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Volumn 47, Issue 2, 1999, Pages 762-769

Chemical models of cytochrome P450 catalyzed insecticide metabolism. Application to the oxidative metabolism of carbamate insecticides

Author keywords

Biomimetic oxidation; Carbamate insecticides; Cytochrome P450; HPLC electrospray MS; Iron(III) tetraarylporphyrins; Metabolite synthesis; Oxidative metabolism

Indexed keywords

CARBAMATE INSECTICIDE; CARBAMIC ACID DERIVATIVE; CARBARIL; CARBOFURAN; CYTOCHROME P450; HYDROGEN PEROXIDE; IRON DERIVATIVE; PIRIMICARB;

EID: 0032968232     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf980347+     Document Type: Article
Times cited : (23)

References (33)
  • 1
    • 0028041384 scopus 로고
    • The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor Tiagabine
    • Andersen, K. E.; Begtrup, M.; Chorghade, M. S.; Lee, E. C.; Lau, J.; Lundt, B. F.; Petersen, H.; Sorensen, P. O.; Thogersen, H. The synthesis of novel GABA uptake inhibitors. Part 2. Synthesis of 5-hydroxytiagabine, a human metabolite of the GABA reuptake inhibitor Tiagabine. Tetrahedron 1994, 50, 8699-8710.
    • (1994) Tetrahedron , vol.50 , pp. 8699-8710
    • Andersen, K.E.1    Begtrup, M.2    Chorghade, M.S.3    Lee, E.C.4    Lau, J.5    Lundt, B.F.6    Petersen, H.7    Sorensen, P.O.8    Thogersen, H.9
  • 2
    • 0000787825 scopus 로고
    • Iron porphyrin-catalyzed oxidation of 1,2 dimethoxyarenes: A discussion of the different reactions involved in the competition between the formation of methoxyquinones or muconic dimethyl esters
    • Artaud, I.; Ben-Aziza, K.; Mansuy, D. Iron Porphyrin-Catalyzed Oxidation of 1,2 Dimethoxyarenes: A Discussion of the Different Reactions Involved in the Competition between the Formation of Methoxyquinones or Muconic Dimethyl Esters. J. Org. Chem. 1993, 58, 3373-3380.
    • (1993) J. Org. Chem. , vol.58 , pp. 3373-3380
    • Artaud, I.1    Ben-Aziza, K.2    Mansuy, D.3
  • 3
    • 0345695283 scopus 로고
    • Synthesis of possible metabolites of methylcarbamate insecticide chemicals. Substituted aryl-N-hydroxymethylcarbamates
    • Balba, M. H.; Singer, M. S.; Slade, M.; Casida, J. E. Synthesis of Possible Metabolites of Methylcarbamate Insecticide Chemicals. Substituted Aryl-N-hydroxymethylcarbamates. J. Agric. Food Chem. 1968, 16, 821-825.
    • (1968) J. Agric. Food Chem. , vol.16 , pp. 821-825
    • Balba, M.H.1    Singer, M.S.2    Slade, M.3    Casida, J.E.4
  • 4
    • 0016212136 scopus 로고
    • Factors influencing the metabolism of mexacarbate by microorganisms
    • Benezet, H. J.; Matsumura, F. Factors influencing the metabolism of Mexacarbate by microorganisms. J. Agric. Food Chem. 1974, 22, 427-430.
    • (1974) J. Agric. Food Chem. , vol.22 , pp. 427-430
    • Benezet, H.J.1    Matsumura, F.2
  • 7
    • 0029821062 scopus 로고    scopus 로고
    • Improved protocol for the synthesis and halogenation of sterically hindered metalloporphyrins
    • Chorghade, M. S.; Dolphin, D.; Dupre, D.; Hill, D. R.; Lee, F. C.; Wijesekera, T. P. Improved Protocol for the Synthesis and Halogenation of Sterically Hindered Metalloporphyrins. Synthesis 1996, 1320-1324.
    • (1996) Synthesis , pp. 1320-1324
    • Chorghade, M.S.1    Dolphin, D.2    Dupre, D.3    Hill, D.R.4    Lee, F.C.5    Wijesekera, T.P.6
  • 8
    • 0024027564 scopus 로고
    • Predicting metabolic pathways by logic programming
    • Darvas, F. Predicting Metabolic Pathways by Logic Programming. J. Mol. Graph. 1988, 6, 80-87.
    • (1988) J. Mol. Graph. , vol.6 , pp. 80-87
    • Darvas, F.1
  • 9
    • 0000794919 scopus 로고    scopus 로고
    • Polyhaloporphyrins: Unusal ligands for metals and metal-catalyzed oxidations
    • Dolphin, D.; Taylor, T. G.; Xie, L. Y. Polyhaloporphyrins: Unusal Ligands for Metals and Metal-Catalyzed Oxidations. Acc. Chem. Res. 1997, 30, 251-259.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 251-259
    • Dolphin, D.1    Taylor, T.G.2    Xie, L.Y.3
  • 10
    • 0000280680 scopus 로고
