix[4]arene (TBMTCA) as adsorbent for metal cations, such as Pb(II) and Fe(III). The synthesized compounds were characterized using FT-IR and 1H-NMR spectroscopy. The adsorption studies were then carried out with contact time as a parameter, while the kinetics were evaluated using the Lagergren and Ho-McKay equations. The isotherms were analyzed using the Langmuir and Freundlich equations. For the kinetics of TBCA adsorbents, Pb(II) cations followed the Ho-McKay model, while Fe(III) was based on Lagergren. Furthermore, for the TBMTCA adsorbent, Pb(II) followed the Lagergren kinetic model, while Fe(III) was based on the Ho-McKay. The cation adsorption isotherms of Pb(II)-TBCA, Pb(II)-TBMTCA, Fe(III)-TBCA, and Fe(III)-TBMTCA are more in line with the Langmuir model. These results indicate that they can be used as heavy metal adsorbents, and recycled to increase their economic value.

This study aims to investigate the application of two calix[4]arene derivatives named 5,11,17,23-tetra-(t-butyl)-25,26,27,28-tetrahydroxycalix[4]arene (TBCA) and 5,11,17,23-tetra-(t-butyl)-26,27,28-tribenzoyloxycalix[4]arene (TBMTCA) as adsorbents of Pb(II) from aqueous solution in a batch system. Adsorption was carried out by varying pH solution, exposure time, and concentration. The kinetics was evaluated based on the adsorption in various exposure times using the Lagergren and Ho equations, while the isotherms were analyzed based on the adsorption in various Pb(II) concentrations using the Langmuir and Freundlich equations. Furthermore, the isotherm model showed the Pb(II) adsorption of TBCA and TBMTCA followed Langmuir model with a capacity of 137.29 and 128.46 mg/g, respectively. Based on the adsorption capacity, both adsorbents are the potential for the removal of heavy metal cations from polluted water.

A new series of xanthyl-cinnamate hybrid compounds (4a-d) have been synthesized and screened through in vitro assay against four human cancer cell lines, i.e., HeLa, T47D, A549, and WiDr. The results revealed that xanthone hybridization with cinnamic acid increases the selectivity of the compounds with SI values of 2.75–209.03 compared to its parent oxygenated-xanthone. Compound 1,3-dihydroxyxanthen-6-yl cinnamate (4c) showed high cytotoxic activity against WiDr cell lines with an IC50 value of 39.57 µM. Molecular docking studies revealed the possible binding modes of all hybrid compounds with EGFR protein. A complex of 3,6-dihydroxyxanthen-1-yl cinnamate (4d)-EGFR, as the best binding model, exhibited higher predicted EGFR inhibitory activity than erlotinib and oxygenated-xanthone with a ΔG and Ki value of -35.02 kJ/mol and 0.74 µM, respectively. Compounds 4c and 4d were chosen as the most potent derivates from the study.

Recently, biodiesel production from palm oils has been thoroughly investigated to substitute crude oil due to its scarcity. However, the biodiesel production process is time-consuming due to its slow kinetics; thus, concentrated sulfuric acid has been used to fasten the reaction process in some industries. Unfortunately, sulfuric acid is a toxic, corrosive, and non-environmentally friendly catalyst. In this study, we prepared sulfated Calix[4]resorcinarene derived from vanillin as an efficient organocatalyst to replace sulfuric acid. The catalytic activity of sulfated Calix[4]resorcinarenes was evaluated through the methylation of palmitic acid and oleic acid as model compounds due to their abundant amounts in palm oil. The Calix[4]resorcinarene and sulfated Calix[4]resorcinarenes have been obtained through a one-pot reaction in 71.8–98.3% yield. Their chemical structures were confirmed by using FTIR, NMR and HRMS spectrometry analyses. The results showed that the sulfated Calix[4]resorcinarene exhibited high catalytic activity for methyl palmitate and methyl oleate productions in 94.8 ± 1.8 and 97.3 ± 2.1% yield, respectively, which was comparable to sulfuric acid (96.3 ± 1.8 and 95.9 ± 2.5%). The optimum condition was achieved by using 0.020 wt equivalent of organocatalyst for 6 h reaction process at 338 K. The methylation of palmitic acid and oleic acid fits well with the first-order kinetic model (R2 = 0.9940–0.9999) with a reaction rate constant of 0.6055 and 1.1403 h-1, respectively. Further investigation reveals that the hydroxyl group of vanillin plays a pivotal role in the organocatalytic activity of sulfated Calix[4]resorcinarene.

Cancer therapy through conventional chemotherapy has been widely applied; however, one of the main disadvantages of chemotherapy is the non-selective targeting of cancer cells which causes various adverse side effects. The development of drug delivery agents that are more selective and effective in cancer therapy needs to be performed so that the drugs have a therapeutic effect and minimize side effects. In this study, the compound C-phenylcalyx[4]resorcinarene epoxide (CFKRE) has acted as a drug delivery agent because it can form host complex interactions with ligands. The CFKRE compound was synthesized through two reaction steps: the condensation and alkylation reactions of the epoxide. The structure was analyzed using FTIR, 1H-, and 13C-NMR spectrophotometers and then tested for in vitro cytotoxicity using the MTT assay. The results showed that 70% yield of CFKRE was obtained. Molecular docking analysis of CFKRE compounds against PDGFR and EGFR proteins showed high binding energy compared to conventional chemotherapeutic agents. Molecular dynamic studies showed that CFKRE compounds could form a host-ligand complex with a −350.4 kcal/mol binding energy. Cytotoxic assay of CFKRE compound against MCF-7 breast cancer cells and Vero cells gave IC50 values of 4.04 and 29.59 μg/mL, respectively. These results indicated that CFKRE compounds are not toxic and have the potential to be utilized as new candidates for drug delivery agents.

Abstract In the present work, three hydroxyxanthones were synthesized in 11.15–33.42% yield from 2,6-dihydroxybenzoic acid as the starting material. The chemical structures of prepared hydroxyxanthones have been elucidated by using spectroscopic techniques. Afterward, the hydroxyxanthones were evaluated as antioxidant agents through radical scavenging assay; and anticancer agents through in vitro assays against WiDr, MCF-7, and HeLa cancer cell lines. Hydroxyxanthone 3b was categorized as a strong antioxidant agent (IC50 = 349 ± 68 µM), while the other compounds were categorized as moderate antioxidant agents (IC50 > 500 µM). On the other hand, hydroxyxanthone 3a exhibited the highest anticancer activity (IC50 = 184 ± 15 µM) and the highest selectivity (SI = 18.42) against MCF-7 cancer cells. From the molecular docking study, it was found that hydroxyxanthone 3a interacted with the active sites of Topoisomerase II protein through Hydrogen bonding with DG13 and π–π stacking interactions with DA12 and DC8. These findings revealed that hydroxyxanthones are potential candidates to be developed as antioxidant and anticancer agents in the future.

