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. 1985 Jan 25;13(2):449–458. doi: 10.1093/nar/13.2.449

Sequence specific damage of DNA induced by reducing sugars.

J Morita, K Ueda, S Nanjo, T Komano
PMCID: PMC341007  PMID: 2987796

Abstract

Reducing sugars induced alkali-labile sites in DNA. The DNA reacted with D-fructose 6-phosphate or D-fructose in the presence of Cu2+ was cleaved by the treatment with aqueous piperidine at 90 degrees C for 30 min. Alkali-labile sites were induced frequently at the pyrimidine residues, especially at the pyrimidine residues in pyrimidine-purine (5'----3') sequences. Transition metal ions such as Cu2+ and oxygen radicals such as hydrogen peroxide were possibly involved in the induction of alkali-labile sites.

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Selected References

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

  1. Ames B. N. Dietary carcinogens and anticarcinogens. Oxygen radicals and degenerative diseases. Science. 1983 Sep 23;221(4617):1256–1264. doi: 10.1126/science.6351251. [DOI] [PubMed] [Google Scholar]
  2. Bearden J. C., Jr, Lloyd R. S., Haidle C. W. Bleomycin-induced breakage of closed-circular DNA. Biochem Biophys Res Commun. 1977 Mar 21;75(2):442–448. doi: 10.1016/0006-291x(77)91062-2. [DOI] [PubMed] [Google Scholar]
  3. Bennett G. N. Formation of alkali labile linkages in DNA by hedamycin and use of hedamycin as a probe of protein-DNA complexes. Nucleic Acids Res. 1982 Aug 11;10(15):4581–4594. doi: 10.1093/nar/10.15.4581. [DOI] [PMC free article] [PubMed] [Google Scholar]
  4. Berlin V., Haseltine W. A. Reduction of adriamycin to a semiquinone-free radical by NADPH cytochrome P-450 reductase produces DNA cleavage in a reaction mediated by molecular oxygen. J Biol Chem. 1981 May 25;256(10):4747–4756. [PubMed] [Google Scholar]
  5. Brawn K., Fridovich I. DNA strand scission by enzymically generated oxygen radicals. Arch Biochem Biophys. 1981 Feb;206(2):414–419. doi: 10.1016/0003-9861(81)90108-9. [DOI] [PubMed] [Google Scholar]
  6. Bucala R., Model P., Cerami A. Modification of DNA by reducing sugars: a possible mechanism for nucleic acid aging and age-related dysfunction in gene expression. Proc Natl Acad Sci U S A. 1984 Jan;81(1):105–109. doi: 10.1073/pnas.81.1.105. [DOI] [PMC free article] [PubMed] [Google Scholar]
  7. Chiou S. H. DNA- and protein-scission activities of ascorbate in the presence of copper ion and a copper-peptide complex. J Biochem. 1983 Oct;94(4):1259–1267. doi: 10.1093/oxfordjournals.jbchem.a134471. [DOI] [PubMed] [Google Scholar]
  8. D'Andrea A. D., Haseltine W. A. Sequence specific cleavage of DNA by the antitumor antibiotics neocarzinostatin and bleomycin. Proc Natl Acad Sci U S A. 1978 Aug;75(8):3608–3612. doi: 10.1073/pnas.75.8.3608. [DOI] [PMC free article] [PubMed] [Google Scholar]
  9. Godson G. N., Barrell B. G., Staden R., Fiddes J. C. Nucleotide sequence of bacteriophage G4 DNA. Nature. 1978 Nov 16;276(5685):236–247. doi: 10.1038/276236a0. [DOI] [PubMed] [Google Scholar]
