메뉴 건너뛰기




Volumn 51, Issue 8, 2008, Pages 2541-2550

Oximes: Metabolic activation and structure-allergenic activity relationships

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLCYCLOHEX 2 ENONE OXIME; 2,3 DIMETHYLCYCLOHEX 2 ENONE OXIME; 3 METHYLCYCLOHEX 2 ENONE OXIME; BENZALDOXIME; CYCLOHEX 2 ENONE OXIME; GLUTATHIONE; HAPTEN; HEX 4 EN 3 ONE OXIME; OXIME; PROHAPTEN;

EID: 43049150746     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701092n     Document Type: Article
Times cited : (21)

References (47)
  • 2
    • 0034973773 scopus 로고    scopus 로고
    • Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity
    • Guengerich, F. P. Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity. Chem. Res. Toxicol. 2001, 14, 611-650.
    • (2001) Chem. Res. Toxicol , vol.14 , pp. 611-650
    • Guengerich, F.P.1
  • 3
    • 0345039474 scopus 로고    scopus 로고
    • Xenobiotics as skin sensitizers: Metabolic activation and detoxification, and protein-binding mechanisms
    • Taylor and Francis: London
    • Smith, C. K.; Hotchkiss, S. A. M. Xenobiotics as skin sensitizers: Metabolic activation and detoxification, and protein-binding mechanisms. Allergic contact dermatitis: Chemical and metabolic mechanisms; Taylor and Francis: London, 2001: pp 119-205.
    • (2001) Allergic contact dermatitis: Chemical and metabolic mechanisms , pp. 119-205
    • Smith, C.K.1    Hotchkiss, S.A.M.2
  • 4
    • 84895316581 scopus 로고    scopus 로고
    • Mechanisms in allergic contact dermatitis
    • 4th ed, Frosch, P. J, Menné, T, Lepoittevin, J. P, Eds, Springer: Berlin, Heidelberg
    • Rustemeyer, T.; van Hoogstraten, I. M. W.; von Blomberg, B. M. E.; Scheper, R. J. Mechanisms in allergic contact dermatitis. In Contact Dermatitis. 4th ed.; Frosch, P. J., Menné, T., Lepoittevin, J. P., Eds.; Springer: Berlin, Heidelberg, 2006: pp 11-43.
    • (2006) Contact Dermatitis , pp. 11-43
    • Rustemeyer, T.1    van Hoogstraten, I.M.W.2    von Blomberg, B.M.E.3    Scheper, R.J.4
  • 6
    • 0035006195 scopus 로고    scopus 로고
    • Allergic contact sensitization in an adult Danish population: Two cross-sectional surveys eight years apart (the Copenhagen Allergy Study)
    • Nielsen, N. H.; Linneberg, A.; Menne, T.; Madsen, F.; Frolund, L.; Dirksen, A.; Jorgensen, T. Allergic contact sensitization in an adult Danish population: Two cross-sectional surveys eight years apart (the Copenhagen Allergy Study). Acta Derm. Venereol. 2001, 81, 31-4.
    • (2001) Acta Derm. Venereol , vol.81 , pp. 31-34
    • Nielsen, N.H.1    Linneberg, A.2    Menne, T.3    Madsen, F.4    Frolund, L.5    Dirksen, A.6    Jorgensen, T.7
  • 8
    • 33845195281 scopus 로고    scopus 로고
    • Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals
    • Gerberick, G. F.; Ryan, C. A.; Dearman, R. J.; Kimber, I. Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals. Methods 2007, 41, 54-60.
    • (2007) Methods , vol.41 , pp. 54-60
    • Gerberick, G.F.1    Ryan, C.A.2    Dearman, R.J.3    Kimber, I.4
  • 9
    • 43049148103 scopus 로고    scopus 로고
    • EU, Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. Off. J. Eur. Union 2006, L 396, 1-849.
    • EU, Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. Off. J. Eur. Union 2006, L 396, 1-849.