Plasmodium falciparum (P. falciparum) is the most fatal among the other Plasmodium parasites that infect humans with the malaria disease. Currently, the resistance of P. falciparum against some antifolate drugs has become a severe problem. On the other hand, xanthone and thioxanthone derivatives have been reported to have remarkable antimalarial activity. However, molecular docking studies have not evaluated thioxanthone derivative compounds as antimalarial agents. Accordingly, this research investigated the binding pose and inhibition mechanism of several thioxanthone derivatives against P. falciparum proteins DHFR (PDB ID: 1J3K) and DHODH (PDB ID: 1TV5) through molecular docking study. The compound structures were geometrically optimized using Gaussian 09 software and docked to the receptors using AutoDock4 software. The results showed that the free binding energy of thioxanthone derivatives ranged between -6.77 to -7.50 and -8.45 to -9.55 kcal mol–1 against pfDHFR and pfDHODH, respectively, with RMSD values of less than 2 Å. Compound F (4-iodo-3,4-dihydroxy-thioxanthone) gave the most substantial free binding energy against both proteins. Furthermore, the hydrogen bond interaction of compound F was the same as the native ligands of pfDHFR and pfDHODH. These results suggested that compound F has a more robust interaction in pfDHFR and pfDHODH. Thus, it is promising to further evaluate the compound as a candidate for a new antimalarial agent.

Anion logam berat Cr2O72– bersifat lebih toksik dibandingkan bentuk kationnya (Cr3+) yang dalam konsentrasi kecil dapat menyebabkan kanker bagi manusia. Salah satu cara yang paling sederhana dalam menyerap zat pencemar yaitu melalui adsorpsi. Senyawa C–4–etoksi–3–metoksifenilkaliks[4]resorsinarena trifenilfosfonium klorida (CKR) telah digunakan sebagai adsorben Cr2O72–. Dalam penelitian ini dilakukan karakterisasi adsorben CKR lebih lanjut dan interaksinya terhadap Cr2O72–. Metode penelitian yang dilakukan adalah (1) karakterisasi adsorben CKR meliputi titik lebur dan sifat kelarutannya; dan (2) studi spektroskopi CKR dan kompleks CKR–Cr2O72– serta desorpsi. Hasil penelitian menunjukkan CKR memiliki titik lebur 259,7°C dan mampu larut dalam aseton, etanol, metanol, dimetilformamida, dan dimetilsulfoksida serta terdistribusi di dalam air dengan baik. CKR berukuran pori 35,50 (mesopori) memiliki luas permukaan spesifik (SBET) sebesar 5,749 m2/g dan total volume pori 10,21×10–3 cc/g. Interaksi antara situs aktif gugus fosfonium kuarterner dengan Cr2O72– dalam kompleks CKR–Cr2O72–melalui pergantian unsur Cl pada CKR oleh Cr2O72–dengan prosentase massa sekitar 0,07%. Regenerasi adsorben CKR melalui desorpsi tunggal belum dapat membebaskan semua Cr2O72– yang telah terikat. Kemisorpsi CKR–Cr2O72– meliputi 13,16% pertukaran ion dan selebihnya diduga merupakan proses kelasi dengan interaksi logam–adsorben yang lebih kuat.

Crude oil is an indispensable energy feedstock for daily activities, although some amounts of metallic porphyrins components with undesired characteristics have been identified. These constituents are assumed to originate from the geochemical process of chlorophyll and heme derivatives. In addition, their chemical structures have been thoroughly characterized using spectroscopy techniques, while several analytical methods were adopted in the detection and concentration quantification in the crude oils. The metallic porphyrins have several demerits, including the deactivation of used catalysts, contamination of the treated petrochemical products, and corrosion of the industrial equipment. Also, the removal process is considered challenging due to the strong interaction with the asphaltene fraction of crude oil. This review article, therefore, provides brief information on the origin, physicochemical properties, and possible removal technology of metallic porphyrins from crude oil samples. Besides, a better understanding of chemistry contributes a useful insight towards the development and establishment of better futuristic processing technology.

This research aims to examine the capability of poly-37,40-diallyl-38,39,41,42,-tetrahydroxy-calix[6]arenes as adsorbent for heavy metal cations such as Cd(II), Cr(III) and Cu(II). The adsorption process was carried out by batch method in the variation of acidity (pH), contact time and initial concentration of metal ions. The adsorption kinetics and adsorption isotherms were also studied. The results of this research showed that the amount of adsorbed metal increased with the increasing of the pH of metal solution. The amount of metal ions Cd(II) and Cr(III) adsorbed was optimum at pH 5, while for metal ion Cu(II) was optimum at pH 4. The optimum contact time for Cd(II), Cr(III) and Cu(II) was 60; 30; and 180 minutes, respectively. The study of adsorption kinetics showed that the adsorption of Cd (II), Cr (III) and Cu (II) metal ions using this adsorbent followed kinetics model of Ho. Isothermal studies showed that the adsorption of the three metal ions tends to follow the Langmuir isotherm. The adsorption capacities of Cd (II), Cr (III) and Cu (II) metal ions with poly-37,40-diallyl-38,39,41,42,-tetrahydroxycalix[6]arenes were 7.06; 14.72 and 38.45 µmol/g, respectively.

Four chalcone derivatives were synthesized and pre-evaluated as broad-spectrum UV protector. Chalcones 1-4 showed a wide range of UV absorbance values and moderate molar absorptivity values. Chalcones 3 and 4 showed better photostability than chalcones 1 and 2 because the lowering of their absorbance was smaller and slower under UVB irradiation. A combination of the spectra of chalcone derivatives 1-4 indicated that a formulation containing all four will provide a broad-spectrum sunscreen protecting the skin from UVA and UVB.

This study describes simple synthetic method to prepare 1-(2-methoxybenzyl)-1,10-phenanthrolin-1-ium bromide from gandapura oil. The salt were synthesized in four steps. Initially, commercial gandapura oil was directly subjected to the alkylation reaction under basic condition using dimethyl sulfate to give methyl 2-methxybenzoate in 86% yield. Next, the produced benzoate ester was reduced by LiAlH4 to produce 2-methoxybenzyl alcohol in 67% yield. The treatment of benzyl alcohol with phosphorus tribromide under solvent free condition produced the corresponding benzyl bromide (in 67% yield), which was directly introduced into bimolecular nucleophilic substitution reaction with 1,10-phenantroline monohydrate to finally give the desired product in 63% yield.

Abstract Background Biofilm is one of the causes of antibiotic resistance. One of the biofilm-producing bacteria is Staphylococcus epidermidis which has been proven to infect long-term users of urinary catheters and implant devices. The 1-monolaurin compound has been known to have an antimicrobial effect. However, its effect on clinical isolates of S. epidermidis in producing biofilm has not been established. This study was conducted to investigate the effect of 1-monolaurin towards biofilm forming clinical isolates of S. epidermidis. Methods The experiment used micro broth dilution technique which consists of test group (1-monolaurin), positive control group (rifampicin), solvent group, negative control group (clinical isolate of S. epidermidis), and media group (TSB media). The Minimal Inhibition Concentration (MIC) was determined by incubating bacteria added with 1-monolaurin (1000–1953 μg/mL) or rifampicin (250–0,488 μg/mL) for 24 h. The MIC was determined visually. After that, the incubated bacteria was cultured in TSA media to determine Minimal Bactericidal Concentration (MBC). The assessment of Biofilm inhibitory Concentration (BIC) and Biofilm Eradication Concentration (BEC) was conducted with the same way, the difference was BIC intervened directly with compound meanwhile BEC was incubated for 24 h in 37 °C before the intervention. Then, the specimen was reincubated to grow biofilm at the microplate, washed with PBS and stained with 1% of crystal violet. The optical density (OD) was measured at a wavelength of 595 nm. The percentage of BIC and BEC then were calculated, continued to probit analysis regression to determine the BIC50, BIC80, BEC50, and BEC80. Results The MIC dan MBC of 1-monolaurin and rifampicin were > 1000 μg/mL, > 1000 μg/mL, ≤0.488 μg/mL, and 1.953 μg/mL respectively. BIC50 and BIC80 of 1-monolaurin and rifampicin were 26.669 μg/mL, 168.688 μg/mL, 0.079 μg/mL, and 0.974 μg/mL respectively. The BEC50 and BEC80 of 1-monolaurin and rifampicin were 322.504 μg/mL, 1338.681 μg/mL, 5.547 μg/mL, dan 17.910 μg/mL respectively. Conclusion The 1-monolaurin can inhibit growth and eradicate the biofilm formed by clinical isolates of S. epidermidis, however, it has neither inhibit nor kill planktonic cells of S. epidermidis.

