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Discovery of HDAC Inhibitors That Lack an Active Site Zn(2+)-Binding Functional Group.

Abstract：

:Natural and synthetic histone deacetylase (HDAC) inhibitors generally derive their strong binding affinity and high potency from a key functional group that binds to the Zn(2+) ion within the enzyme active site. However, this feature is also thought to carry the potential liability of undesirable off-target interactions with other metalloenzymes. As a step toward mitigating this issue, here, we describe the design, synthesis, and structure-activity characterizations of cyclic α3β-tetrapeptide HDAC inhibitors that lack the presumed indispensable Zn(2+)-binding group. The lead compounds (e.g., 15 and 26) display good potency against class 1 HDACs and are active in tissue culture against various human cancer cell lines. Importantly, enzymological analysis of 26 indicates that the cyclic α3β-tetrapeptide is a fast-on/off competitive inhibitor of HDACs 1-3 with K i values of 49, 33, and 37 nM, respectively. Our proof of principle study supports the idea that novel classes of HDAC inhibitors, which interact at the active-site opening, but not with the active site Zn(2+), can have potential in drug design.

journal_name

ACS Med Chem Lett

journal_title

ACS medicinal chemistry letters

authors

Vickers CJ,Olsen CA,Leman LJ,Ghadiri MR

doi

10.1021/ml300081u

subject

Has Abstract

pub_date

2012-04-26 00:00:00

pages

505-8

issue

6

issn

1948-5875

journal_volume

3

pub_type

杂志文章

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