Protein Information

Name cytochrome P450 (protein family or complex)
Synonyms cytochrome P450; cytochrome P 450; CYP450; CYP 450

Compound Information

Name triadimenol
CAS

Reference List

PubMed Abstract RScore(About this table)
3545213 Yoshida Y, Aoyama Y: Interaction of azole antifungal agents with cytochrome P-45014DM purified from Saccharomyces cerevisiae microsomes. Biochem Pharmacol. 1987 Jan 15;36(2):229-35.

Mechanism of action of azole antifungal agents was studied by analyzing interaction of ketoconazole, itraconazole, triadimefon and triadimenol with a purified yeast cytochrome P-450 which catalyzes lanosterol 14 alpha-demethylation (P-45014DM).
31(0,1,1,1) Details
2561184 Vanden Bossche H, Marichal P, Gorrens J, Coene MC, Willemsens G, Bellens D, Roels I, Moereels H, Janssen PA: Biochemical approaches to selective antifungal activity. Mycoses. 1989;32 Suppl 1:35-52.

Azole antifungals (e.g. the imidazoles: miconazole, clotrimazole, bifonazole, imazalil, ketoconazole, and the triazoles: diniconazole, triadimenol, propiconazole, fluconazole and itraconazole) inhibit in fungal cells the 14 alpha-demethylation of lanosterol or 24-methylenedihydrolanosterol.
The consequent inhibition of ergosterol synthesis originates from binding of the unsubstituted nitrogen (N-3 or N-4) of their imidazole or triazole moiety to the heme iron and from binding of their N-1 substituent to the apoprotein of a cytochrome P-450 (P-450 (14) DM) of the endoplasmic reticulum.
1(0,0,0,1) Details
11396979 Lamb DC, Cannieux M, Warrilow AG, Bak S, Kahn RA, Manning NJ, Kelly DE, Kelly SL: Plant sterol 14 alpha-demethylase affinity for azole fungicides. Biochem Biophys Res Commun. 2001 Jun 15;284(3):845-9.

Azole fungicides were thought to have much greater affinity for the fungal cytochrome P450 enzyme, sterol 14 alpha-demthylase (CYP51) than the plant orthologue.
Using purified CYP51 from the plant Sorghum bicolor L Moenech, a direct comparison of the sensitivity to the fungicides triadimenol and tebuconazole has been carried out.
1(0,0,0,1) Details
19572650 Cao X, Hu M, Zhang J, Li F, Yang Y, Liu D, Liu SH: Determination of stereoselective interaction between enantiomers of chiral gamma-aryl-1H-1,2,4-triazole derivatives and Penicillium digitatum. J Agric Food Chem. 2009 Aug 12;57(15):6914-9.

In vitro experiments were indicative of a strong inhibitory effect of all of the compounds on P. digitatum, and seven of the compounds 5 exhibited better inhibition than the commercial fungicides triadimefon and triadimenol.
These observations suggest that P. digitatum discriminates the enantiomers and that the R enantiomer better fits the active site of cytochrome P450.
1(0,0,0,1) Details
20026392 Crowell SR, Henderson WM, Fisher JW, Kenneke JF: Gender and species differences in triadimefon metabolism by rodent hepatic microsomes. Toxicol Lett. 2010 Mar 1;193(1):101-7. Epub 2009 Dec 22.

Understanding the potential differences in metabolic capacity and kinetics between various common laboratory species as well as between genders is an important facet of chemical risk assessment that is often overlooked, particularly for chemicals which undergo non-cytochrome P450 mediated metabolism.
Triadimefon depletion and triadimenol formation were measured in each type of microsomes.
1(0,0,0,1) Details