Effect of a microemulsion system on hapten-peptide reactivity studies: Examples of hydroxycitronellal and citral, fragrance skin sensitizers, with glutathione

Chemical Research in Toxicology

Volumn 23, Issue 9, 2010, Pages 1433-1441

  Merckel, Fabien ^a   Bernard, Guillaume ^a   Mutschler, Julien ^a   Giménez Arnau, Elena ^a   Gerberick, G Frank ^b   Lepoittevin, Jean Pierre ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b PROCTER AND GAMBLE COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ALCOHOL; ALDEHYDE; BUFFER; CHLOROFORM; CITRAL; DODECYLBENZENESULFONATE SODIUM; GLUTATHIONE; HAPTEN; HYDROXYCITRONELLAL; NUCLEOPHILE; PEPTIDE; TERT BUTYL ALCOHOL;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; HYDROPHOBICITY; IN VITRO STUDY; MICHAEL ADDITION; MICROEMULSION; NUCLEAR MAGNETIC RESONANCE; SKIN SENSITIZATION; SOLUBILITY;

ACETONITRILES; CARBON ISOTOPES; CHLOROFORM; EMULSIONS; GLUTATHIONE; HAPTENS; KINETICS; MONOTERPENES; PERFUME; SKIN; SOLUBILITY; SULFHYDRYL COMPOUNDS; TERPENES; TERT-BUTYL ALCOHOL; WATER;

EID: 77956928365     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100043b     Document Type: Article

References (38)

