Erratum: Correction to skin sensitization of epoxyaldehydes: Importance of conjugation (Chem. Res. Toxicol. (2013) 26: 5 (674-684) DOI: 10.1021/tx300465h);Skin sensitization of epoxyaldehydes: Importance of conjugation

Chemical Research in Toxicology

Volumn 26, Issue 5, 2013, Pages 674-684

  Delaine, Tamara ^a   Hagvall, Lina ^a,b   Rudbäck, Johanna ^a   Luthman, Kristina ^a   Karlberg, Ann Therese ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCYSTEINE; ALDEHYDE DERIVATIVE; ALIPHATIC COMPOUND; EPOXIDE; ETHANE; N ACETYL CYSTEINE METHYL ESTER; THIOL; UNCLASSIFIED DRUG; ALDEHYDE; ALLERGEN;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; AUTOOXIDATION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL BOND; CHEMICAL STRUCTURE; CONJUGATION; CONTACT ALLERGY; CONTROLLED STUDY; FEMALE; IN VITRO STUDY; IN VIVO STUDY; LYMPH NODE; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SKIN SENSITIZATION; SYNTHESIS; ANIMAL; CBA MOUSE; CHEMISTRY; DERMATITIS, ALLERGIC CONTACT; LOCAL LYMPH NODE ASSAY; TOXICITY;

ALDEHYDES; ALLERGENS; ANIMALS; DERMATITIS, ALLERGIC CONTACT; EPOXY COMPOUNDS; FEMALE; LOCAL LYMPH NODE ASSAY; MICE; MICE, INBRED CBA;

EID: 84877945452     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx500007v     Document Type: Erratum

References (51)

