A specific and potent inhibitor of brassinosteroid biosynthesis possessing a dioxolane ring.
Screening for brassinosteroid biosynthesis inhibitors was performed to find azole derivatives that induced dwarfism, to resemble brassinosteroid-deficient mutants in Arabidopsis, and which could be rescued by brassinosteroid. Through this screening experiment, propiconazole fungicide was selected as a likely inhibitor of brassinosteroid biosynthesis and, thus, propiconazole derivatives with optimized activity and selectivity were synthesized. The biological activity of these compounds was evaluated by examining cress stem elongation. Among the compounds tested, 2RS,4RS-1-[2-(4-trifluoromethylphenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (12) showed the most potent capability to retard cress stem elongation in the light. The compound-induced hypocotyl dwarfism was restored by the coapplication of 10 nM brassinolide but not by 1 microM gibberellin. These results suggest that 12 should affect brassinosteroid biosynthesis. The potency and specificity of 12 were greater than those of brassinazole, a previously reported brassinosteroid biosynthesis inhibitor.
Sekimata
Katsuhiko
K
Graduate School of Science and Engineering, Saitama University, Saitama 338-8570, Japan.
Han
Sun-Young
SY
Yoneyama
Koichi
K
Takeuchi
Yasutomo
Y
Yoshida
Shigeo
S
Asami
Tadao
T
D060406:Brassinosteroids; D002777:Cholestanols / Q000494:pharmacology; D065607:Cytochrome P-450 Enzyme Inhibitors; D004149:Dioxoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005875:Gibberellins / Q000037:antagonists & inhibitors*; D013260:Steroids, Heterocyclic / Q000494:pharmacology; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
C459439:1-(2-(4-trifluoromethylphenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-triazole; D060406:Brassinosteroids; C451122:Brz2001; D002777:Cholestanols; D065607:Cytochrome P-450 Enzyme Inhibitors; D004149:Dioxoles; D005875:Gibberellins; D013260:Steroids, Heterocyclic; D014230:Triazoles; C045950:propiconazole; C412342:brassinazole; C023623:brassinolide