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2-Substituted-2-amino-6-boronohexanoic acids as arginase inhibitors.

Abstract：

:Substitution at the alpha center of the known human arginase inhibitor 2-amino-6-boronohexanoic acid (ABH) is acceptable in the active site pockets of both human arginase I and arginase II. In particular, substituents with a tertiary amine linked via a two carbon chain show improved inhibitory potency for both enzyme isoforms. This potency improvement can be rationalized by X-ray crystallography, which shows a water-mediated contact between the basic nitrogen and the carboxylic acid side chain of Asp200, which is situated at the mouth of the active site pocket of arginase II (Asp181 in arginase I). We believe that this is the first literature report of compounds with improved arginase inhibitory activity, relative to ABH, and represents a promising starting point for further optimization of in vitro potency and the identification of better tool molecules for in vivo investigations of the potential pathophysiological roles of arginases.

journal_name

Bioorg Med Chem Lett

journal_title

Bioorganic & medicinal chemistry letters

authors

Golebiowski A,Paul Beckett R,Van Zandt M,Ji MK,Whitehouse D,Ryder TR,Jagdmann E,Andreoli M,Mazur A,Padmanilayam M,Cousido-Siah A,Mitschler A,Ruiz FX,Podjarny A,Schroeter H

doi

10.1016/j.bmcl.2013.02.024

subject

Has Abstract

pub_date

2013-04-01 00:00:00

pages

2027-30

issue

7

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(13)00198-4

journal_volume

23

pub_type

杂志文章

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