Design and Synthesis of New Tubulin Polymerization Inhibitors Inspired from Combretastatin A-4: An Anticancer Agent

Akanksha Sharma, Doddabasappa Talimarada, Umesh Prasad Yadav, Nidhi Singh, A. Sudharshan Reddy, Debojyoti Bag, Krishna Biswas, Amit Baidya, Asha N. Borale, Dhananjay Shinde, Sandeep Singh, Harish Holla

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

A series of 30 small hybrid molecules are synthesized inspired from Combretastatin A-4 (CA-4), where ethylene-bridge of CA-4 is replaced with two five-membered heterocyclic rings, viz. isoxazoline and 1, 2, 3-triazole. These are joined by a methylene linker, with substitutions at A and B – ring position of CA-4. The new molecular entities have shown significant cytotoxicity to cancer cell from the IC50 0.49 μM–3.17 μM with 1-((4,5-Dihydro-3-(2,5-dimethoxyphenyl)isoxazol-5-yl)methyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole displayed IC50 0.422±0.07 μM for A-549 -lung cancer cell line and IC50 0.498±0.03 μM for MDA-MB-231-breast cancer cell line. The western blot analysis, confocal staining and also by in vitro tubulin polymerization assay established the target specificity of the molecules as a tubulin polymerization inhibitor. Molecular docking & Molecular dynamics studies confirmed the binding interaction patterns of these molecules at the Colchicine binding site of tubulin and have correlated the observed experimental result with variation in structure satisfactorily.

Original languageEnglish (US)
Pages (from-to)11560-11572
Number of pages13
JournalChemistrySelect
Volume5
Issue number37
DOIs
StatePublished - Oct 8 2020
Externally publishedYes

Keywords

  • Cancer
  • Click Chemistry
  • Colchicine binding site
  • Combretastatin A-4
  • Medicinal Chemistry

ASJC Scopus subject areas

  • General Chemistry

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