Oxidative activation and degradation of organophosphorus pesticides mediated by iron porphyrins
Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II), tolclofos-methyl (III), butamifos (IV) and fenthion (V). The major products from 1-IV were the corresponding phenols and each oxon formed via a phosphox...
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| Published in | Journal of Pesticide Science Vol. 30; no. 2; pp. 103 - 110 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
Tokyo
Pesticide Science Society of Japan
01.01.2005
Japan Science and Technology Agency |
| Subjects | |
| Online Access | Get full text |
| ISSN | 1348-589X 0385-1559 1349-0923 |
| DOI | 10.1584/jpestics.30.103 |
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| Abstract | Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II), tolclofos-methyl (III), butamifos (IV) and fenthion (V). The major products from 1-IV were the corresponding phenols and each oxon formed via a phosphoxathiirane intermediate by oxidation at the P=S moiety similarly as reported for their mammalian metabolism by cytochrome P450 enzymes. Stepwise oxidation of the methylthio sulfur via sulfoxide to sulfone, and ester cleavage and oxidative desulfuration primarily proceeded for V. Both the electron distribution of the highest occupied molecular orbital and its energy level of the pesticides calculated by MNDO-PM3 were shown to control the reaction site and rate of oxidation at sulfur atoms. |
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| AbstractList | Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II), tolclofos-methyl (III), butamifos (IV) and fenthion (V). The major products from I–IV were the corresponding phenols and each oxon formed via a phosphoxathiirane intermediate by oxidation at the P=S moiety similarly as reported for their mammalian metabolism by cytochrome P450 enzymes. Stepwise oxidation of the methylthio sulfur via sulfoxide to sulfone, and ester cleavage and oxidative desulfuration primarily proceeded for V. Both the electron distribution of the highest occupied molecular orbital and its energy level of the pesticides calculated by MNDO-PM3 were shown to control the reaction site and rate of oxidation at sulfur atoms. © Pesticide Science Society of Japan Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II), tolclofos-methyl (III), butamifos (IV) and fenthion (V). The major products from I-IV were the corresponding phenols and each oxon formed via a phosphoxathiirane intermediate by oxidation at the P=S moiety similarly as reported for their mammalian metabolism by cytochrome P450 enzymes. Stepwise oxidation of the methylthio sulfur via sulfoxide to sulfone, and ester cleavage and oxidative desulfuration primarily proceeded for V. Both the electron distribution of the highest occupied molecular orbital and its energy level of the pesticides calculated by MNDO-PM3 were shown to control the reaction site and rate of oxidation at sulfur atoms. INTRODUCTION Oxidative metabolism catalyzed by cytochrome P450 enzymes (P450) is one of the most important degradative pathways for xenobiotics including pesticides. Many types of reactions such as hydroxylation of alkyl and aromatic carbons, dealkylation via stepwise oxidation, epoxidation of alkene and oxidation at nitrogen and sulfur atoms are known to be catalyzed. 1-3) The atomic oxygen originating from molecular oxygen is bound to iron of the protoporphyrin IX moiety in P450 and its transfer to a substrate proceeds in the presence of NADPH. The Fe (valence, IV；spin state, S=1) porphyrin-oxygen cation radical has been strongly suggested as the prosthetic moiety in an active state by extensive theoretical studies and the triplet oxene is considered to be the most appropriate model. 4) In order to examine the mode of action of P450-catalyzed oxidation at a molecular level, Keseru et al. have applied computational methods including molecular orbital (MO) calculations and molecular dynamic simulations to the carbofuran-P450cam complex utilizing the three-dimensional structure of the enzyme. 5) Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II), tolclofos-methyl (III), butamifos (IV) and fenthion (V). The major products from 1-IV were the corresponding phenols and each oxon formed via a phosphoxathiirane intermediate by oxidation at the P=S moiety similarly as reported for their mammalian metabolism by cytochrome P450 enzymes. Stepwise oxidation of the methylthio sulfur via sulfoxide to sulfone, and ester cleavage and oxidative desulfuration primarily proceeded for V. Both the electron distribution of the highest occupied molecular orbital and its energy level of the pesticides calculated by MNDO-PM3 were shown to control the reaction site and rate of oxidation at sulfur atoms. |
| Author | Fujisawa, T.(Sumitomo Chemical Co. Ltd., Takarazuka, Hyogo (Japan)) Katagi, T |
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| Cites_doi | 10.1584/jpestics.1.207 10.1021/jf980347+ 10.1584/jpestics.1.9 10.1002/jlcr.2580130306 10.1021/jo00064a026 10.1093/jee/54.6.1232 10.1016/S0960-894X(01)80830-1 10.1021/jo049879h 10.1021/ja9639372 10.1002/jcc.540141014 10.1016/S0021-9673(01)88831-2 10.1016/0166-1280(90)85045-O 10.1016/0006-291X(86)90265-2 10.1002/jlcr.2580160314 10.1021/bi00224a016 10.1021/es0011663 10.1515/9783112563328 10.1007/BF00128336 10.1584/jpestics.2.119 10.1021/bk-1981-0158.ch002 10.1584/jpestics.6.65 10.1021/ar960126u 10.1002/jlcr.2580130305 10.1021/ic00255a028 10.3109/00498259509046676 |
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| Keywords | Degradation Porphyrin Pesticides organophosphorus pesticides oxidation mediated by iron porphyrin Activation Iron Organophosphorus compounds Oxidation MNDO-PM3 calculations |
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| Snippet | Biomimetic oxidation mediated by three types of iron porphyrins was examined for five organophosphrus pesticides, fenitrothion (I), cyanophos (II),... |
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| SubjectTerms | Biological and medical sciences Biomimetics CITOCROMO P450 COMPOSE ORGANOPHOSPHORE COMPUESTO ORGANICO DEL FOSFORO CYTOCHROME P450 DEGRADACION DEGRADATION FER Fundamental and applied biological sciences. Psychology HIERRO IRON MNDO-PM3 calculations ORGANOPHOSPHORUS COMPOUNDS Organophosphorus pesticides OXIDACION OXIDATION oxidation mediated by iron porphyrin OXYDATION PESTICIDAL PROPERTIES PESTICIDE PESTICIDES Phenols Phytopathology. Animal pests. Plant and forest protection PLAGUICIDAS PORFIRINAS PORPHYRINE PORPHYRINS PROPIEDADES PLAGUICIDAS PROPRIETE DES PESTICIDES RELACION ESTRUCTURA ACTIVIDAD RELATION STRUCTURE ACTIVITE STRUCTURE ACTIVITY RELATIONSHIPS Sulfur |
| Title | Oxidative activation and degradation of organophosphorus pesticides mediated by iron porphyrins |
| URI | https://www.jstage.jst.go.jp/article/jpestics/30/2/30_2_103/_article/-char/en http://mol.medicalonline.jp/en/journal/download?GoodsID=cy3jpesc/2005/003002/006&name=0103-0110e https://www.proquest.com/docview/1444571349 |
| Volume | 30 |
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| ispartofPNX | Journal of Pesticide Science, 2005, Vol.30(2), pp.103-110 |
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