메뉴 건너뛰기




Volumn 57, Issue 11, 2009, Pages 4861-4866

Enzymes and inhibitors in neonicotinoid insecticide metabolism

Author keywords

Aldehyde oxidase; Clothianidin; CYP450; Glucuronide; Imidacloprid; Methylation; Neonicotinoid insecticide; Thiacloprid; Thiamethoxam

Indexed keywords

((E) 1 (2 CHLORO 1,3 THIAZOL 5 YLMETHYL) 3 METHYL 2 NITROGUANIDINE); ((E)-1-(2-CHLORO-1,3-THIAZOL-5-YLMETHYL)-3-METHYL-2-NITROGUANIDINE); ALDEHYDE OXIDASE; CYTOCHROME P450; ENZYME INHIBITOR; GUANIDINE DERIVATIVE; IMIDACLOPRID; IMIDAZOLE DERIVATIVE; INSECTICIDE; NITRO DERIVATIVE; OXAZINE DERIVATIVE; THIAMETHOXAM; THIAZOLE DERIVATIVE;

EID: 67149115255     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf900250f     Document Type: Article
Times cited : (74)

References (34)
  • 1
    • 0037209233 scopus 로고    scopus 로고
    • Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors
    • Tomizawa, M.; Casida, J. E. Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors, Annu. Rev. Entomol. 2003, 48, 339-364.
    • (2003) Annu. Rev. Entomol , vol.48 , pp. 339-364
    • Tomizawa, M.1    Casida, J.E.2
  • 2
    • 13844280231 scopus 로고    scopus 로고
    • Neonicotinoid insecticide toxicology: Mechanisms of selective action
    • Tomizawa, M.; Casida, J. E. Neonicotinoid insecticide toxicology: mechanisms of selective action. Ann. Rev. Pharmacol. Toxicol. 2005, 45, 247-268.
    • (2005) Ann. Rev. Pharmacol. Toxicol , vol.45 , pp. 247-268
    • Tomizawa, M.1    Casida, J.E.2
  • 3
    • 67149086316 scopus 로고    scopus 로고
    • Tomlin, C. D. S., Ed. The Pesticide Manual, 14th ed.; British Crop Protection Council: Alton, Hampshire, U.K., 2006; 1350 pp.
    • Tomlin, C. D. S., Ed. The Pesticide Manual, 14th ed.; British Crop Protection Council: Alton, Hampshire, U.K., 2006; 1350 pp.
  • 4
    • 33746211295 scopus 로고    scopus 로고
    • Chloropyridinyl neonicotinoid insecticides: Diverse molecular substituents contribute to facile metabolism in mice
    • Ford, K. A.; Casida, J. E. Chloropyridinyl neonicotinoid insecticides: diverse molecular substituents contribute to facile metabolism in mice. Chem. Res. Toxicol. 2006, 19, 944-951.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 944-951
    • Ford, K.A.1    Casida, J.E.2
  • 5
    • 33845247120 scopus 로고    scopus 로고
    • Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice
    • Ford, K. A.; Casida, J. E. Unique and common metabolites of thiamethoxam, clothianidin, and dinotefuran in mice. Chem. Res. Toxicol. 2006, 19, 1549-1556.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 1549-1556
    • Ford, K.A.1    Casida, J.E.2
  • 6
    • 19044376121 scopus 로고    scopus 로고
    • Metabolism of pesticides
    • 2nd ed, Krieger R. I, Ed, Academic Press: San Diego, CA
    • Hodgson, E.; Levi, P. E. Metabolism of pesticides. In Handbook of Pesticide Toxicology, 2nd ed., Krieger R. I., Ed.; Academic Press: San Diego, CA, 2001; Vol. 1, pp 531-562.
    • (2001) Handbook of Pesticide Toxicology , vol.1 , pp. 531-562
    • Hodgson, E.1    Levi, P.E.2
  • 7
    • 0041311188 scopus 로고    scopus 로고
    • Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants
    • Nauen, R.; Ebbinghaus-Kintscher, U.; Salgado, V. L.; Kaussman, M. Thiamethoxam is a neonicotinoid precursor converted to clothianidin in insects and plants. Pestic. Biochem. Physiol. 2003, 76, 55-69.
    • (2003) Pestic. Biochem. Physiol , vol.76 , pp. 55-69
    • Nauen, R.1    Ebbinghaus-Kintscher, U.2    Salgado, V.L.3    Kaussman, M.4
  • 8
    • 58149352683 scopus 로고    scopus 로고
    • Comparative metabolism and pharmaco-kinetics of seven neonicotinoid insecticides in spinach
