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Synthesis of 1-benzyl-1H-benzimidazoles as galectin-1 mediated anticancer agents.

Abstract：

:In our pursuit to develop novel non-carbohydrate small molecule Galectin-1 Inhibitors, we have designed a series of 1-benzyl-1H-benzimidazole derivatives and demonstrated their anticancer activity. The compound 6g, 4-(1-benzyl-5-chloro-1H-benzo[d]imidazol-2-yl)-N-(4-hydroxyphenyl) benzamide was found to be most potent with an IC50 of 7.01 ± 0.20 µM and arresting MCF-7 cell growth at G2/M phase and S phase. Induction of apoptosis was confirmed by morphological changes like cell shrinkage, blebbing and cell wall deformation, dose dependent increase in the mitochondrial membrane potential (ΔΨm) and ROS levels. Further, dose dependent decrease in Gal-1 protein levels proves Gal-1 mediated apoptosis by 6g. Molecular docking studies were performed to understand the Gal-1 interaction with compound 6g. In addition, RP-HPLC studies showed 85.44% of 6g binding to Gal-1. Binding affinity studies by fluorescence spectroscopy and Surface Plasmon Resonance (SPR) showed that 6g binds to Gal-1 with binding constant (Ka) of 1.2 × 104 M-1 and equilibrium constant KD value of 5.76 × 10-4 M respectively.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Goud NS,Ghouse SM,Vishnu J,Komal D,Talla V,Alvala R,Pranay J,Kumar J,Qureshi IA,Alvala M

doi

10.1016/j.bioorg.2019.103016

subject

Has Abstract

pub_date

2019-08-01 00:00:00

pages

103016

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(18)30681-3

journal_volume

89

pub_type

杂志文章

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