Design and synthesis of lignostilbene-alpha,beta-dioxygenase inhibitors.
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.
Han
Sun young
Sy
RIKEN, Hirosawa 2-1, Wako, 351-0198, Saitama, Japan.
Inoue
Hiroki
H
Terada
Tamami
T
Kamoda
Shigehiro
S
Saburi
Yoshimasa
Y
Sekimata
Katsuhiko
K
Saito
Tamio
T
Kobayashi
Masatomo
M
Shinozaki
Kazuo
K
Yoshida
Shigeo
S
Asami
Tadao
T
D049308:Dioxygenases; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D010105:Oxygenases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D010105:Oxygenases; D049308:Dioxygenases; C069684:lignostilbene-alpha,beta-dioxygenase