In this study, the chloro-substituted hydroxyxanthones were prepared by cyclodehydration of acid derivatives and substituted phenol in the presence of Eaton reagent, followed by halogenations step to electrophilic substitution of chlorine in a moderate yield. The in vitro anticancer activity study on various cell lines revealed that the chloro functional group increases the anticancer activity of the hydroxyxanthone derivatives. The molecular docking study showed that there was a binding interaction between chloro-hydroxyxanthone and the amino acid residues such as Asp810, Cys809, Ile789, His790, and Leu644 of protein tyrosine kinase receptor (1T46.pdb).

In this study, the microreactor system was investigated and compared with the batch-wise system as rapid and effective extractive Pb(II) separation over Fe(III), Cu(II) and Zn(II) with tetraacetic acid calix[4]arene. By using a microreactor system, the Pb(II) extraction percentages reached the maximum of 73, 89 and 100% in 8 sec residence time at equilibrium pH of 2.00, 2.25 and 2.50, respectively. The stripping percentage was 92% at 8 sec residence time by using a microreactor system with 2.0 M HNO3 as a stripping reagent. Complete separation of Pb(II) over Fe(III), Cu(II) and Zn(II) ions with the tetraacetic acid calix[4]arene in a competitive metal system was achieved at pH 2.00. However, the batch system required 24 h to reach the equilibrium for both extraction and stripping processes. The results suggested that the microreactor system enhanced the Pb(II) extraction and stripping rate up to 104 times faster than the batch-wise system.

Indonesia is rich with essential oils such as anise and clove leave oils. In respect to explore the potential utilization of these resources, it has been conducted the transformation of p-hydroxybenzaldehyde and vanillin (4-hydroxy-3-methoxy benzaldehyde) respectively derived from anise oil and clove leaves oil to a series of C-arylcalix[4]resorcinarenes and C-arylcalix[4]pyrogallolarene macrocycles. Treatment of these aldehydes with resorcinol in the presence of HCl in absolute ethanol at reflux for 8 h afforded C-4-hydroxyphenylcalix[4]resorcinarene (3a) and C-4-hydroxy-3-methoxy phenyl-calix[4]resorcinarene (3b) in good yields. When the aldehydes were treated with pyrogallol under the similar condition, the products were C-4-hydroxyphenyl calix[4]pyrogallolarene (3c) and C-4-hydroxy-3-methoxyphenylcalix[4]pyrogallolarene (3d) which were also obtained in excellent yields. Treatment of these calix[4]resorcinarenes and calix[4]pyrogallolarenes with cinnamoyl chloride and benzoyl chloride in pyridine afforded the corresponding cinnamate esters and benzoate esters in high yields. The resulted C-arylcalix-[4]resorcinarenes and C-arylcalix[4]pyrogallol arenes were subjected to antioxidant activity test using DPPH method and showed strong activity with IC50 values of 15–80 μg/mL. In terms of the synthesized calix cinnamates, the compounds showed UV-B absorption with SPF values of 15–30 at a concentration of 25 ppm which demonstrate their potential to be applied as a UV-B protector. Furthermore, these compounds were also tested for their photostability on the UV-B region and the results showed that the compounds were still unstable under irradiation for 30 min.

Background: Chemotherapy is a common treatment for leukemia as well as in other cancer treatment. The lack of tumor selectivity and development of multi-drug resistance by chemotherapy caused the development of new strategy in cancer treatment become a pressing need. This study was performed to evaluate the anticancer activity and selectivity of seven derivatives of chalcones against K562 and HL-60 leukemia cell lines. Materials and Methods: The cytotoxicity of chalcone’s seven derivatives (compound 1-7) was tested by using MTS (3-(4,5-dimethylthiazol-2-yl)-5-(3-carboxyme-thoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium) method. The percentage of cell mortality data was calculated then the IC50 was analyzed using probit analysis (SPSS 17). The selectivity index (SI) then calculated from IC50 ratio of normal lymphocyte cells and cancerous cells line (HL-60 and K562). Results: The IC50 of almost all seven tested compounds were lower in HL-60 cell lines than K562 cell lines, except for Compound 7. The number and position of methoxy groups in chalcone derivatives influenced the anticancer and cancer selectivity of chalcone derivatives. Conclusion: The results revealed that the number and position of methoxy groups in chalcone derivatives influenced the anticancer and cancer selectivity of chalcone derivatives. Keywords: anticancer, chalcone derivatives, methoxy-4’-amino chalcone, leukemia, cytotoxic, selectivity

This research was conducted to evaluate the anticancer activity of new compounds of benzyl-1,10-phenanthroline derivatives and their selectivity. In vitro anticancer activity of 11 benzyl-1,10-phenanthroline derivatives were conducted on three human cancer cell lines, cervical cancer (HeLa), myeloma (NS-1), and breast cancer (MCF-7) using MTT-based cytotoxicity assay. The cytotoxicity of each compound was assessed to normal Vero cell line by the same method. The in vitro anticancer activity and cytotoxicity was expressed by the concentration inhibiting 50% of the cell growth (IC50), and the selectivity index (SI) was determined by calculating ratio of the IC50 on Vero cell line and the human cancer cell lines. The results showed that among the 11 compounds tested, the (1)-N-(4-butoxybenzyl)-1,10-phenanthrolinium bromide exhibited the best in vitro anticancer activity with an IC50 27.602.76 μM on HeLa, 6.425.53 μM on NS-1 and 9.442.17 μM on MCF-7 cell lines. Its SI were 377.65 39.97 on HeLa, 6158.72 5306.34 on NS-1 and 1140.11 261.85 on MCF-7 cell lines. This study demonstrated that (1)-N-(4-butoxybenzyl)-1,10-phenanthrolinium bromide possessed a potential in vitro anticancer activity on cancer cell lines with high selectivity.

