Abstract
Bis(indolyl)methane appended biaryls were designed, synthesized and evaluated in human cervical cancer cell lines (HeLa) for their anticancer activities and compared against normal rat cardiac myoblasts (H9C2) cells. Compounds 1-12 were synthesized, with variations in one of the phenyl unit, in a single step by condensation of biaryl-2-carbaldehydes with indole in the presence of para-toluenesulfonic acid. Compound 1 exhibited a GI50 value of 11.00 ± 0.707 μM and the derivatives, compounds 4 and 11 showed a GI50 value of 8.33 ± 0.416 μM and 9.13 ± 0.177 μM respectively in HeLa cells and was found to be non-toxic to H9C2 cells up to 20 μM. Furthermore, compounds 1, 4 and 11 induced caspase dependent cellular apoptosis in a concentration-dependent manner, reduced mitochondrial membrane potential, inhibited the cell migration and downregulated the production of MMP-2 and MMP-9 in HeLa cells.
References
Mar 31, 1992·Biochemistry·F A TaniousW D Wilson
Mar 1, 1993·Immunology Today·J J Cohen
Jan 22, 2005·Carcinogenesis·Xiaofei ChangLeonard F Bjeldanes
Jul 11, 2006·Cell Biology International·M S KiranP R Sudhakaran
Sep 16, 2006·Cell Death and Differentiation·Q Bao, Y Shi
Dec 19, 2007·Molecular Carcinogenesis·Jun HongStephen Safe
May 27, 2008·Cancer Letters·Stephen SafeSudhakar Chintharlapalli
Jul 23, 2009·Cancer Research·Saijun FanEliot M Rosen
Dec 2, 2009·European Journal of Cancer Prevention : the Official Journal of the European Cancer Prevention Organisation (ECP)·Kyeong-Hee ChoiSung-Dae Cho
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Nov 13, 2010·Bioorganic & Medicinal Chemistry Letters·C PraveenP T Perumal
May 21, 2011·European Journal of Cancer Prevention : the Official Journal of the European Cancer Prevention Organisation (ECP)·Ji-Ae ShinSung-Dae Cho
May 26, 2012·Mini Reviews in Medicinal Chemistry·Nasir Ali Shafakat AliMazahar Farooqui
Jun 28, 2012·Oncology Reports·Junyong ZhuZuhua Chen
Nov 20, 2012·Future Medicinal Chemistry·Shivaputra A PatilDuane D Miller
Jul 31, 2013·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Terrick AndeyMandip Singh
Aug 8, 2014·Molecular Endocrinology·Syng-Ook LeeStephen Safe
Sep 27, 2014·Organic & Biomolecular Chemistry·Chandrasekhar ChallaRavi S Lankalapalli
Citations
Oct 19, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Graziella ToccoMichela Begala
Jun 2, 2016·Chemical Communications : Chem Comm·Kieran GriffithsGeorge E Kostakis
Nov 18, 2018·Acta Crystallographica. Section E, Crystallographic Communications·Suhaila SapariSiti Aishah Hasbullah
Jul 6, 2021·Beilstein Journal of Organic Chemistry·Thanigaimalai PillaiyarChrista E Müller
Jul 20, 2018·ACS Omega·Chandrasekhar ChallaRavi S Lankalapalli
Apr 23, 2019·Organic Letters·Yuan LingWeidong Rao
Jan 31, 2020·Computers in Biology and Medicine·Ashish BahugunaNeha Garg
Nov 8, 2017·Organic Letters·Lu YeTeck-Peng Loh