Chemical models of cytochrome p450 catalyzed insecticide metabolism. Application to the oxidative metabolism of carbamate insecticides

Citation
Gm. Keseru et al., Chemical models of cytochrome p450 catalyzed insecticide metabolism. Application to the oxidative metabolism of carbamate insecticides, J AGR FOOD, 47(2), 1999, pp. 762-769
Citations number
33
Categorie Soggetti
Agricultural Chemistry","Chemistry & Analysis
Journal title
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
ISSN journal
00218561 → ACNP
Volume
47
Issue
2
Year of publication
1999
Pages
762 - 769
Database
ISI
SICI code
0021-8561(199902)47:2<762:CMOCPC>2.0.ZU;2-S
Abstract
Cytochrome P450 (CP450) catalyzed oxidative metabolism of carbofuran (1), c arbaryl (2), and pirimicarb (3) has been modeled using biomimetic oxidation s catalyzed by iron(III) tetraarylporphyrins. Oxidation products of 1 were identified by comparison of HPLC retention times measured under standardize d conditions for metabolites synthesized and characterized by H-1 and C-13 NMR spectroscopy. Comparison of product distributions to in vivo metabolic profiles revealed that the H2O2/meso-tetrakis(pentafluorophenyl)porphyrin i ron(III) chloride [Fe(TF20PP)] system mimics the action of insect CP450s ag ainst carbofuran. The effectiveness of this system was further demonstrated by the biomimetic oxidation of other carbamate insecticides (2 and 3) moni tored by HPLC/electrospray MS. The predictive power of this biomimetic mode l was compared to that of knowledge-based expert systems. Although similar models were recently applied in pharmaceutical research, the usefulness of this approach has first been demonstrated for the prediction of metabolic p rofiles of agrochemicals.