    • Nature of certain carbamate metabolites of the insecticide sevin
    • Dorough, H. W.; Casida, J. E. Nature of Certain Carbamate Metabolites of the Insecticide Sevin. J. Agric. Food Chem. 1964, 12, 294-304.
    • (1964) J. Agric. Food Chem. , vol.12 , pp. 294-304
    • Dorough, H.W.1    Casida, J.E.2
  • 11
    • 0345263666 scopus 로고
    • Methylenedioxyphenyl derivatives as synergists for carbamate insecticides on susceptible, DDT-and parathion-resistant houseflies
    • Eldefrawi, M. E.; Miskus, R.; Sutcher, V. Methylenedioxyphenyl derivatives as synergists for carbamate insecticides on susceptible, DDT-and parathion-resistant houseflies. J. Econ. Entomol. 1960, 53, 231-234.
    • (1960) J. Econ. Entomol. , vol.53 , pp. 231-234
    • Eldefrawi, M.E.1    Miskus, R.2    Sutcher, V.3
  • 12
    • 0041050976 scopus 로고
    • Molecular biology of insecticide resistance
    • Feyereisen, R. Molecular Biology of Insecticide Resistance. Toxicol. Lett. 1995, 82/83, 83-90.
    • (1995) Toxicol. Lett. , vol.82-83 , pp. 83-90
    • Feyereisen, R.1
  • 13
    • 0010420577 scopus 로고
    • Hard acid and soft nucleophil system. New efficient method for removal of Benzyl Protecting Group
    • Fuju, K.; Ichikawa, K.; Node, M.; Fujita, E. Hard Acid and Soft Nucleophil System. New Efficient Method for Removal of Benzyl Protecting Group. J. Org. Chem. 1979, 44, 1661-1664.
    • (1979) J. Org. Chem. , vol.44 , pp. 1661-1664
    • Fuju, K.1    Ichikawa, K.2    Node, M.3    Fujita, E.4
  • 15
    • 0027731496 scopus 로고
    • Insect cytochrome P-450: Metabolism and resistance to insecticides
    • Hodgson, E.; Rose, R. L.; Goh, D. K. S.; Rock, G. C.; Roe, R. M. Insect cytochrome P-450: metabolism and resistance to insecticides. Biochern. Soc. Trans. 1993, 21, 1060-1065.
    • (1993) Biochern. Soc. Trans. , vol.21 , pp. 1060-1065
    • Hodgson, E.1    Rose, R.L.2    Goh, D.K.S.3    Rock, G.C.4    Roe, R.M.5
  • 16
    • 0001366141 scopus 로고    scopus 로고
    • Improved synthesis of 5,10,15,20-tetrakisaryl and tetrakisalkyl porphyrins
    • Johnstone, R. A. W.; Nunes, P. G.; Pereira, M. M.; Gonsalves, M. A. R. Improved Synthesis of 5,10,15,20-tetrakisaryl and tetrakisalkyl porphyrins. Heterocycles 1996, 43, 1423-1437.
    • (1996) Heterocycles , vol.43 , pp. 1423-1437
    • Johnstone, R.A.W.1    Nunes, P.G.2    Pereira, M.M.3    Gonsalves, M.A.R.4
  • 17
    • 0542430100 scopus 로고
    • Quantitative dealkylation of alkyl ethers via treatment with trimethylsilyl iodide. A new method for ether hydrolyzis
    • Jung, M. E.; Lyster, M. A. Quantitative Dealkylation of Alkyl Ethers via Treatment with Trimethylsilyl Iodide. A New Method for Ether Hydrolyzis. J. Org. Chem. 1977, 42, 3761-3763.
    • (1977) J. Org. Chem. , vol.42 , pp. 3761-3763
    • Jung, M.E.1    Lyster, M.A.2
  • 18
    • 0031609855 scopus 로고    scopus 로고
    • Cytochrome P450 catalyzed insecticide metabolism. Chemical and theoretical models
    • Keserü, G. M. Cytochrome P450 Catalyzed Insecticide Metabolism. Chemical and Theoretical Models. Sci. Prog. 1998, 81, 245-272.
    • (1998) Sci. Prog. , vol.81 , pp. 245-272
    • Keserü, G.M.1
  • 19
    • 0030822772 scopus 로고    scopus 로고
    • Cytochrome P-450 catalysed insecticide metabolism. Prediction of regio-and stereoselectivity in the primer metabolism of carbofuran: A theoretical study
    • Keserü, G. M.; Kolossváry, I.; Bertók, B. Cytochrome P-450 catalysed insecticide metabolism. Prediction of regio-and stereoselectivity in the primer metabolism of carbofuran: a theoretical study. J. Am. Chem. Soc. 1997, 119, 5127-5131.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 5127-5131
    • Keserü, G.M.1    Kolossváry, I.2    Bertók, B.3
  • 20
    • 0033119336 scopus 로고    scopus 로고
    • Metalloporphyrin catalyzed biomimetic oxidation of aryl methyl ethers
    • in press
    • Keserü, G. M.; Balogh, T.; Bokotey, S.; Árvai, G.; Bertók, B. Metalloporphyrin Catalyzed Biomimetic Oxidation of Aryl Methyl Ethers. Tetrahedron 1999, in press.
