Sensitization to p-amino aromatic compounds: Study of the covalent binding of 2,5-dimethyl-p-benzoquinonediimine to a model peptide by electrospray ionization tandem mass spectrometry

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 10, 2008, Pages 5482-5489

  Eilstein, Joan ^a   Giménez Arnau, Elena ^a   Duché, Daniel ^b   Cavusoglu, Nükhet ^b   Hussler, Georges ^b   Rousset, Françoise ^b   Lepoittevin, Jean Pierre ^a  

^a UNIVERSITY HOSPITAL OF STRASBOURG   (France)

^b L ORÉAL RECHERCHE   (France)

Author keywords

Lysine; p Benzoquinonediimine; Peptide binding; Skin sensitization

Indexed keywords

2,5 DIMETHYL 4 BENZOQUINONEDIIMINE; ALDEHYDE DERIVATIVE; AMINE; AMINOADIPIC ACID; AROMATIC COMPOUND; BENZOQUINONE DERIVATIVE; IMINE; LYSINE; PEPTIDE; SCHIFF BASE;

ALLERGENICITY; AMINO ACID SEQUENCE; ARTICLE; CHEMICAL MODIFICATION; COVALENT BOND; CYCLIZATION; DEAMINATION; ELECTROSPRAY MASS SPECTROMETRY; HAPTEN CARRIER COMPLEX; LIQUID CHROMATOGRAPHY; OXIDATION REDUCTION REACTION; PROTEIN DEGRADATION; SENSITIZATION; SKIN ALLERGY; TANDEM MASS SPECTROMETRY;

BINDING SITES; CHROMATOGRAPHY, LIQUID; DERMATITIS, CONTACT; HAPTENS; IMINES; KINETICS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; TIME FACTORS;

EID: 43749105351     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.014     Document Type: Article

References (22)

1. Rustemeyer T., van Hoogstraten I.M.W., von Blomberg B.M.E., and Scheper R.J. In: Frosch P.J., Menné T., and Lepoittevin J.-P. (Eds). Contact Dermatitis (2006), Springer-Verlag, Berlin, Heidelberg, New York 11-43
2. Lepoittevin J.-P. In: Frosch P.J., Menné T., and Lepoittevin J.-P. (Eds). Contact Dermatitis (2006), Springer-Verlag, Berlin, Heidelberg, New York 45-68
3. Merk H.F. In: Lepoittevin J.-P., Basketter D.A., Goossens A., and Karlberg A.-T. (Eds). Allergic Contact Dermatitis: The Molecular Basis (1998), Springer-Verlag, Berlin, Heidelberg, New York 68-80
4. Dupuis G. Br. J. Dermatol. 101 (1979) 617
5. Karlberg A.-T., Basketter D.A., Goossens A., and Lepoittevin J.-P. Contact Dermatitis 40 (1999) 183
6. Matura M., Sköld M., Börje A., Andersen K.E., Bruze M., Frosch P., Goossens A., Johansen J.D., Svedman C., White I.R., and Karlberg A.-T. Contact Dermatitis 52 (2005) 320
7. Le Coz C.J., Lefebvre C., Keller F., and Grosshans E. Arch. Dermatol. 136 (2000) 1515
8. Matulich J., and Sullivan J. Contact Dermatitis 53 (2005) 33
9. th plenary meeting of 27 February 2002. Available athttp://europa.eu.int/comm/health/ph_risk/committees/sccp/sccp_opinions_en.htm.
10. Gerberick G.F., Robinson M.K., Ryan C.A., Dearman R.J., Kimber I., Basketter D.A., Wright Z., and Marks J.G. Am. J. Contact Dermat. 12 (2001) 156
11. Mayer R.L. Progr. Allergy 4 (1954) 79
12. Lisi P., and Hansel K. Contact Dermatitis 39 (1998) 304
13. Eilstein J., Giménez-Arnau E., Duché D., Rousset F., and Lepoittevin J.-P. Chem. Res. Toxicol. 19 (2006) 1248
14. Eilstein J., Giménez-Arnau E., Duché D., Rousset F., and Lepoittevin J.-P. Chem. Res. Toxicol. 20 (2007) 1155
15. Meschkat E., Barrat M.D., and Lepoittevin J.-P. Chem. Res. Toxicol. 14 (2001) 118
16. Alvarez-Sánchez R., Basketter D., Pease C., and Lepoittevin J.-P. Bioorg. Med. Chem. Lett. 14 (2004) 365
17. Gerberick F.G., Vassallo J.D., Bailey R.E., Chaney J.G., Morrall S.W., and Lepoittevin J.-P. Toxicol. Sci. 81 (2004) 332
18. Kagan H.M., and Li W. J. Cell Biochem. 88 (2003) 660
19. Rinaldi A.C., Rescigno A., Rinaldi A., and Sanjust E. Bioorg. Chem. 27 (1999) 253
20. Requena J.R., Chao C.-C., Levine R.L., and Stadtman E.R. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 69
21. Medda R., Mura A., Longu S., Anedda R., Padiglia A., Casu M., and Floris G. Biochimie 88 (2006) 827
22. Smith-Mungo L.I., and Kagan H.M. Matrix Biol. 16 (1998) 387