    • Ford, K. A.; Casida, J. E. Comparative metabolism and pharmaco-kinetics of seven neonicotinoid insecticides in spinach. J. Agric. Food Chem. 2008, 56, 10168-10175.
    • (2008) J. Agric. Food Chem , vol.56 , pp. 10168-10175
    • Ford, K.A.1    Casida, J.E.2
  • 9
    • 0242445125 scopus 로고    scopus 로고
    • Thiamethoxam; pesticide tolerance
    • Environmental Protection Agency
    • Environmental Protection Agency. Thiamethoxam; pesticide tolerance. Fed. Regist. 2002, 68, 66561-66571
    • (2002) Fed. Regist , vol.68 , pp. 66561-66571
  • 10
    • 13844314619 scopus 로고    scopus 로고
    • Clothianidin; pesticide tolerance
    • Environmental Protection Agency
    • Environmental Protection Agency. Clothianidin; pesticide tolerance. Fed, Regist. 2003, 68, 32390-32400
    • (2003) Fed, Regist , vol.68 , pp. 32390-32400
  • 11
    • 26944438720 scopus 로고    scopus 로고
    • Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 1: Mode of action studies in the mouse
    • Green, T.; Toghill, A.; Lee, R.; Waechter, F.; Weber, E.; Noakes, J. Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 1: Mode of action studies in the mouse. Toxicol. Sci. 2005, 86, 36-17.
    • (2005) Toxicol. Sci , vol.86 , pp. 36-17
    • Green, T.1    Toghill, A.2    Lee, R.3    Waechter, F.4    Weber, E.5    Noakes, J.6
  • 12
    • 26944495351 scopus 로고    scopus 로고
    • Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 2: Species differences in response
    • Green, T.; Toghill, A.; Lee, R.; Waechter, F.; Weber, E.; Peffer, R.; Noakes, J.; Robinson, M. Thiamethoxam induced mouse liver tumors and their relevance to humans. Part 2: Species differences in response. Toxicol. Sci. 2005, 86, 48-55.
    • (2005) Toxicol. Sci , vol.86 , pp. 48-55
    • Green, T.1    Toghill, A.2    Lee, R.3    Waechter, F.4    Weber, E.5    Peffer, R.6    Noakes, J.7    Robinson, M.8
  • 13
    • 0043066903 scopus 로고    scopus 로고
    • In vitro human phase I metabolism of xenobiotics 1: Pesticides and related compounds used in agriculture and public health, May 2003
    • Hodgson, E. In vitro human phase I metabolism of xenobiotics 1: Pesticides and related compounds used in agriculture and public health, May 2003. J. Biochem. Mol. Toxicol. 2003, 17, 201-206.
    • (2003) J. Biochem. Mol. Toxicol , vol.17 , pp. 201-206
    • Hodgson, E.1
  • 14
    • 84892246340 scopus 로고    scopus 로고
    • Human cytochrome P450 enzymes
    • Ortiz de Montellano, P. R, Ed, Kluwer Academic/Plenum Publishers: New York
    • Guengerich, F. P. Human cytochrome P450 enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York, 2005; pp 377-530.
    • (2005) Cytochrome P450: Structure, Mechanism, and Biochemistry , pp. 377-530
    • Guengerich, F.P.1
  • 15
    • 84892244187 scopus 로고    scopus 로고
    • Inhibition of cytochrome P450 enzymes
    • Ortiz de Montellano, P. R, Ed, Kluwer Academic/Plenum Publishers: New York
    • Correia, M. A.; Ortiz de Montellano, P. R. Inhibition of cytochrome P450 enzymes. In Cytochrome P450: Structure, Mechanism, and Biochemistry; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York, 2005; pp 247-322.
    • (2005) Cytochrome P450: Structure, Mechanism, and Biochemistry , pp. 247-322
    • Correia, M.A.1    Ortiz de Montellano, P.R.2
  • 16
    • 31844451913 scopus 로고    scopus 로고
    • Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides
    • Dick, R. A.; Kaane, D. B.; Casida, J. E. Substrate specificity of rabbit aldehyde oxidase for nitroguanidine and nitromethylene neonicotinoid insecticides. Chem. Res. Toxicol. 2006, 19, 38-43.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 38-43
    • Dick, R.A.1    Kaane, D.B.2    Casida, J.E.3
