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Discovery of New Lead Compounds as Inhibitors of Allene Oxide Snnthase Based on Ozagrel Scaffold

Keimei Oh, Yuina Todate, and Yuko Yoshizawa
Department of Biotechnology, Faculty of Bioresource Sciences, Akita Prefectural University, Shimoshinjo Nakano, Japan
Abstract—Plant defense responses to herbivore attack and mechanical wounding are regulated by signal transduction pathways. Jasmonates (JAs) are important signal mediators that involve in plant defense signaling. To explore the regulation mechanism of JAs signaling, we have been working on JA biosynthesis inhibitors through design and synthesis small molecules targeting allene oxide synthase (AOS, CYP74A), a key enzyme in JA biosynthesis. In the present work, we report the synthesis of new imidazole-type AOS inhibitors based on ozagrel scaffold. The inhibitory activity of the synthesized compounds against AOS was determined by using purified recombinant protein expressed in E. Coli. Among the nine newly synthesized imidazole derivatives, we found that 6-[4-(2-imidazol-1-yl-ethyl) phenoxy] hexanoic acid ethyl ester (f) exhibits inhibitory activity against AOS with an IC50 value approximately 78±12µM.

Index Terms—allene oxide synthase, Inhibitors, Jasmonic acid biosynthesis, Plant hormone, Plant defense response, Imidazole

Cite: Keimei Oh, Yuina Todate, and Yuko Yoshizawa, "Discovery of New Lead  Compounds as Inhibitors of Allene Oxide Snnthase Based on Ozagrel Scaffold," Journal of Medical and Bioengineering, Vol. 5, No. 1, pp. 45-48, February 2016. Doi: 10.12720/jomb.5.1.45-48
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