19 results on '"indole derivative"'
Search Results
2. Molecular Mechanisms of Skatole-Induced Inflammatory Responses in Intestinal Epithelial Caco-2 Cells: Implications for Colorectal Cancer and Inflammatory Bowel Disease
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Katsunori Ishii, Kazuma Naito, Dai Tanaka, Yoshihito Koto, Koichi Kurata, and Hidehisa Shimizu
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inflammation ,tryptophan metabolites ,indole derivative ,gut microbiota ,intestinal epithelial cells ,Cytology ,QH573-671 - Abstract
Inflammatory cytokines, such as tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6), in intestinal epithelial cells significantly contribute to inflammatory bowel disease (IBD) and colorectal cancer (CRC). Given our previous findings that TNF-α is upregulated in intestinal epithelial Caco-2 cells induced by skatole, a tryptophan-derived gut microbiota metabolite, the present study aimed to explore the relationship between skatole and IL-6, alongside TNF-α. Skatole elevated the promoter activity of IL-6 as well as TNF-α, and increased IL-6 mRNA expression and protein secretion. In addition to activating NF-κB, the NF-κB inhibitor BAY 11-7082 reduced skatole-induced cell survival and the mRNA expression of IL-6 and TNF-α. NF-κB activation was attenuated by the extracellular signal-regulated kinase (ERK) pathway inhibitor U0126 and the p38 inhibitor SB203580, but not by the c-Jun N-terminal kinase (JNK) inhibitor SP600125. U126 and SB203580 also decreased the skatole-induced increase in IL-6 expression. When skatole-induced AhR activation was inhibited by CH223191, in addition to promoting NF-κB activation, IL-6 expression was enhanced in a manner similar to that previously reported for TNF-α. Taken together, these results suggest that skatole-elicited NF-κB activation induces IL-6 and TNF-α expression, although AhR activation partially suppresses this process. The ability of skatole to increase the expression of IL-6 and TNF-α may significantly affect the development and progression of these diseases. Moreover, the balance between NF-κB and AhR activation appears to govern the skatole-induced increases in IL-6 and TNF-α expression. Therefore, the present findings provide new insights into the mechanisms linking tryptophan-derived gut microbiota metabolites with colorectal disease. more...
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- 2024
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Catalog
3. A Novel Indolium-Based Fluorescent Probe for Fast Detection of Cyanide
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Mei Ding, Xiao Xiao, Chen Zhou, Mingxin Luo, and Jing Sun
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cyanide ,fluorescent probe ,indole derivative ,Biotechnology ,TP248.13-248.65 - Abstract
A novel indolium-based fluorescent probe for the detection of CN− was developed based on the conjugation of 1, 2, 3, 3-Tetramethyl-3H-indolium iodide and 2-acetyl benzothiophene. The introduction of external CN− caused a nucleophilic attack to the quaternary amine salt structure in the probe and resulted in the departure of iodide ions and the steric rotation of the index salt group, which caused fluorescence quenching. The titration experiments showed that the probe had rapid qualitative and quantitative analysis capabilities for CN−. Moreover, the relevant biocompatibility experiments also demonstrated the potential application value of the probe. more...