  • 17
    • 0014853596 scopus 로고
    • Mixed-function oxidase involvement in the biochemistry of insecticide synergists
    • Casida, J. E. Mixed-function oxidase involvement in the biochemistry of insecticide synergists. J. Agric. Food Chem. 1970, 18, 753-772.
    • (1970) J. Agric. Food Chem , vol.18 , pp. 753-772
    • Casida, J.E.1
  • 18
    • 0001270581 scopus 로고
    • 3H] imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene- and 2-mtroimino-imidazolidines
    • 3H] imidacloprid binding site in house fly head acetylcholine receptor to insecticidal activity of 2-nitromethylene- and 2-mtroimino-imidazolidines. Pestic. Biochem. Physiol. 1993, 46, 200-206.
    • (1993) Pestic. Biochem. Physiol , vol.46 , pp. 200-206
    • Liu, M.-Y.1    Lanford, J.2    Casida, J.E.3
  • 19
    • 0015083352 scopus 로고
    • Response of hepatic microsomal mixed-function oxidases to various types of insecticide chemical synergists administered to mice
    • Škrinjarić-Špoljar, M.; Matthews, H. B.; Engel, J. L.; Casida, J. E. Response of hepatic microsomal mixed-function oxidases to various types of insecticide chemical synergists administered to mice. Biochem. Pharmacol. 1971, 20, 1607-1618.
    • (1971) Biochem. Pharmacol , vol.20 , pp. 1607-1618
    • Škrinjarić-Špoljar, M.1    Matthews, H.B.2    Engel, J.L.3    Casida, J.E.4
  • 21
    • 67149141076 scopus 로고
    • Dietholate
    • Weed Science Society of America, 6th ed, Champaign
    • Weed Science Society of America. Dietholate. In Herbicide Handbook. 6th ed.; Champaign, 1L, 1989; pp 102-103.
    • (1989) Herbicide Handbook , vol.1 L , pp. 102-103
  • 22
    • 22944464131 scopus 로고
    • Chemical mechanisms of the cytochrome P-450 monooxygenase-catalyzed metabolism of phosphorothionate triesters
    • Sulfur in Pesticide Action and Metabolism; Rosen, R. D, Magee, P. S, Casida, J. E, Eds, American Chemical Society: Washington, DC
    • Neal, R. A. Chemical mechanisms of the cytochrome P-450 monooxygenase-catalyzed metabolism of phosphorothionate triesters. In Sulfur in Pesticide Action and Metabolism; Rosen, R. D., Magee, P. S., Casida, J. E., Eds.; ACS Symposium Series 158; American Chemical Society: Washington, DC, 1981; pp 19-34.
    • (1981) ACS Symposium Series , vol.158 , pp. 19-34
    • Neal, R.A.1
  • 23
    • 25444471829 scopus 로고    scopus 로고
    • Neonicotinoid nitroguanidine insecticide metabolites: Synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives
    • Kanne, D. B.; Dick, R. A.; Tomizawa, M.; Casida, J. E. Neonicotinoid nitroguanidine insecticide metabolites: synthesis and nicotinic receptor potency of guanidines, aminoguanidines, and their derivatives. Chem. Res. Toxicol. 2005, 18, 1479-1484.
    • (2005) Chem. Res. Toxicol , vol.18 , pp. 1479-1484
    • Kanne, D.B.1    Dick, R.A.2    Tomizawa, M.3    Casida, J.E.4
  • 24
    • 13844294285 scopus 로고    scopus 로고
    • Identification of aldehyde oxidase as the neonicotinoid nitroreductase
    • Dick, R. A.; Kanne, D. B.; Casida, I. E. Identification of aldehyde oxidase as the neonicotinoid nitroreductase. Chem. Res. Toxicol. 2005, 18, 317-323.
    • (2005) Chem. Res. Toxicol , vol.18 , pp. 317-323
    • Dick, R.A.1    Kanne, D.B.2    Casida, I.E.3
  • 27
    • 0142150014 scopus 로고    scopus 로고
    • N-Glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases
    • Kuehl, G. E.; Murphy, S. E. N-Glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab. Dispos. 2003, 31, 1361-1368.
    • (2003) Drug Metab. Dispos , vol.31 , pp. 1361-1368
    • Kuehl, G.E.1    Murphy, S.E.2
  • 28
    • 0036707617 scopus 로고    scopus 로고
