Skip to main content
PMC home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1981 Mar 11;9(5):1241–1250. doi: 10.1093/nar/9.5.1241

Conformational changes of poly(dG-dC) . poly(dG-dC) modified by the carcinogen N-acetoxy-N-acetyl-2-aminofluorene.

E Sage, M Leng
PMCID: PMC326749  PMID: 7232216

Abstract

Poly (dG-dC) . poly(dG-dC) was modified by the reaction with N-acetoxy-N-acetyl-2-aminofluorene. The conformations of poly(dG-dC) . poly(dG-dC) and of poly d(G-C)AAF were studied by circular dichroism under various experimental conditions. In 95% ethanol, the two polynucleotides adopt the A-form. In 3.9 M LiCl, the transition B-form-C-form is observed with poly(dG-dC) . poly (dG-dC) but not with poly d(G-C)AAF. In 1 mM phosphate buffer, poly d(G-C)AAF behaves as a mixture of B- and Z-form, the relative percentages depending upon the amounts of modified bases. The percentage of Z-form is decreased by addition of EDTA and is increased by addition of Mg++. Spermine favors the Z-form in modified and unmodified polynucleotides. No defect in the double helix of poly d(G-C)AAF is detected by SI endonuclease.

Full text

PDF
1244

Selected References

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

  1. Arnott S., Chandrasekaran R., Birdsall D. L., Leslie A. G., Ratliff R. L. Left-handed DNA helices. Nature. 1980 Feb 21;283(5749):743–745. doi: 10.1038/283743a0. [DOI] [PubMed] [Google Scholar]
  2. Fuchs R. P. In vitro recognition of carcinogen-induced local denaturation sites native DNA by S1 endonuclease from Aspergillus oryzae. Nature. 1975 Sep 11;257(5522):151–152. doi: 10.1038/257151a0. [DOI] [PubMed] [Google Scholar]
  3. Fuchs R., Daune M. Physical basis of chemical carcinogenesis by N-2-fluorenylacetamide derivatives and analogs. FEBS Lett. 1973 Aug 15;34(2):295–298. doi: 10.1016/0014-5793(73)80815-4. [DOI] [PubMed] [Google Scholar]
  4. Harvan D. J., Hass J. R., Lieberman M. W. Adduct formation between the carcinogen N-acetoxy-2-acetylaminofluorene and synthetic polydeoxyribonucleotides. Chem Biol Interact. 1977 May;17(2):203–210. doi: 10.1016/0009-2797(77)90085-0. [DOI] [PubMed] [Google Scholar]
  5. Ivanov V. I., Minchenkova L. E., Schyolkina A. K., Poletayev A. I. Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism. Biopolymers. 1973;12(1):89–110. doi: 10.1002/bip.1973.360120109. [DOI] [PubMed] [Google Scholar]
  6. Lefèvre J. F., Fuchs R. P., Daune M. P. Comparative studies on the 7-iodo and 7-fluoro derivatives of N-acetoxy-N-2-acetylaminofluorene: binding sites on DNA and conformational change of modified deoxytrinucleotides. Biochemistry. 1978 Jun 27;17(13):2561–2567. doi: 10.1021/bi00606a016. [DOI] [PubMed] [Google Scholar]
  7. Leng M., Ptak M., Rio P. Conformation of acetylaminofluorene and aminofluorene modified guanosine and guanosine derivatives. Biochem Biophys Res Commun. 1980 Oct 16;96(3):1095–1102. doi: 10.1016/0006-291x(80)90064-9. [DOI] [PubMed] [Google Scholar]
  8. Mercado C. M., Tomasz M. Circular dichroism of mitomycin-DNA complexes. Evidence for a conformational change in DNA. Biochemistry. 1977 May 3;16(9):2040–2046. doi: 10.1021/bi00628a044. [DOI] [PubMed] [Google Scholar]
  9. Nelson J. H., Grunberger D., Cantor C. R., Weinstein I. B. Modification of ribonucleic acid by chemical carcinogens. IV. Circular dichroism and proton magnetic resonance studies of oligonucleotides modified with N-2-acetylaminofluorene. J Mol Biol. 1971 Dec 14;62(2):331–346. doi: 10.1016/0022-2836(71)90431-1. [DOI] [PubMed] [Google Scholar]
  10. Patel D. J., Canuel L. L., Pohl F. M. "Alternating B-DNA" conformation for the oligo(dG-dC) duplex in high-salt solution. Proc Natl Acad Sci U S A. 1979 Jun;76(6):2508–2511. doi: 10.1073/pnas.76.6.2508. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Pohl F. M., Jovin T. M. Salt-induced co-operative conformational change of a synthetic DNA: equilibrium and kinetic studies with poly (dG-dC). J Mol Biol. 1972 Jun 28;67(3):375–396. doi: 10.1016/0022-2836(72)90457-3. [DOI] [PubMed] [Google Scholar]
  12. Pohl F. M. Polymorphism of a synthetic DNA in solution. Nature. 1976 Mar 25;260(5549):365–366. doi: 10.1038/260365a0. [DOI] [PubMed] [Google Scholar]
  13. Ramstein J., Leng M. Salt-dependent dynamic structure of poly(dG-dC) x poly(dG-dC). Nature. 1980 Nov 27;288(5789):413–414. doi: 10.1038/288413a0. [DOI] [PubMed] [Google Scholar]
  14. Simpson R. T., Shindo H. Conformation of 145 base pair length poly (dG-dC) . poly (dG-dC) in solution and in association with histones. Nucleic Acids Res. 1980 May 10;8(9):2093–2103. doi: 10.1093/nar/8.9.2093. [DOI] [PMC free article] [PubMed] [Google Scholar]
  15. Tunis-Schneider M. J., Maestre M. F. Circular dichroism spectra of oriented and unoriented deoxyribonucleic acid films--a preliminary study. J Mol Biol. 1970 Sep 28;52(3):521–541. doi: 10.1016/0022-2836(70)90417-1. [DOI] [PubMed] [Google Scholar]
  16. Wang A. H., Quigley G. J., Kolpak F. J., Crawford J. L., van Boom J. H., van der Marel G., Rich A. Molecular structure of a left-handed double helical DNA fragment at atomic resolution. Nature. 1979 Dec 13;282(5740):680–686. doi: 10.1038/282680a0. [DOI] [PubMed] [Google Scholar]
  17. Yamasaki H., Leffler S., Weinstein I. B. Effect of N-2-acetylaminofluorene modification on the structure and template activity of DNA and reconstituted chromatin. Cancer Res. 1977 Mar;37(3):684–691. [PubMed] [Google Scholar]
  18. Zimmerman S. B., Pheiffer B. H. Does DNA adopt the C form in concentrated salt solutions or in organic solvent water mixtures? An x-ray diffraction study of DNA fibers immersed in various media. J Mol Biol. 1980 Sep 25;142(3):315–330. doi: 10.1016/0022-2836(80)90275-2. [DOI] [PubMed] [Google Scholar]
  19. de Murcia G., Lang M. C., Freund A. M., Fuchs R. P., Duane M. P., Sage E., Leng M. Electron microscopic visualization of N-acetoxy-N-2-acetylaminofluorene binding sites in ColE1 DNA by means of specific antibodies. Proc Natl Acad Sci U S A. 1979 Dec;76(12):6076–6080. doi: 10.1073/pnas.76.12.6076. [DOI] [PMC free article] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES