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Design and synthesis of silicon-containing tubulin polymerization inhibitors: replacement of the ethylene moiety of combretastatin A-4 with a silicon linker.

Abstract：

:Silicon-containing combretastatin analogs were designed, synthesized and evaluated for stability and biological activities. Among them, compound 31 exhibited strong tubulin polymerization-inhibitory activity and very potent tumor cell growth-inhibitory activity (IC50=0.007 μM) in MCF-7 cell proliferation assay. This compound also potently inhibited [(3)H]colchicine binding (90.7% inhibition at 3 μM). These activities were comparable to those of combretastatin A-4 (CA-4) (1). In addition, compound 31 was physico-chemically more stable than 1. These results suggest that a silicon linker can act as a bioisoster of a cis carbon-carbon double bond.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Nakamura M,Kajita D,Matsumoto Y,Hashimoto Y

doi

10.1016/j.bmc.2013.09.046

subject

Has Abstract

pub_date

2013-12-01 00:00:00

pages

7381-91

issue

23

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00826-2

journal_volume

21

pub_type

杂志文章

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