Activation of promutagens by porphyrinic biomimetic systems

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Abstract

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.

Original languageEnglish
Pages (from-to)243-250
Number of pages8
JournalMutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
Volume269
Issue number2
DOIs
Publication statusPublished - 1992

Fingerprint

Biomimetics
Oxygen
Amines
tert-Butylhydroperoxide
2-amino-3-methylimidazo(4,5-f)quinoline
Mutagens
Cytochrome P-450 Enzyme System
2-Acetylaminofluorene
Methylcholanthrene
Benzo(a)pyrene
Polycyclic Aromatic Hydrocarbons
Quercetin
Heme
Carcinogens
Chlorides
Metals

Keywords

  • Ames assay
  • Biomimetic systems
  • Carcinogen activation
  • Oxidative activation

Cite this

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title = "Activation of promutagens by porphyrinic biomimetic systems",
abstract = "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.",
keywords = "Ames assay, Biomimetic systems, Carcinogen activation, Oxidative activation",
author = "J. Rueff and A. Rodrigues and A. Laires and J. Gaspar",
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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

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U2 - 10.1016/0027-5107(92)90206-H

DO - 10.1016/0027-5107(92)90206-H

M3 - Article

VL - 269

SP - 243

EP - 250

JO - Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

JF - Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis

SN - 0027-5107

IS - 2

ER -