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The crystal structure of anthraquinone-2-carboxylic acid has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional theory techniques. Anthraquinone-2-carboxylic acid crystallizes in space group P -1 (#2) with a = 3.7942(2), b = 13.266(5), c = 22.835(15) Å, α = 73.355(30), β = 89.486(6), γ = 86.061(1)°, V = 1098.50(7) Å3, and Z = 4. The crystal structure contains two independent molecules of anthraquinone-2-carboxylic acid. Although the expected hydrogen-bonded dimers are present, the dimers are not centrosymmetric. The dimer contains one molecule of each planar low-energy conformation. The crystal structure consists of a herringbone array of centrosymmetric pairs of molecules parallel to the bc -plane. The molecules stack along the short a -axis. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™ (PDF®). [ABSTRACT FROM AUTHOR]

Infections linked to Staphylococcus spp. are difficult to treat with current antibiotic therapy, resulting in increased antibiotic resistance populations. One of the leading strategies to overcome this issue is the novel combination of antibacterial nanoparticles (NPs) and sustainable natural compounds. This study reported the identification of a new synergistic combination of copper oxide (CuO) NPs, a well-known antibacterial agent against Staphylococcus spp., and anthraquinone-2-carboxylic acid (AQ), a plant-derived antimicrobial compound, with a potent and specific fashion in killing Staphylococcus spp. CuO NPs were synthesized using the one-pot coprecipitation method and characterized by using X-ray diffraction and transmission electron microscopy. Further checkerboard analysis showed that CuO NPs and AQ increased the antibacterial activity of individual agents against Staphylococcus aureus among Staphylococcus spp. by four- to eightfold compared to individual materials. Additional mechanistic studies on the synergy revealed that the inhibition of biofilm formation and loss of cytoplasmic volume with cell shrinkage are the major actions of the combination in expressing the phenotype. This study clearly showed that the combination of CuO NPs and AQ would be a novel strategy to eradicate S. aureus infections. [ABSTRACT FROM AUTHOR]

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β-Cyclodextrin (CD) derivatives containing an aromatic triazole ring were studied as potential carriers of the following drugs containing an anthraquinone moiety: anthraquinone-2-sulfonic acid (AQ2S); anthraquinone-2-carboxylic acid (AQ2CA); and a common anthracycline, daunorubicin (DNR). UV-Vis and voltammetry measurements were carried out to determine the solubilities and association constants of the complexes formed, and the results revealed the unique properties of the chosen CDs as effective pH-dependent drug complexing agents. The association constants of the drug complexes with the CDs containing a triazole and lipoic acid (βCDLip) or galactosamine (βCDGAL), were significantly larger than that of the native βCD. The AQ2CA and AQ2S drugs were poorly soluble, and their solubilities increased as a result of complex formation with βCDLip and βCDGAL ligands. AQ2CA and AQ2S are negatively charged at pH 7.4. Therefore, they were less prone to form an inclusion complex with the hydrophobic CD cavity than at pH 3 (characteristic of gastric juices) when protonated. The βCDTriazole and βCDGAL ligands were found to form weaker inclusion complexes with the positively charged drug DNR at an acidic pH (pH 5.5) than in a neutral medium (pH 7.4) in which the drug dissociates to its neutral, uncharged form. This pH dependence is favorable for antitumor applications.

Anthraquinone-2-carboxlic acid (9,10-dihydro-9,10-dioxo-2-anthracenecarboxylic acid, AQCA) was identified as one of the major anthraquinones in Brazilian taheebo. Since there was no report explaining its immunopharmacological actions, in this study, we aimed to investigate the molecular mechanism of AQCA-mediated anti-inflammatory activity using reporter gene assays, kinase assays, immunoblot analyses, and overexpression strategies with lipopolysaccharide (LPS)-treated macrophages. AQCA was found to suppress the release of nitric oxide (NO) and prostaglandin (PG) E2 from LPS-treated peritoneal macrophages without displaying any toxic side effects. Molecular analysis revealed that AQCA was able to inhibit the activation of the nuclear factor (NF)-ĸB and activator protein (AP)-1 pathways by direct suppression of upstream signaling enzymes including interleukin-1 receptor-associated kinase 1 (IRAK1) and spleen tyrosine kinase (Syk). Therefore, our data strongly suggest that AQCA-mediated suppression of inflammatory responses could be managed by a direct interference of signaling cascades including IRAK and Syk, linked to the activation of NF-ĸB and AP-1. [ABSTRACT FROM AUTHOR]

