Activation of non-sensitizing or low-sensitizing fragrance substances into potent sensitizers - Prehaptens and prohaptens

Contact Dermatitis

Volumn 69, Issue 6, 2013, Pages 323-334

  Karlberg, Ann Therese ^a   Börje, Anna ^a   Duus Johansen, Jeanne ^b   Lidén, Carola ^c   Rastogi, Suresh ^d   Roberts, David ^e   Uter, Wolfgang ^f   White, Ian R ^g  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c KAROLINSKA INSTITUTE   (Sweden)

^d Liverpool John Moores University ^*

^e LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^f UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^g ST THOMAS HOSPITAL   (United Kingdom)

Author keywords

abiotic and biotic activation; autoxidation; directive 76 768 ECC; fragrance allergens; prehaptens; prohaptens; SCCS; scientific opinion

Indexed keywords

ALLERGEN; ESSENTIAL OIL; FRAGRANCE; HAPTEN; PHOTOSENSITIZING AGENT; PROHAPTEN; UNCLASSIFIED DRUG;

AUTOOXIDATION; CHEMICAL STRUCTURE; CONTACT ALLERGY; HUMAN; NONHUMAN; REVIEW; SENSITIZATION;

ABIOTIC AND BIOTIC ACTIVATION; AUTOXIDATION; DIRECTIVE 76/768/ECC; FRAGRANCE ALLERGENS; PREHAPTENS; PROHAPTENS; SCCS; SCIENTIFIC OPINION;

ALLERGENS; DERMATITIS, ALLERGIC CONTACT; HAPTENS; HUMANS; OILS, VOLATILE; PERFUME;

EID: 84888001224     PISSN: 01051873     EISSN: 16000536     Source Type: Journal    
DOI: 10.1111/cod.12127     Document Type: Review

References (67)

