Oxidation of 2-Mercaptobenzothiazole in Latex Gloves and Its Possible Haptenation Pathway

Details

• Personal Author:
  Chipinda I ; Hettick JM ; Siegel, Paul D. ; Simoyi RH
• Description:
  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. [Description provided by NIOSH]
• Subjects:
  Dermatitis Enzymes Epoxy Compounds Hypersensitivity Mass Spectrometry Occupational Health Personal Protective Equipment Safety Skin Sulfhydryl Compounds
• Keywords:
  Allergies Enzyme-activity Epoxides Gloves Immune-system Mass-spectrometry Mercaptans Oxidation Personal-protective-equipment Proteins Skin-exposure Skin-irritants Thiols

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• ISSN:
  0893-228X
• Document Type:
  Text
• Genre:
  Journal Article
• Place as Subject:
  Oregon ; OSHA Region 10 ; OSHA Region 3 ; West Virginia
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Division:
  HELD - Health Effects Laboratory Division
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Volume:
  20
• Issue:
  8
• NIOSHTIC Number:
  nn:20032359
• Citation:
  Chem Res Toxicol 2007 Aug; 20(8):1084-1092
• Contact Point Address:
  National Institute for Occupational Safety and Health, Health Effects Laboratory Division, Allergy and Clinical Immunology Branch, 1095 Willowdale Road, Morgantown, West Virginia 26505-2888
• CAS Registry Number:
  2-Mercaptobenzothiazole (CAS RN 149-30-4) ; Accelerator DM (CAS RN 120-78-5) ; Propionic acid (CAS RN 79-09-4)
• Federal Fiscal Year:
  2007
• Peer Reviewed:
  True
• Source Full Name:
  Chemical Research in Toxicology
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:c1fdc9e9093fc66af1b71628670274013c45d12c08c386ab83667a31a56c324ee38435d9d110da0e6afa10c1893fea7ca31999da412b1ebe7ac367619e8dbab2
• Download URL:
  https://stacks.cdc.gov/view/cdc/186371/cdc_186371_DS1.pdf
• File Type:
  [PDF - 539.50 KB ]