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. 1977 Jul;4(7):2487–2494. doi: 10.1093/nar/4.7.2487

Photoproducts from DNA pyrimidine bases and polycyclic aromatic hydrocarbons

G Michael Blackburn 1, R G Fenwick 1, G Lockwood 1, G M Williams 1
PMCID: PMC342581  PMID: 909781

Abstract

The major photoproduct formed between benzo[a]pyrene and thymine is identified as 1-(benzo[a]pyren-6-yl)-thymine by means of spectroscopic analysis and isotopic syntheses. Irradiation of 1-methylcytosine hydrochloride and anthracene gives two isolable photoproducts of which one is assigned the structure 5-(anthracen-9-yl)-1-methylcytosine.

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Selected References

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

  1. Blackburn G. M., Buckingham J., Fenwick R. G., Taussig P., Thompson M. H. Photochemical binding of anthracene and other aromatic hydrocarbons to deoxyribonucleic acid with attendant loss of tritium. J Chem Soc Perkin 1. 1973;22:2809–2813. doi: 10.1039/p19730002809. [DOI] [PubMed] [Google Scholar]
  2. Cavalieri E., Calvin M. Photochemical coupling of benzo(a)pyrene with 1-methylcytosine; photoenhancement of carcinogenicity. Photochem Photobiol. 1971 Nov;14(5):641–653. doi: 10.1111/j.1751-1097.1971.tb06202.x. [DOI] [PubMed] [Google Scholar]
  3. HELLER W. Experimentelle Untersuchungen uber den Lichtkrebs; Lichtkrebserzeugung durch Photosensibilisierung. Strahlentherapie. 1950;81(4):529–548. [PubMed] [Google Scholar]
  4. Hoffmann H. D., Lesko S. A., Jr, Ts'o P. O. Chemical linkage of polycyclic hydrocarbons to deoxyribonucleic acids and polynucleotides in aqueous solution and in a buffer-ethanol solvent system. Biochemistry. 1970 Jun 23;9(13):2594–2604. doi: 10.1021/bi00815a006. [DOI] [PubMed] [Google Scholar]
  5. Jeffrey A. M., Jennette K. W., Blobstein S. H., Weinstein I. B., Beland F. A., Harvey R. G., Kasal H., Miura I., Nakanishi K. Letter: Benzo[a]pyrene-nucleic acid derivative found in vivo: structure of a benzo[a]pyrenetetrahydrodiol epoxide-guanosine adduct. J Am Chem Soc. 1976 Sep 1;98(18):5714–5715. doi: 10.1021/ja00434a060. [DOI] [PubMed] [Google Scholar]
  6. Nery R. Carcinogenic mechanisms: a critical review and a suggestion that oncogenesis may be adaptive ontogenesis. Chem Biol Interact. 1976 Feb;12(2):145–169. doi: 10.1016/0009-2797(76)90096-x. [DOI] [PubMed] [Google Scholar]
  7. Rice J. M., Dudek G. O., Barber M. Mass spectra of nucleic acid derivatives. Pyrimidines. J Am Chem Soc. 1965 Oct 20;87(20):4569–4576. doi: 10.1021/ja00948a029. [DOI] [PubMed] [Google Scholar]
  8. Santamaria L., Giordano G. G., Alfisi M., Cascione F. Effects of light on 3,4-benzpyrene carcinogenesis. Nature. 1966 May 21;210(5038):824–825. doi: 10.1038/210824a0. [DOI] [PubMed] [Google Scholar]
  9. Selkirk J. K., Croy R. G., Gelboin H. V. Benzo(a)pyrene metabolites: efficient and rapid separation by high-pressure liquid chromatography. Science. 1974 Apr 12;184(4133):169–171. doi: 10.1126/science.184.4133.169. [DOI] [PubMed] [Google Scholar]
  10. TSO P. O., LU P. INTERACTION OF NUCLEIC ACIDS, II. CHEMICAL LINKAGE OF THE CARCINOGEN 3,4-BENZPYRENE TO DNA INDUCED BY PHOTORADIATION. Proc Natl Acad Sci U S A. 1964 Feb;51:272–280. doi: 10.1073/pnas.51.2.272. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Varghese A. J. Photocyclo addition of acetone to uracil and cytosine. Photochem Photobiol. 1975 Mar;21(3):147–151. doi: 10.1111/j.1751-1097.1975.tb06644.x. [DOI] [PubMed] [Google Scholar]
  12. Warshawsky D., Calvin M. Tritium incorporation at specific positions in benzo(a)pyrene. Biochem Biophys Res Commun. 1975 Apr 7;63(3):541–547. doi: 10.1016/s0006-291x(75)80418-9. [DOI] [PubMed] [Google Scholar]
  13. Wood A. W., Wislocki P. G., Chang R. L., Levin W., Lu A. Y., Yagi J., Hernandez O., Herina D. M., Conney A. H. Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides. Cancer Res. 1976 Sep;36(9 PT1):3358–3366. [PubMed] [Google Scholar]

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