Design and synthesis of lignostilbene-alpha,beta-dioxygenase inhibitors

Sun young Han; Hiroki Inoue; Tamami Terada; Shigehiro Kamoda; Yoshimasa Saburi; Katsuhiko Sekimata; Tamio Saito; Masatomo Kobayashi; Kazuo Shinozaki; Shigeo Yoshida; Tadao Asami

doi:10.1016/s0960-894x(02)00126-9

Design and synthesis of lignostilbene-alpha,beta-dioxygenase inhibitors

Bioorg Med Chem Lett. 2002 Apr 22;12(8):1139-42. doi: 10.1016/s0960-894x(02)00126-9.

Authors

Sun young Han¹, Hiroki Inoue, Tamami Terada, Shigehiro Kamoda, Yoshimasa Saburi, Katsuhiko Sekimata, Tamio Saito, Masatomo Kobayashi, Kazuo Shinozaki, Shigeo Yoshida, Tadao Asami

Affiliation

¹ RIKEN, Hirosawa 2-1, Wako, 351-0198, Saitama, Japan.

PMID: 11934574
DOI: 10.1016/s0960-894x(02)00126-9

Abstract

Lignostilbene-alpha,beta-dioxygenase cleaves the olefinic double bond of phenolic stilbenes by a mechanism similar to that of 9-cis-epoxycarotenoid dioxygenase, a key enzyme in abscisic acid biosynthesis. Several analogues of stilbene were designed and synthesized, and their efficacy as inhibitors of lignostilbene-alpha,beta-dioxygenase was examined. The compound (Z)-1-(4-hydroxyphenyl)-1-fluoro-2-phenylethene (2) was found to be a potent inhibitor of this enzyme with an IC(50) of 3 microM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Dioxygenases*
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry*
Oxygenases / antagonists & inhibitors*

Substances

Enzyme Inhibitors
Oxygenases
Dioxygenases
lignostilbene-alpha,beta-dioxygenase