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Volumn 43, Issue 11, 2005, Pages 1627-1636

An α, β-unsaturated oxime identified as a strong contact allergen: Indications of antigen formation via several pathways

Author keywords

Allergic contact dermatitis; Guinea pigs; Metabolism; Mice; Sensitization; Structure activity relationships

Indexed keywords

5 ISOPROPENYL 2 METHYL 2 CYCLOHEXEN 1 ONE O METHYLOXIME; 5 ISOPROPENYL 2 METHYL 2 CYCLOHEXEN 1 ONE OXIME; 5 ISOPROPENYL 2 METHYLCYCLOHEXANONE OXIME; 5 ISOPROPENYL 2,3 DIMETHYL 2 CYCLOHEXEN 1 ONE OXIME; ANTIGEN; CONTACT ALLERGEN; OXIME DERIVATIVE; UNCLASSIFIED DRUG;

EID: 24644438681     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2005.05.004     Document Type: Article
Times cited : (24)

References (42)
  • 1
    • 0018133951 scopus 로고
    • Contact allergy to toothpaste flavors
    • K.E. Andersen Contact allergy to toothpaste flavors Contact Dermatitis 4 1978 195 198
    • (1978) Contact Dermatitis , vol.4 , pp. 195-198
    • Andersen, K.E.1
  • 2
    • 0033091308 scopus 로고    scopus 로고
    • Validation and subsequent development of the DEREK skin sensitization rulebase by analysis of the BgVV list of contact allergens
    • M.D. Barratt, and J.J. Langowski Validation and subsequent development of the DEREK skin sensitization rulebase by analysis of the BgVV list of contact allergens J. Chem. Inf. Comput. Sci. 39 1999 294 298
    • (1999) J. Chem. Inf. Comput. Sci. , vol.39 , pp. 294-298
    • Barratt, M.D.1    Langowski, J.J.2
  • 3
    • 0032776406 scopus 로고    scopus 로고
    • A comparison of statistical approaches to derivation of EC3 values from local lymph node assay dose responses
    • D.A. Basketter, L.J. Lea, A. Dickens, D. Briggs, I. Pate, R.J. Dearman, and I. Kimber A comparison of statistical approaches to derivation of EC3 values from local lymph node assay dose responses J. Appl. Toxicol. 19 1999 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
  • 5
    • 15144358594 scopus 로고    scopus 로고
    • Contact allergens from surfactants. Atmospheric oxidation of polyoxyethylene alcohols, formation of ethoxylated aldehydes, and their allergenic activity
    • M. Bergh, L.P. Shao, G. Hagelthorn, E. Gäfvert, J.L.G. Nilsson, and A.-T. Karlberg Contact allergens from surfactants. Atmospheric oxidation of polyoxyethylene alcohols, formation of ethoxylated aldehydes, and their allergenic activity J. Pharm. Sci. 87 1998 276 282
    • (1998) J. Pharm. Sci. , vol.87 , pp. 276-282
    • Bergh, M.1    Shao, L.P.2    Hagelthorn, G.3    Gäfvert, E.4    Nilsson, J.L.G.5    Karlberg, A.-T.6
  • 6
    • 0037568107 scopus 로고    scopus 로고
    • Structure elucidation, synthesis, and contact allergenic activity of a major hydroperoxide formed at autoxidation of the ethoxylated surfactant C12E5
    • A. Bodin, M. Linnerborg, J.L.G. Nilsson, and A.-T. Karlberg Structure elucidation, synthesis, and contact allergenic activity of a major hydroperoxide formed at autoxidation of the ethoxylated surfactant C12E5 Chem. Res. Toxicol. 16 2003 575 582
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 575-582
    • Bodin, A.1    Linnerborg, M.2    Nilsson, J.L.G.3    Karlberg, A.-T.4
  • 7
    • 0023837816 scopus 로고
    • Experiences with Freund's complete adjuvant test (FCAT) when screening for contact allergens in colophony
    • A. Boman, A.-T. Karlberg, and J.E. Wahlberg Experiences with Freund's complete adjuvant test (FCAT) when screening for contact allergens in colophony Contact Dermatitis 18 1988 25 29
    • (1988) Contact Dermatitis , vol.18 , pp. 25-29
    • Boman, A.1    Karlberg, A.-T.2    Wahlberg, J.E.3
  • 8
    • 0034898074 scopus 로고    scopus 로고