    • (1999) Tetrahedron
    • Keserü, G.M.1    Balogh, T.2    Bokotey, S.3    Árvai, G.4    Bertók, B.5
  • 23
    • 0242712014 scopus 로고
    • Status and future of synergists in resistance management
    • Ragsdale, N. N., Kearney, P. C., Plimmer, J. R., Eds.; ACS Conference Proceedings Series; American Chemical Society: Washington, DC
    • Lamoureux, G. L.; Rusness, D. G. Status and Future of Synergists in Resistance Management. In 8th IUPAC Congress of Pesticides; Ragsdale, N. N., Kearney, P. C., Plimmer, J. R., Eds.; ACS Conference Proceedings Series; American Chemical Society: Washington, DC, 1995; pp 350-366.
    • (1995) 8th IUPAC Congress of Pesticides , pp. 350-366
    • Lamoureux, G.L.1    Rusness, D.G.2
  • 24
    • 0000845585 scopus 로고    scopus 로고
    • Oxygen activation by metal complexes and alkyl hydroperoxides. Application ol mechanistic probes to explore the role of alkyloxy radicals in alkane functionalization
    • MacFaul, P. A.; Arends, I. W. C.; Ingold, K. U.; Wayner, D. M. Oxygen Activation by Metal Complexes and Alkyl Hydroperoxides. Application ol Mechanistic Probes to Explore the Role of Alkyloxy Radicals in Alkane Functionalization. J. Chem. Soc., Perkin Trans. 2 1997, 135-144.
    • (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 135-144
    • MacFaul, P.A.1    Arends, I.W.C.2    Ingold, K.U.3    Wayner, D.M.4
  • 25
    • 0344400411 scopus 로고    scopus 로고
    • Metabolite, MDL Information Systems, San Leandro, CA, 1997
    • Metabolite, MDL Information Systems, San Leandro, CA, 1997.
  • 26
    • 33947309684 scopus 로고
    • Metabolism of 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-N-methylcarbamate (Furadan) in plants, insects and mammals
    • Metcalf, R. C.; Borck, K.; El-Aziz Munoz, S. A.; Casillo, C. C. Metabolism of 2,2-dimethyl-2,3-dihydrobenzofuranyl-7-N-methylcarbamate (Furadan) in Plants, Insects and Mammals. J. Agric. Food Chem. 1968, 16, 300-311.
    • (1968) J. Agric. Food Chem. , vol.16 , pp. 300-311
    • Metcalf, R.C.1    Borck, K.2    El-Aziz Munoz, S.A.3    Casillo, C.C.4
  • 29
    • 0025266069 scopus 로고
    • Application of chemical P-450 model systems to drug metabolism III. Metabolism of 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine
    • Nagatsu, Y.; Higuchi, T.; Hirobe, M. Application of chemical P-450 model systems to drug metabolism III. Metabolism of 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine. Chem. Pharm. Bull. 1993, 38, 400-403.
    • (1993) Chem. Pharm. Bull. , vol.38 , pp. 400-403
    • Nagatsu, Y.1    Higuchi, T.2    Hirobe, M.3
  • 31
    • 0004058001 scopus 로고    scopus 로고
    • British Crop Protection Council: Farnham, UK
    • The Pesticide Manual, 11th ed.; British Crop Protection Council: Farnham, UK, 1997.
    • (1997) The Pesticide Manual, 11th Ed.
  • 32
    • 37049098026 scopus 로고
    • Sterically protected hemins with electronegative substituents: Efficient catalysts for hydroxylation and epoxidation
    • Traylor, P. S.; Dolphin, D.; Traylor, T. G. Sterically protected hemins with electronegative substituents: efficient catalysts for hydroxylation and epoxidation. J. Chem. Soc., Chem. Commun. 1984, 279-280.
    • (1984) J. Chem. Soc., Chem. Commun. , pp. 279-280
    • Traylor, P.S.1    Dolphin, D.2    Traylor, T.G.3
  • 33
    • 0032559285 scopus 로고    scopus 로고
    • Investigation of photochemical behavior of pesticides in a photolysis reactor coupled on-line with a liquid chromatography-electrospray ionization tandem mass spectrometry system. Application to trace and confirmatory analyses in food samples
    • Volmer, D. A. Investigation of photochemical behavior of pesticides in a photolysis reactor coupled on-line with a liquid chromatography-electrospray ionization tandem mass spectrometry system. Application to trace and confirmatory analyses in food samples. J Chromatogr. A 1998, 794, 129-146.
    • (1998) J Chromatogr. A , vol.794 , pp. 129-146
    • Volmer, D.A.1


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