The previous study showed that xanthone had antiplasmodial activity. Xanthone, with additional hydroxyl groups, was synthesized to increase its antiplasmodial activity. One of the strategies to evaluate a compound that can be developed into an antimalarial drug is by testing its mechanism in inhibiting heme polymerization. In acidic condition, hematin can be polymerized to β-hematin in vitro, which is analog with hemozoin in Plasmodium. This study was conducted to evaluate the antiplasmodial activity of hydroxyxanthone derivative compounds on two strains of Plasmodium falciparum 3D-7 and FCR-3, to assess inhibition of heme polymerization activity and determine the selectivity of hydroxyxanthone derivative compounds. The antiplasmodial activity of each compound was tested on Plasmodium falciparum 3D-7 and FCR-3 with 72 hours incubation period, triplicated in three replications with the microscopic method. The compound that showed the best antiplasmodial activity underwent flow cytometry assay. Heme polymerization inhibition test was performed using the in vitro heme polymerization inhibition activity (HPIA) assay. The antiplasmodial activity and heme polymerization inhibition activity were expressed as the 50% inhibitory concentration (IC50). In vitro cytotoxicity was tested using the MTT assay method on Vero cell lines to determine its selectivity index. The results showed that among 5-hydroxyxanthone derivative compounds, the 1,6,8-trihydroxyxanthone had the best in vitro antiplasmodial activity on both 3D-7 and FCR-3 Plasmodium falciparum strains with IC50 values of 6.10 ± 2.01 and 6.76 ± 2.38 μM, respectively. The 1,6,8-trihydroxyxanthone showed inhibition activity of heme polymerization with IC50 value of 2.854 mM and showed the high selectivity with selectivity index of 502.2–556.54. In conclusion, among 5-hydroxyxanthone derivatives tested, the 1,6,8-trihydroxyxantone showed the best antiplasmodial activity and has heme polymerization inhibition activity and high selectivity.

ABSTRACT: Background: The increasing rate of cancer chemoresistance and adverse side effects of therapy have led to the wide use of various chemotherapeutic combinations in cancer management, including lymphoid malignancy. Objective: We investigated the effects of a combination of 1,3,6-trihydroxy-4,5,7-trichloroxanthone (TTX) and doxorubicin on the Raji lymphoma cell line. Methods: Raji cells were treated with different concentrations of TTX, doxorubicin, or combinations thereof. Cancer cell growth inhibition was evaluated using 3-(4,5-dimethyltiazol-2-yl)-2,5- diphenyltetrazolium bromide/MTT assay to determine the half-maximal inhibitory concentration. Combination index values were calculated using CompuSyn (ComboSyn, Inc, Paramus, NJ). Molecular docking was conducted using a Protein-Ligand ANT System. Results: The mean (SD) half-maximal inhibitory concentration values of TTX and doxorubicin were 15.948 (3.101) µM and 25.432 (1.417) µM, respectively. The combination index values of the different combinations ranged from 0.057 to 0.285, indicating strong to very strong synergistic effects. The docking study results reveal that TTX docks at the active site of Raf-1 and c-Jun N-kinase receptors with predicted free energies of binding of −79.37 and −75.42 kcal/mol, respectively. Conclusions: The xanthone-doxorubicin combination showed promising in vitro activity against lymphoma cells. The results also indicate that the TTX and doxorubicin combination's effect was due to the interaction between TTX with Raf-1 and c-Jun N-kinase receptors, 2 determinants of doxorubicin resistance progression.

A synthesis and kinetic study of the urea controlled-release composite material based on isolated Na-lignosulfonate, Na-alginate and tapioca was carried out. This experiment’s aims were to isolate Na-lignosulfonate from wood sawdust and to applicate this isolated Na-lignosulfonate, along with tapioca and Na-alginate as urea control release composite material. A kinetic study of urea released from the composite materials was also conducted. Na-lignosulfonate was isolated by Kraft lignin method to give a brown solid yield of 16.92% and was characterized by FT-IR spectrophotometer and SEM-EDX. The composite materials were synthesized by blending urea as the active compound with composite material as the carrier compound. Three types of material were prepared: complete material (A), low-concentration Na-lignosulfonate material (B) and material without tapioca (C). The composite material had a spherical form with 0.79 mm radius and 2.16 mm swollen radius. Urea content inside material was 40.425 mg urea/g material. The urea diffusivity coefficient for material A, B, and C were 7.27 x 10–6; 15.50 x 10–6 and 0.94 x 10–6 m2 h–1, respectively. Modelling analysis showed the experiment obeyed around only 15% of the Korsmeyer–Peppas model, but there was good correlation (80%) with the unsteady-state diffusion model.

Isnatin Miladiyah,1,2 Jumina Jumina,3 Sofia Mubarika Haryana,4 Mustofa Mustofa5 1Pharmacology Department, Faculty of Medicine, Islamic University of Indonesia, 2Doctorate Program of Medical Science and Health, Faculty of Medicine, 3Chemistry Department, Faculty of Mathematics and Natural Sciences, 4Histology and Cell Biology Department, Faculty of Medicine, 5Pharmacology and Therapeutic Department, Faculty of Medicine, Gadjah Mada University, Yogyakarta, Indonesia Background: Xanthone derivatives have a wide range of pharmacological activities, such as those involving antibacterial, antiviral, antimalarial, anthelmintic, anti-inflammatory, antiprotozoal, and anticancer properties. Among these, we investigated the anticancer properties of xanthone. This research aimed to analyze the biological activity of ten novel xanthone derivatives, to investigate the most contributing-descriptors for their cytotoxic activities, and to examine the possible mechanism of actions of xanthone compound through molecular docking. Materials and methods: The cytotoxic tests were carried out on WiDR and Vero cell lines, by a 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyl-tetrazolium bromide (MTT) assay method. The structural features required for xanthone’s anticancer activity were conducted by using the semi-empirical Austin Model-1 method, and continued with quantitative structure-activity relationship (QSAR) analysis using BuildQSAR program. The study of the possible mechanism of actions of the selected xanthone compound was done through molecular docking with PLANTS. Results: The three novel xanthone derivatives (compounds 5, 7, and 8) exhibited cytotoxic activity with compound 5 showed the highest degree of cytotoxicity at concentration 9.23 µg/mL (37.8 µM). The following best equation model was obtained from the BuildQSAR calculation: log 1/IC50 = -8.124 qC1 -35.088 qC2 -6.008 qC3 + 1.831 u + 0.540 logP -9.115 (n = 10, r = 0.976, s = 0.144, F = 15.920, Q2 = 0.651, SPRESS = 0.390). This equation model generated 15 proposed new xanthone compounds with better-predicted anticancer activities. A molecular docking study of compound 5 showed that xanthone formed binding interactions with some receptors involved in cancer pathology, including telomerase, tumor-promoting inflammation (COX-2), and cyclin-dependent kinase-2 (CDK2) inhibitor. Conclusion: The results suggested that compound 5 showed the best cytotoxic activity among the xanthone derivatives tested. QSAR analysis showed that the descriptors contributed to xanthone’s cytotoxic activity were the net atomic charge at qC1, qC2, and qC3 positions, also dipole moment and logP. Compound 5 was suspected to be cytotoxic by its inhibition of telomerase, COX-2, and CDK2 receptors. Keywords: xanthones, anticancer, semiempirical AM1, BuildQSAR, molecular docking

Studies on the synthesis of polyurethane/silica modified epoxy polymer using 1,3-propanediol has been conducted. Synthesis of polymers made by reaction of tolonate and 1,3-propanediol (ratio NCO/OH=2.5) as the building blocks of polyurethane with diglycidyl ether bisphenol A (DGEBA) epoxy and catalyst dibutyltin dilaurate (DBTL).The total weight of the polyurethane used was 20% (w/w) of the total epoxy. Based on Fourier Transform Infrared (FTIR) and 1H-Nuclear Magnetic Resonance (1H-NMR) spectra indicated the existence of a new bond that is formed from the reaction of isocyanate group and hydroxyl group, where the hydroxyl groups derived from epoxy and 1,3-propanediol. The addition of silica (5, 10, and 15% w/w to epoxy) into the epoxy-modified polyurethane has been carried out through sol-gel reaction of tetraethyl orthosilicate (TEOS). The isocyanate conversion rate for the addition of silica 5, 10, and 15% are 95.69; 100, and 100%, respectively. The morphology and element identification by Scanning Electron Microscopy/Energy Dispersive X-Ray Analysis (SEM/EDX), showed that Si element has been successfully added in the polymer. From the tensile strength and elongation analysis, also thermal stability analysis using Thermal Gravimetric Analyzer (TGA), the increase of silica amount into the polyurethane modified epoxy did not significantly affect to thermal properties, but decrease the tensile strength of the polymer.