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- 2024
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4. A New Indole Derivative, LWX-473, Overcomes Glucocorticoid Resistance in Jurkat Cells by Activating Mediators of Apoptosis
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Jingrui Song, Kun Yang, Babu Gajendran, Krishnapriya M. Varier, Wenxue Li, Qin Liu, Qing Rao, Yubing Hang, Xiangchun Shen, Sheng Liu, Lei Huang, Mei Xu, and Yanmei Li
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leukemia ,glucocorticoid resistance ,indole derivative ,jurkat cells ,apoptosis ,Biochemistry ,QD415-436 ,Biology (General) ,QH301-705.5 - Abstract
Background: Glucocorticoids (GCs) are commonly used as the primary chemotherapy for lymphoid malignancies, including acute lymphoblastic leukemia (ALL). However, the development of GC resistance limits their prolonged use. Methods: In this study, we investigated the potential of a newly synthesized indole derivative called LWX-473, in combination with the classic GC Dexamethasone (DEX), to enhance the responsiveness of Jurkat cells to GC treatment. Results: Our findings demonstrate that LWX-473 alone or in combination with DEX significantly improves GC-induced cell apoptosis and arrests the cell cycle in the G1 phase. Notably, the combination of LWX-473 and DEX exhibits superior efficacy in killing Jurkat cells compared to LWX-473 alone. Importantly, this compound demonstrates reduced toxicity towards normal cells. Conclusions: Our study reveals that LWX-473 has the ability to restore the sensitivity of Jurkat cells to DEX by modulating the mitochondrial membrane potential, activating the expression of DEX-liganded glucocorticoid receptor (GR), and inhibiting key molecules in the JAK/STAT signaling pathway. These findings suggest that LWX-473 could be a potential therapeutic agent for overcoming GC resistance in lymphoid malignancies. more...
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- 2024
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5. Investigation of the Vibrational Characteristics of 6-Isocyano-1-Methyl-1H-Indole: Utilizing the Isonitrile Group as an Infrared Probe
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Min You, Zilin Gao, Liang Zhou, Changyuan Guo, and Qiang Guo
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indole derivative ,infrared probe ,isonitrile group ,vibrational characteristics ,infrared spectroscopy ,theoretical calculations ,Organic chemistry ,QD241-441 - Abstract
Indole derivatives have garnered considerable attention in the realm of biochemistry due to their multifaceted properties. In this study, we undertake a systematic investigation of the vibrational characteristics of a model indole derivative, 6-isocyano-1-methyl-1H-indole (6ICMI), by employing a combination of FTIR, IR pump-probe spectroscopy, and theoretical calculations. Our findings demonstrate a strong dependence of the isonitrile stretching frequency of 6ICMI on the polarizability of protic solvents and the density of hydrogen-bond donor groups in the solvent when the isonitrile group is bonded to aromatic groups. Both experimental and theoretical analyses unveil a significant correlation between the isonitrile stretch vibration of 6ICMI and the solvent acceptor number of alcohols. Furthermore, the polarization-controlled infrared pump-probe conducted on 6ICMI in dimethyl sulfoxide provides additional support for the potential use of the isonitrile stretching mode of 6ICMI as an effective infrared probe for local environments. more...
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- 2023
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6. The role of the microbiome in ovarian cancer: mechanistic insights into oncobiosis and to bacterial metabolite signaling
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Adrienn Sipos, Gyula Ujlaki, Edit Mikó, Eszter Maka, Judit Szabó, Karen Uray, Zoárd Krasznai, and Péter Bai
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Ovarian cancer ,Microbiome ,EMT ,Microbial metabolite ,Indole derivative ,Lipopolysaccharide ,Therapeutics. Pharmacology ,RM1-950 ,Biochemistry ,QD415-436 - Abstract
Abstract Ovarian cancer is characterized by dysbiosis, referred to as oncobiosis in neoplastic diseases. In ovarian cancer, oncobiosis was identified in numerous compartments, including the tumor tissue itself, the upper and lower female genital tract, serum, peritoneum, and the intestines. Colonization was linked to Gram-negative bacteria with high inflammatory potential. Local inflammation probably participates in the initiation and continuation of carcinogenesis. Furthermore, local bacterial colonies in the peritoneum may facilitate metastasis formation in ovarian cancer. Vaginal infections (e.g. Neisseria gonorrhoeae or Chlamydia trachomatis) increase the risk of developing ovarian cancer. Bacterial metabolites, produced by the healthy eubiome or the oncobiome, may exert autocrine, paracrine, and hormone-like effects, as was evidenced in breast cancer or pancreas adenocarcinoma. We discuss the possible involvement of lipopolysaccharides, lysophosphatides and tryptophan metabolites, as well as, short-chain fatty acids, secondary bile acids and polyamines in the carcinogenesis of ovarian cancer. We discuss the applicability of nutrients, antibiotics, and probiotics to harness the microbiome and support ovarian cancer therapy. The oncobiome and the most likely bacterial metabolites play vital roles in mediating the effectiveness of chemotherapy. Finally, we discuss the potential of oncobiotic changes as biomarkers for the diagnosis of ovarian cancer and microbial metabolites as possible adjuvant agents in therapy. more...
