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Benzodiazepine peptidomimetic inhibitors of farnesyltransferase.

Abstract：

:A structural survey of protein Zn2+ binding geometries was instigated based upon the functional requirement of Ras farnesyltransferase for Zn2+. The Cys-X-X-Cys motif found in Zn(2+)-binding proteins such as aspartate transcarbamylase was used as a template to devise a bidentate-coordination model for Cys-A1-A2-X peptide inhibitors. Accordingly, replacement of the central dipeptide with the hydrophobic scaffold 3-amino-1-carboxymethyl-2,3-dihydro-5- phenyl-1H-1,4-benzodiazepin-2-one (BZA) yielded a peptidomimetic inhibitor, Cys(BZA)Met, of moderate potency (IC50 = 400 nM). N-Methylation of the cysteine amide improved potency almost 100-fold (IC50 = 0.3-1 nM). The increased affinity presumably correlates with a preferred conformation of the inhibitor which maximizes a hydrophobic interaction between the scaffold and the enzyme, and the proper presentation of cysteine and methionine to allow bidentate coordination at Zn2+. These non-peptide inhibitors have been shown to block farnesylation of the Ras protein in intact cells and provide lead compounds for the development of new cancer therapeutic agents.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Marsters JC Jr,McDowell RS,Reynolds ME,Oare DA,Somers TC,Stanley MS,Rawson TE,Struble ME,Burdick DJ,Chan KS

doi

10.1016/s0968-0896(00)82044-1

subject

Has Abstract,Author List Incomplete

pub_date

1994-09-01 00:00:00

pages

949-57

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(00)82044-1

journal_volume

2

pub_type

杂志文章

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