Synthesis and in vitro test of C-methylcalix[4]resorcinaryl octacinnamate as the sunscreen has been conducted. The C-methylcalix[4]resorcinaryl octacinnamate was synthesized in 2 steps. They were synthesis of C-methylcalix[4]resorcinarene via acid catalyzed condensation of resorcinol and acetaldehyde, followed by estherification using cinnamoyl chloride and pyridine catalyst. The characterization of the target molecule was performed by infra red spectrophotometer, proton-NMR, carbon-NMR and mass spectromether. The sunscreen activity test was conducted by spectroscopic method and MTT-assay. Spectroscopic analysis (UV) showed that the target molecule absorbed the dangerous ultraviolet radiation between 280 and 320 nm (UV B) wave length with the maximum absorption at 290 nm (ε = 31.535 M-1 cm-1). The MTT-assay indicated that the IC50 of C-methylcalix[4]resorcinaryl octacinnamate is 12.006 ppm. The sunscreen activity of C-methylcalix[4]resorcinaryl octacinnamate is stronger than commercial sunscreen Intersun (IC50 = 18.235 ppm).

The annual number of cancer deaths continues increasing every day; thus, it is urgent to search for and find active, selective, and efficient anticancer drugs as soon as possible. Among the available anticancer drugs, almost all of them contain heterocyclic moiety in their chemical structure. Xanthone is a heterocyclic compound with a dibenzo-γ-pyrone framework and well-known to have “privileged structures” for anticancer activities against several cancer cell lines. The wide anticancer activity of xanthones is produced by caspase activation, RNA binding, DNA cross-linking, as well as P-gp, kinase, aromatase, and topoisomerase inhibition. This anticancer activity depends on the type, number, and position of the attached functional groups in the xanthone skeleton. This review discusses the recent advances in the anticancer activity of xanthone derivatives, both from natural products isolation and synthesis methods, as the anticancer agent through in vitro, in vivo, and clinical assays.

Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in the present work, we synthesized eight chalcone derivatives through Claisen–Schmidt condensation at room temperature. The evaluation of the optical properties of each chalcone derivatives in the UV region was conducted through spectroscopic and computational studies. The synthesized chalcones were obtained in good yields and they were active in the UV region. The results revealed that more methoxy substituents to chalcone leads toward red shift. All chalcone derivatives have high molar absorptivity value (21,000–56,000) demonstrating that they have the potential to be used as the sunscreen agent. The cytotoxicity assay showed that chalcone derivatives were demonstrating low toxicity toward normal human fibroblast cell, which is remarkable. Therefore, we concluded that the synthesized chalcones in this work were potential to be developed as novel sunscreen agents in real application.

Lithium extraction remains a challenge in the hydrometallurgy process due to its economic value and maldistribution sources. Employing calix[4]arene derivatives in solvent extraction techniques results in high selectivity and extraction capability, but a slow extraction rate. The slow kinetics of batch-wise extraction can be drastically accelerated by using a T-type microreactor system. Therefore, a combination of calix[4]arene and a microreactor system serves as an ideal platform for efficient lithium extraction. In this work, the fluid dynamics of lithium extraction using a monoacetic acid calix[4]arene derivative in a T-type microreactor system were studied. Increasing the O/A ratio increases the average length, surface area, and volume of the organic droplets, but decreases the specific surface area. In contrast, increasing the Reynolds number decreases the average length, surface area, and volume of the organic droplets, but increases the specific surface area. It was found that shorter diffusion distance, larger specific surface area, and faster vortex velocity were the factors that play the most pivotal roles in achieving great extraction rate enhancement in T-type microreactor systems compared to batch-wise systems. These findings represent an important new concept in the study of the fluid dynamics of lithium extraction using monoacetic acid calix[4]arene derivatives in T-type microreactor systems.

The study of xanthone derivatives as cytotoxic agents in cancer is increasing. This study was conducted to explore the Quantitative Structure-Activity Relationship (QSAR) of xanthones as cytotoxic agents in HepG2 cells, to find compounds with better potency. The data set were taken from the previous study, involving 26 xanthone derivates and their cytotoxic activities in Inhibitory Concentration 50% (IC50). The parameters (descriptors) were obtained from quantum mechanics calculation using semiempirical AM1 method and QSAR models determined with principle component regression, with log (1/IC50) as a dependent variable and five latent variables as independent variables. From the 26 main descriptors, PCR reduced them to five latent variables (1st– 5th LV). The QSAR analysis gave the best model as follows: log (1/IC50) = 4.592 – 0.204 LV1 + 0.295 LV2 + 0.028 LV3 (n = 26, r = 0.571, SE = 0.234, Fcount/Ftable ratio = 1.165, PRESS value = 3.766). The study concluded that the descriptors contributed to anticancer activity were volume, mass, surface area, log P, dipole moment, HOMO energy, LUMO energy, and atomic net charge of some atoms. Modifications of substitution that would contribute to cytotoxic activity can be performed at phenyl ring A and C, but not at B.

Fe-Ionic Imprinted Polymer (IIP) from polyeugenol as base polymer and polyethylene glycol diglycidyl ether (PEGDE) as cross-linking agent had been synthesized to adsorb Fe(III) from aqueous media. The non-imprinting material (NIP) and polyeugenol were used in the adsorption study as control. Synthesis work included polymerization, template uploading, crosslinking and template removal, optimized for different template ion upload pH and concentrations. The polymers were characterized by FTIR spectroscopy, XRD and SEM-EDX, followed by adsorption test to study the adsorption kinetics and isotherms for all adsorbents. Selective adsorption study of IIP was carried out using binary mixtures of Fe(III) and Cr(III), Pb(II), Cd(II). Experimental results showed that the optimum conditions for the synthesis was template upload pH of 3, Fe/polyeugenol ratio of 1 mg/g, while the optimum adsorption pH was 3. The adsorption mechanism of Fe(III) on all adsorbents was dominated by hydrogen bond formation. The adsorption kinetics followed the pseudo-second-order model while the equilibrium data was best explained by the Langmuir isotherm model. The adsorption capacity of Fe(III) on the IIP was 12.73 mg/g, higher than that of the other adsorbents. Results also show that IIP-Fe was more selective toward Fe than NIP by 2.69 (Cd), 1.66 (Cr) and 1.6 (Pb) fold, respectively.

