Enlarged analogues of uniconazole, new azole containing inhibitors of ABA 8'-hydroxylase CYP707A

Bioorg Med Chem Lett. 2009 Oct 1;19(19):5782-6. doi: 10.1016/j.bmcl.2009.07.137. Epub 2009 Aug 3.

Abstract

We enlarged the uniconazole (UNI) molecule to find a specific inhibitor of abscisic acid (ABA) 8'-hydroxylase, and synthesized various UNI derivatives that were substituted with hydrophilic and hydrophobic groups at the 4-chlorine of the phenyl group of UNI using click chemistry. Considering its potency in ABA 8'-hydroxylase inhibition, its small effect on seedling growth, and its ease of application, UT4, the UNI derivative containing the C4 alkyltriazole, was the best candidate for a highly selective inhibitor of ABA 8'-hydroxylase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cytochrome P-450 Enzyme Inhibitors*
  • Cytochrome P-450 Enzyme System / metabolism
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology
  • Malus / growth & development
  • Oryza / growth & development
  • Plant Proteins
  • Recombinant Proteins / antagonists & inhibitors
  • Recombinant Proteins / metabolism
  • Seedlings / drug effects
  • Seedlings / growth & development
  • Triazoles / chemical synthesis
  • Triazoles / chemistry*
  • Triazoles / pharmacology

Substances

  • Cytochrome P-450 Enzyme Inhibitors
  • Enzyme Inhibitors
  • Plant Proteins
  • Recombinant Proteins
  • Triazoles
  • Cytochrome P-450 Enzyme System
  • abscisic acid 8'-hydroxylase
  • uniconazole