Abstract
Polycyclic aromatic hydrocarbons (PAH) are widespread environmental contaminants that may be metabolically activated to mutagenic or carcinogenic derivatives (Particulate Polycyclic Organic Matter, 1972; Gelboin and Ts’o, 1978). Intensive research indicates that PAH are promutagens or procarcinogens containing the bay region geometric feature (Jerina et al., 1978). Studies show that the biological activity of these compounds results from metabolism to bay region diol-epoxides, which are capable of forming covalent adducts at nucleophilic sites within DNA.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Ames, B.N., J. McCann, and E. Yamasaki. 1975. Methods of detecting carcinogens and mutagens with the Salmonella/ mammalian-microsome mutagenicity test. Mutation Res. 31: 347–364.
Bruice, P.Y., T.C. Bruice, P.M. Dansette, H.G. Selander, H. Yagi, and D.M. Jerina. 1976. Comparison of the mechanisms of solvolysis and rearrangement of K-region vs. non-K-region arene oxides of phenanthrene.; comparison solvolytic rate constants of K-region and non-K-region arene oxides. J. Am. Chem. Soc. 98: 2965–2973.
Clive, D., K.O. Johnson, J.F.S. Spector, A.G. Batson, and M.M.M. Brown. 1979. Validation and characterization of the L5178/TK+/- mouse lymphoma mutagen assay system. Mutation Res. 59: 61–108.
Clive, D., and J.F.S. Spector. 1975. Laboratory procedures for assessing specific locus mutations at the TK locus in cultures L5178Y mouse lymphoma cells. Mutation Res. 31: 17–29.
Eisenstadt, E., and A. Gold. 1978. Cyclopenta(cd)pyrene: a highly mutagenic polycyclic aromatic hydrocarbon. Proc. Nat. Acad. Sci. USA 75: 1667–1669.
Gehly, E.B., W.E. Fahl, C.R. Jefcoate, and C. Heidelberger. 1979. The metabolism of benzo(a)pyrene by cytochrome P450 in transformable and non-transformable C3H mouse fibroblasts. J. Biol. Chem. 254: 5041–5048.
Gelboin, H.V., and P.O.P. Ts’o, eds. Polycyclic Hydrocarbons and Cancer, Vols. 1 and 2. Academic Press: New York.
Gold, A. 1975. Carbon black adsorbate: separation and identification of a carcinogen and some oxygenated polyaromatics. Anal. Chem. 47: 1469–1472.
Gold, A., J. Brewster, and E. Eisenstadt. 1979. Synthesis of cyclopenta(cd)pyrene-3,4-epoxide, the ultimate mutagenic metabolite of the environmental carcinogen cyclopenta(cd)pyrene. J. Chem. Soc. Chem. Commun. 903–904.
Gold, A., J. Schultz, and E. Eisenstadt. 1978. Relative reactivities of pyrene ring positions: cyclopenta(cd)pyrene via an intramolecular Friedel-Crafts acylation. Tetrahedron Lett. 4491–4494.
Gold, A., J. Schultz, and E. Eisenstadt. 1979. Synthesis and metabolism of cyclopenta(cd)pyrene. In: Polynuclear Aromatic Hydrocarbons. P.W. Jones and P. Leber, eds. Ann Arbor Science: Ann Arbor, MI. pp. 695–704.
Grimmer, G. 1977. ‘ARC monographs on the evaluation of carcinogenic risk of chemicals to man, Vol. 16. International Agency for Research on Cancer, Lyon, France. p. 29.
Ittah, Y., and D.M. Jerina. 1978. Synthesis of cyclopenta(cd)pyrene. Tetrahedron Lett. 4495–4498.
Jerina, D.M., H. Yagi, R.E. Lehr, D.R. Thakker, M. Schaeffer-Ridder, J.M. Karle, W. Levin, A.W. Wood, R.L. Chang, and A.H. Conney. 1978. Bay region theory of carcinogenesis by polycyclic aromatic hydrocarbons. In: Polycyclic Hydrocarbons and Cancer, Vol. 1. H.V. Gelboin and P.O.P. Ts’o, eds. Academic Press: New York. pp. 173–188.