The inhibitory activity of heme polymerization of (1)-N-(2-nitrobenzyl)-1,10- phenantrolinium iodide and (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide have been done. This study aims to analyse the (1)-N-(2-nitrobenzyl)-1,10-phenantrolinium iodide and (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide as inhibitory of polimerization heme. Analysis of heme inhibtory polimerization activity used the experimental in vitro method. The activity showed by IC50 (the capable concentration of extract to inhibiting polymerization heme 172 Pharmaҫiana, Vol. 4, No. 2, 2014: 171-176 by 50% ). The IC50 value acquired by probit analysis. Assess IC50 of (1)-N-(2-nitrobenzyl)- 1,10-phenantrolinium iodide not to be identified, (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide and chloroquine by successively are 0,571±0,071; 25,498±1,876 mg/mL. The result showed the (1)-N-(4-nitrobenzyl)-1,10-phenantrolinium iodide had the highest value of the heme polymerization inhibitory activity than chloroquin, (1)-N-(2-nitrobenzyl)-1,10- phenantrolinium iodide hadn’t the heme polymerization inhibitory activity.

A new phosphonate modified silica (PMS) has been investigated for adsorption of Co(II), Ni(II), Cu(II), and Zn(II) in aqueous solution. The adsorbent was modified of silica by immobilizing aminoethyl dihydrogen phosphate (AEPH2) on 1,4-dibromobutane grafted silica. The physicochemical of the adsorbent was investigated using Fourier Transform Infra-red (FTIR) spectroscopy, X-ray Fluorescence (XRF), and N2 gas adsorption/desorption. The adsorption study was carried out in a batch system by mixing solution of metal ions at various pHs, contact times, and initial metal ion concentrations. The unadsorbed metals were determined by Flame Atomic Absorption Spectrophotometry (FAAS). Result of characterization showed that PMS has been successfully prepared. The product contained 45.99% (w/w) silica and 1.33% (w/w) phosphorous with surface area, pore volume, and pore size of 115.3 m2g-1; 0.7578 mLg-1; and 131.44 Å, respectively. Adsorption of metal ions on PMS occurred quite fast, less than 30 min. Modification of phosphonate on silica increased the adsorption capability, up to 8 times higher than that of unmodified silica, depending on metal ion type and pH solution. The capacity order of the metals adsorption was Cu(II)>Co(II)>Ni(II)>Zn(II). Based on the adsorption characteristic, the adsorbent is promising to be applied as a material for solid phase extraction of transition metal ions.

The aims of this research is to synthesize Pb(II) imprinted polymers with carboxymethyl chitosan (CMC) as polymers and bisphenol A diglycidyl ether (BADGE) as cross-linker (Pb-IIP). Chitosan (CTS), non imprinted polymer (NIP) and Pb-IIP were characterized using infrared (IR) spectroscopy, X-ray diffraction (XRD), surface area analyzer (SAA), scanning electron microscopy (SEM), and energy dispersive X-ray (EDX) spectroscopy. The result showed that the adsorption was optimum at pH 5 and contact time of 250 min. Adsorption of Pb(II) ion with all of adsorbents followed pseudo-second order kinetic equation. Adsorption of Pb(II) ion on CTS followed Freundlich isotherm while that on NIP and Pb-IIP followed the Langmuir adsorption isotherm. The adsorbent of Pb-IIP give higher capacity than the NIP and CTS. Adsorption capacity of Pb-IIP, NIP and CTS were 167.1, 128.9 and 76.1 mg/g, respectively. NIP gave higher adsorption selectivity for Pb(II)/Ni(II) and Pb(II)/Cu(II), whereas Pb-IIP showed higher adsorption selectivity for Pb(II)/Cd(II).The hydrogen bonding dominated interaction between Pb(II) ion on NIP and Pb-IIP.

A new upper rim-functionalized benzoyl C-phenylcalix[4]resorcinaryl octaacetate and cinnamoyl C-phenylcalix[4]resorcinarene have been synthesized and evaluated as the absorbers for ultraviolet radiation. The benzoyl C-phenylcalix[4]resorcinaryl octaacetate was synthesized in 3 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation and Friedel-Craft benzoylation. The cinnamoyl C-phenylcalix[4]resorcinarene was synthesized in 4 steps. They were synthesis of C-phenilcalix[4]resorcinarene via acid-catalyzed-condensation of resorcinol and benzaldehyde, followed by O-acetylation, Friedel-Craft cinnamoylation and hydrolysis. Spectroscopic analysis (UV) showed that the target molecule absorbed the ultraviolet radiation between 200 and 400 nm with the maximum absorption at 240.50 nm (ε = 10.135 M-1 cm-1) and 243.50 nm (ε = 12.135 M-1 cm-1).

The aims of this research is to synthesize a chitosan derivative insoluble in acidic aqueous medium and that has high adsorption capacity for Pb(II) ions by cross-linking and grafting. Cross-linking and grafting were done using ethylene glycol diglycidyl ether (EGDE) and chloroacetic acid, respectively. The modified chitosan was characterized using FTIR spectrophotometer, XRD and TG-DTA. Chitosan and Chit-EGDE-Acetate was applied as adsorbent of Pb(II) ions in a batch system. The concentration of Pb(II) in adsorption medium was quantified using AAS. The result showed that the adsorption was optimum at pH 5, contact time of 200 min for chitosan and 300 min for Chit-EGDE-Acetate. Adsorption of Pb(II) ions on both adsorbents followed pseudo second order kinetic equation. Adsorption of Pb(II) ions on chitosan followed Freundlich isotherm while that on Chit-EGDE-Acetate followed the Langmuir adsorption isotherm. The adsorption capacity of Chit-EGDE-Acetate for Pb(II) ions was 200.0 mg L-1 while that for chitosan was 166.7 mg L-1. Interaction type of Pb(II) ions on adsorbent was determined by sequential desorption.

The synthesis of (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide had been conducted from vanillin. Heme polymerization inhibitory activity assay of the synthesized antiplasmodium has also been carried out. The first step of reaction was methylation of vanillin using dimethylsulfate and NaOH. The mixture was refluxed for 2 h to yield veratraldehyde in the form of light yellow solid (79% yield). Methylation product was reduced using sodium borohydride (NaBH4) with grinding method and yielded veratryl alcohol in the form of yellow liquid (98% yield). Veratryl alcohol was brominated using PBr3 to yield yellowish black liquid (85% yield). The final step was benzylation of 1,10-phenanthroline monohydrate with the synthesized veratryl bromide under reflux condition in acetone for 14 h to afford (1)-N-(3,4-dimethoxy-benzyl)-1,10-phenanthrolinium bromide (84%) as yellow solid with melting point of 166-177 °C. The structures of products were characterized by FT-IR, GC-MS and 1H-NMR spectrometers. The results of heme polymerization inhibitory activity assay of (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide showed that it had IC50 HPIA of 3.63 mM, while chloroquine had IC50 of4.37 mM. These results indicated that (1)-N-(3,4-dimethoxybenzyl)-1,10-phenanthrolinium bromide was more potential antiplasmodium than chloroquine.

