Characterization of novel imidazole derivative, JM-8686, a potent inhibitor of allene oxide synthase.

Keimei Oh, Tadao Asami, Kenji Matsui, Gregg A Howe, Noboru Murofushi

Department of Biotechnology, Faculty of Bio-resource Sciences, Akita Prefectural University, Akita 010-0195, Japan. jmwang@akita-pu.ac.jp

FEBS letters 2006 Oct 16

filter terms:

The inhibitory properties of a first synthetic jasmonic acid biosynthesis inhibitor, JM-8686, were investigated. Steady-state kinetic analysis indicates that the compound is a competitive inhibitor of allene oxide synthase (AOS) with a K(i) value of approximate 0.62+/-0.15 microM. Dialysis experiment indicates that AOS inactivation by JM-8686 is reversible. The optical difference spectroscopy analysis of JM-8686 and AOS interaction indicates that JM-8686 induced type II binding spectra with a K(d) value of approximate 1.6+/-0.2 microM, suggesting that JM-8686 binds to the prosthetic heme iron of AOS. Comparison of the inhibitory potency of the compound against HPL (CYP74B) from tomato revealed that JM-8686 was a highly selective inhibitor for AOS.

Citation

Keimei Oh, Tadao Asami, Kenji Matsui, Gregg A Howe, Noboru Murofushi. Characterization of novel imidazole derivative, JM-8686, a potent inhibitor of allene oxide synthase. FEBS letters. 2006 Oct 16;580(24):5791-6