1. Gerberick, G. F., Ryan, C. A., Dearman, R. J., and Kimber, I. (2007) Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals Methods 41, 54-60
2. Karlberg, A.-T., Bergström, M. A., Börje, A., Luthman, K., and Nilsson, J. L. G. (2008) Allergic contact dermatitis - Formation, structural requirements, and reactivity of skin sensitizers Chem. Res. Toxicol. 21, 53-69
3. Vandebriel, R. J. and Loveren, H. V. (2010) Non-animal sensitization testing: State-of-the-art Crit. Rev. Toxicol. 40, 389-404
4. Aeby, P., Ashikaga, T., Bessou-Touya, S., Schepky, A., Gerberick, F., Kern, P., Marrec-Fairley, M., Maxwell, G., Ovigne, J. M., Sakaguchi, H., Reisinger, K., Tailhardat, M., Martinozzi-Teissier, S., and Winkler, P. (2010) Identifying and characterizing chemical skin sensitizers without animal testing: Colipa's research and method development program Toxicol. in Vitro 24, 1465-1473
5. Kimber, I., Basketter, D. A., Gerberick, G. F., Ryan, C. A., and Dearman, R. J. (2011) Chemical allergy: Translating biology into hazard characterization Toxicol. Sci. 120, S238-S268
6. Peiser, M., Tralau, T., Heidler, J., Api, A. M., Arts, J. H. E., Basketter, D. A., English, J., Diepgen, T. L., Fuhlbrigge, R. C., Gaspari, A. A., Johansen, J. D., Karlberg, A. T., Kimber, I., Lepoittevin, J. P., Liebsch, M., Maibach, H. I., Martin, S. F., Merk, H. F., Platzek, T., Rustemeyer, T., Schnuch, A., Vandebriel, R. J., White, I. R., and Luch, A. (2012) Allergic contact dermatitis: Epidemiology, molecular mechanisms, in vitro methods and regulatory aspects Cell. Mol. Life Sci. 69, 763-781
7. Landsteiner, K. and Jacobs, J. (1936) Studies on the sensitization of animals with simple chemicals compounds. II J. Exp. Med. 64, 625-639
8. Rustemeyer, T. and Fartasch, M. (2012) Immunology and Barrier Function of the Skin, in Karnerva's Occupational Dermatology (Rustemeyer, T., Elsner, P., John, S. M., and Maibach, H. I., Eds.) pp 3-8, Springer-Verlag, Berlin, Germany.
9. Divkovic, M., Pease, C. K., Gerberick, G. F., and Basketter, D. A. (2005) Hapten-protein binding: from theory to practical application in the in vitro prediction of skin sensitization Contact Dermatitis 53, 189-200
10. Gerberick, G. F., Vassallo, J. D., Bailey, R. E., Chaney, J. G., Morrall, S. W., and Lepoittevin, J.-P. (2004) Development of a peptide reactivity assay for screening contact allergens Toxicol. Sci. 81, 332-343
11. Gerberick, G. F., Vassallo, J. D., Foertsch, L. M., Price, B. B., Chaney, J. G., and Lepoittevin, J.-P. (2007) Quantification of chemical peptide reactivity for screening contact allergens: A classification tree model approach Toxicol. Sci. 97, 417-427
12. Bergstrom, M. A., Luthman, K., Nilsson, J. L. G., and Karlberg, A.-T. (2006) 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. 19, 760-769
13. Hagvall, L., Bäcktorp, C., Svensson, S., Nyman, G., Börje, A., and Karlberg, A.-T. (2007) Fragrance compound geraniol forms contact allergens on air exposure. Identification and quantification of oxidation products and effect on skin sensitization Chem. Res. Toxicol. 20, 807-814
14. Hagvall, L., Baron, J. M., Börje, A., Weidolf, L., Merk, H., and Karlberg, A.-T. (2008) Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens Toxicol. Appl. Pharmacol. 233, 308-313
15. Rudbäck, J., Bergström, M. A., Börje, A., Nilsson, U., and Karlberg, A.-T. (2012) α-Terpinene, an antioxidant in tea tree oil, autoxidizes rapidly to skin allergens on air exposure Chem. Res. Toxicol. 25, 713-721
16. Basketter, D. A. (1992) Skin sensitazation to cinnamic alcohol-the role of skin metabolism Acta Derm.-Venereol. 72, 264-265
17. Cheung, C., Hotchkiss, S. A. M., and Pease, C. K. S. (2003) Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency J. Dermatol. Sci. 31, 9-19
18. Niklasson, I. B., Delaine, T., Islam, M. N., Karlsson, R., Luthman, K., and Karlberg, A.-T. (2013) Cinnamyl alcohol oxidizes rapidly upon air exposure Contact Dermatitis 68, 129-138
19. NAr domain Chem. Res. Toxicol. 24, 1003-1011
20. Natsch, A., Gfeller, H., Haupt, T., and Brunner, G. (2012) Chemical reactivity and skin sensitization potential for benzaldehydes: Can Schiff base formation explain everything? Chem. Res. Toxicol. 25, 2203-2215
21. Bergström, M. A., Andersson, S. I., Broo, K., Luthman, K., and Karlberg, A.-T. (2008) Oximes: Metabolic activation and structure-allergenic activity relationships J. Med. Chem. 51, 2541-2550
22. Patlewicz, G. Y., Basketter, D. A., Smith Pease, C. K., Wilson, K., Wright, Z. M., Roberts, D. W., Bernard, G., Arnau, E. G., and Lepoittevin, J.-P. (2004) Further evaluation of quantitative structure-activity relationship models for the prediction of the skin sensitization potency of selected fragrance allergens Contact Dermatitis 50, 91-97
23. Nilsson, A. M., Bergstrom, M. A., Luthman, K., Nilsson, J. L. G., and Karlberg, A.-T. (2005) A conjugated diene identified as a prohapten: Contact allergenic activity and chemical reactivity of proposed epoxide metabolites Chem. Res. Toxicol. 18, 308-316
24. Niklasson, I. B., Broo, K., Jonsson, C., Luthman, K., and Karlberg, A.-T. (2009) Reduced sensitizing capacity of epoxy resin systems: A structure-activity relationship study Chem. Res. Toxicol. 22, 1787-1794
25. Niklasson, I. B., Delaine, T., Luthman, K., and Karlberg, A. T. (2011) Impact of a heteroatom in a structure-activity relationship study on analogues of phenyl glycidyl ether (PGE) from epoxy resin systems Chem. Res. Toxicol. 24, 542-548
26. Delaine, T., Niklasson, I. B., Emter, R., Luthman, K., Karlberg, A. T., and Natsch, A. (2011) Structure-activity relationship between the in vivo skin sensitizing potency of analogues of phenyl glycidyl ether and the induction of Nrf2-dependent luciferase activity in the KeratinoSens in vitro assay Chem. Res. Toxicol. 24, 1312-1318
