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. 1979 Jun;30:185–189. doi: 10.1289/ehp.7930185

Mutagenic and carcinogenic properties of polycyclic aromatic hydrocarbons.

Y V Pashin, L M Bakhitova
PMCID: PMC1637690  PMID: 446450

Abstract

The rapid development of the chemical industry, combustion of fossil fuels, and smoking of tobacco have resulted in contact of the general population with benzo(a)pyrene and other carcinogenic aromatic hydrocarbons. Persons especially at risk occupationally are those engaged in thermal processing of oil shale, coal, and heavy residual petroleum. It has been shown that polycyclic aromatic hydrocarbons require metabolic activation before they can act as mutagens or carcinogens. This metabolic activation results from interaction with microsomal enzymes present in many body cells, yielding reactive epoxides which react with DNA and produce mutations in the count frame shift or participate in covalent bounding. While opinions differ regarding the relative role of these processes in mutagenesis, considerable evidence exists which links mutagenesis and carcinogenesis. Metabolites of the polycyclic aromatic hydrocarbons which are carcinogenic are usually mutagenic, which supports the hypothesis that damage to chromosomes plays an important role in carcinogenesis. These facts open the possibility to monitoring the spread of carcinogenic substances in the biosphere by relatively simple tests whose endpoint is mutagenesis.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Aaronson S. A., Todaro G. J. Basis for the acquisition of malignant potential by mouse cells cultivated in vitro. Science. 1968 Nov 29;162(3857):1024–1026. doi: 10.1126/science.162.3857.1024. [DOI] [PubMed] [Google Scholar]
  2. Albert A. Relations between molecular structure 6501 and biological activity: stages in the evolution of current concepts. Annu Rev Pharmacol. 1971;11:13–36. doi: 10.1146/annurev.pa.11.040171.000305. [DOI] [PubMed] [Google Scholar]
  3. Ames B. N. A combined bacterial and liver test system for detection and classification of carcinogens as mutagens. Genetics. 1974 Sep;78(1):91–95. doi: 10.1093/genetics/78.1.91. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Ames B. N. Carcinogens are mutagens: their detection and classification. Environ Health Perspect. 1973 Dec;6:115–118. doi: 10.1289/ehp.7306115. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Ames B. N., Lee F. D., Durston W. E. An improved bacterial test system for the detection and classification of mutagens and carcinogens. Proc Natl Acad Sci U S A. 1973 Mar;70(3):782–786. doi: 10.1073/pnas.70.3.782. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Ames B. N., Sims P., Grover P. L. Epoxides of carcinogenic polycyclic hydrocarbons are frameshift mutagens. Science. 1972 Apr 7;176(4030):47–49. doi: 10.1126/science.176.4030.47. [DOI] [PubMed] [Google Scholar]
  7. Arcos J. C., Argus M. F. Molecular geometry and carcinogenic activity of aromatic compounds. New perspectives. Adv Cancer Res. 1968;11:305–471. doi: 10.1016/s0065-230x(08)60390-5. [DOI] [PubMed] [Google Scholar]
  8. BROOKES P., LAWLEY P. D. EVIDENCE FOR THE BINDING OF POLYNUCLEAR AROMATIC HYDROCARBONS TO THE NUCLEIC ACIDS OF MOUSE SKIN: RELATION BETWEEN CARCINOGENIC POWER OF HYDROCARBONS AND THEIR BINDING TO DEOXYRIBONUCLEIC ACID. Nature. 1964 May 23;202:781–784. doi: 10.1038/202781a0. [DOI] [PubMed] [Google Scholar]
  9. Boyland E. The correlation of experimental carcinogenesis and cancer in man. Prog Exp Tumor Res. 1969;11:222–234. doi: 10.1159/000391396. [DOI] [PubMed] [Google Scholar]
  10. Brookes P. Covalent interaction of carcinogens with DNA. Life Sci. 1975 Feb 1;16(3):331–344. doi: 10.1016/0024-3205(75)90254-4. [DOI] [PubMed] [Google Scholar]
  11. Brookes P., Heidelberger C. Isolation and degradation of DNA from cells treated with tritium-labeled 7,12-dimethylbenz(a)anthracene: studies on the nature of the binding of this carcinogen to DNA. Cancer Res. 1969 Jan;29(1):157–165. [PubMed] [Google Scholar]
  12. Brookes P. Quantitative aspects of the reaction of some carcinogens with nucleic acids and the possible significance of such reactions in the process of carcinogenesis. Cancer Res. 1966 Sep;26(9):1994–2003. [PubMed] [Google Scholar]