1. Hagvall L, Baron J M, Börje A, Weidolf L, Merk H, Karlberg A T,. Cytochrome P450-mediated activation of the fragrance compound geraniol forms potent contact allergens. Toxicol Appl Pharmacol 2008: 233: 308-313.
2. Hagvall L, Bäcktorp C, Svensson S, Nyman G, Börje 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.
3. Elahi E N, Wright Z, Hinselwood D, Hotchkiss S A, Basketter D A, Pease C K,. Protein binding and metabolism influence the relative skin sensitization potential of cinnamic compounds. Chem Res Toxicol 2004: 17: 301-310.
4. Basketter D A,. Skin sensitization to cinnamic alcohol-the role of skin metabolism. Acta Derm Venereol 1992: 72: 264-265.
5. Niklasson I B, Delaine T, Islam M N, Karlsson R, Luthman K, Karlberg A T,. Cinnamyl alcohol oxidizes rapidly upon air exposure. Contact Dermatitis 2013: 68: 129-138.
6. Rudbäck J, Bergström M A, Börje A, Nilsson U, Karlberg A T,. alpha-Terpinene, an antioxidant in tea tree oil, autoxidizes rapidly to skin allergens on air exposure. Chem Res Toxicol 2012: 25: 713-721.
7. Bergström M A, Luthman K, Nilsson J L, 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.
8. Hagvall L, Bäcktorp C, Norrby P O, Karlberg A T, Börje A,. Experimental and theoretical investigations of the autoxidation of geranial: a dioxolane hydroperoxide identified as a skin sensitizer. Chem Res Toxicol 2011: 24: 1507-1515.
9. Uter W D J J, Börje A, Karlberg A T, Lidén C, Rastogi S, Roberts D, White I,. Categorisation of fragrance contact allergens for prioritisation of preventive meaures: clinical and experimental data and consideration of structure activity relationships. Contact Dermatitis 2013: 69: 196-230.
10. Bråred Christensson J, Matura M, Bäcktorp C, Börje A, Nilsson J L, Karlberg A T,. Hydroperoxides form specific antigens in contact allergy. Contact Dermatitis 2006: 55: 230-237.
11. Karlberg A T, Bergström M A, Börje A, Luthman K, Nilsson J L,. Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers. Chem Res Toxicol 2008: 21: 53-69.
12. Karlberg A T, Boman A, Melin B,. Animal experiments on the allergenicity of d-limonene-the citrus solvent. Ann Occup Hyg 1991: 35: 419-426.
13. Karlberg A T, Magnusson K, Nilsson U,. Air oxidation of d-limonene (the citrus solvent) creates potent allergens. Contact Dermatitis 1992: 26: 332-340.
14. Karlberg A T, Shao L P, Nilsson U, Gafvert E, Nilsson J L,. Hydroperoxides in oxidized d-limonene identified as potent contact allergens. Arch Dermatol Res 1994: 286: 97-103.
15. Sköld M, Börje A, Matura M, Karlberg A T,. Studies on the autoxidation and sensitizing capacity of the fragrance chemical linalool, identifying a linalool hydroperoxide. Contact Dermatitis 2002: 46: 267-272.
16. Sköld M, Börje 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: 1697-1705.
17. Sköld M, Hagvall L, Karlberg A T,. Autoxidation of linalyl acetate, the main component of lavender oil, creates potent contact allergens. Contact Dermatitis 2008: 58: 9-14.
18. Christensson J B, Johansson S, Hagvall L, Jonsson C, Börje A, Karlberg A T,. Limonene hydroperoxide analogues differ in allergenic activity. Contact Dermatitis 2008: 59: 344-352.
19. 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.
20. Sköld M, Karlberg A T, Matura M, Börje A,. The fragrance chemical beta-caryophyllene-air oxidation and skin sensitization. Food Chem Toxicol 2006: 44: 538-545.
21. Gerberick G F, Ryan C A, Kern P S, Schlatter H, Dearman R J, Kimber I, Patlewicz G Y, Basketter D A,. Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis 2005: 16: 157-202.
22. Hagvall L, Sköld M, Bråred-Christensson J, Borje A, Karlberg A T,. Lavender oil lacks natural protection against autoxidation, forming strong contact allergens on air exposure. Contact Dermatitis 2008: 59: 143-150.
23. Matura M, Sköld M, Börje A, et al. Not only oxidized R-(+)- but also S-(-)-limonene is a common cause of contact allergy in dermatitis patients in Europe. Contact Dermatitis 2006: 55: 274-279.
24. Matura M, Goossens A, Bordalo O, Garcia-Bravo B, Magnusson K, Wrangsjö K, Karlberg A T,. Patch testing with oxidized R-(+)-limonene and its hydroperoxide fraction. Contact Dermatitis 2003: 49: 15-21.
