Abstract
Aims: In this study experiments were carried out to explore antioxidant, antimicrobial, cytotoxic properties of novel indole derivative 1-ethyl-2-phenyl-3-phenylethyl-3-thiophen-2-yl-1Hindole (EPI) together with its effect on glutathione S-transferases (GST) activities in human liver carcinoma (HepG2) cells.
Background: Indoles probably represent one of the most important heterocyclic structures that have been attracting the interest of many scientists in drug discovery.
Objective: The present study was carried out to explore antioxidant, antimicrobial, cytotoxic properties of novel indole derivative 1-ethyl-2-phenyl-3-phenylethyl-3-thiophen-2-yl-1H-indole (EPI) and its effect on glutathione S-transferases (GST) activities in human liver carcinoma (HepG2) cells.
Materials and Methods: Pd-catalyst Sonogashira coupling reactions, MTT Assay, Antioxidant capacity test, Antimicrobial test, GST enzyme activity test.
Results: 1-ethyl-2-phenyl-3-(phenylethynyl)-1H-indole had antioxidant and antimicrobial properties. It displayed significant induction in glutathione S-transferases (GST) enzyme activity in human liver cancer cell lines (HepG2), but cytotoxic effect on all tested cancer cell lines could not be observed.
Conclusion: All of these results showed that 1-ethyl-2-phenyl-3-(phenylethynyl)-1H-indole had antioxidant and antimicrobial properties without cytotoxic effect, which could make it a promising active component with further studies.
Keywords: Indole, heteroaromatic compounds, antioxidant, cytotoxicity, antimicrobial, small molecules.
Graphical Abstract
[http://dx.doi.org/10.3390/md13084814] [PMID: 26287214]
[http://dx.doi.org/10.1016/j.matchemphys.2016.12.040]
[http://dx.doi.org/10.6023/cjoc201907047]
[http://dx.doi.org/10.1016/j.bmcl.2013.02.090] [PMID: 23540647]
[http://dx.doi.org/10.2174/1389557511313120009] [PMID: 22625410]
[http://dx.doi.org/10.1007/7081_2007_074]
[PMID: 28782480]
[http://dx.doi.org/10.2147/IDR.S208757] [PMID: 31413605]
[http://dx.doi.org/10.1016/j.ijbiomac.2015.04.042] [PMID: 25934105]
[http://dx.doi.org/10.1016/j.bmc.2006.02.014] [PMID: 16504522]
[http://dx.doi.org/10.1016/j.ejmech.2010.05.067] [PMID: 20594623]
[http://dx.doi.org/10.1021/jo500131h] [PMID: 24512551]
[http://dx.doi.org/10.21873/anticanres.13720] [PMID: 31570421]
[http://dx.doi.org/10.1039/C9CC04172A] [PMID: 31407744]
[http://dx.doi.org/10.1021/acschemneuro.9b00297] [PMID: 31545596]
[http://dx.doi.org/10.1016/j.ejmech.2014.10.065] [PMID: 25462257]
[http://dx.doi.org/10.1016/j.ejmech.2018.10.037] [PMID: 30359819]
[http://dx.doi.org/10.1016/j.bioorg.2019.103021] [PMID: 31176854]
[http://dx.doi.org/10.1126/scitranslmed.3004404] [PMID: 23253612]
[http://dx.doi.org/10.1093/cid/ciu598] [PMID: 25352626]
[http://dx.doi.org/10.1155/2019/5283948] [PMID: 31354829]
[http://dx.doi.org/10.1371/journal.pmed.1002184] [PMID: 27898664]
[http://dx.doi.org/10.2174/1385272054863989]
[http://dx.doi.org/10.1002/slct.201904783] [PMID: 32328514]
[http://dx.doi.org/10.1016/j.molstruc.2016.08.021]
[http://dx.doi.org/10.1016/j.ejmech.2018.01.026] [PMID: 29339254]
[http://dx.doi.org/10.1016/j.ejmech.2016.03.021] [PMID: 27017546]
[http://dx.doi.org/10.1021/acs.jmedchem.6b00021] [PMID: 27149641]
[http://dx.doi.org/10.1016/j.bmc.2015.12.008] [PMID: 26707844]
[http://dx.doi.org/10.1016/j.tetlet.2016.01.071]
[http://dx.doi.org/10.2174/1570178616666181116100232]
[http://dx.doi.org/10.1007/s12039-018-1523-3]
[http://dx.doi.org/10.1038/sj.onc.1206940] [PMID: 14576844]
[http://dx.doi.org/10.1017/S0007485309006725] [PMID: 19413913]
[http://dx.doi.org/10.1021/jf0715166] [PMID: 17902627]
[http://dx.doi.org/10.1039/c3cc43204a] [PMID: 23936897]
[http://dx.doi.org/10.1007/s11745-998-0216-8] [PMID: 9590623]
[http://dx.doi.org/10.1006/abio.1999.4019] [PMID: 10222007]
[http://dx.doi.org/10.1006/abio.1996.0292] [PMID: 8660627]
[http://dx.doi.org/10.1007/s10565-012-9214-1] [PMID: 22392284]
[http://dx.doi.org/10.1007/s11696-018-0640-2]
[http://dx.doi.org/10.1002/slct.202000685]
[http://dx.doi.org/10.1021/jo201119e] [PMID: 21739980]
[http://dx.doi.org/10.3109/10715762.2014.996146] [PMID: 25511471]
[http://dx.doi.org/10.1039/c2cc36531f] [PMID: 23125978]
[http://dx.doi.org/10.3390/antiox9020143] [PMID: 32041310]
[http://dx.doi.org/10.1016/j.ejmech.2019.111691] [PMID: 31536895]
[http://dx.doi.org/10.1021/jf800401d] [PMID: 18717566]