  • 10
    • 43049131905 scopus 로고    scopus 로고
    • EU, Directive 2003/15/EC of the European Parliament and of the Council of 27 February 2003 amending Council Directive 76/768/EEC on the approximation of the laws of the Member States relating to cosmetic products. Off. J. Eur. Union 2003, L 66, 26-35.
    • EU, Directive 2003/15/EC of the European Parliament and of the Council of 27 February 2003 amending Council Directive 76/768/EEC on the approximation of the laws of the Member States relating to cosmetic products. Off. J. Eur. Union 2003, L 66, 26-35.
  • 13
    • 33745290408 scopus 로고    scopus 로고
    • Conjugated dienes as prohaptens in contact allergy: In vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation
    • Bergstrom, M. A.; Luthman, K.; Nilsson, J. L. G.; Karlberg, A.-T. Conjugated dienes as prohaptens in contact allergy: In vivo and in vitro studies of structure-activity relationships, sensitizing capacity, and metabolic activation. Chem. Res. Toxicol. 2006, 19, 760-769.
    • (2006) Chem. Res. Toxicol , vol.19 , pp. 760-769
    • Bergstrom, M.A.1    Luthman, K.2    Nilsson, J.L.G.3    Karlberg, A.-T.4
  • 14
    • 34447118901 scopus 로고    scopus 로고
    • Metabolic epoxidation of an α,β-unsaturated oxime generates sensitizers of extreme potency. Are nitroso intermediates responsible
    • Bergstrom, M. A.; Luthman, K.; Karlberg, A.-T. Metabolic epoxidation of an α,β-unsaturated oxime generates sensitizers of extreme potency. Are nitroso intermediates responsible. Chem. Res. Toxicol. 2007, 20, 927-936.
    • (2007) Chem. Res. Toxicol , vol.20 , pp. 927-936
    • Bergstrom, M.A.1    Luthman, K.2    Karlberg, A.-T.3
  • 15
    • 0023745415 scopus 로고
    • Contact allergy to colophony. Chemical identifications of allergens, sensitization experiments and clinical experiences
    • Karlberg, A. T. Contact allergy to colophony. Chemical identifications of allergens, sensitization experiments and clinical experiences. Acta Derm. Venereol. Suppl. (Stockholm) 1988, 139, 1-13.
    • (1988) Acta Derm. Venereol. Suppl. (Stockholm) , vol.139 , pp. 1-13
    • Karlberg, A.T.1
  • 16
    • 34250765328 scopus 로고    scopus 로고
    • Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization
    • Hagvall, L.; Backtorp, C.; Svensson, S.; Nyman, G.; Borje, A.; Karlberg, A. T. Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization. Chem. Res. Toxicol. 2007, 20, 807-814.
    • (2007) Chem. Res. Toxicol , vol.20 , pp. 807-814
    • Hagvall, L.1    Backtorp, C.2    Svensson, S.3    Nyman, G.4    Borje, A.5    Karlberg, A.T.6
  • 17
    • 10844260755 scopus 로고    scopus 로고
    • Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization
    • Skold, M.; Borje, A.; Harambasic, E.; Karlberg, A. T. Contact allergens formed on air exposure of linalool. Identification and quantification of primary and secondary oxidation products and the effect on skin sensitization. Chem. Res. Toxicol. 2004, 17, 1697-705.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 1697-1705
    • Skold, M.1    Borje, A.2    Harambasic, E.3    Karlberg, A.T.4
  • 18
    • 33845459807 scopus 로고    scopus 로고
    • Addressing metabolic activation as an integral component of drug design
    • Doss, G. A.; Baillie, T. A. Addressing metabolic activation as an integral component of drug design. Drug Metab. Rev. 2006, 38, 641-649.