25. Matura M, Goossens A, Bordalo O, Garcia-Bravo B, Magnusson K, Wrangsjö K, Karlberg A T,. Oxidized citrus oil (R-limonene): a frequent skin sensitizer in Europe. J Am Acad Dermatol 2002: 47: 709-714.
26. Karlberg A T, Dooms-Goossens A,. Contact allergy to oxidized d-limonene among dermatitis patients. Contact Dermatitis 1997: 36: 201-206.
27. Bråred Christensson J, Andersen K E, Bruze M, et al. Air-oxidized linalool: a frequent cause of fragrance contact allergy. Contact Dermatitis 2012: 67: 247-259.
28. Christensson J B, Matura M, Gruvberger B, Bruze M, Karlberg A T,. Linalool-a significant contact sensitizer after air exposure. Contact Dermatitis 2010: 62: 32-41.
29. Matura M, Sköld M, Börje A, et al. Selected oxidized fragrance terpenes are common contact allergens. Contact Dermatitis 2005: 52: 320-328.
30. Buckley D A,. Allergy to oxidized linalool in the UK. Contact Dermatitis 2011: 64: 240-241.
31. Bråred Christensson J, Andersen K E, Bruze M, et al. An international multicentre study on the allergenic activity of air-oxidized R-limonene. Contact Dermatitis 2013: 68: 214-223.
32. Hagvall L, Karlberg A T, Christensson J B,. Finding the optimal patch test material and test concentration to detect contact allergy to geraniol. Contact Dermatitis 2013: 68: 224-231.
33. Hagvall L, Karlberg A T, Christensson J B,. Contact allergy to air-exposed geraniol: clinical observations and report of 14 cases. Contact Dermatitis 2012: 67: 20-27.
34. Berglund V,. Master Thesis, How do small differences in chemical reactivity and sensitizing capacity affect the frequency of contact allergy to common fragrances? University of Gothenburg, 2011.
35. Santucci B, Cristaudo A, Cannistraci C, Picardo M,. Contact dermatitis to fragrances. Contact Dermatitis 1987: 16: 93-95.
36. Fregert S, Hjorth N,. Results of standard patch tests with substances abandoned. Contact Dermatitis Newsletter 1969: 5: 85-86.
37. Frosch P J, Pilz B, Andersen K E, et al. Patch testing with fragrances: results of a multicenter study of the European Environmental and Contact Dermatitis Research Group with 48 frequently used constituents of perfumes. Contact Dermatitis 1995: 33: 333-342.
38. Uter W, Geier J, Frosch P J, Schnuch A,. Contact allergy to fragrances: current patch test results (2005 to 2008) from the IVDK network. Contact Dermatitis 2010: 63: 254-261.
39. Frosch P J, Johansen J D, Menné T, et al. Further important sensitizers in patients sensitive to fragrances. I. Reactivity to 14 frequently used chemicals. Contact Dermatitis 2002: 47: 78-85.
40. Schnuch A, Uter W, Geier J, Lessmann H, Frosch P J,. Sensitization to 26 fragrances to be labelled according to current European regulation. Results of the IVDK and review of the literature. Contact Dermatitis 2007: 57: 1-10.
41. van Oosten E J, Schuttelaar M L, Coenraads P J,. Clinical relevance of positive patch test reactions to the 26 EU-labelled fragrances. Contact Dermatitis 2009: 61: 217-223.
42. de Groot A C, Liem D H, Nater J P, van Ketel W G,. Patch tests with fragrance materials and preservatives. Contact Dermatitis 1985: 12: 87-92.
43. de Groot A C, Coenraads P J, Bruynzeel D P, et al. Routine patch testing with fragrance chemicals in The Netherlands. Contact Dermatitis 2000: 42: 184-185.
44. Frosch P J, Johansen J D, Menné T, et al. Further important sensitizers in patients sensitive to fragrances. II. Reactivity to essential oils. Contact Dermatitis 2002: 47: 279-287.
45. Karlberg A T, Magnusson K, Nilsson U,. Influence of an anti-oxidant on the formation of allergenic compounds during auto-oxidation of d-limonene. Ann Occup Hyg 1994: 38: 199-207.
46. Ruberto G, Baratta M T, Deans S G, Dorman H J,. Antioxidant and antimicrobial activity of Foeniculum vulgare and Crithmum maritimum essential oils. Planta Med 2000: 66: 687-693.
47. Kim H J, Chen F, Wu C, Wang X, Chung H Y, Jin Z,. Evaluation of antioxidant activity of Australian tea tree (Melaleuca alternifolia) oil and its components. J Agric Food Chem 2004: 52: 2849-2854.
