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NOVEL RESVERATROL ANALOGUES WITH AROMATIC HETERO MOIETIES: DESIGNING, ONE-POT SYNTHESIS AND IN VITRO BIOLOGICAL EVALUATION

LAIRIKYENGBAM DEEPTI ROY 1#, JYOTSNA KUMAR 1#*, JUDY JAYS 2, GEETA KRISHNAMURTHY 1, POOJA GOUR 1, SHIVANJALI ESTHER ARLAND 1

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In the present work, resveratrol was used as a precursor, extracted, isolated and purified from green grapes (Vitis vinifera), and subjected to synthetic manipulations to acquire a series of novel resveratrol analogues. The docking results demonstrated that all three novel resveratrol analogues (ResA1, ResA2 and ResA3) can fit into the ERα (oestrogen receptor alpha) binding pockets via a hydrogen bond, hydrophobic and π-π interactions. In vitro antioxidant activity was carried out by using 1,1-diphenyl-2picrylhydrazyl (DPPH). Results reflected that ResA2 and ResA3 exhibited high antioxidant activities than ascorbic acid used as a control. The antimicrobial activity of novel synthesized resveratrol analogues shows that Streptococcus pneumoniae, exhibited strong resistance to ResA3 at all concentrations. In vitro cytotoxic evaluation of these novel compounds on a panel of ER-positive and ER-negative human breast cancer cell lines (MCF-7, MDA-MB-231) carried out by 3-(4, 5-dimethylthiazol2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay demonstrate that ResA2 and ResA3 have potent anti-proliferative effects on both the cell lines (inhibitory concentration i.e., IC50 values are 390.16 µg/mL and 327.70 µg/mL; 203.72 µg/mL and 186.58 µg/mL respectively for MCF-7 and MDA-MB-231). Synthesized resveratrol analogues had demonstrated more than 70% cell viability inhibition against human breast epithelial cell lines (MCF-10A cells), even at 500 µg/mL. This study showed that the proposed novel resveratrol analogues could be used as a plausible pharmacophore for targeting ERα protein and will be supportive for exploring the new series of resveratrol analogues as potential anticancer agents.