    • (2006) Drug Metab. Rev , vol.38 , pp. 641-649
    • Doss, G.A.1    Baillie, T.A.2
  • 19
    • 1642281756 scopus 로고    scopus 로고
    • Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development
    • Evans, D. C.; Watt, A. P.; Nicoll-Griffith, D. A.; Baillie, T. A. Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 2004, 17, 3-16.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 22
    • 30644477451 scopus 로고    scopus 로고
    • Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization
    • Aptula, A. O.; Patlewicz, G.; Roberts, D. W.; Schultz, T. W. Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization. Toxicol. In Vitro 2006, 20, 239-247.
    • (2006) Toxicol. In Vitro , vol.20 , pp. 239-247
    • Aptula, A.O.1    Patlewicz, G.2    Roberts, D.W.3    Schultz, T.W.4
  • 23
    • 35649009496 scopus 로고    scopus 로고
    • Utility and limitations of a peptide reactivity assay to predict fragrance allergens in vitro
    • Natsch, A.; Gfeller, H.; Rothaupt, M.; Ellis, G. Utility and limitations of a peptide reactivity assay to predict fragrance allergens in vitro. Toxicol. In Vitro 2007, 21, 1220-1226.
    • (2007) Toxicol. In Vitro , vol.21 , pp. 1220-1226
    • Natsch, A.1    Gfeller, H.2    Rothaupt, M.3    Ellis, G.4
  • 24
    • 33750067066 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of a novel class of rofecoxib analogues us dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs)
    • Chen, Q. H.; Rao, P. N. P.; Knaus, E. E. Synthesis and biological evaluation of a novel class of rofecoxib analogues us dual inhibitors of cyclooxygenases (COXs) and lipoxygenases (LOXs). Bioorg. Med. Chem. 2006, 14, 7898-7909.
    • (2006) Bioorg. Med. Chem , vol.14 , pp. 7898-7909
    • Chen, Q.H.1    Rao, P.N.P.2    Knaus, E.E.3
  • 26
    • 33751171517 scopus 로고    scopus 로고
    • Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate poisoning
    • Jokanovic, M.; Stojiljkovic, M. P. Current understanding of the application of pyridinium oximes as cholinesterase reactivators in treatment of organophosphate poisoning. Eur. J. Pharmacol. 2006, 553, 10-17.
    • (2006) Eur. J. Pharmacol , vol.553 , pp. 10-17
    • Jokanovic, M.1    Stojiljkovic, M.P.2
  • 27
    • 0036179745 scopus 로고    scopus 로고
    • Metabolism of 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5- carboxamide, a potent anti-epileptic drug
    • Hainzl, D.; Loureiro, A. I.; Parada, A.; Soares-Da-Silva, P. Metabolism of 10,11-dihydro-10-hydroxyimino-5H-dibenz[b,f]azepine-5- carboxamide, a potent anti-epileptic drug. Xenobiotica 2002, 32, 131-140.
    • (2002) Xenobiotica , vol.32 , pp. 131-140
    • Hainzl, D.1    Loureiro, A.I.2    Parada, A.3    Soares-Da-Silva, P.4
  • 28
    • 0036156569 scopus 로고    scopus 로고
    • P450-mediated metabolism of 1-[3-(aminomethyl)phenyl]-N-[3- fluoro-2′-(methylsulfonyl)-[1,1′-biphenyl]-4-y1]-3-(trifluoromethyl) -1H-pyrazole-5-carboxamide (DPC 423) and its analogues to aldoximes. Characterization of glutathione conjugates of postulated intermediates derived from aldoximes
    • Mutlib, A. E.; Chen, S. Y.; Espina, R. J.; Shockeor, J.; Prakash, S. R.; Gan, L. S. P450-mediated metabolism of 1-[3-(aminomethyl)phenyl]-N-[3- fluoro-2′-(methylsulfonyl)-[1,1′-biphenyl]-4-y1]-3-(trifluoromethyl) -1H-pyrazole-5-carboxamide (DPC 423) and its analogues to aldoximes. Characterization of glutathione conjugates of postulated intermediates derived from aldoximes. Chem. Res. Toxicol. 2002, 15, 63-75.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 63-75
    • Mutlib, A.E.1    Chen, S.Y.2    Espina, R.J.3    Shockeor, J.4    Prakash, S.R.5    Gan, L.S.6
  • 29
    • 24644438681 scopus 로고    scopus 로고
    • An α,β-unsaturated oxime identified as a strong contact allergen. Indications of antigen formation via several pathways
    • Nilsson, A. M.; Bergstrom, M. A.; Luthman, K.; Nilsson, J. L.; Karlberg, A. T. An α,β-unsaturated oxime identified as a strong contact allergen. Indications of antigen formation via several pathways. Food Chem. Toxicol. 2005, 43, 1627-36.
