Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests

Natsch, Andreas; Emter, Roger; Badertscher, Remo P.; Brunner, Gerhard; Granier, Thierry; Kern, Susanne; Ellis, Graham

doi:10.1021/acs.chemrestox.5b00039

Publication type:	Article in scientific journal
Type of review:	Peer review (publication)
Title:	Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests
Authors:	Natsch, Andreas Emter, Roger Badertscher, Remo P. Brunner, Gerhard Granier, Thierry Kern, Susanne Ellis, Graham
et. al:	No
DOI:	10.1021/acs.chemrestox.5b00039
Published in:	Chemical Research in Toxicology
Volume(Issue):	28
Issue:	6
Page(s):	1205
Pages to:	1208
Issue Date:	15-Jun-2015
Publisher / Ed. Institution:	American Chemical Society
ISSN:	0893-228X 1520-5010
Language:	English
Subjects:	Hydrogen peroxide; Molecular structure; Oxidation-reduction; Tryptophan; Diagnostic test, routine
Subject (DDC):	540: Chemistry
Abstract:	Hydroperoxides can act as specific haptens and oxidatively modify proteins. Terpene hydroperoxides trigger unusually high frequencies of positive skin reactions in human patients if tested at high concentrations. It is unknown whether this is due to specific hapten formation. Here, we show that both terpene hydroperoxides and the endogenous hydroperoxide formed from squalene can oxidatively modify tryptophan. Oxidative modifications of Trp were recently postulated to explain cross-sensitization between unrelated photosensitizers. Current observations may extend this hypothesis: Oxidative events triggered by endogenous hydroperoxides and hydroperoxides/oxidants derived from xenobiotics might lead to a sensitized state detected by patch tests with high concentrations of hydroperoxides.
URI:	https://digitalcollection.zhaw.ch/handle/11475/23984
Fulltext version:	Published version
License (according to publishing contract):	Licence according to publishing contract
Departement:	Life Sciences and Facility Management
Organisational Unit:	Institute of Chemistry and Biotechnology (ICBT)
Appears in collections:	Publikationen Life Sciences und Facility Management

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Natsch, A., Emter, R., Badertscher, R. P., Brunner, G., Granier, T., Kern, S., & Ellis, G. (2015). Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests. Chemical Research in Toxicology, 28(6), 1205–1208. https://doi.org/10.1021/acs.chemrestox.5b00039

Natsch, A. et al. (2015) ‘Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests’, Chemical Research in Toxicology, 28(6), pp. 1205–1208. Available at: https://doi.org/10.1021/acs.chemrestox.5b00039.

A. Natsch et al., “Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests,” Chemical Research in Toxicology, vol. 28, no. 6, pp. 1205–1208, Jun. 2015, doi: 10.1021/acs.chemrestox.5b00039.

NATSCH, Andreas, Roger EMTER, Remo P. BADERTSCHER, Gerhard BRUNNER, Thierry GRANIER, Susanne KERN und Graham ELLIS, 2015. Oxidative tryptophan modification by terpene- and squalene-hydroperoxides and a possible link to cross-reactions in diagnostic tests. Chemical Research in Toxicology. 15 Juni 2015. Bd. 28, Nr. 6, S. 1205–1208. DOI 10.1021/acs.chemrestox.5b00039

Natsch, Andreas, Roger Emter, Remo P. Badertscher, Gerhard Brunner, Thierry Granier, Susanne Kern, and Graham Ellis. 2015. “Oxidative Tryptophan Modification by Terpene- and Squalene-Hydroperoxides and a Possible Link to Cross-Reactions in Diagnostic Tests.” Chemical Research in Toxicology 28 (6): 1205–8. https://doi.org/10.1021/acs.chemrestox.5b00039.

Natsch, Andreas, et al. “Oxidative Tryptophan Modification by Terpene- and Squalene-Hydroperoxides and a Possible Link to Cross-Reactions in Diagnostic Tests.” Chemical Research in Toxicology, vol. 28, no. 6, June 2015, pp. 1205–8, https://doi.org/10.1021/acs.chemrestox.5b00039.