Skip to main content
NCBI home page
Proceedings of the National Academy of Sciences of the United States of America logoLink to Proceedings of the National Academy of Sciences of the United States of America
. 1992 May 1;89(9):3967–3971. doi: 10.1073/pnas.89.9.3967

Preferential hydroxylation by the chemical nuclease meso-tetrakis-(4-N-methylpyridiniumyl)porphyrinatomanganeseIII pentaacetate/KHSO5 at the 5' carbon of deoxyriboses on both 3' sides of three contiguous A.T base pairs in short double-stranded oligonucleotides.

M Pitié 1, G Pratviel 1, J Bernadou 1, B Meunier 1
PMCID: PMC525612  PMID: 1570321

Abstract

Selected double-stranded oligodeoxyribonucleotides have been used to probe, at the molecular level, DNA chain breakages induced by the chemical nuclease mesotetrakis(4-N- methylpyridiniumyl)porphyrinatomanganeseIII pentaacetate/KHSO5. The results show that cleavage selectively occurs on the two 3' sides of three contiguous A.T base pairs (an A.T triplet). Hydroxylation at 5' carbon of the deoxyribose targets represents the initial damage on the sugar-phosphodiester backbone and leaves a 3' phosphate and a 5' aldehyde at the ends. The fragments were separated by HPLC and unambiguously identified through chemical and biochemical reactions and/or sequencing after enzymatic conversion to mononucleosides. Also studied was the degradation of a 22-nucleotide DNA molecule containing two A.T triplets. Gel electrophoresis analyses on the corresponding 5'-32P-end-labeled substrate supported the above cleavage specificity and mechanism.