In this study, in situ surface-enhanced Raman scattering (SERS) spectroelectrochemistry and angle-resolved X-ray photoelectron spectroscopy (AR-XPS) are used to investigate the redox reaction and adsorption behavior of anthraquinone-2-carboxylic acid (AQ-2-COOH) on an Ag electrode at different pH values. The obtained results indicate that AQ-2-COOH is adsorbed tilted on the Ag electrode through O-atom of ring carbonyl in a potential range from −0.3 to −0.5 V vs. SCE, but the orientation turns to more tilted orientation with both O-atom of the ring carbonyl and carboxylate group in positive potential region for pH 6.0 and 7.4. However, at pH 10.0, the orientation adopts tilted conformation constantly on the Ag electrode with both O-atom of the anthraquinone ring and carboxylate group in the potential range from −0.3 to −0.5 V vs. SCE or at positive potentials. Moreover, the adsorption behavior of AQ-2-COOH has been further confirmed by AR-XPS on the Ag surface. Proposed reasons for the observed changes in orientation are presented. [ABSTRACT FROM AUTHOR]

Metal-free and several metallo-porphyrazines (M = Mg, 2H, Co, Cu, or Zn) carrying eight (3-thiopropyl anthraquinone-2-carboxylate) groups at the peripheral positions were synthesized from octakis(3-hydroxypropylthio)porphyrazinato] Mg(II). Symmetrically functionalized porphyrazines with eight ester units were soluble in common organic solvents. Chloro-octakis(3-thiopropyl anthraquinone-2-carboxylate) porphyrazinato iron(III) (FePzCl) was prepared by the reaction of metal-free porphyrazine with iron(II) acetate and further treatment with hydrochloric acid solution. The oligomeric structure [FePz(pyz)]nand the monomeric compound [FePz(py)2] were formed as stable complexes by reacting FePzCl with pyrazine and pyridine, respectively. The porphyrazine compounds were characterized by different spectroscopic methods. Metal-free and metallo-porphyrazines (M = Mg, 2H, Co, Cu, Zn, or ClFe) with eight (3-thiopropyl anthraquinone-2-carboxylate) units appending on the periphery through flexible alkylthio-bridges have been synthesized through esterification of octakis(hydroxypropylthio) porphyrazinato magnesium with anthraquinone-2-carboxylic acid in the presence of dicyclohexylcarbodiimide (DCCI) and toluene-p-sulfonic acid. The synthesized compounds were characterized by FT-IR, UV–vis,1H and13C NMR, mass spectrometry, and elemental analysis. [ABSTRACT FROM AUTHOR]

• AQCA/CMK-3 nanohybrid was employed as a new redox nanoprobe for the first time. • Urchin-like Ce-MOFs were used as favorable platform to accelerate electron transfer. • Sandwich-type aptasensor was constructed with excellent sensitivity and specificity. • This approach was utilized to detect MPT64 in human serum with satisfactory results. Rapid and sensitive tuberculosis (TB) diagnoses remain big challenges to current detection tools. In this work, a sensitive electrochemical aptasensor was constructed for the determination of Mycobacterium tuberculosis antigen MPT64 using a new redox nanoprobe. We found that anthraquinone derivative, anthraquinone-2-carboxylic acid (AQCA), a redox mediator, could be confined in ordered mesoporous carbon material of CMK-3. Due to the large loading amount of AQCA, as well as the confined space and electron transfer promotion effect of CMK-3, the obtained AQCA/CMK-3 nanohybrid with mass ratio of 2:1 showed excellent electroactivity and was employed as a new redox nanoprobe for signal amplification for the first time. Additionally, urchin-like Ce-MOFs were used to load a large amount of deposited gold nanocrystals (dep-Au), leading to dense immobilization of capture probe. The proposed electrochemical aptasensor for MPT64 detection showed a good linear relationship in the range from 100 fg/mL to 10 ng/mL with a low detection limit of 67.6 fg/mL. Besides, the aptasensor was utilized to detect MTP64 in human serum samples for TB diagnosis and presented satisfactory results. [ABSTRACT FROM AUTHOR]

Abstract: We developed an efficient method for the generation of hydrogen peroxide by aerobic photooxidation of 2-propanol using anthraquinone-2-carboxylic acid and molecular oxygen in air and visible light from fluorescent lamps. One-pot epoxidation of α,β-unsaturated ketones using the generated hydrogen peroxide is also reported. [Copyright &y& Elsevier]

Abstract: The adsorption state of anthraquinone-2-carboxylic acid (AQ-2-COOH) deposited from acetone solutions (0.01–1.00mg/ml) on native oxide surfaces of Al films was characterized by inelastic electron tunneling spectroscopy, infrared reflection absorption spectroscopy, and X-ray photoelectron spectroscopy. The oxide was prepared on evaporated Al films at room temperature in an oxygen-dc glow discharge. The morphology of the deposited AQ-2-COOH on the oxide surfaces was observed and analyzed by atomic force microscopy. These surface analyses showed that AQ-2-COOH is adsorbed predominantly as a uniform nanometer-scale film of carboxylate anions on the oxide surfaces deposited from solutions with concentrations lower than or equal to 0.02mg/ml. It was found that AQ-2-COOH is adsorbed as both a uniform film of anions and as micron-sized particles of neutral molecules with heights of a few tens of nanometers when AQ-2-COOH is deposited from solutions with concentrations higher than 0.02mg/ml. A comparison of the results obtained by these surface analytical techniques clearly shows the features and advantages of these analytical techniques. [Copyright &y& Elsevier]

