Does the extreme skin sensitization potency of benzoquinone result from special chemistry?

Contact Dermatitis

Volumn 61, Issue 6, 2009, Pages 332-336

  Roberts, David W ^a   Aptula, Aynur O ^b  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

Contact allergy; LLNA; Mechanism; Reactivity; Read across

Indexed keywords

BENZOQUINONE;

ARTICLE; CONTROLLED STUDY; LYMPH NODE; MICHAEL ADDITION; QUANTITATIVE ANALYSIS; SKIN SENSITIZATION; THEORETICAL MODEL;

ALLERGENS; BENZOQUINONES; DATABASES, FACTUAL; DERMATITIS, ALLERGIC CONTACT; LOCAL LYMPH NODE ASSAY; MODELS, THEORETICAL; MOLECULAR STRUCTURE; PREDICTIVE VALUE OF TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SKIN; TOXICITY TESTS;

EID: 72149122917     PISSN: 01051873     EISSN: 16000536     Source Type: Journal    
DOI: 10.1111/j.1600-0536.2009.01646.x     Document Type: Article

References (22)

1. EU (2003). 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 ("7th Amendment to the European Cosmetics Directive"). Official Journal of the European Union L 66, 26 35.
2. Aptula A O, Roberts D W. Mechanistic applicability domains for non-animal based toxicological endpoints. General principles and application to reactive toxicity. Chem Res Toxicol 2006 : 19 : 1097 1105.
3. Roberts D W, Aptula A O, Patlewicz G. Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published data set of 106 chemicals tested in the mouse Local Lymph Node Assay. Chem Res Toxicol 2007 : 20 : 44 60.
4. Roberts D W, Aptula A O. Determinants of skin sensitisation potential. J Appl Toxicol 2008 : 28 : 377 387.
5. Lepoittevin J-P, Basketter D A, Goosssens A, Karlberg A-T (Eds) (1997) Allergic Contact Dermatitis. The Molecular Basis, Springer, Heidelberg.
6. Gerberick G F, Vassallo J D, Foertsch L M, Price B B, Chaney J G, Lepoittevin J-P. Quantification of chemical peptide reactivity for screening contact allergens: a classification tree model approach. Toxicol Sci 2007 : 97 : 417 427.
7. Karlberg A-T, Bergström M, Börje A, Luthman K, Nilsson J. Allergic contact dermatitis - formation, sructural requirements, and reactivity of skin sensitizers. Chem Res Toxicol 2008 : 21 : 53 69.
8. Natsch A, Gfeller H. LC-MS based characterization of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitization potential. Toxicol Sci 2008 : 106 : 464 478.
9. Aleksic M, Thain E, Roger D, Saib O, Davies M, Li J, Aptula A, Raniero Z. Reactivity profiling: Covalent modification of single nucleophile peptides for skin sensitisation risk assessment. Toxicol Sci 2009 : 108 : 401 411.
10. Enoch S J, Madden J C, Cronin M T D. Identification of mechanisms of toxic action for skin sensitisation, using a SMARTS pattern based approach. SAR QSAR Environ Res 2008 : 19 : 555 578.
11. Alvarez-Sanchez R, Basketter D, Pease C, Lepoittevin J-P. Studies of chemical selectivity of hapten, reactivity, and skin sensitization. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C-labelled skin sensitisers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI). Chem Res Toxicol 2003 : 16 : 627 636.
12. Landsteiner K, Jacobs J. Studies on the sensitisation of animals with simple chemical compounds. J Exp Med 1935 : 61 : 643 656.
13. http://www.epa.gov/ttnatw01/hlthef/quinone.html (last accessed 05 September 2009)
14. 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.
15. Roberts D W, Aptula A O, Cronin M T D, Hulzebos E, Patlewicz G. Global (Q)SARs for skin sensitization-assessment against OECD principles, SAR QSAR Environ Res 2007 : 18 : 343 365.
16. Aptula A O, Roberts D W, Patlewicz G. Mechanistic applicability domains for non-animal based toxicological endpoints. QSAR analysis of the Schiff Base applicability domain for skin sensitization. Chem Res Toxicol 2006 : 19 : 1228 1233.
17. Roberts D, Natsch A. High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of Michael acceptor electrophiles. Chem Res Tox 2009 : 22 : 592 603.
18. Perrin D D, Dempsey B, Serjeant E P. (1981) pKa Prediction for Organic Acids and Bases. Chapman and Hall, London.
19. Basketter D A, Blaikie L, Dearman R J et al. Use of the local lymph node assay for the estimation of relative contact allergenic potency. Contact Dermatitis 2000 : 42 : 344 348.
20. Butler J, Hoey B M. Reactions of glutathione and glutathione radicals with benzoquinones. Free Radic Biol Med 1992 : 12 : 337 345.
21. Schultz T W, Yarbrough J W, Johnson E L. Structure-activity relationships for reactivity of carbonyl-containing compounds with glutathione. SAR QSAR Environ Res 2005 : 16 : 313 322.
22. Roberts D W, Patlewicz G, Kern P et al. Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitisation. Chem Res Toxicol 2007 : 20 : 1019 1030. (Pubitemid 47204815)