Mercaptobenzothiazole allergenicity-role of the thiol group.

Article Details

Citation
Copy to clipboard

Chipinda I, Zhang XD, Simoyi RH, Siegel PD

Mercaptobenzothiazole allergenicity-role of the thiol group.

Cutan Ocul Toxicol. 2008;27(2):103-16. doi: 10.1080/15569520701713008.

PubMed ID
18568896 [ View in PubMed
]
Abstract

The rubber accelerator, 2-mercaptobenzothiazole (MBT), is known to cause allergic contact dermatitis (ACD), but the mechanism is unknown. The role of the thiol group in MBT's allergenicity was investigated in the present study. Guinea pigs were sensitized to MBT using a modified guinea pig maximization test (GPMT) and reactivity was assessed toward 2-mercaptobenzothiazole disulfide (MBTS), 2-hydroxybenzothiazole (HBT; thiol-substituted), 2-(methylthio)benzothiazole (MTBT; thiol-blocked), and benzothiazole (BT; thiol-lacking). MBT and MBTS, but not BT, HBT, or MTBT, elicited ACD in MBT-sensitized animals, demonstrating that the thiol group is critical to MBT's allergenicity. In addition, both MBT and MBTS were shown to inhibit both glutathione reductase and thioredoxin reductase, and thus contribute to the stability of MBT-protein mixed disulfides. It is concluded that the probable haptenation mechanism of MBT is through initial oxidation to MBTS with subsequent reduction to form mixed disulfides with proteins.

DrugBank Data that Cites this Article

Drugs