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- 2021
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7. Green and Facile Synthesis of Spirocyclopentanes Through NaOH-Promoted Chemo- and Diastereo-Selective (3 + 2) Cycloaddition Reactions of Activated Cyclopropanes and Enamides
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Xun Zhu, Dingwu Pan, Chengli Mou, Bo Zhou, Lutai Pan, and Zhichao Jin
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green ,NaOH ,donor-acceptor cyclopropane ,(3 + 2) cycloaddition ,spirocyclopentane ,indole derivative ,Chemistry ,QD1-999 - Abstract
A chemo- and diastereo-selective (3 + 2) cycloaddition reacition between Donor-Acceptor (D-A) cyclopropanes and α,β-unsaturated enamides is developed for efficient access to spiro(cyclopentane-1,3'-indoline) derivatives. Simple, inexpensive and readily available NaOH is used as the sole catalyst for this process. A broad range of D-A cyclopropanes could be used as the C-3 synthons to react with oxindole-derived α,β-unsaturated enamides. The structurally sophisticated spiro(cyclopentane-1,3'-indoline) derivatives bearing up to 3 adjacent chiral centers are afforded in excellent yields as single diastereomers. more...
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- 2020
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8. Fe3O4 magnetic nanoparticles (MNPs) as an effective catalyst for synthesis of indole derivatives
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Zohreh Rostami, Masoumeh Rouhanizadeh, Navabeh Nami, and Daryoush Zareyee
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fe3o4 magnetic nanoparticles ,indole derivative ,green chemistry ,easily separation ,Chemical technology ,TP1-1185 ,Chemistry ,QD1-999 - Abstract
The principal aim of this research is the application of Fe3O4 (MNPs) in the synthesis of some indole derivatives. Fe3O4 MNPs were prepared by Co-Precipitation method from the reaction of FeCl2.4H2O and FeCl3.6H2O in ammonia solution. Morphology and structure of Fe3O4 MNPs were determined by FT-IR, X-Ray diffraction (XRD), transmission electron microscopy (TEM) and scanning electron microscopy (SEM). Fe3O4 (MNPs) has been used as a highly efficient catalyst for the synthesis of some Indole derivatives like 6H-Indole [2,3-b] quinoxaline, 3-methyl–6H-Indole [2,3-b] quinoxaline and (z)-3-(pyridine-2-yl-imino)-Indole-2-one. The reaction was carried out using various amounts of Fe3O4 nanoparticles in various solvents and solvent-free conditions. The optimum amount of nano-Fe3O4 was 5 mol% in THF under reflux conditions. The structures of indole derivatives were further established by NMR, and FT-IR spectra. In view of excellent catalytic capacity, the exceedingly simple workup procedure, environmentally friendly reaction and good yield, Fe3O4 (MNPs) was proved to be the good catalyst for this reaction. more...
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- 2018
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9. Synthesis of 1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole and Evaluation of Its Antiprotozoal Activity
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Jean Guillon, Clotilde Boudot, Anita Cohen, Solène Savrimoutou, Sandra Rubio, Vittoria Milano, Mathieu Marchivie, Nadine Azas, Catherine Mullié, Pascal Sonnet, and Bertrand Courtioux
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indole derivative ,antimalarial activity ,antileishmanial activity ,antitrypanosomal activity ,Inorganic chemistry ,QD146-197 - Abstract
1H-3-{4-[(3-Dimethylaminopropyl)aminomethyl]phenyl}-2-phenylindole was synthesized via a multi-step pathway starting from 2-iodoaniline. Structure characterization of this new indole compound was achieved by 1H-NMR, 13C-NMR and ESI-MS spectral analysis. The title compound was screened in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Biological results showed antiparasitic activity with IC50 values in the μM range. more...