  10. Hashimoto Y., Shudo K. Sequence selective modification of DNA with muta-carcinogenic 2-amino-6-methyldipyrido[1,2-a:3',2'-d]imidazole. Biochem Biophys Res Commun. 1983 Nov 15;116(3):1100–1106. doi: 10.1016/s0006-291x(83)80255-1. [DOI] [PubMed] [Google Scholar]
  11. Henner W. D., Grunberg S. M., Haseltine W. A. Sites and structure of gamma radiation-induced DNA strand breaks. J Biol Chem. 1982 Oct 10;257(19):11750–11754. [PubMed] [Google Scholar]
  12. Kasai H., Nishimura S. Hydroxylation of deoxyguanosine at the C-8 position by ascorbic acid and other reducing agents. Nucleic Acids Res. 1984 Feb 24;12(4):2137–2145. doi: 10.1093/nar/12.4.2137. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Kashimura N., Morita J., Komano T. Autoxidation and phagocidal action of some reducing sugar phosphates. Carbohydr Res. 1979 Apr;70(1):C3–C7. doi: 10.1016/s0008-6215(00)83286-3. [DOI] [PubMed] [Google Scholar]
  14. Lesko S. A., Lorentzen R. J., Ts'o P. O. Role of superoxide in deoxyribonucleic acid strand scission. Biochemistry. 1980 Jun 24;19(13):3023–3028. doi: 10.1021/bi00554a029. [DOI] [PubMed] [Google Scholar]
  15. Marshall L. E., Graham D. R., Reich K. A., Sigman D. S. Cleavage of deoxyribonucleic acid by the 1,10-phenanthroline-cuprous complex. Hydrogen peroxide requirement and primary and secondary structure specificity. Biochemistry. 1981 Jan 20;20(2):244–250. doi: 10.1021/bi00505a003. [DOI] [PubMed] [Google Scholar]
  16. Maxam A. M., Gilbert W. A new method for sequencing DNA. Proc Natl Acad Sci U S A. 1977 Feb;74(2):560–564. doi: 10.1073/pnas.74.2.560. [DOI] [PMC free article] [PubMed] [Google Scholar]
  17. Samuni A., Chevion M., Czapski G. Unusual copper-induced sensitization of the biological damage due to superoxide radicals. J Biol Chem. 1981 Dec 25;256(24):12632–12635. [PubMed] [Google Scholar]
  18. Sanger F., Coulson A. R., Friedmann T., Air G. M., Barrell B. G., Brown N. L., Fiddes J. C., Hutchison C. A., 3rd, Slocombe P. M., Smith M. The nucleotide sequence of bacteriophage phiX174. J Mol Biol. 1978 Oct 25;125(2):225–246. doi: 10.1016/0022-2836(78)90346-7. [DOI] [PubMed] [Google Scholar]
  19. Sugimura T., Sato S. Mutagens-carcinogens in foods. Cancer Res. 1983 May;43(5 Suppl):2415s–2421s. [PubMed] [Google Scholar]
  20. Takeshita M., Grollman A. P., Ohtsubo E., Ohtsubo H. Interaction of bleomycin with DNA. Proc Natl Acad Sci U S A. 1978 Dec;75(12):5983–5987. doi: 10.1073/pnas.75.12.5983. [DOI] [PMC free article] [PubMed] [Google Scholar]
  21. Thornalley P., Wolff S., Crabbe J., Stern A. The autoxidation of glyceraldehyde and other simple monosaccharides under physiological conditions catalysed by buffer ions. Biochim Biophys Acta. 1984 Feb 14;797(2):276–287. doi: 10.1016/0304-4165(84)90131-4. [DOI] [PubMed] [Google Scholar]
  22. Totter J. R. Spontaneous cancer and its possible relationship to oxygen metabolism. Proc Natl Acad Sci U S A. 1980 Apr;77(4):1763–1767. doi: 10.1073/pnas.77.4.1763. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Ueda K., Morita J., Komano T. Sequence specificity of heat-labile sites in DNA induced by mitomycin C. Biochemistry. 1984 Apr 10;23(8):1634–1640. doi: 10.1021/bi00303a008. [DOI] [PubMed] [Google Scholar]

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