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Chemical mechanisms for skin sensitization by aromatic compounds with hydroxy and amino groups.

Abstract：

:It is well-known that aromatic diamino-, dihydroxy-, and amino-hydroxy compounds, with NH(2) and OH groups in ortho- or para-positions relative to each other, are strong skin sensitizers. In this paper, we analyze published potency and cross-reactivity data, whereby animals sensitized to one of these compounds are challenged with other compounds. The data are consistent with two parallel chemical reaction mechanisms: oxidation to electrophilic (protein reactive) quinones or quinone imines or formation of protein-reactive free radicals such as the Wurster salt, which can be formed by para-phenylene diamine. Compounds with NH(2) and OH groups meta to each other have also been found to be skin sensitizers, in some cases quite strong sensitizers. For these compounds, direct formation of quinones or quinone imines is not possible, and free radicals of the Wurster salt type are not favored. Here, we present a molecular mechanism to rationalize the sensitization potential of such compounds and, using the results of quantum mechanics calculations, show how this mechanism can explain observed structure-potency trends.

journal_name

Chem Res Toxicol

journal_title

Chemical research in toxicology

authors

Aptula AO,Enoch SJ,Roberts DW

doi

10.1021/tx9000336

subject

Has Abstract

pub_date

2009-09-01 00:00:00

pages

1541-7

issue

9

eissn

0893-228X

issn

1520-5010

journal_volume

22

pub_type

杂志文章

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