    • N-Glucuronidation of nicotine and cotinine in human: Formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases
    • Ghosheh, I.; Hawes, E.M. N-Glucuronidation of nicotine and cotinine in human: formation of cotinine glucuronide in liver microsomes and lack of catalysis by 10 examined UDP-glucuronosyltransferases. Drug Metab. Dispos. 2002, 30, 991-996.
    • (2002) Drug Metab. Dispos , vol.30 , pp. 991-996
    • Ghosheh, I.1    Hawes, E.M.2
  • 29
    • 0021168439 scopus 로고
    • Nicotinamide methylation: Tissue distribution, developmental and neoplastic changes
    • Seifert, R.; Hoshino, J.; Kröger, H. Nicotinamide methylation: tissue distribution, developmental and neoplastic changes. Biochim. Biophys. Acta 1984, 801, 259-264.
    • (1984) Biochim. Biophys. Acta , vol.801 , pp. 259-264
    • Seifert, R.1    Hoshino, J.2    Kröger, H.3
  • 30
    • 0034629412 scopus 로고    scopus 로고
    • Gas chro-matographic-mass spectrometric procedures for determination of the catechol-O-methyltransferase (COMT) activity and for detection of unstable catecholic metabolites in human and rat liver preparations after COMT catalyzed in statu nascendi derivatiza-tion using S-adenosylmethionine
    • Maurer, H. H.; Bickeboeller-Friedrich, J.; Kraemer, T. Gas chro-matographic-mass spectrometric procedures for determination of the catechol-O-methyltransferase (COMT) activity and for detection of unstable catecholic metabolites in human and rat liver preparations after COMT catalyzed in statu nascendi derivatiza-tion using S-adenosylmethionine. J. Chromatogr., B 2008, 739, 325-335.
    • (2008) J. Chromatogr., B , vol.739 , pp. 325-335
    • Maurer, H.H.1    Bickeboeller-Friedrich, J.2    Kraemer, T.3
  • 31
    • 26944456635 scopus 로고    scopus 로고
    • Case study: Weight of evidence evaluation of the human health relevance of thiamethoxam-related mouse liver tumors
    • Pastoor, T.; Rose, P.; Lloyd, S.; Peffer, R.; Green, T. Case study: weight of evidence evaluation of the human health relevance of thiamethoxam-related mouse liver tumors. Toxicol. Sci. 2005, 86, 56-60.
    • (2005) Toxicol. Sci , vol.86 , pp. 56-60
    • Pastoor, T.1    Rose, P.2    Lloyd, S.3    Peffer, R.4    Green, T.5
  • 32
    • 0037035949 scopus 로고    scopus 로고
    • Imidacloprid insecticide metabolism: Human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction
    • Schulz-Jander, D. A.; Casida, J. E. Imidacloprid insecticide metabolism: human cytochrome P450 isozymes differ in selectivity for imidazolidine oxidation versus nitroimine reduction. Toxicol. Lett. 2002, 132, 65-70.
    • (2002) Toxicol. Lett , vol.132 , pp. 65-70
    • Schulz-Jander, D.A.1    Casida, J.E.2
  • 33
    • 0035207207 scopus 로고    scopus 로고
    • DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid
    • Daborn, P.; Boundy, S.; Yen, J.; Pittendrigh, B.; ffrench-Constant, R. DDT resistance in Drosophila correlates with Cyp6g1 over-expression and confers cross-resistance to the neonicotinoid imidacloprid. Mol. Genet. Genomics 2001, 266, 556-563.
    • (2001) Mol. Genet. Genomics , vol.266 , pp. 556-563
    • Daborn, P.1    Boundy, S.2    Yen, J.3    Pittendrigh, B.4    ffrench-Constant, R.5
  • 34
    • 1842496203 scopus 로고    scopus 로고
    • Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci (Hemiptera: Aleyrodidae)
    • Rauch, N.; Nauen, R. Identification of biochemical markers linked to neonicotinoid cross resistance in Bemisia tabaci (Hemiptera: Aleyrodidae). Arch. Insect Biochem. Physiol. 2003, 54, 165-176.
    • (2003) Arch. Insect Biochem. Physiol , vol.54 , pp. 165-176
    • Rauch, N.1    Nauen, R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.