TY - JOUR
T1 - Activation of promutagens by porphyrinic biomimetic systems
AU - Rueff, J.
AU - Rodrigues, A.
AU - Laires, A.
AU - Gaspar, J.
PY - 1992
Y1 - 1992
N2 - Biomimetic oxidative systems using tetraarylporphyrins, which can bind various metals, and exogenous oxygen donors have been extensively studied as models of the natural heme prosthetic group. Those systems were shown to catalyze oxidations in a manner consistent with cytochromes P-450 and usefully contributed to an understanding of the mechanisms of the cytochromes P-450-dependent reactions when using oxygen donors. The usage of those systems in mutagenicity studies showed that some promutagens could be activated to proximate mutagens. In the present work we report on the activation of benzo[a]pyrene, 3-methylcholanthrene, 7,12-dimethylbenz[a]anthracene; 2-aminofluorene, 2-acetylaminofluorene and the heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to Ames assay mutagens using tetraphenylporphinatoiron(III) chloride and various oxygen donors, namely iodosylbenzene, cumene hydroperoxide, tert-butylhydroperoxide and H2O2. Our results demonstrate that IQ could be activated using any of the oxygen donors. However, a pattern of specificity for the oxygen donor could be identified. Polycyclic aromatic hydrocarbons displayed higher levels of mutagenicity with iodosylbenzene, whereas aromatic amines were preferentially activated when tert-butylhydroperoxide was used. For the heterocyclic amine IQ the higher responses were obtained using cumene hydroperoxide. The putative non-carcinogen pyrene and the controversial carcinogen quercetin were not activated irrespective of the oxygen donor used.
AB - Biomimetic oxidative systems using tetraarylporphyrins, which can bind various metals, and exogenous oxygen donors have been extensively studied as models of the natural heme prosthetic group. Those systems were shown to catalyze oxidations in a manner consistent with cytochromes P-450 and usefully contributed to an understanding of the mechanisms of the cytochromes P-450-dependent reactions when using oxygen donors. The usage of those systems in mutagenicity studies showed that some promutagens could be activated to proximate mutagens. In the present work we report on the activation of benzo[a]pyrene, 3-methylcholanthrene, 7,12-dimethylbenz[a]anthracene; 2-aminofluorene, 2-acetylaminofluorene and the heterocyclic amine 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) to Ames assay mutagens using tetraphenylporphinatoiron(III) chloride and various oxygen donors, namely iodosylbenzene, cumene hydroperoxide, tert-butylhydroperoxide and H2O2. Our results demonstrate that IQ could be activated using any of the oxygen donors. However, a pattern of specificity for the oxygen donor could be identified. Polycyclic aromatic hydrocarbons displayed higher levels of mutagenicity with iodosylbenzene, whereas aromatic amines were preferentially activated when tert-butylhydroperoxide was used. For the heterocyclic amine IQ the higher responses were obtained using cumene hydroperoxide. The putative non-carcinogen pyrene and the controversial carcinogen quercetin were not activated irrespective of the oxygen donor used.
KW - Ames assay
KW - Biomimetic systems
KW - Carcinogen activation
KW - Oxidative activation
UR - http://www.scopus.com/inward/record.url?scp=0026675201&partnerID=8YFLogxK
U2 - 10.1016/0027-5107(92)90206-H
DO - 10.1016/0027-5107(92)90206-H
M3 - Article
C2 - 1383708
AN - SCOPUS:0026675201
SN - 0027-5107
VL - 269
SP - 243
EP - 250
JO - Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
JF - Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
IS - 2
ER -