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- 2019
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10. Synthesis and structure of 1-(2-bromophenyl)-2-chloro-3-(2-chloracetyl)-1H-indole
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Ting-ting Zhang, Bing Wang, Qing Lu, Jun-fang Zhao, Hong Lei, and Qi Fang
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synthesis ,crystal structure ,indole derivative ,hydrogen bonding ,centrosymmetric dimer ,Crystallography ,QD901-999 - Abstract
In the title indole derivative, C16H10BrCl2NO, the dihedral angle between the mean plane of the indole ring system and the mean plane of the disordered 2-bromophenyl ring is 77.6 (1)°. The non-H atoms of the chloracetyl group are essentially coplanar with the indole core. In the crystal, pairs of molecules are face-to-face embraced via two weak C—H...O hydrogen bonds, forming inversion dimers with an interplanar distance between two parallel indole planes of 3.360 (3) Å. These dimers are connected by head-to-head Cl...Cl intermolecular contacts to build a two-dimensional molecular sheet parallel to (101). Neighbouring molecular sheets are stacked together to construct the three-dimensional structure by further short Cl...Cl intermolecular contacts. The atoms of the bromophenyl group were refined as disordered over two sets of sites with refined occupancies of 0.61 (2) and 0.39 (2). more...
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- 2016
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11. Indole Derivative Interacts with Estrogen Receptor Beta and Inhibits Human Ovarian Cancer Cell Growth
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Laura Verardi, Jessica Fiori, Vincenza Andrisano, Alessandra Locatelli, Rita Morigi, Marina Naldi, Carlo Bertucci, Elena Strocchi, Carla Boga, Gabriele Micheletti, and Natalia Calonghi
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indole derivative ,ovarian cancer ,estrogen receptor beta ,histones ,LC/ESI/MS ,molecular docking ,Organic chemistry ,QD241-441 - Abstract
Ovarian cancer remains the leading cause of mortality among gynecological tumors. Estrogen receptor beta (ERβ) expression has been suggested to act as a tumor suppressor in epithelial ovarian cancer by reducing both tumor growth and metastasis. ERβ expression abnormalities represent a critical step in the development and progression of ovarian cancer: for these reasons, its re-expression by genetic engineering, as well as the use of targeted ERβ therapies, still constitute an important therapeutic approach. 3-{[2-chloro-1-(4-chlorobenzyl)-5-methoxy-6-methyl-1H-indol-3-yl]methylene}-5-hydroxy-6-methyl-1,3-dihydro-2H-indol-2-one, referred to here as compound 3, has been shown to have cytostatic as well cytotoxic effects on various hormone-dependent cancer cell lines. However, the mechanism of its anti-carcinogenic activity is not well understood. Here, we offer a possible explanation of such an effect in the human ovarian cancer cell line IGROV1. Chromatin binding protein assay and liquid chromatography mass spectrometry were exploited to localize and quantify compound 3 in cells. Molecular docking was used to prove compound 3 binding to ERβ. Mass spectrometry-based approaches were used to analyze histone post-translational modifications. Finally, gene expression analyses revealed a set of genes regulated by the ERβ/3 complex, namely CCND1, MYC, CDKN2A, and ESR2, providing possible molecular mechanisms that underline the observed antiproliferative effects. more...
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- 2020
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12. 1-Methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole
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Jean Guillon, Solène Savrimoutou, Sandra Rubio, and Vanessa Desplat
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indole derivative ,leukemia ,antiproliferative activity ,Inorganic chemistry ,QD146-197 - Abstract
The 1-methyl-3-{4-[(4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidin-1-yl)benzyl]}-2-phenylindole compound has been successfully synthesized via a multistep pathway starting from 2-phenylindole. Structure characterization of this new indole derivative was done by FTIR, 1H-NMR, 13C-NMR, and HRMS spectral analysis. The title compound showed high cytotoxic potential against five leukemia cell lines (K562, HL60, U937, U266, and Jurkat cell lines). more...