Abstract: The growth-inhibiting activity of Tabebuia impetiginosa Martius ex DC dried inner bark-derived constituents against Helicobacter pylori ATCC 43504 was examined using paper disc diffusion and minimum inhibitory concentration (MIC) bioassays. The activity of the isolated compounds was compared to that of the commercially available anti-Helicobacter pylori agents, amoxicillin, metronidazole, and tetracycline. The biologically active components of Tabebuia impetiginosa dried inner bark (taheebo) were characterized by spectroscopic analysis as 2-(hydroxymethyl)anthraquinone, anthraquinone-2-carboxylic acid, and 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol). With the paper disc diffusion assay 2-(hydroxymethyl)anthraquinone exhibited strong activity against Helicobacter pylori ATCC 43504 at 0.01mg/disc. Anthraquinone-2-carboxylic acid, lapachol and metronidazole were less effective, exhibiting moderate anti-Helicobacter pylori activity at 0.1mg/disc. Amoxicillin and tetracycline were the most potent compounds tested, displaying very strong activity at 0.005mg/disc. 2-(Hydroxymethyl)anthraquinone exhibited moderate activity at this dose. Tetracycline still had strong activity at 0.001mg/disc while amoxicillin had little activity at this dose. In the MIC bioassay, 2-(hydroxymethyl)anthraquinone (2μg/mL), anthraquinone-2-carboxylic acid (8μg/mL), and lapachol (4μg/mL) were more active than metronidazole (32μg/mL) but less effective than amoxicillin (0.063μg/mL) and tetracycline (0.5μg/mL). The anti-Helicobacter pylori activity of seven 1,4-naphthoquinone derivatives (structurally related to lapachol), 1,4-naphthoquinone, 5,8-dihydroxy-1,4-naphthoquinone (naphthazarin), 2-methyl-1,4-naphthoquinone (menadione), 2-hydroxy-1,4-naphthoquinone (lawsone), 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin), 5-hydroxy-1,4-naphthoquinone (juglone), and 2,3-dichloro-1,4-naphthoquinone (dichlone) was also evaluated using the paper disc assay. Menadione and plumbagin were the most potent compounds tested with the later still exhibiting very strong activity at 0.001mg/disc. Menadione, juglone and tetracycline had strong activity at this low dose while the latter two compounds and amoxicillin had very strong activity at 0.005mg/disc. Lawsone was unusual in that it had very strong activity at 0.1 and 0.05mg/disc but weak activity at doses of 0.01mg/disc and lower. Naphthazalin, lapachol and dichlone had similar activities while metronidazole had the lowest activity of all compounds tested. These results may be an indication of at least one of the pharmacological actions of taheebo. The Tabebuia impetiginosa dried inner bark-derived materials, particularly 2-(hydroxymethyl)anthraquinone, merit further study as potential Helicobacter pylori eradicating agents or lead compounds. [Copyright &y& Elsevier]

β-Cyclodextrin (CD) derivatives containing an aromatic triazole ring were studied as potential carriers of the following drugs containing an anthraquinone moiety: anthraquinone-2-sulfonic acid (AQ2S); anthraquinone-2-carboxylic acid (AQ2CA); and a common anthracycline, daunorubicin (DNR). UV-Vis and voltammetry measurements were carried out to determine the solubilities and association constants of the complexes formed, and the results revealed the unique properties of the chosen CDs as effective pH-dependent drug complexing agents. The association constants of the drug complexes with the CDs containing a triazole and lipoic acid (βCDLip) or galactosamine (βCDGAL), were significantly larger than that of the native βCD. The AQ2CA and AQ2S drugs were poorly soluble, and their solubilities increased as a result of complex formation with βCDLip and βCDGAL ligands. AQ2CA and AQ2S are negatively charged at pH 7.4. Therefore, they were less prone to form an inclusion complex with the hydrophobic CD cavity than at pH 3 (characteristic of gastric juices) when protonated. The βCDTriazole and βCDGAL ligands were found to form weaker inclusion complexes with the positively charged drug DNR at an acidic pH (pH 5.5) than in a neutral medium (pH 7.4) in which the drug dissociates to its neutral, uncharged form. This pH dependence is favorable for antitumor applications. [ABSTRACT FROM AUTHOR]

We developed the aerobic photooxidative bromination of aromatic compounds using carbon tetrabromide in the presence of anthraquinone-2-carboxylic acid under visible light irradiation. [ABSTRACT FROM AUTHOR]