Synthesis and Biological Activity of an Azido Derivative of Paclobutrazol, an Inhibitor of Gibberellin Biosynthesis

Abstract

A photolabile azido derivative of the kaurene oxidase inhibitor 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-l-yl) pentan-3-ol (paclobutrazol) has been synthesized for use as a photoaffinity labeling agent. The compound was tested as an inhibitor of the oxidation of ent-kaurene catalyzed by cell-free preparations from endosperm of Cucurbita maxima. The I(50) of the azido derivative was 9.5 nanomolar, which compares well with that of paclobutrazol (6.3 nanomolar in our measurements). The azido compound bound to Cytochrome P-450 in microsomes from Cucurbita maxima, and induced a Type II spectral change, with an apparent binding constant of 0.24+/-0.04 micromolar.