Electrophilic reactivity and skin sensitization potency of SnAr electrophiles

Chemical Research in Toxicology

Volumn 27, Issue 2, 2014, Pages 240-246

  Roberts, D W ^a   Aptula, A O ^b  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNILEVER RESEARCH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALLERGENS; CYSTEINE; DERMATITIS, ALLERGIC CONTACT; MODELS, BIOLOGICAL; NITROBENZENES; PEPTIDES;

EID: 84894237710     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400355n     Document Type: Article

References (25)

1. Roberts, D. W. and Aptula, A. O. (2008) Determinants of skin sensitisation potential J. Appl. Toxicol. 28, 377-387
2. Roberts, D. W. and Williams, D. L. (1982) The derivation of quantitative correlations between skin sensitisation and physicochemical parameters for alkylating agents and their application to experimental data for sultones J. Theor. Biol. 99, 807-825
3. Roberts, D. W., Aptula, A. O., and Patlewicz, G. (2006) Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization Chem. Res. Toxicol. 19, 1228-1233
4. Roberts, D. W., Aptula, A. O., and Patlewicz, G. (2007) 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. 20, 44-60
5. Roberts, D. W. and Natsch, A. (2009) High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of Michael acceptor electrophiles Chem. Res. Toxicol. 22, 592-603
6. Landsteiner, K. and Jacobs, J. (1936) Studies on the sensitization of animals with simple chemical compounds J. Exp. Med. 64, 643-655
7. NAr ectrophiles Chem. Res. Toxicol. 8, 545-551
8. NAr alectrophiles Chem. Res. Toxicol. 10, 994-1000
9. NAr domain Chem. Res. Toxicol. 24, 1003-1011
10. Terrier, F. (2013) Modern Nucleophilic Aromatic Substiution, Wiley, Weinheim, Germany.
11. N2-reactive chemicals Chem. Res. Toxicol. 24, 2018-2027
12. Bartoli, G. and Todesco, P. E. (1977) Nucleophilic substitution. Linear free energy relationships between reactivity and physical properties of leaving groups and substrates Acc. Chem. Res. 10, 125-132
13. Giles, D. E. and Parker, A. J. (1973) Mechanisms of aromatic nucleophilic substitution by the ambident thiocyanate ion Aust. J. Chem. 26, 273-299
14. Reddy, V. A. (1983) Atypical reaction of 'essential' sulfhydryl groups of malic enzyme with 2-nitro-5-thiocyanobenzoate and 2,4-dinitrophenylthiocyanate Biochim. Biophys. Acta 743, 268-280
15. Perrin, D. D., Dempsey, B., and Serjeant, E. P. (1981) pKa Prediction for Organic Acids and Bases, Chapman and Hall, London.
16. Broxton, T. J., Muir, D. M., and Parker, A. J. (1975) Aromatic nucleophilic substitution reactions of ambident nucleophiles. 111. Reactivity of the nitrite ion J. Org. Chem. 40, 3230-3233
17. Lamm, B. (1959) A halogen exchange reaction in a diazonium compound Acta Chem. Scand. 13, 1254-1255
18. Suschitzky, H. and Wakefield, B. J. (2000) Aromatic Fluorine Chemistry at Salford, in Fluorine Chemistry at the Millennium; Fascinated by Fluorine (Banks, R. E., Ed.), Elsevier Science, Oxford, U.K.
19. Elbayed, K., Berl, V., Debeuckelaere, C., Moussallieh, F.-M., Piotto, M., Namer, I.-J., and Lepoittevin, J.-P. (2013) HR-MAS NMR spectroscopy of reconstructed human epidermis: Potential for the in situ investigation of the chemical interactions between skin allergens and nucleophilic amino acids Chem. Res. Toxicol. 26, 136-145
20. OECD. (2012a. The Adverse Outcome Pathway for skin sensitisation initiated by covalent binding to proteins. Part 1. Series on Testing and Assessment. No. 168. ENV/JM/MONO(2012)10/PART1.
21. OECD. (2012b. The Adverse Outcome Pathway for skin sensitisation initiated by covalent binding to proteins. Part 2: Use of the AOP to develop chemical categories and integrated assessment and testing approaches. Series on Testing and Assessment. No. 168. ENV/JM/MONO(2012)/PART2.
22. MacKay, C., Davies, M., Summerfield, V., and Maxwell, G. (2013) From pathways to people: applying the adverse outcome pathway (AOP) for skin sensitisation to risk assessment ALTEX 30, 473-486
23. 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
24. Gutsell, S. and Russell, P. (2013) The role of chemistry in developing understanding of adverse outcome pathways and their application in risk assessment Toxicol. Res. 2, 299-307
25. Voelker, A. E. and Viswanathan, R. (2013) Synthesis of a suite of bioorthogonal glutathione S-transferase substrates and their enzymatic incorporation for protein immobilization J. Org. Chem. 78, 9647-9658