The definition of the applicability domain relevant to skin sensitization for the aromatic nucleophilic substitution mechanism

SAR and QSAR in Environmental Research

Volumn 23, Issue 7-8, 2012, Pages 649-663

  Enoch, S J ^a   Schultz, T W ^b   Cronin, M T D ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF TENNESSEE   (United States)

Author keywords

adverse outcome pathways; electrophilic reaction chemistry; in chemico; structural alerts

Indexed keywords

ADVERSE OUTCOME PATHWAY; ADVERSE OUTCOMES; AROMATIC NUCLEOPHILIC SUBSTITUTION; ELECTROPHILIC REACTION; ELECTROPHILIC REACTION CHEMISTRY; IN CHEMICO; REACTION CHEMISTRY; SKIN SENSITIZATION; STRUCTURAL ALERT; SUBSTITUTION MECHANISMS;

AROMATIC COMPOUNDS;

EID: 84869484459     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2012.679691     Document Type: Article

References (39)

1. Combes, R and Balls, M. 2005. Intelligent testing strategies for chemicals testing - A case of more haste, less speed?. ATLA, 33: 289-297.
2. Enoch, SJ. 2010. Chemical category formation and read-across for the prediction of toxicity, in Recent advances in QSAR studies: Methods and applications, Edited by: Puzyn, T, Leszczynski, J and Cronin, MTD. 209-219. UK: Springer.
3. OECD, Guidance on Grouping of Chemicals. (available from: http://www.oecd.org/LongAbstract/0,3425,en_2649_34379_39404999_119829_1_1_37407,00.html), 2007
4. Dimitrov, S and Mekenyan, O. 2010. "An introduction to read-across for the prediction of the effects of chemicals". In In Silico Toxicology: Principles and Applications, Edited by: Cronin, MTD and Madden, JC. 371-384. Cambridge, UK: RSC.
5. Diderich, B. 2010. "Tools for category formation and read-across. Overview of the OECD (Q)SAR Application Toolbox". In In Silico Toxicology: Principles and Applications, Edited by: Cronin, MTD and Madden, JC. 385-407. Cambridge, UK: RSC.
6. Schultz, TW. 2010. "Adverse outcome pathways: A way of linking chemical structure to in vivo toxicological hazards". In In silico Toxicology: Principles and Applications, Edited by: Cronin, MTD and Madden, JC. 346-371. Cambridge, UK: RSC.
7. OECD, The OECD QSAR Application Toolbox; software available athttp://www.qsartoolbox.org/
8. Enoch, SJ, Cronin, MTD and Ellison, CM. 2011. The use of a chemistry based profiler for covalent DNA binding in the development of chemical categories for read-across for genotoxicity. ATLA, 39: 131-145.
9. Enoch, SJ, Roberts, DW and Cronin, MTD. 2010. Mechanistic category formation for the prediction of respiratory sensitisation. Chem. Res. Toxicol., 23: 1547-1555.
10. Kimber, I, Basketter, DA, Gerberick, F and Dearman, RJ. 2002. Allergic contact dermatitis. Int. Immunopharmacol., 2: 201-211.
11. Karlberg, AT, Bergstrom, MA, Borje, A, Luthman, K and Nilsson, JLG. 2008. Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitisers. Chem. Res. Toxicol., 21: 53-69.
12. Buehler, EV. 1965. Delayed contact hypersensitivity in the guinea pig. Arch. Dermatol., 91: 171-177.
13. Magnusson, B and Kligman, AM. 1969. The identification of contact allergens by animal assay, the guinea pig maximisation test method. J. Invest. Dermatol., 52: 268-276.
14. Basketter, DA, Gerberick, GF, Kimber, I and Loveless, SE. 1996. The local lymph node assay: A viable alternative to currently accepted skin sensitisation tests. Fd.Chem. Toxicol., 34: 985-997.
15. Landsteiner, K and Jacobs, J. 1935. Studies on the sensitisation of animals with simple chemical compounds. J. Exp. Med., 61: 643-656.
16. Landsteiner, K and Jacobs, J. 1936. Studies on the sensitisation of animals with simple chemical compounds II. J. Exp. Med., 64: 625-639.
17. Gerberick, F, Aleksic, M, Basketter, D, Casati, S, Karlberg, A, Kern, P, Kimber, I, Lepoittevin, D, Natsch, A, Ovigne, JM, Rovida, C, Sakaguchi, H and Schultz, TW. 2008. Chemical reactivity measurement and the predictive identification of skin sensitisers. ATLA, 36: 215-242.
18. Aptula, AO and Roberts, DW. 2006. Mechanistic applicability domains for nonanimal-based prediction of toxicological end points: General principles and application to reactive toxicity. Chem. Res. Toxicol., 19: 1097-1105.
19. Gerberick, GF, Ryan, CA, Kern, PS, Schlatter, H, Dearman, RJ, Kimber, I, Patlewicz, GY and Basketter, DA. 2005. Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods. Dermatitis, 16: 157-202.