    • (2005) Food Chem. Toxicol , vol.43 , pp. 1627-1636
    • Nilsson, A.M.1    Bergstrom, M.A.2    Luthman, K.3    Nilsson, J.L.4    Karlberg, A.T.5
  • 30
    • 0037997262 scopus 로고
    • Reduction of conjugated cyclohexenome oximes with aluminium hydride
    • Zaidlewicz, M.; Uzarewicz, I. G. Reduction of conjugated cyclohexenome oximes with aluminium hydride. Pol. J. Chem. 1988, 62, 143-150.
    • (1988) Pol. J. Chem , vol.62 , pp. 143-150
    • Zaidlewicz, M.1    Uzarewicz, I.G.2
  • 31
    • 0035528012 scopus 로고    scopus 로고
    • Direct C-nitration of cyclic α,β-unsaturated oximes under the action of sodium nitrite and acetic acid in methanol
    • Chibiryaev, A. M.; Denisov, A. Y.; Pyshnyi, D. V.; Tkachev, A. V. Direct C-nitration of cyclic α,β-unsaturated oximes under the action of sodium nitrite and acetic acid in methanol. Russ. Chem. Bull. 2001, 50, 1410-1418.
    • (2001) Russ. Chem. Bull , vol.50 , pp. 1410-1418
    • Chibiryaev, A.M.1    Denisov, A.Y.2    Pyshnyi, D.V.3    Tkachev, A.V.4
  • 32
    • 0032391484 scopus 로고    scopus 로고
    • Reaction of cyclic allylic acefates with aliphatic alcohols in the presence of cerium(III) chloride
    • Uzarewicz, A.; Dresler, R. Reaction of cyclic allylic acefates with aliphatic alcohols in the presence of cerium(III) chloride. Pol. J. Chem. 1998, 72, 1921-1930.
    • (1998) Pol. J. Chem , vol.72 , pp. 1921-1930
    • Uzarewicz, A.1    Dresler, R.2
  • 33
    • 0032855641 scopus 로고    scopus 로고
    • CMR spectra of N-oxygenated pyrazoles I. 3,5-Dialkyl- and 3-alkyl-5-phenyl-4-oxo-4H- pyrazole 1,2-dioxides
    • Zeller, W. E.; Zeller, L. S.; Hansen, J. F. CMR spectra of N-oxygenated pyrazoles I. 3,5-Dialkyl- and 3-alkyl-5-phenyl-4-oxo-4H- pyrazole 1,2-dioxides. Heterocycles 1999, 51, 145-155.
    • (1999) Heterocycles , vol.51 , pp. 145-155
    • Zeller, W.E.1    Zeller, L.S.2    Hansen, J.F.3
  • 36
    • 3042807182 scopus 로고    scopus 로고
    • Identification of the structural requirements for mutagenicity by incorporating molecular flexibility and metabolic activation of chemicals I: TA100 model
    • Mekenyan, O.; Dimitrov, S.; Serafimova, R.; Thompson, E.; Kotov, S.; Dimitrova, N.; Walker, J. D. Identification of the structural requirements for mutagenicity by incorporating molecular flexibility and metabolic activation of chemicals I: TA100 model. Chem. Res. Toxicol. 2004, 17, 753-66.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 753-766
    • Mekenyan, O.1    Dimitrov, S.2    Serafimova, R.3    Thompson, E.4    Kotov, S.5    Dimitrova, N.6    Walker, J.D.7
  • 37
    • 34248597840 scopus 로고    scopus 로고
    • Identification of the structural requirements for mutagencitiy, by incorporating molecular flexibility and metabolic activation of chemicals. II. General Ames mutagenicity model
    • Serafimova, R.; Todorov, M.; Pavlov, T.; Kotov, S.; Jacob, E.; Aptula, A.; Mekenyan, O. Identification of the structural requirements for mutagencitiy, by incorporating molecular flexibility and metabolic activation of chemicals. II. General Ames mutagenicity model. Chem. Res. Toxicol. 200720, 662-76.