Microbial infections remains a serious challenge in food industries due to their resistance to some of the well-known antibacterial and antifungal agents. In this work, a novel monomyristoyl ester (fructosyl monomyristate) and two other derivatives (i.e., glucosyl and galactosyl monomyristates) were successfully synthesized from myristic acid and monosaccharides in two-step reactions. First, the myristic acid was converted to myristoyl chloride, and then the myristoyl chloride was reacted with fructose, glucose and galactose separately to produce the corresponding monosaccharide monomyristate derivatives. The structures of the synthesized products were confirmed by Fourier transform infrared (FTIR), proton and carbon nuclear magnetic resonance (1H- and 13C-NMR), and mass spectral (MS) data. The monomyristates esters were obtained in reaction yields of 45.80%−79.49%. The esters were then evaluated for their antimicrobial activity using the disc diffusion test. It was found that the esters exhibited a medium antibacterial activity against gram-positive bacteria; however, they showed a weak antibacterial activity against gram-negative bacteria. Amongst the esters, galactosyl myristate yielded the highest antibacterial activity against Salmonella typhimurium, Staphylococcus aureus and Bacillus subtilis, while glucosyl monomyristate exhibited the highest antibacterial activity only against Escherichia coli. Additionally, all products showed remarkable antifungal activity against Candida albicans. These findings demonstrate that monosaccharide monomyristate derivatives are promising for use as biocompatible antimicrobial agents in the future.

Some chalcones have been designed and synthesized using Claisen-Schmidt reactions as inhibitors of the ferredoxin and ferredoxin-NADP+ reductase interaction to pursue a new selective antimalaria agent. The synthesized compounds exhibited inhibition interactions between PfFd-PfFNR in the range of 10.94%–50%. The three strongest inhibition activities were shown by (E)-1-(4-aminophenyl)-3-(4-methoxyphenyl)prop-2-en-1-one (50%), (E)-1-(4-aminophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one (38.16%), and (E)-1-(4-aminophenyl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one (31.58%). From the docking experiments we established that the amino group of the methoxyamino chlacone derivatives plays an important role in the inhibition activity by electrostatic interaction through salt bridges and that it forms more stable and better affinity complexes with FNR than with Fd.

A research has been conducted to synthesize tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide from vanillin and investigate its antidote capability for Cr(VI) intoxication. The synthesis was carried out in four steps i.e. (1) O-alkylation of 4-hydroxy-3-methoxybenzaldehyde, (2) HCl-catalyzed condensation of 3,4-dimethoxybenzaldehyde with resorcinol, (3) Mannich reaction of C-3,4-dimethoxyphenylcalix[4]resorcinarene with formaldehyde and dimethylamine in the presence of HCl to yield tetrakis-N,N-dimethylaminomethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene, and (4) treatment the Mannich base with methyl iodide to produce the quaternary ammonium salt of tetrakis-N,N,N-trimethylammoniummethyl-C-3,4-dimethoxyphenylcalix[4]resorcinarene iodide. According to the analysis of 1H-NMR spectrometer, the targeted compounds tend to exist in the chair (C2h) conformation. The capability of resorcinarene for Cr(VI) antidote was examined by orally injection method on mice groups. Based on LD50 determination, the resorcinarene was classified as non toxic compound according to Loomis criteria. Therapeutic using quaternary ammonium-modified resorcinarene was able to reduce metal concentrations of Cr(VI) in liver, kidney, and serum in the magnitude of 78.30; 85.72, and 88.79%, respectively. The higher dose of drug administered the greater decrease in the level of heavy metal. Judging from the amount of milligrams of reduced chromium per gram of organ, kidney is the organ having highest decreasing metal concentrations.

ABSTRAK Pada penelitian ini dipelajari kemampuan dari senyawa poli-monoaliloksi-kaliks[6]arena (PMK[6]H) sebagai antidotum keracunan Cd pada mencit. Penelitian ini mengikuti rancangan acak lengkap dengan menggunakan mencit jantan, galur Balb/C, sehat, umur 2-3 bulan dan mempunyai bobot badan yang seragam. Subjek uji sebanyak 30 ekor dikelompokkan menjadi 6 kelompok. Kelompok 1 adalah kelompok mencit yang diberi pakan normal dan larutan CMC 0,5%. Kelompok 2 (kontrol negatif ) diberi pakan normal dan dicekok larutan CdCl2 (3,15 mg selama 14 hari pada setiap pagi). Kelompok 3 adalah kelompok kontrol positif (kontrol antidotum) dan kelompok 4-6 adalah kelompok eksperimen. Kelompok 3-6 diberi pakan normal dan dicekok larutan CdCl2 selama 14 hari pada setiap pagi dan sore harinya diobati dengan dimerkaprol (0,65 mg/Kg BB) untuk kelompok 3 dan PMK[6]H untuk kelompok eksperimen dengan dosis masing-masing 0,22; 0,65; dan 1,95 mg/Kg BB dalam CMC 0,5%. Pengamatan gejala toksik dilakukan selama 14 hari. Pada akhir masa uji, mencit dikorbankan untuk selanjutnya diambil ginjal dan hatinya untuk diukur kadar Cd dengan menggunakan spektrofotometer serapan atom (AAS) dan untuk pengamatan histopatologi. Hasil penelitian menunjukkan adanya penurunan kadar Cd dalam ginjal mencit pada kelompok 3-6 yaitu berturut-turut sebesar 14,98; 15,22; 30,92; dan 45,61 %. sedangkan kadar Cd dalam hati mengalami penurunan masing-masing sebesar 23,37; 25,79; 31,82; dan 35,66 %. Berdasarkan data tersebut, maka PMK[6]H dapat menurunkan kadar Cd dalam ginjal dan hati mencit yang telah diracuni dengan CdCl2 bahkan pada tingkat dosis yang sama, PMK[6]H memberikan penurunan kadar Cd yang lebih besar dari dimerkaprol. ABSTRACT The efficacy of poly-monoallyloxycalix[6]arene (PMK[6]H) as antidote in the Cd intoxication was studied in mice. This research used completely randomized design. The animal test was Balb/C male mice, healthy, age 2-3 months with uniform body weight. Thirty mice were grouped into 6 groups. Group 1was normal group were fed with normal mice chow and administration of 0.5 % CMC. Group 2 was negative control group were fed with normal mice chow and administration of CdCl2 (3.15 mg for 14 days on each morning). Group 3 was positive control group (antidote control) and group 4-6 were experimental groups. Group 3-6 were fed with normal mice chow and administration of CdCl2 (3.15 mg for 14 days on each morning and late afternoon treatment with dimercaprol (0.65 mg/Kg BW) for groups 3 and PMK[6]H for the experimental groups. The dosage of PMK[6]H were 0.22; 0.65; and 1.95 mg/Kg BW in 0.5 % CMC, respectively. Evaluation of the toxic symptoms was done for 14 days. In the end of the evaluation, all mice were killed to take the kidneys and livers for histopathologic examination and the Cd levels were measured using atomic absorption spectrophotometer (AAS). The results showed a decline in levels of Cd in the kidneys of mice in group 3-6 were 14.98; 15.22; 30.92; and 45.61 %, respectively, while the Cd levels in livers decreased by 23.37; 25.79; 31.82; and 35.66 %, respectively. Based on the data, it showed that PMK[6]H can reduce the Cd toxicity in mice and at the same dosage, PMK[6]H can provide a reduction in Cd levels greater than dimercaprol.

The hydration of α-pinene has been studied in the presence of Y-zeolite (Si/Al = 2.89) as a solid acid catalyst. The reaction was performed in batch reactor in isopropyl alcohol at various temperature and reaction time with magnetic stirrer. The acid catalyst hydration reaction of a-pinene yields a complex mixture of monoterpenes, alcohols and hydrocarbons. The selectivity of α-terpineol (the monocyclic alcohol) as main product was 59.20% with a conversion of 83.83% and the non alcoholic as the isomerization co-product as 30% after 60 min at 65 °C. The conversion and selectivity to α-terpineol increase significantly with in increase in temperature and reaction times.