Full text

PDF
3967

Images in this article

3971Image
on p.3971

Selected References

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

  1. Barton J. K. Metals and DNA: molecular left-handed complements. Science. 1986 Aug 15;233(4765):727–734. doi: 10.1126/science.3016894. [DOI] [PubMed] [Google Scholar]
  2. Bernadou J., Pratviel G., Bennis F., Girardet M., Meunier B. Potassium monopersulfate and a water-soluble manganese porphyrin complex, [Mn(TMPyP)](OAc)5, as an efficient reagent for the oxidative cleavage of DNA. Biochemistry. 1989 Sep 5;28(18):7268–7275. doi: 10.1021/bi00444a019. [DOI] [PubMed] [Google Scholar]
  3. Boutorine A. S., Le Doan T., Battioni J. P., Mansuy D., Dupré D., Hélène C. Rapid routes of synthesis of chemically reactive and highly radioactively labeled alpha- and beta-oligonucleotide derivatives for in vivo studies. Bioconjug Chem. 1990 Sep-Oct;1(5):350–356. doi: 10.1021/bc00005a009. [DOI] [PubMed] [Google Scholar]
  4. Dabrowiak J. C., Ward B., Goodisman J. Quantitative footprinting analysis using a DNA-cleaving metalloporphyrin complex. Biochemistry. 1989 Apr 18;28(8):3314–3322. doi: 10.1021/bi00434a029. [DOI] [PubMed] [Google Scholar]
  5. Ding L., Bernadou J., Meunier B. Oxidative degradation of cationic metalloporphyrins in the presence of nucleic acids: a way to binding constants? Bioconjug Chem. 1991 Jul-Aug;2(4):201–206. doi: 10.1021/bc00010a002. [DOI] [PubMed] [Google Scholar]
  6. Ding L., Etemad-Moghadam G., Cros S., Auclair C., Meunier B. Syntheses and in vitro evaluation of water-soluble "cationic metalloporphyrin-ellipticine" molecules having a high affinity for DNA. J Med Chem. 1991 Mar;34(3):900–906. doi: 10.1021/jm00107a005. [DOI] [PubMed] [Google Scholar]
  7. Ding L., Etemad-Moghadam G., Meunier B. Oxidative cleavage of DNA mediated by hybrid metalloporphyrin-ellipticine molecules and functionalized metalloporphyrin precursors. Biochemistry. 1990 Aug 28;29(34):7868–7875. doi: 10.1021/bi00486a013. [DOI] [PubMed] [Google Scholar]
  8. Drew H. R., Travers A. A. DNA structural variations in the E. coli tyrT promoter. Cell. 1984 Jun;37(2):491–502. doi: 10.1016/0092-8674(84)90379-9. [DOI] [PubMed] [Google Scholar]
  9. Frolova E. I., Ivanova E. M., Zarytova V. F., Abramova T. V., Vlassov V. V. Porphyrin-linked oligonucleotides. Synthesis and sequence-specific modification of ssDNA. FEBS Lett. 1990 Aug 20;269(1):101–104. doi: 10.1016/0014-5793(90)81129-c. [DOI] [PubMed] [Google Scholar]
  10. Gasmi G., Pasdeloup M., Pratviel G., Pitié M., Bernadou J., Meunier B. 31P NMR characterization of terminal phosphates induced on DNA by the artificial nuclease 'Mn-TMPyP/KHSO5' in comparison with DNases I and II. Nucleic Acids Res. 1991 Jun 11;19(11):2835–2839. doi: 10.1093/nar/19.11.2835. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Goldberg I. H. Free radical mechanisms in neocarzinostatin-induced DNA damage. Free Radic Biol Med. 1987;3(1):41–54. doi: 10.1016/0891-5849(87)90038-4. [DOI] [PubMed] [Google Scholar]
  12. Moser H. E., Dervan P. B. Sequence-specific cleavage of double helical DNA by triple helix formation. Science. 1987 Oct 30;238(4827):645–650. doi: 10.1126/science.3118463. [DOI] [PubMed] [Google Scholar]
  13. Nelson H. C., Finch J. T., Luisi B. F., Klug A. The structure of an oligo(dA).oligo(dT) tract and its biological implications. Nature. 1987 Nov 19;330(6145):221–226. doi: 10.1038/330221a0. [DOI] [PubMed] [Google Scholar]
  14. Sigman D. S. Chemical nucleases. Biochemistry. 1990 Oct 2;29(39):9097–9105. doi: 10.1021/bi00491a001. [DOI] [PubMed] [Google Scholar]
  15. Van Atta R. B., Bernadou J., Meunier B., Hecht S. M. On the chemical nature of DNA and RNA modification by a hemin model system. Biochemistry. 1990 May 22;29(20):4783–4789. doi: 10.1021/bi00472a006. [DOI] [PubMed] [Google Scholar]
  16. Ward B., Skorobogaty A., Dabrowiak J. C. DNA binding specificity of a series of cationic metalloporphyrin complexes. Biochemistry. 1986 Dec 2;25(24):7827–7833. doi: 10.1021/bi00372a007. [DOI] [PubMed] [Google Scholar]
  17. Ward B., Skorobogaty A., Dabrowiak J. C. DNA cleavage specificity of a group of cationic metalloporphyrins. Biochemistry. 1986 Nov 4;25(22):6875–6883. doi: 10.1021/bi00370a021. [DOI] [PubMed] [Google Scholar]
  18. Weiner P. K., Langridge R., Blaney J. M., Schaefer R., Kollman P. A. Electrostatic potential molecular surfaces. Proc Natl Acad Sci U S A. 1982 Jun;79(12):3754–3758. doi: 10.1073/pnas.79.12.3754. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Yoon C., Privé G. G., Goodsell D. S., Dickerson R. E. Structure of an alternating-B DNA helix and its relationship to A-tract DNA. Proc Natl Acad Sci U S A. 1988 Sep;85(17):6332–6336. doi: 10.1073/pnas.85.17.6332. [DOI] [PMC free article] [PubMed] [Google Scholar]
  20. Zein N., Sinha A. M., McGahren W. J., Ellestad G. A. Calicheamicin gamma 1I: an antitumor antibiotic that cleaves double-stranded DNA site specifically. Science. 1988 May 27;240(4856):1198–1201. doi: 10.1126/science.3240341. [DOI] [PubMed] [Google Scholar]

Articles from Proceedings of the National Academy of Sciences of the United States of America are provided here courtesy of National Academy of Sciences

RESOURCES