  13. Cavalieri E., Calvin M. Molecular characteristics of some carcinogenic hydrocarbons. Proc Natl Acad Sci U S A. 1971 Jun;68(6):1251–1253. doi: 10.1073/pnas.68.6.1251. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Cookson M. J., Sims P., Grover P. L. Mutagenicity of epoxides of polycyclic hydrocarbons correlates with carcinogenicity of parent hydrocarbons. Nat New Biol. 1971 Dec 8;234(49):186–187. doi: 10.1038/newbio234186a0. [DOI] [PubMed] [Google Scholar]
  15. De Serres F. J. Editorial: The correlation between carcinogenic and mutagenic activity in short-term tests for mutation-induction and DNA repair. Mutat Res. 1975 Aug;31(4):203–204. doi: 10.1016/0165-1161(75)90001-1. [DOI] [PubMed] [Google Scholar]
  16. Epstein S. S. Environmental determinants of human cancer. Cancer Res. 1974 Oct;34(10):2425–2435. [PubMed] [Google Scholar]
  17. Evans C. H., DiPaolo J. A. Neoplastic transformation of guinea pig fetal cells in culture induced by chemical carcinogens. Cancer Res. 1975 Apr;35(4):1035–1044. [PubMed] [Google Scholar]
  18. Fishbein L. Mutagens and potential mutagens in the biosphere. I. DDT and its metabolites, polychlorinated biphenyls, chlorodioxins, polycyclic aromatic hydrocarbons, haloethers. Sci Total Environ. 1974 Jul;2(4):305–340. doi: 10.1016/0048-9697(74)90001-1. [DOI] [PubMed] [Google Scholar]
  19. Grover P. L., Sims P., Huberman E., Marquardt H., Kuroki T., Heidelberger C. In vitro transformation of rodent cells by K-region derivatives of polycyclic hydrocarbons. Proc Natl Acad Sci U S A. 1971 Jun;68(6):1098–1101. doi: 10.1073/pnas.68.6.1098. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Hammond E. C. The epidemiological approach to the etiology of cancer. Cancer. 1975 Mar;35(3):652–654. doi: 10.1002/1097-0142(197503)35:3<652::aid-cncr2820350317>3.0.co;2-y. [DOI] [PubMed] [Google Scholar]
  21. Harris C. C., Genta V. M., Frank A. L., Kaufman D. G., Barrett L. A., McDowell E. M., Trump B. F. Carcinogenic polynuclear hydrocarbons bind to macromolecules in cultured human bronchi. Nature. 1974 Nov 1;252(5478):68–69. doi: 10.1038/252068a0. [DOI] [PubMed] [Google Scholar]
  22. Huberman E., Aspiras L., Heidelberger C., Grover P. L., Sims P. Mutagenicity to mammalian cells of epoxides and other derivatives of polycyclic hydrocarbons. Proc Natl Acad Sci U S A. 1971 Dec;68(12):3195–3199. doi: 10.1073/pnas.68.12.3195. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Huberman E. Mammalian cell transformation and cell-mediated mutagenesis by carcinogenic polycyclic hydrocarbons. Mutat Res. 1975 Aug;29(2):285–291. doi: 10.1016/0027-5107(75)90181-5. [DOI] [PubMed] [Google Scholar]
  24. Huberman E., Sachs L. Cell-mediated mutagenesis of mammalian cells with chemical carcinogens. Int J Cancer. 1974 Mar 15;13(3):326–333. doi: 10.1002/ijc.2910130308. [DOI] [PubMed] [Google Scholar]
  25. Kier L. D., Yamasaki E., Ames B. N. Detection of mutagenic activity in cigarette smoke condensates. Proc Natl Acad Sci U S A. 1974 Oct;71(10):4159–4163. doi: 10.1073/pnas.71.10.4159. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. Kuroki T., Heidelberger C. The binding of polycyclic aromatic hydrocarbons to the DNA, RNA, and proteins of transformable cells in culture. Cancer Res. 1971 Dec;31(12):2168–2176. [PubMed] [Google Scholar]
  27. Maugh T. H., 2nd Chemical carcinogenesis: a long-neglected field blossoms. Science. 1974 Mar 8;183(4128):940–944. doi: 10.1126/science.183.4128.940. [DOI] [PubMed] [Google Scholar]
  28. Ong T. M., De Serres F. J. Mutagenicity of chemical carcinogens in Neurospora crassa. Cancer Res. 1972 Sep;32(9):1890–1893. [PubMed] [Google Scholar]
  29. Sugiyama T. Chromosomal aberrations and carcinogenesis by various benz(a)anthracene derivatives. Gan. 1973 Dec;64(6):637–639. [PubMed] [Google Scholar]
  30. Weekes U., Brusick D. In vitro metabolic activation of chemical mutagens. II. The relationships among mutagen formation, metabolism and carcinogenicity for dimethylnitrosamine and diethylnitrosamine in the livers, kidneys and lungs of BALB/cJ, C57BL/6J and RF/J mice. Mutat Res. 1975 Jun;31(3):175–183. doi: 10.1016/0165-1161(75)90087-4. [DOI] [PubMed] [Google Scholar]

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