20. Kern, PS, Gerberick, GF, Ryan, CA, Kimber, I, Aptula, AO and Basketter, DA. 2010. Local lymph node data for the evaluation of skin sensitisation alternatives: A second compilation. Dermatitis, 21: 8-32.
21. Roberts, DW, Aptula, AO and Patlewicz, GY. 2011. Chemistry-based risk assessment for skin sensitisation: Quantitative mechanistic modelling for the SNAr domain. Chem. Res. Toxicol., 24: 1003-1011.
22. Schultz, TW, Rogers, K and Aptula, AO. 2009. Read-across to rank skin sensitisation potential: Subcategories for the Michael acceptor domain. Contact Derm., 60: 21-31.
23. Aptula, AO, Patlewicz, G, Roberts, DW and Schultz, TW. 2006. Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization. Toxicol. In Vitr., 20: 239-247.
24. Enoch, SJ, Madden, JC and Cronin, MTD. 2008. Identification of mechanisms of toxic action for skin sensitisation using a SMARTS pattern based approach. SAR QSAR Environ. Res., 19: 555-578.
25. Roberts, DW. 1995. Linear free-energy relationships for reactions of electrophilic halobenzenes and pseudohalobenzenes, and their application in prediction of skin sensitization potential for SNAr electrophiles. Chem. Res. Toxicol., 8: 545-551.
26. Roberts, DW and Natsch, A. 2009. High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitisation potency of Michael acceptor electrophiles. Chem. Res. Toxicol., 22: 592-603.
27. Natsch, A and Gfeller, H. 2008. LC-MS-based characterisation of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitisation potential. Toxicol. Sci., 106: 464-478.
28. Ankley, GT, Bennett, RS, Erickson, RJ, Hoff, DJ, Hornung, MW, Johnson, RD, Mount, DR, Nichols, JW, Russom, CL, Schmieder, PK, Tietge, JE and Villeneuve, DL. 2010. Adverse outcome pathways: A conceptual framework to support ecotoxicology research and risk assessment. Environ. Toxicol. Chem., 29: 730-741.
29. Schwobel, JAH, Koleva, YK, Enoch, SJ, Bajot, F, Hewitt, M, Madden, JC, Roberts, DW, Schultz, TW and Cronin, MTD. 2011. Measurement and estimation of electrophilic reactivity for predictive toxicology. Chem. Rev., 111: 2562-2596.
30. Emter, R, Ellis, G and Natsch, A. 2010. Performance of a novel keratinocyte-based reporter cell line to screen skin sensitisers in vitro. Toxicol. App. Pharmacol., 245: 281-290.
31. Natsch, A and Emter, R. 2008. Skin sensitisers induce antioxidant response element dependent genes: Applications to the in vitro testing of the sensitisation potential of chemicals. Toxicol. Sci., 102: 110-119.
32. McKim, JM, Keller, DJ and Gorski, JR. 2010. A new method for identifying chemical sensitisers combining peptide binding with ARE/EpRE-mediated gene expression in human skin cells. Cutan. Ocular Toxicol., 29: 171-192.
33. dos Santos, GG, Reinders, J, Ouwehand, K, Rustemeyer, T, Scheper, RJ and Gibbs, S. 2009. Progress on the development of human in vitro dendritic cell based assays for assessment of the sensitising potential of a compound. Toxicol. App. Pharmacol., 236: 372-382.
34. dos Santos, GG, Speikstra, SW, Sampat-Sardjoepersad, SC, Reinders, J, Scheper, RJ and Gibbs, S. 2011. A potential in vitro epidermal equivalent assay to determine sensitiser potency. Toxicol. In Vitro, 25: 347-357.
35. Vandebriel, RJ, Pennings, JLA, Baken, KA, Pronk, TE, Boorsma, A, Gottschalk, R and van Loveren, H. 2010. Keratinocyte gene expression profiles discriminate sensitising and irritating compounds. Toxicol. Sci., 117: 81-89.
36. Ashikaga, T, Sakaguchi, H, Sono, S, Kosaka, N, Ishikawa, M, Nukada, Y, Miyazawa, M, Ito, Y, Nishiyama, N and Itagaki, H. 2010. A comparative evaluation of in vitro skin sensitisation tests: The human cell-line activation test (h-CLAT) versus the local lymph node assay (LLNA). ATLA, 38: 275-284.
37. Aptula, AO, Patlewicz, G and Roberts, DW. 2005. Skin sensitization: Reaction mechanistic applicability domains for structure-activity relationships. Chem. Res. Toxicol., 18: 1420-1426.
38. Roberts, DW, Patlewicz, G, Kern, PS, Gerberick, F, Kimber, I, Dearman, RJ, Ryan, CA, Basketter, DA and Aptula, AO. 2007. Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitization. Chem. Res. Toxicol., 20: 1019-1030.
39. Schultz, TW, Yarbrough, JW, Hunter, RS and Aptula, AO. 2007. Verification of the structural alerts for Michael acceptors. Chem. Res. Toxicol., 20: 1359-1363.