Inhibitory effect of hemin, chlorophyllin and related pyrrole pigments on the mutagenicity of benzo[a]pyrene and its metabolites

Sakae Arimoto, Kazuko Kan-yama, Haruki Rai, Hikoya Hayatsu

Research output: Contribution to journalArticle

34 Citations (Scopus)

Abstract

Hemin and chlorophyllin are known to inhibit strongly the mutagenicity of benzo[a]pyrene in the Salmonella assay. To further investigate this phenomenon, a series of these pyrrole pigments including pure samples of Cu- and Fe-chlorins were tested for their potency to inhibit the mutagenicity of benzo[a]pyrene and its metabolites, benzo[a]pyrene-7,8-diol, benzo[a]pyrene4,5-epoxide, and benzo[a]pyrene-7,8-diol-9,10-epoxide. Hemin was the most potent amongthe pigments tested for these inhibitions. Both hemin and Cu-chlorin accelerated efficiently the degradation of benzo[a]pyrene-7,8-diol-9,10-epoxide, and this acceleration seemed to be the predominant mechanism by which these pigments inhibit the overall mutagenicity of benzo[a]pyrene in Salmonella. Based on spectroscopic evidence, we speculate that a complex formation between hemin and benzo[a]pyrene-7,8-diol-9,10-epoxide takes place and that this complexing is the cause of the accelerated degradation.

Original languageEnglish
Pages (from-to)127-135
Number of pages9
JournalMutation Research/Genetic Toxicology
Volume345
Issue number3-4
DOIs
Publication statusPublished - 1995

Fingerprint

Hemin
Pyrroles
Benzo(a)pyrene
7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
Metabolites
Pigments
Salmonella
Degradation
Epoxy Compounds
Assays
chlorophyllin

Keywords

  • 3-hydroxybenzo[a]pyrene
  • 3-OH-BP
  • 4,5-dihydrobenzo[a]pyrene-4,5-epoxide
  • Antimutagenicity
  • benzo[a]pyrene
  • Benzo[a]pyrene
  • Benzo[a]pyrene-7,8-diol-9,10-epoxide
  • benzo[a]pyrene-trans-7,8-dihydrodiol
  • benzo[a]pyrene-trans-7,8-dihydrodiol-9,10-epoxide (anti)
  • BP
  • BP(4,5)E
  • BP(7,8)D
  • BP(7,8)D(9,10)E
  • Chlorin
  • Chlorophyllin
  • chlorophyllin Na lacking the central metal
  • copper chlorophyllin Na
  • Cu-chlorin
  • Fe-chlorin
  • Hemin
  • iron chlorophyllin Na

ASJC Scopus subject areas

  • Genetics
  • Toxicology

Cite this

Inhibitory effect of hemin, chlorophyllin and related pyrrole pigments on the mutagenicity of benzo[a]pyrene and its metabolites. / Arimoto, Sakae; Kan-yama, Kazuko; Rai, Haruki; Hayatsu, Hikoya.

In: Mutation Research/Genetic Toxicology, Vol. 345, No. 3-4, 1995, p. 127-135.

Research output: Contribution to journalArticle

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abstract = "Hemin and chlorophyllin are known to inhibit strongly the mutagenicity of benzo[a]pyrene in the Salmonella assay. To further investigate this phenomenon, a series of these pyrrole pigments including pure samples of Cu- and Fe-chlorins were tested for their potency to inhibit the mutagenicity of benzo[a]pyrene and its metabolites, benzo[a]pyrene-7,8-diol, benzo[a]pyrene4,5-epoxide, and benzo[a]pyrene-7,8-diol-9,10-epoxide. Hemin was the most potent amongthe pigments tested for these inhibitions. Both hemin and Cu-chlorin accelerated efficiently the degradation of benzo[a]pyrene-7,8-diol-9,10-epoxide, and this acceleration seemed to be the predominant mechanism by which these pigments inhibit the overall mutagenicity of benzo[a]pyrene in Salmonella. Based on spectroscopic evidence, we speculate that a complex formation between hemin and benzo[a]pyrene-7,8-diol-9,10-epoxide takes place and that this complexing is the cause of the accelerated degradation.",
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T1 - Inhibitory effect of hemin, chlorophyllin and related pyrrole pigments on the mutagenicity of benzo[a]pyrene and its metabolites

AU - Arimoto, Sakae

AU - Kan-yama, Kazuko

AU - Rai, Haruki

AU - Hayatsu, Hikoya

PY - 1995

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N2 - Hemin and chlorophyllin are known to inhibit strongly the mutagenicity of benzo[a]pyrene in the Salmonella assay. To further investigate this phenomenon, a series of these pyrrole pigments including pure samples of Cu- and Fe-chlorins were tested for their potency to inhibit the mutagenicity of benzo[a]pyrene and its metabolites, benzo[a]pyrene-7,8-diol, benzo[a]pyrene4,5-epoxide, and benzo[a]pyrene-7,8-diol-9,10-epoxide. Hemin was the most potent amongthe pigments tested for these inhibitions. Both hemin and Cu-chlorin accelerated efficiently the degradation of benzo[a]pyrene-7,8-diol-9,10-epoxide, and this acceleration seemed to be the predominant mechanism by which these pigments inhibit the overall mutagenicity of benzo[a]pyrene in Salmonella. Based on spectroscopic evidence, we speculate that a complex formation between hemin and benzo[a]pyrene-7,8-diol-9,10-epoxide takes place and that this complexing is the cause of the accelerated degradation.

AB - Hemin and chlorophyllin are known to inhibit strongly the mutagenicity of benzo[a]pyrene in the Salmonella assay. To further investigate this phenomenon, a series of these pyrrole pigments including pure samples of Cu- and Fe-chlorins were tested for their potency to inhibit the mutagenicity of benzo[a]pyrene and its metabolites, benzo[a]pyrene-7,8-diol, benzo[a]pyrene4,5-epoxide, and benzo[a]pyrene-7,8-diol-9,10-epoxide. Hemin was the most potent amongthe pigments tested for these inhibitions. Both hemin and Cu-chlorin accelerated efficiently the degradation of benzo[a]pyrene-7,8-diol-9,10-epoxide, and this acceleration seemed to be the predominant mechanism by which these pigments inhibit the overall mutagenicity of benzo[a]pyrene in Salmonella. Based on spectroscopic evidence, we speculate that a complex formation between hemin and benzo[a]pyrene-7,8-diol-9,10-epoxide takes place and that this complexing is the cause of the accelerated degradation.

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