    • Oxidation of the ketoxime acetoxime to nitric oxide by oxygen radical-generating systems
    • A.A. Caro, A.I. Cederbaum, and D.A. Stoyanovsky Oxidation of the ketoxime acetoxime to nitric oxide by oxygen radical-generating systems Nitric Oxide-Biol. Chem. 5 2001 413 424
    • (2001) Nitric Oxide-Biol. Chem. , vol.5 , pp. 413-424
    • Caro, A.A.1    Cederbaum, A.I.2    Stoyanovsky, D.A.3
  • 10
    • 0010521593 scopus 로고
    • Lithium and potassium trialkylborohydrides. Reagent for direct reduction of alpha-beta unsaturated carbonyl compounds to synthetically versatile enolate anions
    • J.M. Fortunato, and B.J. Ganem Lithium and potassium trialkylborohydrides. Reagent for direct reduction of alpha-beta unsaturated carbonyl compounds to synthetically versatile enolate anions J. Org. Chem. 41 1976 2194 2200
    • (1976) J. Org. Chem. , vol.41 , pp. 2194-2200
    • Fortunato, J.M.1    Ganem, B.J.2
  • 11
    • 0023679173 scopus 로고
    • A scheme for the prediction and ranking of relative potencies of dermal sensitizers based on data from several systems
    • S.C. Gad A scheme for the prediction and ranking of relative potencies of dermal sensitizers based on data from several systems J. Appl. Toxicol. 8 1988 361 368
    • (1988) J. Appl. Toxicol. , vol.8 , pp. 361-368
    • Gad, S.C.1
  • 12
    • 0032746777 scopus 로고    scopus 로고
    • In vivo production of nitric oxide after administration of cyclohexanone oxime
    • R.E. Glover, J.T. Corbett, L.T. Burka, and R.P. Mason In vivo production of nitric oxide after administration of cyclohexanone oxime Chem. Res. Toxicol. 12 1999 952 957
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 952-957
    • Glover, R.E.1    Corbett, J.T.2    Burka, L.T.3    Mason, R.P.4
  • 14
    • 0000632422 scopus 로고
    • The ORD, CD and UV spectra of sulphides derived from carvone
    • M. Hargreaves, and L. Rabari The ORD, CD and UV spectra of sulphides derived from carvone Monatsh. Chem. 114 1983 195 210
    • (1983) Monatsh. Chem. , vol.114 , pp. 195-210
    • Hargreaves, M.1    Rabari, L.2
  • 15
    • 0026745146 scopus 로고
    • Occupational allergic contact dermatitis from ethyl chloro oximido acetate
    • B.M. Hausen Occupational allergic contact dermatitis from ethyl chloro oximido acetate Contact Dermatitis 27 1992 277
    • (1992) Contact Dermatitis , vol.27 , pp. 277
    • Hausen, B.M.1
  • 16
    • 0032497909 scopus 로고    scopus 로고
    • Microsomal cytochrome P450 dependent oxidation of N-hydroxyguanidines, amidoximes, and ketoximes: Mechanism of the oxidative cleavage of their CN(OH) bond with formation of nitrogen oxides
    • A. Jousserandot, J.L. Boucher, Y. Henry, B. Niklaus, B. Clement, and D. Mansuy Microsomal cytochrome P450 dependent oxidation of N-hydroxyguanidines, amidoximes, and ketoximes: mechanism of the oxidative cleavage of their CN(OH) bond with formation of nitrogen oxides Biochemistry 37 1998 17179 17191
    • (1998) Biochemistry , vol.37 , pp. 17179-17191
    • Jousserandot, A.1    Boucher, J.L.2    Henry, Y.3    Niklaus, B.4    Clement, B.5    Mansuy, D.6
  • 17
    • 0026534530 scopus 로고
    • Air oxidation of d-limonene (the citrus solvent) creates potent allergens
    • A.T. Karlberg, K. Magnusson, and U. Nilsson Air oxidation of d-limonene (the citrus solvent) creates potent allergens Contact Dermatitis 26 1992 332 340
    • (1992) Contact Dermatitis , vol.26 , pp. 332-340
    • Karlberg, A.T.1    Magnusson, K.2    Nilsson, U.3
  • 18
    • 0028414136 scopus 로고
    • Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene
    • A.-T. Karlberg, K. Magnusson, and U. Nilsson Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene Ann. Occup. Hyg. 38 1994 199 207
    • (1994) Ann. Occup. Hyg. , vol.38 , pp. 199-207
