Sensitization to p-amino aromatic compounds: study of the covalent binding of 2, 5-dimethyl-p-benzoquinonediimine to a model peptide by electrospray ionization …

J Eilstein, E Giménez-Arnau, D Duché… - Bioorganic & medicinal …, 2008 - Elsevier
To understand the hapten–protein complex formation in the context of skin contact allergy to
p-amino aromatic derivatives, 2, 5-dimethyl-p-benzoquinonediimine was used as a model …

A Mechanistic Investigation into the Irreversible Protein Binding and Antigenicity of p-Phenylenediamine

C Jenkinson, RE Jenkins, JL Maggs… - Chemical research in …, 2009 - ACS Publications
Exposure to the skin sensitizer p-phenylenediamine (PPD) is associated with allergic
contact dermatitis; however, the ability of PPD to modify protein has not been fully …

Synthesis and Reactivity Toward Nucleophilic Amino Acids of 2,5-[13C]-Dimethyl-p-benzoquinonediimine

J Eilstein, E Giménez-Arnau, D Duché… - Chemical research in …, 2006 - ACS Publications
2, 5-[13C]-Dimethyl-p-benzoquinonediimine was synthesized, and its reactivity toward
several nucleophilic amino acids was studied by associated 13C and 1H {13C} NMR …

Reactivity profiling: Covalent modification of single nucleophile peptides for skin sensitization risk assessment

M Aleksic, E Thain, D Roger, O Saib… - Toxicological …, 2009 - academic.oup.com
The molecular basis of chemical allergy is rooted in the ability of an allergen (hapten) to
modify endogenous proteins. This mechanistic understanding aided development of …

Mechanistic Studies on the Lysine-Induced N-Formylation of 2,5-Dimethyl-p-benzoquinonediimine

J Eilstein, E Giménez-Arnau, D Duché… - Chemical research in …, 2007 - ACS Publications
2, 5-Dimethyl-p-benzoquinonediimine was used as a model to study the reactivity of p-
benzoquinonediimines, the first oxidation intermediates of allergenic p-amino aromatic …

Chemical reactivity and skin sensitization potential for benzaldehydes: can Schiff base formation explain everything?

A Natsch, H Gfeller, T Haupt… - Chemical Research in …, 2012 - ACS Publications
Skin sensitizers chemically modify skin proteins rendering them immunogenic. Sensitizing
chemicals have been divided into applicability domains according to their suspected …

Electrochemistry/liquid chromatography/mass spectrometry to demonstrate irreversible binding of the skin allergen p‐phenylenediamine to proteins

S Jahn, H Faber, R Zazzeroni… - … Communications in Mass …, 2012 - Wiley Online Library
RATIONALE para‐Phenylenediamine (PPD) is a potent and well‐known allergen, which is
commonly used in hair or fur dyes and can cause severe allergic contact dermatitis. In this …

LC-MS–Based Characterization of the Peptide Reactivity of Chemicals to Improve the In Vitro Prediction of the Skin Sensitization Potential

A Natsch, H Gfeller - Toxicological Sciences, 2008 - academic.oup.com
A key step in the skin sensitization process is the formation of a covalent adduct between
skin sensitizers and endogenous proteins and/or peptides in the skin. Based on this …

Adducts between nucleophilic amino acids and hexahydrophthalic anhydride, a structure inducing both types I and IV allergy

SR Ahlfors, MH Kristiansson, CH Lindh, BAG Jönsson… - Biomarkers, 2005 - Taylor & Francis
Haptens causing type I allergy have been shown to predominantly form lysine adducts in the
carrier protein, while many haptens giving rise to type IV allergy preferentially form adducts …

Mass spectrometric identification of covalent adducts of the skin allergen 2, 4-dinitro-1-chlorobenzene and model skin proteins

M Aleksic, CK Pease, DA Basketter, M Panico… - Toxicology in vitro, 2008 - Elsevier
A large proportion of allergic skin reactions are considered to be the result of skin exposure
to small organic chemicals that possess the intrinsic ability to covalently modify skin proteins …