Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene

Edmond J. LaVoie, Stephen S. Hecht, Shantilal Amin, Victoria Bedenko, Dietrich Hoffmann

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

The metabolism of the environmental agents benzo(j) fluoranthene and benzo(k)fluoranthene was investigated using supernatants from the livers of Aroclor 1254-pretreated rats, which are effective in activating benzo(j)fluoranthene and benzo(k)fluoranthene to metabolites mutagenic toward Sal monella typhimurium TA 100. Six bands of metabolites of benzo(j)fluoranthene were separated by high-pressure liquid chromatography, and each band was tested for mutagenicity toward S. typhimurium TA 100 with activation. The major mutagenic band contained two dihydrodiols, one of which was identified as 9,10-dihydro-9,10-dihydroxybenzoOfluoran-thene by comparison to a synthetic reference standard. 9 was mutagenic toward S. typhimurium TA 100 with activation, presumably as a result of conversion to the corresponding dihydrodiol-epoxide. The major dihydrodiol metabolite of benzo-fluoranthene was identified, by comparison to a synthetic standard, as 8,9-dihydro-8,9-dihydroxybenzof 8 This dihydrodiol, which could also be converted to a dihydrodiol-epoxide, was mutagenic toward S. typhimurium TA 100 with activation. The results of this study indicate that metabolism to dihydrodiols is one pathway in the activation of benzoOfluoranthene and benzof fluoranthene to ultimate mutagens for S. typhimurium TA 100.

Original languageEnglish (US)
Pages (from-to)4528-4532
Number of pages5
JournalCancer Research
Volume40
Issue number12
StatePublished - Dec 1 1980

Fingerprint

Epoxy Compounds
Chlorodiphenyl (54% Chlorine)
Mutagens
fluoranthene
trans-1,2-dihydro-1,2-naphthalenediol
High Pressure Liquid Chromatography
Liver
benzo(j)fluoranthene
benzo(k)fluoranthene

All Science Journal Classification (ASJC) codes

  • Oncology
  • Cancer Research

Cite this

LaVoie, E. J., Hecht, S. S., Amin, S., Bedenko, V., & Hoffmann, D. (1980). Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene. Cancer Research, 40(12), 4528-4532.
LaVoie, Edmond J. ; Hecht, Stephen S. ; Amin, Shantilal ; Bedenko, Victoria ; Hoffmann, Dietrich. / Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene. In: Cancer Research. 1980 ; Vol. 40, No. 12. pp. 4528-4532.
@article{cedec173383947fd90bbdf9e3ec83eb9,
title = "Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene",
abstract = "The metabolism of the environmental agents benzo(j) fluoranthene and benzo(k)fluoranthene was investigated using supernatants from the livers of Aroclor 1254-pretreated rats, which are effective in activating benzo(j)fluoranthene and benzo(k)fluoranthene to metabolites mutagenic toward Sal monella typhimurium TA 100. Six bands of metabolites of benzo(j)fluoranthene were separated by high-pressure liquid chromatography, and each band was tested for mutagenicity toward S. typhimurium TA 100 with activation. The major mutagenic band contained two dihydrodiols, one of which was identified as 9,10-dihydro-9,10-dihydroxybenzoOfluoran-thene by comparison to a synthetic reference standard. 9 was mutagenic toward S. typhimurium TA 100 with activation, presumably as a result of conversion to the corresponding dihydrodiol-epoxide. The major dihydrodiol metabolite of benzo-fluoranthene was identified, by comparison to a synthetic standard, as 8,9-dihydro-8,9-dihydroxybenzof 8 This dihydrodiol, which could also be converted to a dihydrodiol-epoxide, was mutagenic toward S. typhimurium TA 100 with activation. The results of this study indicate that metabolism to dihydrodiols is one pathway in the activation of benzoOfluoranthene and benzof fluoranthene to ultimate mutagens for S. typhimurium TA 100.",
author = "LaVoie, {Edmond J.} and Hecht, {Stephen S.} and Shantilal Amin and Victoria Bedenko and Dietrich Hoffmann",
year = "1980",
month = "12",
day = "1",
language = "English (US)",
volume = "40",
pages = "4528--4532",
journal = "Cancer Research",
issn = "0008-5472",
number = "12",

}

LaVoie, EJ, Hecht, SS, Amin, S, Bedenko, V & Hoffmann, D 1980, 'Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene', Cancer Research, vol. 40, no. 12, pp. 4528-4532.

Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene. / LaVoie, Edmond J.; Hecht, Stephen S.; Amin, Shantilal; Bedenko, Victoria; Hoffmann, Dietrich.

In: Cancer Research, Vol. 40, No. 12, 01.12.1980, p. 4528-4532.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Identification of Mutagenic Dihydrodiols As Metabolites Of Benzo(J)Fluoranthene And Benzo(K)Fluoranthene

AU - LaVoie, Edmond J.

AU - Hecht, Stephen S.

AU - Amin, Shantilal

AU - Bedenko, Victoria

AU - Hoffmann, Dietrich

PY - 1980/12/1

Y1 - 1980/12/1

N2 - The metabolism of the environmental agents benzo(j) fluoranthene and benzo(k)fluoranthene was investigated using supernatants from the livers of Aroclor 1254-pretreated rats, which are effective in activating benzo(j)fluoranthene and benzo(k)fluoranthene to metabolites mutagenic toward Sal monella typhimurium TA 100. Six bands of metabolites of benzo(j)fluoranthene were separated by high-pressure liquid chromatography, and each band was tested for mutagenicity toward S. typhimurium TA 100 with activation. The major mutagenic band contained two dihydrodiols, one of which was identified as 9,10-dihydro-9,10-dihydroxybenzoOfluoran-thene by comparison to a synthetic reference standard. 9 was mutagenic toward S. typhimurium TA 100 with activation, presumably as a result of conversion to the corresponding dihydrodiol-epoxide. The major dihydrodiol metabolite of benzo-fluoranthene was identified, by comparison to a synthetic standard, as 8,9-dihydro-8,9-dihydroxybenzof 8 This dihydrodiol, which could also be converted to a dihydrodiol-epoxide, was mutagenic toward S. typhimurium TA 100 with activation. The results of this study indicate that metabolism to dihydrodiols is one pathway in the activation of benzoOfluoranthene and benzof fluoranthene to ultimate mutagens for S. typhimurium TA 100.

AB - The metabolism of the environmental agents benzo(j) fluoranthene and benzo(k)fluoranthene was investigated using supernatants from the livers of Aroclor 1254-pretreated rats, which are effective in activating benzo(j)fluoranthene and benzo(k)fluoranthene to metabolites mutagenic toward Sal monella typhimurium TA 100. Six bands of metabolites of benzo(j)fluoranthene were separated by high-pressure liquid chromatography, and each band was tested for mutagenicity toward S. typhimurium TA 100 with activation. The major mutagenic band contained two dihydrodiols, one of which was identified as 9,10-dihydro-9,10-dihydroxybenzoOfluoran-thene by comparison to a synthetic reference standard. 9 was mutagenic toward S. typhimurium TA 100 with activation, presumably as a result of conversion to the corresponding dihydrodiol-epoxide. The major dihydrodiol metabolite of benzo-fluoranthene was identified, by comparison to a synthetic standard, as 8,9-dihydro-8,9-dihydroxybenzof 8 This dihydrodiol, which could also be converted to a dihydrodiol-epoxide, was mutagenic toward S. typhimurium TA 100 with activation. The results of this study indicate that metabolism to dihydrodiols is one pathway in the activation of benzoOfluoranthene and benzof fluoranthene to ultimate mutagens for S. typhimurium TA 100.

UR - http://www.scopus.com/inward/record.url?scp=0019160427&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0019160427&partnerID=8YFLogxK

M3 - Article

C2 - 7002294

AN - SCOPUS:0019160427

VL - 40

SP - 4528

EP - 4532

JO - Cancer Research

JF - Cancer Research

SN - 0008-5472

IS - 12

ER -