    • (2007) Chem. Res. Toxicol , vol.20 , pp. 662-676
    • Serafimova, R.1    Todorov, M.2    Pavlov, T.3    Kotov, S.4    Jacob, E.5    Aptula, A.6    Mekenyan, O.7
  • 38
    • 28444479129 scopus 로고    scopus 로고
    • The local lymph node assay being too sensitive
    • Vohr, H.-W.; Ahr, H. J. The local lymph node assay being too sensitive. Arch. Toxicol. 2005, 79, 721-28.
    • (2005) Arch. Toxicol , vol.79 , pp. 721-728
    • Vohr, H.-W.1    Ahr, H.J.2
  • 40
    • 3042844427 scopus 로고    scopus 로고
    • Gerberick, G. F.; Ryan, C. A.; Kern, P. S.; Dearman, R. J.; Kimber, I.; Patlewicz, G. Y.; Basketter, D. A. A chemical dataset for evaluation of alternative approaches to skin-sensitization testing. Contact Dermatitis 2004, 50, 274-88.
    • Gerberick, G. F.; Ryan, C. A.; Kern, P. S.; Dearman, R. J.; Kimber, I.; Patlewicz, G. Y.; Basketter, D. A. A chemical dataset for evaluation of alternative approaches to skin-sensitization testing. Contact Dermatitis 2004, 50, 274-88.
  • 41
    • 0025786629 scopus 로고
    • Metabolism and disposition of cyclohexanone oxime in male F344 rats
    • Parmar, D.; Burka, L. T. Metabolism and disposition of cyclohexanone oxime in male F344 rats. Drug Metab. Dispos. 1991, 19, 1101-1107.
    • (1991) Drug Metab. Dispos , vol.19 , pp. 1101-1107
    • Parmar, D.1    Burka, L.T.2
  • 43
    • 43049138153 scopus 로고
    • 2-Chloro-2- methylcyclohexane and 2-methyl-2-cyclohexenone
    • Warnhoff, E. W.; Martin, D. G.; Johnson, W. S. 2-Chloro-2- methylcyclohexane and 2-methyl-2-cyclohexenone. Org. Synth. 1957, 37, 8-12.
    • (1957) Org. Synth , vol.37 , pp. 8-12
    • Warnhoff, E.W.1    Martin, D.G.2    Johnson, W.S.3
  • 45
    • 0032776406 scopus 로고    scopus 로고
    • A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses
    • Basketter, D. A.; Lea, L. J.; Dickens, A.; Briggs, D.; Pate, I.; Dearman, R. J.; Kimber, I. A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses. J. Appl. Toxicol. 1999, 19, 261-266.
    • (1999) J. Appl. Toxicol , vol.19 , pp. 261-266
    • Basketter, D.A.1    Lea, L.J.2    Dickens, A.3    Briggs, D.4    Pate, I.5    Dearman, R.J.6    Kimber, I.7
  • 46
    • 3042708376 scopus 로고    scopus 로고
    • Contact sensitization: Classification according to potency
    • European Centre for Ecotoxicology and Toxicology of Chemicals ECETOC, Technical report no. 87; ECETOC: Brussels, Belgium
    • European Centre for Ecotoxicology and Toxicology of Chemicals (ECETOC). Contact sensitization: classification according to potency. Technical report no. 87; ECETOC: Brussels, Belgium, 2003.
    • (2003)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.