Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.

Naphthalene is a volatile polycyclic aromatic hydrocarbon generated during combustion and is a ubiquitous chemical in the environment. Short term exposures of rodents to air concentrations less than the current OSHA standard yielded necrotic lesions in the airways and nasal epithelium of the mouse,...

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Autores principales:	Nathalie T Pham, William T Jewell, Dexter Morin, A Daniel Jones, Alan R Buckpitt
Formato:	article
Lenguaje:	EN
Publicado:	Public Library of Science (PLoS) 2012
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/6359ec9c9d5d4f6f9fe69df6cf3f1eb0
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spelling	oai:doaj.org-article:6359ec9c9d5d4f6f9fe69df6cf3f1eb02021-11-18T07:09:50ZCharacterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.1932-620310.1371/journal.pone.0042053https://doaj.org/article/6359ec9c9d5d4f6f9fe69df6cf3f1eb02012-01-01T00:00:00Zhttps://www.ncbi.nlm.nih.gov/pmc/articles/pmid/22870282/?tool=EBIhttps://doaj.org/toc/1932-6203Naphthalene is a volatile polycyclic aromatic hydrocarbon generated during combustion and is a ubiquitous chemical in the environment. Short term exposures of rodents to air concentrations less than the current OSHA standard yielded necrotic lesions in the airways and nasal epithelium of the mouse, and in the nasal epithelium of the rat. The cytotoxic effects of naphthalene have been correlated with the formation of covalent protein adducts after the generation of reactive metabolites, but there is little information about the specific sites of adduction or on the amino acid targets of these metabolites. To better understand the chemical species produced when naphthalene metabolites react with proteins and peptides, we studied the formation and structure of the resulting adducts from the incubation of model peptides with naphthalene epoxide, naphthalene diol epoxide, 1,2-naphthoquinone, and 1,4-naphthoquinone using high resolution mass spectrometry. Identification of the binding sites, relative rates of depletion of the unadducted peptide, and selectivity of binding to amino acid residues were determined. Adduction occurred on the cysteine, lysine, and histidine residues, and on the N-terminus. Monoadduct formation occurred in 39 of the 48 reactions. In reactions with the naphthoquinones, diadducts were observed, and in one case, a triadduct was detected. The results from this model peptide study will assist in data interpretation from ongoing work to detect peptide adducts in vivo as markers of biologic effect.Nathalie T PhamWilliam T JewellDexter MorinA Daniel JonesAlan R BuckpittPublic Library of Science (PLoS)articleMedicineRScienceQENPLoS ONE, Vol 7, Iss 8, p e42053 (2012)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Nathalie T Pham William T Jewell Dexter Morin A Daniel Jones Alan R Buckpitt Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
description	Naphthalene is a volatile polycyclic aromatic hydrocarbon generated during combustion and is a ubiquitous chemical in the environment. Short term exposures of rodents to air concentrations less than the current OSHA standard yielded necrotic lesions in the airways and nasal epithelium of the mouse, and in the nasal epithelium of the rat. The cytotoxic effects of naphthalene have been correlated with the formation of covalent protein adducts after the generation of reactive metabolites, but there is little information about the specific sites of adduction or on the amino acid targets of these metabolites. To better understand the chemical species produced when naphthalene metabolites react with proteins and peptides, we studied the formation and structure of the resulting adducts from the incubation of model peptides with naphthalene epoxide, naphthalene diol epoxide, 1,2-naphthoquinone, and 1,4-naphthoquinone using high resolution mass spectrometry. Identification of the binding sites, relative rates of depletion of the unadducted peptide, and selectivity of binding to amino acid residues were determined. Adduction occurred on the cysteine, lysine, and histidine residues, and on the N-terminus. Monoadduct formation occurred in 39 of the 48 reactions. In reactions with the naphthoquinones, diadducts were observed, and in one case, a triadduct was detected. The results from this model peptide study will assist in data interpretation from ongoing work to detect peptide adducts in vivo as markers of biologic effect.
format	article
author	Nathalie T Pham William T Jewell Dexter Morin A Daniel Jones Alan R Buckpitt
author_facet	Nathalie T Pham William T Jewell Dexter Morin A Daniel Jones Alan R Buckpitt
author_sort	Nathalie T Pham
title	Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
title_short	Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
title_full	Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
title_fullStr	Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
title_full_unstemmed	Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
title_sort	characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.
publisher	Public Library of Science (PLoS)
publishDate	2012
url	https://doaj.org/article/6359ec9c9d5d4f6f9fe69df6cf3f1eb0
work_keys_str_mv	AT nathalietpham characterizationofmodelpeptideadductswithreactivemetabolitesofnaphthalenebymassspectrometry AT williamtjewell characterizationofmodelpeptideadductswithreactivemetabolitesofnaphthalenebymassspectrometry AT dextermorin characterizationofmodelpeptideadductswithreactivemetabolitesofnaphthalenebymassspectrometry AT adanieljones characterizationofmodelpeptideadductswithreactivemetabolitesofnaphthalenebymassspectrometry AT alanrbuckpitt characterizationofmodelpeptideadductswithreactivemetabolitesofnaphthalenebymassspectrometry
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Characterization of model peptide adducts with reactive metabolites of naphthalene by mass spectrometry.

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