1. Russel, W. H. S. and Burch, R. L. (1959) The Principle of the Humane Experimental Technique, p 238, Methuen, London.
2. EEC (1967) EEC Council Directive 67/548/EEC on the approximation of the laws, regulations and administrative provisions relating to the classification, packaging and labeling of dangerous substances. Off. J. Eur. Commun. 196, 1-98.
3. EU (1999) Directive 1999/45/EC of the European Parliament and the Council of 31 May 1999 concerning the approximation of the laws, regulation and administrative provisions of the Member States relating to the classification, packaging and labeling of dangerous preparations. Off. J. Eur. Commun. L200, 1-68.
4. EC (2006) Regulation (EC) No 1907/2006 of the European Parliament and of the Council of the 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency. Off. J. Eur. Union L396, 1-849.
5. 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. Off. J. Eur. Union L66, 26-35.
6. Magnusson, B. and Kligman, A. M. (1970) Allergic Contact Dermatitis in the Guinea Pig pp 141, Charles C. Thomas, Springfield, IL.
7. Buehler, E. V. (1965) Delayed contact hypersensitivity in the guinea pig Arch. Dermatol. 91, 171-177
8. Kimber, I. and Basketter, D. A. (1992) The murine local lymph node assay; collaborative studies and new directions: A commentary Food Chem. Toxicol. 30, 165-169
9. Casati, S., Aeby, P., Basketter, D. A., Cavani, A., Gennari, A., Gerberick, G. F., Griem, P., Hartung, T., Kimber, I., Lepoittevin, J.-P., Meade, B. J., Pallardy, M., Rougier, N., Rousset, F., Rubinstenn, G., Sallusto, F., Verheyen, G. R., and Zuang, V. (2005) Dendritic cells as a tool for the predictive identification of skin sensitization hazard Altern. Lab. Anim. 33, 47-62
10. Gerberick, G. F., Aleksic, M., Basketter, D. A., Casati, S., Karlberg, A.-T., Kern, P., Kimber, I., Lepoittevin, J.-P., Natsch, A., Ovigne, J.-M., Rovida, C., Sakagushi, H., and Schultz, T. (2008) Chemical reactivity measurement and the predictive identification of skin sensitizers Altern. Lab. Anim. 36, 215-242
11. Kato, H., Okamoto, M., Yamashita, K., Nakamura, Y., Fukumori, Y., Nakai, K., and Kaneko, H. (2003) Peptide-binding assessment using mass spectrometry as a new screening method for skin sensitization J. Toxicol. Sci. 28, 19-24
12. Schultz, T. W., Yarbrough, J. W., and Johnson, E. L. (2005) Structure-activity relationships for reactivity of carbonyl-containing compounds with glutathione SAR QSAR Environ. Res. 16, 313-322
13. Aptula, A. O., Patlewicz, G., Roberts, D. W., and Schultz, T. W. (2006) Non-enzymatic glutathione reactivity and in vitro toxicity: a non-animal approach to skin sensitization Toxicol. in Vitro 20, 239-247
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
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
16. Natsch, A. and Gfeller, H. (2008) LC-MS-based characterization of peptide reactivity of chemicals to improve the in vitro prediction of skin sensitization potential Toxicol. Sci. 106, 464-478
17. Kimber, I., Basketter, D. A., Butler, M., Gamer, A., Garrigue, J.-L., Gerberick, G. F., Newsome, C., Steiling, W., and Vohr, H. W. (2003) Classification of contact allergens according to potency: proposals Food Chem. Toxicol. 41, 1799-1809
18. Schwuger, M. J. and Stickdorn, K. (1995) Microemulsions in technical processes Chem. Rev. 95, 849-864
19. Holmberg, K. (2007) Organic reactions in microemulsions Eur. J. Org. Chem. 731-742
20. Paul, B. K. and Moulik, S. P. (2001) Uses and applications of microemulsions Curr. Sci. 80, 990-1001
21. Menger, F. M. and Elrington, A. R. (1991) Organic reactivity in microemulsion systems J. Am. Chem. Soc. 113, 9621-9624
22. Frosch, P. J., Pirker, C., Rastogi, S., Andersen, K. E., Bruze, M., Svedman, C., Goossens, A., White, I., Uter, W., Giménez-Arnau, E., Lepoittevin, J.-P., Johansen, J. D., and Menné, T. (2005) Patch testing with a new fragrance mix detects additional patients sensitive to perfumes and missed by the current fragrance mix Contact Dermatitis 52, 207-215
23. Tanner, J. E. (1970) Use of stimulated echo in NMR diffusion studies J. Chem. Phys. 52, 2523-26
24. Cotts, R. M., Hoch, M. J. R., Sun, T., and Markert, J. T. (1989) Pulsed field gradient stimulated echo methods for improved NMR diffusion measurements in heterogeneous systems J. Magn. Reson. 83, 252-266
25. Delsuc, M. A. and Malliavin, T. E. (1998) Maximum entropy processing of DOSY NMR spectra Anal. Chem. 70, 2146-48
26. 13C]-hexane- 1,3-sultones to human serum albumin Chem. Res. Toxicol. 14, 118-126
27. Alvarez-Sanchez, R., Divkovic, M., Basketter, D., Pease, C., Panico, M., Dell, A., Morris, H., and Lepoittevin, J.-P. (2004) Effect of glutathione on the covalent binding of the 13C-labeled skin sensitizer 5-chloro-2- methylisothiazol-3-one (MCI) to human serum albumin: identification of adducts by NMR, MALDI-MS and nano-ES MS/MS Chem. Res. Toxicol. 17, 1280-1288
28. 13C]-dimethyl- para -benzoquinonediimine Chem. Res. Toxicol. 19, 1248-1256
29. Ahlfors, S. R., Sterner, O., and Hansson, C. (2003) Reactivity of contact allergenic haptens to amino acid residues in a model carrier peptide, and characterization of formed peptide-hapten adducts Skin Pharmacol. Appl. Skin Physiol. 16, 59-68
30. Bergstrom, M. A., Ott, H., Carlson, A., Neis, M., Zwadlo-Klarwasser, G., Jonsson, C. A., Merk, H. F., Karlberg, A.-T., and Baron, J. M. (2007) A skin-like cytochrome P450 cocktail activates prohaptens to contact allergenic metabolites J. Invest. Dermatol. 127, 1145-1153
31. 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
32. 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
33. Gonzalez, A. and Holt, S. L. (1981) Formation of macrocyclic lactones in microemulsions J. Org. Chem. 46, 2594-2596
34. Gonzalez, A. and Holt, S. L. (1982) Effect of microemulsions on the Diels-Alder reaction: Endo/exo ratios in the reaction of cyclopentadiene and methyl methacrylate J. Org. Chem. 47, 3186-3188
35. Sjoblom, J., Lindberg, R., and Friberg, S. E. (1996) Microemulsions: phase equilibria characterization, structures, applications and chemical reactions Adv. Colloid Interface Sci. 95, 125-287
36. 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 lymph node data for evaluation of skin sensitization alternative methods Dermatitis 16, 157-202
37. Andersen, K. E., White, I. R., and Goossens, A. (2006) In Contact Dermatitis (Frosch, P. J., Menné, T., and Lepoittevin, J.-P., Eds.) 5 th ed., pp 453-492, Springer, Berlin, Germany.
38. Alvarez-Sanchez, R., Basketter, D. A., Pease, C., and Lepoittevin, J.-P. (2004) Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2- methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione Bioorg. Med. Chem. Lett. 14, 365-368