48. Foti M C, Ingold K U,. Mechanism of inhibition of lipid peroxidation by gamma-terpinene, an unusual and potentially useful hydrocarbon antioxidant. J Agric Food Chem 2003: 51: 2758-2765.
49. Rudbäck J, Islam M N, Nilsson U, Karlberg A T,. A sensitive method for determination of allergenic fragrance terpene hydroperoxides using liquid chromatography coupled with tandem mass spectrometry. J Sep Sci 2013: 36: 1370-1378.
50. Smith C K, Hotchkiss S A,. Enzymes and mechanisms of xenobiotic metabolism. In: Allergic Contact Dermatitis Chemical and Metabolic Mechanisms, London and New York, Taylor and Francis, 2001: pp. 45-87.
51. Kalgutkar A S, Gardner I, Obach R S, et al. A comprehensive listing of bioactivation pathways of organic functional groups. Curr Drug Metab 2005: 6: 161-225.
52. Nilsson A M, Bergström M A, Luthman K, Nilsson J L, Karlberg A T,. A conjugated diene identified as a prohapten: contact allergenic activity and chemical reactivity of proposed epoxide metabolites. Chem Res Toxicol 2005: 18: 308-316.
53. Bergström M A, Ott H, Carlsson A, et al. A skin-like cytochrome P450 cocktail activates prohaptens to contact allergenic metabolites. J Invest Dermatol 2007: 127: 1145-1153.
54. Smith C K, Moore C A, Elahi E N, Smart A T, Hotchkiss S A,. Human skin absorption and metabolism of the contact allergens, cinnamic aldehyde, and cinnamic alcohol. Toxicol Appl Pharmacol 2000: 168: 189-199.
55. Cheung C, Hotchkiss S A, Pease C K,. Cinnamic compound metabolism in human skin and the role metabolism may play in determining relative sensitisation potency. J Dermatol Sci 2003: 31: 9-19.
56. Ott H, Wiederholt T, Bergström M A, et al. High-resolution transcriptional profiling of chemical-stimulated dendritic cells identifies immunogenic contact allergens, but not prohaptens. Skin Pharmacol Physiol 2010: 23: 213-224.
57. Bertrand F, Basketter D A, Roberts D W, Lepoittevin J P,. Skin sensitization to eugenol and isoeugenol in mice: possible metabolic pathways involving ortho-quinone and quinone methide intermediates. Chem Res Toxicol 1997: 10: 335-343.
58. Melles D, Vielhaber T, Baumann A, Zazzeroni R, Karst U,. In chemico evaluation of skin metabolism: investigation of eugenol and isoeugenol by electrochemistry coupled to liquid chromatography and mass spectrometry. J Chromatogr B 2013: 913-914: 106-112.
59. Götz C, Pfeiffer R, Tigges J, et al. Xenobiotic metabolism capacities of human skin in comparison with a 3D epidermis model and keratinocyte-based cell culture as in vitro alternatives for chemical testing: activating enzymes (Phase I). Exp Dermatol 2012: 21: 358-363.
60. Götz C, Pfeiffer R, Tigges J, et al. Xenobiotic metabolism capacities of human skin in comparison with a 3D-epidermis model and keratinocyte-based cell culture as in vitro alternatives for chemical testing: phase II enzymes. Exp Dermatol 2012: 21: 364-369.
61. Modi B G, Neustadter J, Binda E, et al. Langerhans cells facilitate epithelial DNA damage and squamous cell carcinoma. Science 2012: 335: 104-108.
62. Ott H, Bergström M A, Heise R, Skazik C, Zwadlo-Klarwasser G, Merk H F, Baron J M, Karlberg A T,. Cutaneous metabolic activation of carvoxime, a self-activating, skin-sensitizing prohapten. Chem Res Toxicol 2009: 22: 399-405.
63. Hartung T, Bremer S, Casati S, et al. A modular approach to the ECVAM principles on test validity. Altern Lab Anim 2004: 32: 467-472.
64. Goebel C, Aeby P, Ade N, et al. Guiding principles for the implementation of non-animal safety assessment approaches for cosmetics: skin sensitisation. Regul Toxicol Pharmacol 2012: 63: 40-52.
65. White I R, Johansen J D, Arnau E G, et al. Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? Contact Dermatitis 1999: 41: 272-275.
66. Tanaka S, Royds C, Buckley D, et al. Contact allergy to isoeugenol and its derivatives: problems with allergen substitution. Contact Dermatitis 2004: 51: 288-291.
67. Rastogi S C, Johansen J D,. Significant exposures to isoeugenol derivatives in perfumes. Contact Dermatitis 2008: 58: 278-281.