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Docking and hydropathic scoring of polysubstituted pyrrole compounds with antitubulin activity.

Abstract：

:Compounds that bind at the colchicine site of tubulin have drawn considerable attention with studies indicating that these agents suppress microtubule dynamics and inhibit tubulin polymerization. Data for 18 polysubstituted pyrrole compounds are reported, including antiproliferative activity against human MDA-MB-435 cells and calculated free energies of binding following docking the compounds into models of alphabeta-tubulin. These docking calculations coupled with HINT interaction analyses are able to represent the complex structures and the binding modes of inhibitors such that calculated and measured free energies of binding correlate with an r(2) of 0.76. Structural analysis of the binding pocket identifies important intermolecular contacts that mediate binding. As seen experimentally, the complex with JG-03-14 (3,5-dibromo-4-(3,4-dimethoxyphenyl)-1H-pyrrole-2-carboxylic acid ethyl ester) is the most stable. These results illuminate the binding process and should be valuable in the design of new pyrrole-based colchicine site inhibitors as these compounds have very accessible syntheses.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tripathi A,Fornabaio M,Kellogg GE,Gupton JT,Gewirtz DA,Yeudall WA,Vega NE,Mooberry SL

doi

10.1016/j.bmc.2007.11.076

subject

Has Abstract

pub_date

2008-03-01 00:00:00

pages

2235-42

issue

5

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(07)01044-9

journal_volume

16

pub_type

杂志文章

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