27. Guengerich, F. P. and Shimada, T. (1991) Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes Chem. Res. Toxicol. 4, 391-407
28. Guengerich, F. P. (2001) Common and uncommon cytochrome P450 reactions related to metabolism and chemical toxicity Chem. Res. Toxicol. 14, 611-650
29. Gafvert, E., Shao, L. P., Karlberg, A.-T., Nilsson, U., and Nilsson, J. L. G. (1994) Contact allergy to resin acid hydroperoxides. Hapten binding via free radicals and epoxides Chem. Res. Toxicol. 7, 260-266
30. Ponten, A., Zimerson, E., Sorensen, O., and Bruze, M. (2002) Sensitizing capacity and cross-reaction pattern of the isomers of diglycidyl ether of bisphenol F in the guinea pig Contact Dermatitis 47, 293-298
31. Patlewicz, G., Basketter, D. A., Smith, C. K., Hotchkiss, S. A. M., and Roberts, D. W. (2001) Skin-sensitization structure-activity relationships for aldehydes Contact Dermatitis 44, 331-336
32. O'Boyle, N. M., Delaine, T., Luthman, K., Natsch, A., and Karlberg, A.-T. (2012) Analogues of the epoxy resin monomer diglycidyl ether of bisphenol F: Effects on contact allergenic potency and cytotoxicity Chem. Res. Toxicol. 25, 2469-2478
33. Nacro, K., Baltas, M., Escudier, J.-M., and Gorrichon, L. (1996) Enhanced diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes obtained from nerol and geraniol Tetrahedron 52, 9047-9056
34. Martins, R. R. L., Neves, M. G. P. M. S., Silvestre, A. J. D., Simões, M. M. Q., Silva, A. M. S., Tomé, A. C., Cavaleiro, J. A. S., Tagliatesta, P., and Crestini, C. (2001) Oxidation of unsaturated monoterpenes with hydrogen peroxide catalysed by manganese(III) porphyrin complexe J. Mol. Catal. A: Chem. 172, 33-42
35. Bezard, M., Karlberg, A.-T., Montelius, J., and Lepoittevin, J.-P. (1997) Skin sensitization to linalyl hydroperoxide: Support for radical intermediates Chem. Res. Toxicol. 10, 987-993
36. Khan, N., Loeber, D. E., Toube, T. P., and Weedon, B. C. L. (1975) Carotenoids and related compounds. Part XXX. Stereochemistry and synthesis of phytoene J. Chem. Soc., Perkin Trans. 1, 1457-1464
37. Vasil'ev, A. and Engman, L. (2000) Novel preparation of α,β-unsaturated aldehydes. Benzeneselenolate promotes elimination of HBr from α-bromoacetals J. Org. Chem. 65, 2151-2162
38. Sköld, M., Hagvall, L., and Karlberg, A.-T. (2008) Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens Contact Dermatitis 58, 9-14
39. Dess, D. B. and Martin, J. C. (1991) A useful 12-I-5 triacetoxyperiodinane (the Dess-Martin periodinane) for the selective oxidation of primary or secondary alcohols and a variety of related 12-I-5 species J. Am. Chem. Soc. 113, 7277-7287
40. Ahlfors, S. R., Sterner, O., and Hansson, C. (2003) Reactivity of contact allergenic haptens to amino acid residues in a model carrier peptide, and characterization of formed peptide-hapten adducts Skin Pharmacol. Appl. Skin Physiol. 16, 59-68
41. Ahlfors, S. R., Kristiansson, M. H., Lindh, C. H., Jonsson, B. A. G., and Hansson, C. (2005) Adducts between nucleophilic amino acids and hexahydrophthalic anhydride, a structure inducing both types I and IV allergy Biomarkers 10, 321-335
42. Bergstrom, M. A., Luthman, K., and Karlberg, A.-T. (2007) Metabolic epoxidation of an alpha,beta-unsaturated oxime generates sensitizers of extreme potency. Are nitroso intermediates responsible? Chem. Res. Toxicol. 20, 927-936
43. Merckel, F., Bernard, G., Mutschler, J., Giménez-Arnau, E., Gerberick, G. F., and Lepoittevin, J.-P. (2010) Effect of a microemulsion system on hapten-peptide reactivity studies: Examples of hydroxycitronellal and citral, fragrance skin sensitizers, with glutathione Chem. Res. Toxicol. 23, 1433-1441
44. Natsch, A. and Gfeller, H. (2008) LC-MS-based characterization of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitization potential Toxicol. Sci. 106, 464-478
45. Aleksic, M., Thain, E., Roger, D., Saib, O., Davies, M., Li, J., Aptula, A., and Zazzeroni, R. (2009) Reactivity profiling: Covalent modification of single nucleophile peptides for skin sensitization risk assessment Toxicol. Sci. 108, 401-411
46. Gerberick, F., Aleksic, M., Basketter, D., Casati, S., Karlberg, A.-T., Petra Kern, I. K., Lepoittevin, J. P., Natsch, A., Ovigne, J. M., Rovida, C., Sakaguchi, H., and Schultz, T. (2008) Chemical reactivity measurement and the predictive identification of skin sensitisers ATLA 36, 214-242
47. Sköld, M., Börje, A., Harambasic, E., and Karlberg, A.-T. (2004) 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, 1697-1705
48. Gerberick, F. G., Ryan, C. A., Kern, P. S., Schlatter, H., Dearman, R. J., Kimber, I., Patlewicz, G. Y., and Basketter, D. A. (2005) Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods Dermatitis 16, 157-202
49. Hagvall, L., Bäcktorp, C., Norrby, P.-O., Karlberg, A.-T., and Börje, A. (2011) Experimental and theoretical investigations of the autoxidation of geranial: A dioxolane hydroperoxide identified as a skin sensitizer Chem. Res. Toxicol. 24, 1507-1515
50. Baron, J. M., Wiederholt, T., Heise, R., Merk, H. F., and Bickers, D. R. (2008) Expression and function of cytochrome P450-dependent enzymes in human skin cells Curr. Med. Chem. 15, 2258-2264
51. Modi, B. G., Neustadter, J., Binda, E., Lewis, J., Filler, R. B., Roberts, S. J., Kwong, B. Y., Reddy, S., Overton, J. D., Galan, A., Tigelaar, R., Cai, L., Fu, P., Shlomchik, M., Kaplan, D. H., Hayday, A., and Girardi, M. (2012) Langerhans cells facilitate epithelial DNA damage and squamous cell carcinoma Science 335, 104-108