Malaria is a global health problem, especially in the tropics. Efforts to decrease the incidence of malaria plagued the plasmodium resistance to existing antimalarial drugs. Benzyl Phenanthrolium Iodide derivates have been proved has antimalarial activity. The aim of this study is synthesis the nitro benzyl phenanthrolium. The research that has been done was the synthesis of (1)-N-(2-nitrobenzyl) phenantrolium iodide and(1)-N-(4-nitrobenzyl)-1,10-phenantrolium iodide. Synthesis of (1)-N-(2-nitrobenzyl)-1,10-phenantrolium iodide through a two-steps reaction SN-2 is the reaction of (1)N-(2- nitrobenzyl) chloride and potassium iodide followed by reaction phenantroline 1:10 monohydrate, whether the second product was 4-nitrobenzil bromida as starting material. The reaction were started by reflucting the nitro subtituted benzil halida with potassium iodide for 1 hour, yielded nitro subtituted benzyl iodide. Then followed by reflucting nitro substituted benzyl iodide with 1,10-phenanthroline for 11 hours. The final product isolated and purificated by suitable solvent. The melting point was conducted by melting poin apparatus. The structures of product was characterized by IR and UV-Vis spectroscopy. Results obtained in the form of thick liquid light yellow with a melting point of 54.2-63.5oC. While the compound (1)-N-(4-nitrobenzyl)-1,10-phenantrolium iodide is synthesized from 4-nitrobenzylbromide and potassium iodide followed by reaction phenantroline 1:10 monohydrate. Synthesis results in the form of pale yellow crystals with a melting point of 221​​–225oC . The resulting yield of 32.87%. The interpretation of UV-Vis and Infra red spectras indicated that nitro benzyl iodide have been condensed with 1,10 phenantroline as the end of the product.

This paper discusses the preparation, characterization, and the evaluation of adsorption properties of resin poly-tetra-p-allylcalix[4]arene tetra acetic acid from the p-t-butylphenol. The synthesized resins were applied as an adsorbent for Cr(III) and Pb(II) metal ions. The adsorption was conducted in a batch system by investigating the effects of acidity (pH), contact time and initial concentration of a heavy metal solution. The adsorption of Cr(III) and Pb(II) metal ions on the resin had the optimum pH rating in region of 4–6 and reached the equilibrium condition in 40 minutes. The adsorption of Cr(III) and Pb(II) metal ions on the resin follows the Langmuir isothermal pattern with the linearity constant (R2 ) of Cr(III) and Pb(II) adsorption, whose results were 0.9640 and 0.9716, respectively. The adsorption capacity of Cr(III) and Pb(II) metal ions is 323.0 µmole/g and 33.4 µmole/g, while the adsorption energy is 30.4 kJ/mole and 39.7 kJ/mole, respectively. Most parameters in batch systems confirm that resin is a good adsorbent for Cr(III) and Pb(II), though Cr(III) adsorption was more favorable than that of Pb(II). The outstanding adsorption abilities for Cr(III) and Pb(II) metal ions have exhibited good prospects for disposal application of polluted water and environmental protection.

ABSTRACT The aim research is application of poly-5-allyl-calix[4]arene tetraester as adsorbent of heavy metal cations. Adsorption was carried out towards Pb(II), Cd(II) and Cr(III) ions in batch system. Several variables including pH, contact time and initial concentration of metal ions were determined. The optimum adsorption conditions were achieved at pH 4.0 for Pb(II) and Cd(II), while at pH 6.0 for Cr(III) ions. In addition, the optimum contact time of Cd(II) and Cr(III) ions adsorption were 135 minutes, while those for Pb(II) ion was 180 minutes. The adsorption kinetics of Pb(II), Cd(II) and Cr(III) ions using the calixarene polymer adsorbent followed a pseudo 2nd order kinetics model, with adsorption rate constants of 10-3, 9x10-3 dan 3,6x10-2 g mole-1 min-1, respectively. Furthermore, The adsorption isotherm of Pb(II) ion tends to follow the Freundlich isotherm, whereas the adsorption of Cd(II) and Cr (III) ions tends to follow the Langmuir isotherm. The adsorption capacity of Pb(II), Cd(II) and Cr(III) metal ions were 187.63, 45.63 and 197.25 μmole/g, with adsorption energy of 23.14, 15.18 and 27.15 KJ / mole, respectively. ABSTRAK Penelitian ini bertujuan untuk mengkaji pemanfaatan poli-5-allilkaliks[4]arena tetraester sebagai adsorben kation logam berat. Adsorpsi dilakukan dengan metode batch pada variasi keasaman (pH), waktu kontak dan konsentrasi awal ion logam. Hasil eksperimen menunjukkan bahwa pH optimum adsorpsi adalah pH 4,0 untuk ion logam Pb(II) dan Cd(II), sedangkan untuk Cr(III) pada pH 6,0. Waktu kontak optimum adsorpsi ion logam Cd(II) dan Cr(III) adalah 135 menit, sedangkan untuk ion logam Pb(II) adalah 180 menit. Kajian kinetika adsorpsi menunjukkan bahwa adsorpsi ion logam Pb(II), Cd(II) dan Cr(III) menggunakan adsorben poli-5-allilkaliks[4]arena tetraester mengikuti model kinetika Ho, pseudo orde 2, dengan konstanta laju adsorpsi berturut-turut 10-3, 9x10-3 dan 3,6x10-2 g mol-1 menit-1. Kajian isotherm menunjukkan bahwa adsorpsi ion logam Pb(II) cenderung mengikuti isotherm Freundlich, sedangkan adsorpsi ion Cd(II) dan Cr(III) cenderung mengikuti isotherm Langmuir. Kapasitas maksimum adsorpsi ion logam Pb(II), Cd(II) dan Cr(III) masing-masing sebesar 187,63; 45,63 dan 197,25 µmol/g, dengan energi adsorpsi berturut-turut 23,14; 15,18 dan 27,15 KJ/mol.

The synthesis of 5-nitro-1,10-phenanthroline hydrate 2 derivatives from 1,10-phenanthroline monohydrate as starting material has been carried out. The 5-nitro-1,10-phenanthroline hydrate 2 was obtained through nitration reaction using H2SO4 and HNO3 as catalyst and reagent, respectively. Synthesis of (1)-N-alkyl-6-nitro- and (1)-N-benzyl-6-nitro-1,10-phenanthrolinium have been prepared using dimethyl sulphate (DMS), diethyl sulphate (DES), benzyl chloride, benzyl bromine, and benzyl iodide. The reagents of benzyl bromine, and benzyl iodide were synthesized from benzyl chloride using NaBr in ethanol absolute and NaI in acetone, respectively. The five compounds of 5-nitro-1,10-phenanthroline hydrate 2 derivatives were conducted to evaluate the in vitro antiplasmodial activity. The in vitro antiplasmodial was evaluated on strains of Plasmodium falciparum FCR-3 resistant chloroquine and D10 sensitive chloroquine. The 50% inhibition concentration (IC50) of the five compounds ranged from 2.41±1.41 to 0.07±0.01 μM. The results showed that the (1)-N-benzyl-6-nitro-1,10-phenanthrolinium iodide had highest antiplasmodial activity.