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- 2018
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13. Isonitrile-Derivatized Indole as an Infrared Probe for Hydrogen-Bonding Environments
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Min You, Liang Zhou, Xinyue Huang, Yang Wang, and Wenkai Zhang
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infrared probe ,isonitrile group ,indole derivative ,hydrogen-bonding environments ,infrared spectroscopy ,Organic chemistry ,QD241-441 - Abstract
The isonitrile (NC) group has been shown to be a promising infrared probe for studying the structure and dynamics of biomolecules. However, there have been no systematic studies performed on the NC group as an infrared probe, when it is bonded to an indole ring. Here, we systematically study the NC stretching mode of two model compounds, 5-isocyano-1H-indole (5ICI) and 5-isocyano-1-methyl-1H-indole (NM5ICI), using Fourier transform infrared (FTIR) spectroscopy. The NC stretching frequency is shown to be strongly dependent on the polarizability of protic solvents and the density of hydrogen-bond donor groups in the solvent when NC is bonded to an indole ring. Infrared pump–probe studies of 5ICI in DMSO and in EtOH further support that the NC stretching mode could be used as a site-specific infrared probe for local environments when NC is bonded to an indole ring. more...
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- 2019
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14. Crystal structure of (2-methyl-1-phenylsulfonyl-1H-indol-3-yl)(phenyl)methanone
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M. Umadevi, V. Saravanan, R. Yamuna, A. K. Mohanakrishnan, and G. Chakkaravarthi
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Indole derivative ,crystal structure ,C—H...O hydrogen bonds ,Crystallography ,QD901-999 - Abstract
In the title compound, C22H17NO3S, the sulfonyl-bound phenyl ring is almost orthogonal to the indole ring system, making a dihedral angle of 84.89 (7)°. The carbonyl-bound phenyl ring forms a dihedral angle of 57.32 (5)° with the indole ring system. The two phenyl rings are inclined at 52.68 (7)°. The S atom has a distorted tetrahedral configuration. In the crystal, weak C—H...O interactions link the molecules, forming a helical chain along the b-axis direction. more...
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- 2015
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15. 2-(5-Bromo-1H-indol-3-yl)-4-(4-bromophenyl)-5-(4-chlorobenzoyl)-1H-pyrrole-3-carbonitrile dimethyl sulfoxide monosolvate
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Y. AaminaNaaz, Jayabal Kamalraja, G. Vimala, Paramasivam T. Perumal, and A. SubbiahPandi
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crystal structure ,indole derivative ,pyrrole-3-carbonitrile ,N—H...O hydrogen bonding ,Crystallography ,QD901-999 - Abstract
In the title solvated compound, C26H14Br2ClN3O·C2H6OS, the indole ring is inclined to the central pyrrole ring by 25.7 (2)°. The chlorobenzene ring and the bromobenzene rings subtend dihedral angles of 56.5 (2) and 53.4 (2)°, respectively, with the central pyrrole ring. In the crystal, molecules are bridged by N—H...O hydrogen bonds, involving the dimethyl sulfoxide solvent molecule, forming chains along [010]. There are no other significant intermolecular interactions present. more...
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- 2016
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16. 1-[(4-Methoxyphenyl)sulfonyl]-1H-indole-3-carbaldehyde
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E. A. Jithesh Babu, K. S. Vinay Kumar, Chandra, M. P. Sadashiva, and M. Mahendra
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crystal structure ,indole derivative ,hydrogen bonding ,Crystallography ,QD901-999 - Abstract
In the molecule of the title compound, C16H13NO4S, the mean plane of the indole ring system and that of the methoxyphenyl ring, which are bridged by a sulfonyl group, are inclined at a dihedral angle of 88.98 (9)°. The crystal structure is stabilized by intermolecular C—H...O hydrogen bonds. more...
