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Primary aromatic amines: their N-oxidative bioactivation

Walther-Straub-Institut für Pharmakologie und Toxikologie der Universität München, Nussbaumstrasse 26, D-80336 München

I. Golly

Hermes Arzneimittel GmbH, Georg-Kalb-Strasse 5-8, D-82049 Grosshesselohe, Germany

M. Lehnerer

Walther-Straub-Institut für Pharmakologie und Toxikologie der Universität München, Nussbaumstrasse 26, D-80336 München

J. Schulze

Walther-Straub-Institut für Pharmakologie und Toxikologie der Universität München, Nussbaumstrasse 26, D-80336 München

There exists a diversity of pathways in mammalian cells serving to activate primary aromatic amines.

1 N-Oxidative mixed-function turnover usually involves participation of the cytochrome P450 superfamily, while catalysis by the flavin-containing monooxy genases is restricted to a few amines capable of forming imine tautomers. Surprisingly, haemoglobin metabo lizes cytotoxic and carcinogenic arylamines via a monooxygenase-like mechanism, but peroxygenase activity is also operative.

2 In extrahepatic tissues that exhibit only a low level of monooxygenases, peroxidative transformations, as are brought about by prostaglandin H synthase, myeloperoxidase or lactoperoxidase, predominate in amine activation. Non-mammalian peroxidases fre quently used as model systems include horseradish peroxidase and chloroperoxidase.

3 Non-enzymatic, light-induced conversion of aromatic amines to free radical or N-oxy products proceeds either via direct photolysis of the nitrogenous com pounds or through attack by lipid-derived reactive intermediates generated during irradiation.

4 The interplay of the various tissue-specific processes of arylamine activation serves to explain differences in susceptibility toward the biological actions of primary aromatic amines.

Key Words: primary arylamines • N-oxygenation • enzymology • toxicity

Human & Experimental Toxicology, Vol. 16, No. 8, 441-448 (1997)
DOI: 10.1177/096032719701600805


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