Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of hetrocyclic amines with hydrogen peroxide

Masaki Mifune, Daiki Hino, Hikaru Sugita, Akimasa Iwado, Youji Kitamura, Noriko Motohashi, Ikuko Tsukamoto, Yutaka Saito

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metaltetrakis( sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of MTSPPrs. Among six M-TSPP rs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f ]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.

Original languageEnglish
Pages (from-to)1006-1010
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume53
Issue number8
DOIs
Publication statusPublished - Aug 2005

Fingerprint

Anion Exchange Resins
Porphyrins
Hydrogen Peroxide
Peroxidase
Amines
Catalyst activity
Metals
Raphanus
Sodium Hypochlorite
Oxidation
Oxidants
Nuclear magnetic resonance
Catalysts

Keywords

  • Hetrocyclic amine
  • Metal-porphyrin
  • Oxidative reaction
  • Peroxidase-like activity

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of hetrocyclic amines with hydrogen peroxide. / Mifune, Masaki; Hino, Daiki; Sugita, Hikaru; Iwado, Akimasa; Kitamura, Youji; Motohashi, Noriko; Tsukamoto, Ikuko; Saito, Yutaka.

In: Chemical and Pharmaceutical Bulletin, Vol. 53, No. 8, 08.2005, p. 1006-1010.

Research output: Contribution to journalArticle

Mifune, Masaki ; Hino, Daiki ; Sugita, Hikaru ; Iwado, Akimasa ; Kitamura, Youji ; Motohashi, Noriko ; Tsukamoto, Ikuko ; Saito, Yutaka. / Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of hetrocyclic amines with hydrogen peroxide. In: Chemical and Pharmaceutical Bulletin. 2005 ; Vol. 53, No. 8. pp. 1006-1010.
@article{e9943960dc6545e99bc1e24b03e4d3ff,
title = "Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of hetrocyclic amines with hydrogen peroxide",
abstract = "To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metaltetrakis( sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of MTSPPrs. Among six M-TSPP rs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f ]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.",
keywords = "Hetrocyclic amine, Metal-porphyrin, Oxidative reaction, Peroxidase-like activity",
author = "Masaki Mifune and Daiki Hino and Hikaru Sugita and Akimasa Iwado and Youji Kitamura and Noriko Motohashi and Ikuko Tsukamoto and Yutaka Saito",
year = "2005",
month = "8",
doi = "10.1248/cpb.53.1006",
language = "English",
volume = "53",
pages = "1006--1010",
journal = "Chemical and Pharmaceutical Bulletin",
issn = "0009-2363",
publisher = "Pharmaceutical Society of Japan",
number = "8",

}

TY - JOUR

T1 - Peroxidase-like catalytic activity of anion-exchange resins modified with metal-porphyrins in oxidative reaction of hetrocyclic amines with hydrogen peroxide

AU - Mifune, Masaki

AU - Hino, Daiki

AU - Sugita, Hikaru

AU - Iwado, Akimasa

AU - Kitamura, Youji

AU - Motohashi, Noriko

AU - Tsukamoto, Ikuko

AU - Saito, Yutaka

PY - 2005/8

Y1 - 2005/8

N2 - To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metaltetrakis( sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of MTSPPrs. Among six M-TSPP rs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f ]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.

AB - To elucidate the peroxidase (POD)-like catalytic activity of anion-exchange resins modified with metaltetrakis( sulfophenyl)porphine (M-TSPPrs), an oxidative reaction of seven mutagenic heterocyclic amines (HCAs) with hydrogen peroxide, which reaction is catalyzed by horse radish POD, was investigated in the presence of MTSPPrs. Among six M-TSPP rs tested, Mn- and Fe-TSPPrs were found to have a relatively strong POD-like activity for HCAs, in particular for a typical HCA, 2-amino-3-methyl-imidazo[4,5-f ]quinoline (IQ). The optimal condition for the POD-like activity was selected using Fe- and Mn-TSPPrs. For evaluation of an oxidation product of IQ produced in the presence of Fe-TSPPr, the absorption, NMR and FAB-mass spectra thereof were compared with those of an oxidation product of IQ produced by horse radish POD or a chemical oxidizing agent, sodium hypochlorite. When Fe-TSPPr was present as a catalysts, IQ was converted into the dimmer (hydorazone type) which has no mutagenic activity in umu-test. It was revealed that Fe- and Mn-TSPPrs exhibit a POD-like catalytic activity in oxidative reaction of HCAs with hydrogen peroxide.

KW - Hetrocyclic amine

KW - Metal-porphyrin

KW - Oxidative reaction

KW - Peroxidase-like activity

UR - http://www.scopus.com/inward/record.url?scp=24944559281&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=24944559281&partnerID=8YFLogxK

U2 - 10.1248/cpb.53.1006

DO - 10.1248/cpb.53.1006

M3 - Article

C2 - 16079536

AN - SCOPUS:24944559281

VL - 53

SP - 1006

EP - 1010

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 8

ER -