Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway.

Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Research Abstract Details 

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Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Abstract Text:

Itai Chipinda,Justin M Hettick,Reuben H Simoyi,Paul D Siegel,

The rubber accelerator, 2-mercaptobenzothiazole (MBT), has been reported to cause allergic contact dermatitis from gloves and other rubber products, but its chemical fate when exposed to occupational oxidants and the mechanism of its pathogenesis are not known. It was hypothesized that the thiol group is critical to MBT's (its oxidation products or metabolites) covalent binding and/or haptenation to nucleophilic protein residues. Oxidative transformation of MBT to the disulfide 2,2'-dithiobis(benzothiazole) (MBTS) was observed within the glove matrix when hypochlorous acid, iodine, and hydrogen peroxide were used as oxidants. Cysteine reduced MBTS to MBT with subsequent formation of the mixed disulfide 2-amino-3-(benzothiazol-2-yl disulfanyl)propionic acid which was identified and characterized. Spectrophotometry and mass spectrometry experiments demonstrated the simultaneous reduction of MBTS and disulfide formation with Cys34 on bovine serum albumin, suggesting a potential route of protein haptenation through covalent bonding between protein cysteinyl residues and the MBT/MBTS thiol moiety. Metabolism of MBT using isoniazid and dexamethasone-induced rat liver microsomes, to give a protein reactive epoxide intermediate and provide an alternative protein haptenation mechanism, was not observed. The data suggest that the critical functional group on MBT is the thiol, and haptenation is via the formation of mixed disulfides between the thiol group on MBT and a protein sulfhydryl group.

Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Publishing Authors By Initials

I Chipinda,JM Hettick,RH Simoyi,PD Siegel,

For similar natural sciences: time: time factors research abstracts see: natural sciences: time: time factors research

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Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Journal Published:

PUBLICATION TYPE: Research Support, N.I.H., Extr

Journal: Chemical research in toxicology

VOLUME: 20

Page Numbers: 1084-92

Journal Abbreviation: Chem. Res. Toxicol.

ISSN: 0893-228X

DAY: 13

MONTH: 07

YEAR: 2007

Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Information

Number of References:

LANGUAGE: eng

NlmUniqueID: 8807448

Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Keywords Mesh Terms:

KEYWORDS: Time Factors

MESH TERMS: toxicity

Chemical & Substance for Abstract: Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Information

Substance Name: Cysteine

Registry Number: 52-90-4

Grant and Affiliation Information for Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway.

AFFILIATION: Allergy and Clinical Immunology Branch, Health Effects Laboratory Division, National Institute for Occupational Safety and Health, 1095 Willowdale Road, Morgantown, WV 26505-2888, USA.

Country: United States

AGENCY: United States NIEHS

GRANT: Y01 ES0001-06

ACRONYM: ES

MEDLINETA: Chem Res Toxicol

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