Syntheses and identification of benzo[c]chrysene metabolites

Dhimant Desai, Jacek Krzeminski, Jyh Ming Lin, Anju Chadha, Naoki Miyata, Haruhiko Yagi, Donald M. Jerina, Shantu Amin

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Like other PAHs, chiysenes are thought to exert their carcimogenicity via metabolic activation of proximally carcinogenic dihydrodiols to diol epoxides as ultimate carcinogens. Benzo[c] chrysene (B[c]C) is structurally intriguing among the PAH because it features both a bay region and a fjord region. Although B[c]C is carcinogenic and mutagenic, few data are available on its metabolic activation or the nature of its metabolites. We have synthesized the B[c]C trans-1,2-, 7,8-, and 9,10-dihydrodiols from the appropriate methoxy-substituted bisnaphthyl olefins by photochemical cyclization. B[c]C was metabolized with S9 liver fraction from phenobarbital/β-naphthoflavone-treated rats. Dihydrodiols were formed on both terminal rings as well as in the K-region. 2-, 3-, and 10-HydroxyB[c]C were also identified as metabolites. In mutagenicity studies toward S. typhimurium TA100, 1,2-dihydrodiol was more mutagenic than B[c]C at doses above 1.25 μg/plate, whereas 9,10-dihydrodiol was toxic at doses above 1.25 μg/plate.

Original languageEnglish (US)
Pages (from-to)255-264
Number of pages10
JournalPolycyclic Aromatic Compounds
Volume16
Issue number1-4
StatePublished - Dec 1 1999

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Polycyclic aromatic hydrocarbons
Metabolites
Chemical activation
Carcinogens
Cyclization
Liver
Olefins
Rats
Poisons
Epoxy Compounds
Alkenes
Phenobarbital
trans-1,2-dihydro-1,2-naphthalenediol
benzo(c)chrysene

All Science Journal Classification (ASJC) codes

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

Cite this

Desai, Dhimant ; Krzeminski, Jacek ; Lin, Jyh Ming ; Chadha, Anju ; Miyata, Naoki ; Yagi, Haruhiko ; Jerina, Donald M. ; Amin, Shantu. / Syntheses and identification of benzo[c]chrysene metabolites. In: Polycyclic Aromatic Compounds. 1999 ; Vol. 16, No. 1-4. pp. 255-264.
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Syntheses and identification of benzo[c]chrysene metabolites. / Desai, Dhimant; Krzeminski, Jacek; Lin, Jyh Ming; Chadha, Anju; Miyata, Naoki; Yagi, Haruhiko; Jerina, Donald M.; Amin, Shantu.

In: Polycyclic Aromatic Compounds, Vol. 16, No. 1-4, 01.12.1999, p. 255-264.

Research output: Contribution to journalArticle

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T1 - Syntheses and identification of benzo[c]chrysene metabolites

AU - Desai, Dhimant

AU - Krzeminski, Jacek

AU - Lin, Jyh Ming

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AU - Miyata, Naoki

AU - Yagi, Haruhiko

AU - Jerina, Donald M.

AU - Amin, Shantu

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