Kaden, D.A., R.A. Hites, and W.G. Thilly. 1979. Mutagenicity of soot and associated polycyclic aromatic hydrocarbons to Salmonella typhimurium. Cancer Res. 39: 4152–4159.
Keller, J.W., and C. Heidelberger. 1976. Polycyclic K-region arene oxides; products and kinetics of solvolysis. J. Am. Chem. Soc. 98: 2328–2336.
Konieczny, M., and R.G. Harvey. 1979. Synthesis of cyclopenta(cd)pyrene. J. Org. Chem. 44: 2158–2160.
Lee, M.L., P.G. Prado, J.B. Howard, and R.A. Rites. 1977. Source identification of urban airborne polycyclic aromatic hydrocarbons by gas chromatographic mass spectrometry and high resolution mass spectrometry. Biomed. Mass Spectrum. 4: 182–186.
Maher, V.M., and J.M. McCormick. 1978. Mammalian cell mutagenesis by polycyclic aromatic hydrocarbons and their derivatives. In: Polycyclic Hydrocarbons and Cancer, Vol. 2. H.V. Gelboin and P.O.P. Ts’o, eds. Academic Press: New York. pp. 137–160.
Nesnow, S., and C. Heidelberger. 1976. The effect of modifiers of microsomal enzymes on chemical oncogenesis in cultures of C3H mouse cell lines. Cancer Res. 36: 1801–1080.
Particulate Polycyclic Organic Matter. 1972. National Academy of Sciences: Washington, DC.
Reznikoff, C.A., J.S. Bertram, D.W. Brankow, and C. Heidelberger. 1973. Quantitative and qualitative studies of chemical transformation of cloned C3H mouse embryo cells sensitive to postconfluence inhibition of cell division. Cancer Res. 33: 3239–3249.
Rosen, A.A., and F.M. Middleton. 1955. Identification of petroleum refinery wastes in surface waters. Anal. Chem. 27: 790–794.
Ruehle, P.H., D.L. Fischer, and J.C. Wiley. 1979. Synthesis of cyclopenta(cd)pyrene, a ubiquitous environmental carcinogen. J. Chem. Soc. Chem. Commun. 302–303.
Snook, M.E., R.E. Severson, R.F. Arrendale, H.C. Highman, and O.T. Chortyk. 1977. The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate. Beitrage zur Tabakforsch. 9: 97–101.
Wallcave, L., D.L. Nagel, J.W. Smith, and R.D. Waniska. 1975. Two pyrene derivatives of widespread environmental distribution: cyclopenta(cd)pyrene and acepyrene. Environ. Sci. Technol. 9: 143–145.
Wood, A.N., W. Levin, R.L. Chang, M. Huang, D.E. Ryan, P.E. Thomas, R.E. Lehy, S. Kumer, M. Koreeda, H. Akagi, Y. Ittah, P.M. Dansette, H. Yagi, D.M. Jerina, and A.H. Conney. 1980. Mutagenicity and tumor-initiating activity of cyclopenta(cd)pyrene and structurally related compounds. Cancer Res. 40: 642–649.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1980 Springer Science+Business Media New York
About this chapter
Cite this chapter
Gold, A. et al. (1980). Mutagenicity and Carcinogenicity of a Recently Characterized Carbon Black Adsorbate: Cyclopenta(Cd) Pyrene. In: Waters, M.D., Sandhu, S.S., Huisingh, J.L., Claxton, L., Nesnow, S. (eds) Short-Term Bioassays in the Analysis of Complex Environmental Mixtures II. Environmental Science Research, vol 22. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-4121-5_33
Download citation
DOI: https://doi.org/10.1007/978-1-4684-4121-5_33
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4684-4123-9
Online ISBN: 978-1-4684-4121-5
eBook Packages: Springer Book Archive