- Published
- 2016
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17. Chemical composition of white currant seed extract
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Gođevac Dejan, Vajs Vlatka, Milosavljević Slobodan, Đorđević Boban, Zdunić Gordana, and Tešević Vele
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white currant ,seeds ,sesquiterpenoid glucoside ,dihydrophaseic acid derivative ,indole derivative ,2D NMR ,Chemistry ,QD1-999 - Abstract
From the seeds of white currant (Ribes rubrum, cv. White Champagne), a new sesquiterpenoid glucoside (1) was isolated, along with two known compounds: dihydrophaseic acid 3’-O-β-Dglucopyranoside (2), and 3-carboxymethyl-indole-1-N-β-Dglucopyranoside (3). The structure of the new compound was identified as dihydrophaseic acid 3’-O-β-D-glucopyranosyl-1,6-β-D-glucopyranoside, based on extensive NMR and MS spectral studies. more...
- Published
- 2011
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18. A Novel Synthetic Dihydroindeno[1,2-b] Indole Derivative (LS-2-3j) Reverses ABCB1- and ABCG2-Mediated Multidrug Resistance in Cancer Cells
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Chao Guo, Fangyuan Liu, Jie Qi, Jiahui Ma, Shiqi Lin, Caiyun Zhang, Qian Zhang, Hangyu Zhang, Rong Lu, and Xia Li
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indole derivative ,multidrug resistance ,K562/A02 cell line ,MCF-7/ABCG2 cell line ,ABCB1 ,ABCG2 ,Organic chemistry ,QD241-441 - Abstract
10-oxo-5-(3-(pyrrolidin-1-yl) propyl)-5,10-dihydroindeno [1,2-b] indol-9-yl propionate (LS-2-3j) is a new chemically synthesized indole compound and some related analogues are known to be inhibitors (such as alectinib and Ko143) of ATP-binding cassette (ABC) transporters, especially the ABC transporter subfamily B member 1 (ABCB1) and the ABC transporter subfamily G member 2 (ABCG2). This study aimed to evaluate the multidrug resistance (MDR) reversal effects and associated mechanisms of LS-2-3j in drug-resistant cancer cells. The inhibition of cell proliferation in tested agents was evaluated by the 3-(4,5-dimethylthiazol)-2,5-diphenyltetrazolium bromide (MTT) assay. Accumulation or efflux of chemotherapy drugs was analyzed by flow cytometry. The ATPase activity was measured using an ATPase activity assay kit. The mRNA transcripts and protein expression levels were detected by real-time PCR and Western blot, respectively. In this connection, LS-2-3j significantly enhanced the activity of chemotherapeutic drugs in MDR cells and could significantly increase the intracellular accumulation of doxorubicin (DOX) and mitoxantrone (MITX) by inhibiting the function of the efflux pumps in ABCB1- or ABCG2-overexpressing cells. Furthermore, reduced ATPase activity, mRNA transcription, and protein expression levels of ABCB1 and ABCG2 were observed in a concentration dependent manner in MDR cancer cells. more...
- Published
- 2018
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19. Crystal structure of (E)-diethyl 2-[(1-phenylsulfonyl-1H-indol-3-yl)methylidene]succinate
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M. Umadevi, Potharaju Raju, R. Yamuna, Arasambattu K. Mohanakrishnan, and G. Chakkaravarthi
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crystal structure ,indole derivative ,hydrogen bonding ,Crystallography ,QD901-999 - Abstract
In the title compound, C23H23NO6S, the phenyl ring is perpendicular [dihedral angle = 89.34 (9)°] to the indole ring system. In the molecule, the ethoxy groups are each disordered over two sets of sites with occupancy ratios of 0.671 (6):0.329 (6) and 0.75 (3):0.25 (3). The molecular conformation is consolidated by a weak C—H...O interaction, which generates an S(6) graph–set motif. The packing of the molecules in the crystal structure features weak C—H...π interactions. more...
- Published
- 2015
- Full Text
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