    • Karlberg, A.-T.1    Magnusson, K.2    Nilsson, U.3
  • 23
    • 0022326228 scopus 로고
    • The Freund's complete adjuvant test and the open epicutaneous test. a complementary test procedure for realistic assessment of allergenic potential
    • G. Klecak The Freund's complete adjuvant test and the open epicutaneous test. A complementary test procedure for realistic assessment of allergenic potential Curr. Probl. Derm. 14 1985 152 171
    • (1985) Curr. Probl. Derm. , vol.14 , pp. 152-171
    • Klecak, G.1
  • 24
    • 0026634830 scopus 로고
    • Acetoxime is metabolized by human and rodent hepatic cytochrome P450 enzymes to the genotoxic and carcinogen propane 2-nitronate
    • C. Kohl, C.D. Schiller, A. Gescher, P.B. Farmer, and E. Bailey Acetoxime is metabolized by human and rodent hepatic cytochrome P450 enzymes to the genotoxic and carcinogen propane 2-nitronate Carcinogenesis 13 1992 1091 1094
    • (1992) Carcinogenesis , vol.13 , pp. 1091-1094
    • Kohl, C.1    Schiller, C.D.2    Gescher, A.3    Farmer, P.B.4    Bailey, E.5
  • 25
    • 0036327617 scopus 로고    scopus 로고
    • Catecholoximes as powerful antioxidants for highly unsaturated lipids
    • J.P. Ley, and H.J. Bertram Catecholoximes as powerful antioxidants for highly unsaturated lipids Eur. J. Lipid. Sci. Technol. 104 2002 319 323
    • (2002) Eur. J. Lipid. Sci. Technol. , vol.104 , pp. 319-323
    • Ley, J.P.1    Bertram, H.J.2
  • 26
    • 0026662459 scopus 로고
    • A convergent approach to the dihydrotachysterol diene system. Application to the synthesis of dihydrotachystarol2 (DHT2), 25-hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R), 19-dihydro-(5E)-3-epivitamin D2 and 25-hydroxy-10 (R), 19-dihydro-(5E)-3-epivitamin D2
    • M.A. Maestro, L. Castedo, and A. Mourino A convergent approach to the dihydrotachysterol diene system. Application to the synthesis of dihydrotachystarol2 (DHT2), 25-hydroxydihydrotachysterol2 (25-OH-DHT2), 10(R), 19-dihydro-(5E)-3-epivitamin D2 and 25-hydroxy-10 (R), 19-dihydro-(5E)-3- epivitamin D2 J. Org. Chem. 57 1992 5208 5213
    • (1992) J. Org. Chem. , vol.57 , pp. 5208-5213
    • Maestro, M.A.1    Castedo, L.2    Mourino, A.3
  • 27
    • 0030576307 scopus 로고    scopus 로고
    • Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: Implications for immune mediated toxicity
    • D.J. Naisbitt, P.M. O'Neill, M. Pirmohamed, and B.K. Park Synthesis and reactions of nitroso sulphamethoxazole with biological nucleophiles: implications for immune mediated toxicity Bioorg. Med. Chem. Lett. 6 1996 1511 1516
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1511-1516
    • Naisbitt, D.J.1    O'Neill, P.M.2    Pirmohamed, M.3    Park, B.K.4
  • 28
    • 0035006195 scopus 로고    scopus 로고
    • Allergic contact sensitization in an adult Danish population: Two cross-sectional surveys eight years apart (The Copenhagen allergy study)
    • N.H. Nielsen, A. Linneberg, T. Menne, F. Madsen, L. Frolund, A. Dirksen, and T. Jorgensen Allergic contact sensitization in an adult Danish population: two cross-sectional surveys eight years apart (The Copenhagen allergy study) Acta. Derm. Venereol. 81 2001 31 34
    • (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
  • 30
    • 13844292704 scopus 로고    scopus 로고
    • A conjugated diene identified as a prohapten: Contact allergenic activity and chemical reactivity of proposed epoxide metabolites
    • A.M. Nilsson, M.A. Bergström, K. Luthman, J.L.G. Nilsson, and A.T. Karlberg A conjugated diene identified as a prohapten: contact allergenic activity and chemical reactivity of proposed epoxide metabolites Chem. Res. Toxicol. 18 2005 306 316
    • (2005) Chem. Res. Toxicol. , vol.18 , pp. 306-316
