High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of Michael acceptor electrophiles

Chemical Research in Toxicology

Volumn 22, Issue 3, 2009, Pages 592-603

  Roberts, David W ^a   Natsch, Andreas ^b  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOL 3(2H) ONE; 2 BENZISOTHIAZOLINONE; 2 DECANAL; 2 HEXENAL; 2 METHYL 4 ISOTHIAZOLIN 3 ONE; 2 METHYL 4 ISOTHIAZOLINONE; 4 VINYLPYRIDINE; ACRYLIC ACID ETHYL ESTER; ALDEHYDE DERIVATIVE; ALPHA DAMASCONE; ALPHA METHYLCINNAMIC ALDEHYDE; CINNAMALDEHYDE; CINNAMIC ACID BENZYL ESTER; CITRAL; DIPHENYLCYCLOPROPENE; ELECTROPHILE; ETHYLENE GLYCOL DIMETHACRYLATE; FARNESAL; GALBANONE; GLUTATHIONE; KETONE DERIVATIVE; MALEIC ACID DIETHYL ESTER; METHYL 2 NONYNOATE; NUCLEOPHILE; OXAZOLONE; PEPTIDE; PERILLALDEHYDE; POMAROSE; SAFRANAL; SPIROGALBANONE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; COVALENT BOND; HIGH THROUGHPUT SCREENING; HYDROPHOBICITY; LYMPH NODE; MICHAEL ADDITION; MODEL; MOUSE; NONHUMAN; PROTEIN BINDING; SKIN SENSITIZATION; SOLUBILITY;

ANIMAL TESTING ALTERNATIVES; ANIMALS; COSMETICS; HIGH-THROUGHPUT SCREENING ASSAYS; KINETICS; MICE; MODELS, CHEMICAL; PEPTIDES; SKIN; SKIN TESTS;

ANIMALIA; MURINAE;

EID: 65949100117     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800431x     Document Type: Article

References (24)

1. Basketter, D. A., Evans, P., Fielder, R. J., Gerberick, G. F., Dearman, R. J., and Kimber, I. (2002) Local lymph node assaysValidation, conduct and use in practice. Food Chem. Toxicol. 40, 593-598. (Pubitemid 34310424)
2. Jowsey, I. R., Basketter, D. A., Westmoreland, C., and Kimber, I. (2006) A future approach to measuring relative skin sensitising potency: A proposal. J. Appl. Toxicol. 26, 341-350. (Pubitemid 44064933)
3. Grindon, C., Combes, R., Cronin, M. T. D., Roberts, D. W., and Garrod, J. (2007) An integrated decision-tree testing strategy for skin sensitization with respect to the requirements of the EU REACH legislation. ATLA 35, 683-697. (Pubitemid 46883166)
4. Patlewicz, G., Aptula, A. O., Roberts, D. W., and Uriarte, E. (2007) A mini review of available (Q)SARs and expert systems for skin sensitisation. QSAR Comb. Sci. 27, 60-76.
5. Landsteiner, K., and Jacobs, J. (1936) Studies on the sensitization of animals with simple chemical compounds. J. Exp. Med. 64, 643-655.
6. Dupuis, G., and Benezra, C. Contact Dermatitis to Simple Chemicals: A Molecular Approach; Marcel Dekker: New York, 1982.
7. Roberts, D. W., Patlewicz, G., Kern, P., Gerberick, F., Kimber, I., Dearman, R., Ryan, C., Basketter, D., and Aptula, A. O. (2007) Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitisation. Chem. Res. Toxicol. 20, 1019-1030. (Pubitemid 47204815)
8. Aptula, A. O., and Roberts, D. W. (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. (Pubitemid 44384841)
9. Roberts, D. W., and Aptula, A. O. (2008) Determinants of skin sensitisation potential. J. Appl. Toxicol. 28, 377-387.
10. Roberts, D. W., Aptula, A. O., and Patlewicz, G. (2007) Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classification for a published dataset of 106 chemicals tested in the mouse local lymph node assay. Chem. Res. Toxicol. 20, 44-60. (Pubitemid 46220154)
11. Roberts, D. W., and Lepoittevin, J.-P. In Hapten-protein interactions; Lepoittevin, J.-P., Basketter, D. A., Goosssens, A., Karlberg, A.-T., Eds.; Allergic Contact Dermatitis. The Molecular Basis: Springer, Heidelberg, 1998; pp 129-154.
12. Schultz, T. W., Yarbrough, J. W., and Johnson, E. L. (2005) Structuresactivity relationships for reactivity of carbonyl-containing compounds with glutathione. SAR QSAR Environ. Res. 16, 313-322. (Pubitemid 41283776)
13. Roberts, D. W., Aptula, A. O., Patlewicz, G., and Pease, C. (2008) Chemical reactivity indices and mechanism-based read-across for nonanimal based assessment of skin sensitisation potential. J. Appl. Toxicol. 28, 443-454.
14. 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. (Pubitemid 39377963)
15. 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. (Pubitemid 47073857)
16. 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.
17. Natsch, A., Gfeller, H., Rothaupt, M., and Ellis, G. (2007) Utility and limitations of a peptide reactivity assay to predict fragrance allergens in vitro. Toxicol. In Vitro 21, 1220-1226. (Pubitemid 350030873)
18. Gerberick, G. F., 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. (Pubitemid 43053764)
19. Natsch, A., and Emter, R. (2008) Skin sensitizers induce antioxidant response element dependent genes: Application to the in vitro testing of the sensitization potential of chemicals. Toxicol. Sci. 102, 110-119.
20. Schultz, T. W., Rogers, K. L. N., and Aptula, A. O. (2009) Read-across to rank skin sensitization potential: Subcategories for the Michael acceptor domain. Contact Dermatitis 60, 21-31.
21. Dearman, R. J., Betts, C. J., Farr, C., McLaughlin, J., Berdasco, N., Wiench, K., and Kimber, I. (2007) Comparative analysis of skin sensitization potency of acrylates (methyl acrylate, ethyl acrylate, butyl acrylate, and ethylhexyl acrylate) using the local lymph node assay. Contact Dermatitis 57, 242-247.
22. Eicher, T., and Weber, J. L. Structure and reactivity of cyclopropenones and triafulvenes. Cyclic compounds. Topics in Current Chemistry; Springer: Berlin/Heidelberg, 1975; Vol. 57, pp 1109.
23. Aptula, A. O., Roberts, D. W., and Patlewicz, G. (2006) Mechanistic applicability domains for non-animal based toxicological endpoints. QSAR analysis of the Schiff Base applicability domain for skin sensitization. Chem. Res. Toxicol. 19, 1228-1233. (Pubitemid 44454040)
24. Enoch, S. J., Cronin, M. T. D., Schultz, T. W., and Madden, J. C. (2008) Quantitative and Mechanistic Read Across for Predicting the Skin Sensitization Potential of Alkenes Acting via Michael Addition. Chem. Res. Toxicol. 21, 513-520.