152170-28-0Relevant academic research and scientific papers
Deoxygenation of polyphenols by ascomycetes : kinetic behaviour of the NADPH-dependent naphthol dehydrogenase and inhibition by tricyclazole and its analogues
Viviani, F.,Vors, J. P.,Gaudry, M.,Marquet, A.
, p. 395 - 404 (2007/10/02)
The mode of action of tricyclazole, a systemic fungicide that specifically inhibits the biosynthesis of fungal melanins, has been studied with the purified naphthol reductase from Pyricularia oryzae.The NADPH-dependent naphthol reductase transforms 1,3,6,8-tetrahydroxy-naphthalene (T4HN) into (+)scytalone and 1,3,8-trihydroxynaphthalene (T3HN) into (-)vermelone, and is very strongly inhibited by tricyclazole.Kinetic analysis reveals that the inhibition is noncompetitive with respect to T4HN or T3HN, and uncompetitive with respect to NADPH.An aza-analogue of tricyclazole has been synthesized and tested.Unexpectedly, it appears to be a competitive inhibitor of T4HN in spite of its similarity to tricyclazole. Keywords: melanin biosynthesis / polyphenol deoxygenation / naphthol dehydrogenase
