71.アブシジン酸8'-水酸化酵素CYP707A特異的阻害剤アブシナゾールEの開発(口頭発表)

概要

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Uniconazole (UNI), which is well known as a plant growth regulator, is a triazole-containing inhibitor of GA biosynthetic enzyme (CYP701A). UNI is a low selective P450 inhibitor that inhibits multiple P450 enzymes including abscisic acid (ABA) 8'-hydroxylase (CYP707A), which is a key enzyme for ABA catabolism. Based on our speculation that the low selectivity of UNI may be resulted from its small molecule, we designed and synthesized enlarged UNI analogues of UNI (UT) that have a 1,2,3-triazolyl alkyl chain at C4 of chlorophenyl group of UNI. Although UT compounds showed the strong inhibitory activity against CYP707A, the biological activity of most of UT compounds, especially those with a long alkyl chain (>C4), was not tested because of their water-insolubility. On the other hand, the introduction of protic functional groups in the alkyl chain diminished the inhibitory activity against CYP707A. Thus we designed and synthesized UT1-E2Ts that has a diethylene glycol chain as a novel, water-soluble UT analogue, and examined its water solubility, inhibitory activity against CYP707A, and biological activity. UT1-E2Ts showed strong inhibitory activity against CYP707A and good water-solubility, equivalent to UNI, whereas it did not inhibit the growth of rice seedlings, contrary to UNI.
植物化学調節学会の論文
2009-10-06