    • Nilsson, A.M.1    Bergström, M.A.2    Luthman, K.3    Nilsson, J.L.G.4    Karlberg, A.T.5
  • 31
    • 0030862229 scopus 로고    scopus 로고
    • Syntheses and absolute configurations of the marine sponge purines (+)-agelasimine-A and (+)-agelasimine-B
    • M. Ohba, K. Iizuka, H. Ishibashi, and T. Fujii Syntheses and absolute configurations of the marine sponge purines (+)-agelasimine-A and (+)-agelasimine-B Tetrahedron 53 1997 16977 16986
    • (1997) Tetrahedron , vol.53 , pp. 16977-16986
    • Ohba, M.1    Iizuka, K.2    Ishibashi, H.3    Fujii, T.4
  • 32
    • 0035156257 scopus 로고    scopus 로고
    • Allergic contact dermatitis from pharmaceutical grade BHA in thimodine, with no patch test reaction to analytical grade BHA
    • D.I. Orton, and S. Shaw Allergic contact dermatitis from pharmaceutical grade BHA in thimodine, with no patch test reaction to analytical grade BHA Contact Dermatitis 44 2001 191 192
    • (2001) Contact Dermatitis , vol.44 , pp. 191-192
    • Orton, D.I.1    Shaw, S.2
  • 34
    • 0025786629 scopus 로고
    • Metabolism and disposition of cyclohexanone oxime in male F-344 rats
    • D. Parmar, and L. Burka Metabolism and disposition of cyclohexanone oxime in male F-344 rats Drug. Metab. Dispos. 19 1991 1101 1107
    • (1991) Drug. Metab. Dispos. , vol.19 , pp. 1101-1107
    • Parmar, D.1    Burka, L.2
  • 36
    • 0027292070 scopus 로고
    • Carvone: An overlooked contact allergen cross-reacting with sesquiterpene lactones
    • E. Paulsen, K.E. Andersen, L. Carlsen, and H. Edsgaard Carvone: an overlooked contact allergen cross-reacting with sesquiterpene lactones Contact Dermatitis 29 1993 138 143
    • (1993) Contact Dermatitis , vol.29 , pp. 138-143
    • Paulsen, E.1    Andersen, K.E.2    Carlsen, L.3    Edsgaard, H.4
  • 37
    • 0002093068 scopus 로고    scopus 로고
    • Hapten-protein interactions
    • J.P. Lepoittevin D.A. Basketter A. Goossens A.T. Karlberg Springer Verlag Berlin
    • D.W. Roberts, and J.P. Lepoittevin Hapten-protein interactions J.P. Lepoittevin D.A. Basketter A. Goossens A.T. Karlberg Allergic Contact Dermatitis. The Molecular Basis 1998 Springer Verlag Berlin 81 111
    • (1998) Allergic Contact Dermatitis. the Molecular Basis , pp. 81-111
    • Roberts, D.W.1    Lepoittevin, J.P.2
  • 39
    • 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
    • M. Skold, A. Börje, E. Harambasic, and A.-T. Karlberg 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. 17 2004 1697 1705
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 1697-1705
    • Skold, M.1    Börje, A.2    Harambasic, E.3    Karlberg, A.-T.4
  • 40
    • 0028815974 scopus 로고
    • Reaction of certain α, β-unsaturated terpenic oximes with sodium nitrite in acetic acid: A facile synthesis of allylic nitro-compounds
    • A.V. Tkachev, A.M. Chibiryaev, A.Y. Denisov, and Y.V. Gatilov Reaction of certain α, β-unsaturated terpenic oximes with sodium nitrite in acetic acid: a facile synthesis of allylic nitro-compounds Tetrahedron 51 1995 1789 1808
    • (1995) Tetrahedron , vol.51 , pp. 1789-1808
    • Tkachev, A.V.1    Chibiryaev, A.M.2    Denisov, A.Y.3    Gatilov, Y.V.4
  • 41
    • 0345085694 scopus 로고    scopus 로고
    • Slow oxidation of acetoxime and methylethyl ketoxime to the corresponding nitronates and hydroxy nitronates by liver microsomes from rats, mice, and humans
    • W. Völkel, N. Wolf, M. Derelanko, and W. Dekant Slow oxidation of acetoxime and methylethyl ketoxime to the corresponding nitronates and hydroxy nitronates by liver microsomes from rats, mice, and humans Toxicol. Sci. 47 1999 144 150
    • (1999) Toxicol. Sci. , vol.47 , pp. 144-150
    • Völkel, W.1    Wolf, N.2    Derelanko, M.3    Dekant, W.4


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