Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1984 Oct 25;12(20):7915–7927. doi: 10.1093/nar/12.20.7915

Conformations of poly(dG-dC).poly(dG-dC) modified by the O-acetyl derivative of the carcinogen 4-hydroxyaminoquinoline 1-oxide.

B Bailleul, S Galiègue-Zouitina, M H Loucheux-Lefebvre
PMCID: PMC320215  PMID: 6093058

Abstract

Poly(dG-dC).poly(dG-dC) has been modified by reaction with 4-acetoxyaminoquinoline 1-oxide (Ac-4 HAQO), the ultimate carcinogen of 4-nitroquinoline 1-oxide. The circular dichroism (CD) spectra of the modified and unmodified polymers have been compared under various experimental conditions. The CD spectra were recorded in 1 mM phosphate, 50% (v/v) ethanol, 3.8 M LiCl and 95% (v/v) ethanol, conditions in which poly(dG-dC).poly(dG-dC) adopts the B-, Z-, C- and A-form respectively. In 1 mM phosphate buffer, poly(dG-dC).poly(dG-dC) modified by Ac-4 HAQO seems not to contain regions in the Z-form. Z-form induction could be progressively obtained by the addition of ethanol as follows: in the buffer with about 30% ethanol the modified polymer started to adopt the Z structure, while 40% of ethanol in the buffer was necessary for the unmodified polymer. In the 50% ethanol-1 mM phosphate buffer mixture (v/v), poly(dG-dC).poly(dG-dC) was entirely in the Z-form while poly(dG-dC).poly(dG-dC) modified by Ac-4 HAQO remained partially in the B-form. Enzymatic digestions with the nuclease S1 which is specific of the single-stranded DNA were carried out in order to support the modified poly(dG-dC).poly(dG-dC) CD study conclusions. The role played by the two major adducts on the conformational characteristics of modified polymer is discussed.

Full text

PDF
7915

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. Bailleul B., Galiègue S., Loucheux-Lefebvre M. H. Adducts from the reaction of O,O'-diacetyl or O-acetyl derivatives of the carcinogen 4-hydroxyaminoquinoline 1-oxide with purine nucleosides. Cancer Res. 1981 Nov;41(11 Pt 1):4559–4565. [PubMed] [Google Scholar]
  3. Broyde S., Hingerty B. Conformation of 2-aminofluorene-modified DNA. Biopolymers. 1983 Nov;22(11):2423–2441. doi: 10.1002/bip.360221109. [DOI] [PubMed] [Google Scholar]
  4. Evans F. E., Miller D. W., Beland F. A. Sensitivity of the conformation of deoxyguanosine to binding at the C-8 position by N-acetylated and unacetylated 2-aminofluorene. Carcinogenesis. 1980;1(11):955–959. doi: 10.1093/carcin/1.11.955. [DOI] [PubMed] [Google Scholar]
  5. 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]
  6. Fuchs R. P., Lefevre J. F., Pouyet J., Daune M. P. Comparative orientation of the fluorene residue in native DNA modified by N-acetoxy-N-2-acetylaminofluorene and two 7-halogeno derivatives. Biochemistry. 1976 Jul 27;15(15):3347–3351. doi: 10.1021/bi00660a027. [DOI] [PubMed] [Google Scholar]
  7. Fuchs R., Daune M. Physical studies on deoxyribonucleic acid after covalent binding of a carcinogen. Biochemistry. 1972 Jul 4;11(14):2659–2666. doi: 10.1021/bi00764a017. [DOI] [PubMed] [Google Scholar]
  8. Galiègue-Zouitina S., Bailleul B., Loucheux-Lefebvre M. H. Guanyl-C8-arylamination of DNA by the ultimate carcinogen of 4-nitroquinoline-1-oxide: a spectrophotometric titration. Anal Biochem. 1984 May 1;138(2):454–457. doi: 10.1016/0003-2697(84)90839-x. [DOI] [PubMed] [Google Scholar]
  9. Galiègue-Zouitina S., Bailleul B., Loucheux-Lefebvre M. H. In vitro DNA reaction with an ultimate carcinogen model of 4-nitroquinoline-1-oxide: the 4-acetoxyaminoquinoline-1-oxide. Enzymatic degradation of the modified DNA. Carcinogenesis. 1983;4(3):249–254. doi: 10.1093/carcin/4.3.249. [DOI] [PubMed] [Google Scholar]
  10. Galiègue S., Bailleul B., Loucheux-Lefebvre M. H., Laval J. In vitro enzymatic recognition of DNA modified by O,O'-diacetyl or O-acetyl derivatives of the carcinogen 4-hydroxyaminoquinoline-1-oxide. Carcinogenesis. 1982;3(4):435–438. doi: 10.1093/carcin/3.4.435. [DOI] [PubMed] [Google Scholar]
  11. Galiègue S., Lecocq G., Loucheux-Lefebvre M. H. In vitro DNA reaction with a carcinogen: the O,O'-diacetyl-4-hydroxyaminoquinoline 1-oxide changes of stability of modified DNA. Biochim Biophys Acta. 1980 Oct 17;609(3):383–391. doi: 10.1016/0005-2787(80)90112-4. [DOI] [PubMed] [Google Scholar]
  12. Grunberger D., Nelson J. H., Cantor C. R., Weinstein I. B. Coding and conformational properties of oligonucleotides modified with the carcinogen N-2-acetylaminofluorene. Proc Natl Acad Sci U S A. 1970 Jun;66(2):488–494. doi: 10.1073/pnas.66.2.488. [DOI] [PMC free article] [PubMed] [Google Scholar]
  13. Hanau L. H., Santella R. M., Grunberger D., Erlanger B. F. An immunochemical examination of acetylaminofluorene-modified poly(dG-dC) X poly(dG-dC) in the Z-conformation. J Biol Chem. 1984 Jan 10;259(1):173–178. [PubMed] [Google Scholar]
  14. 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]
  15. Hingerty B., Broyde S. AAF linked to the guanine amino group: a B-Z junction. Nucleic Acids Res. 1983 May 25;11(10):3241–3254. doi: 10.1093/nar/11.10.3241. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Kadlubar F. F. A transversion mutation hypothesis for chemical carcinogenesis by N2-substitution of guanine in DNA. Chem Biol Interact. 1980 Sep;31(3):255–263. doi: 10.1016/0009-2797(80)90014-9. [DOI] [PubMed] [Google Scholar]
  17. Kawazoe Y., Araki M. Studies on chemical carcinogens. V. O,O'-diacetyl-4-hydroxyaminoquinoline 1-oxide. Gan. 1967 Oct;58(5):485–487. [PubMed] [Google Scholar]
  18. 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]
  19. Miller E. C. Some current perspectives on chemical carcinogenesis in humans and experimental animals: Presidential Address. Cancer Res. 1978 Jun;38(6):1479–1496. [PubMed] [Google Scholar]
  20. 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]
  21. 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]
  22. Sage E., Leng M. Conformation of poly(dG-dC) . poly(dG-dC) modified by the carcinogens N-acetoxy-N-acetyl-2-aminofluorene and N-hydroxy-N-2-aminofluorene. Proc Natl Acad Sci U S A. 1980 Aug;77(8):4597–4601. doi: 10.1073/pnas.77.8.4597. [DOI] [PMC free article] [PubMed] [Google Scholar]
  23. Sage E., Leng M. Conformational changes of poly(dG-dC) . poly(dG-dC) modified by the carcinogen N-acetoxy-N-acetyl-2-aminofluorene. Nucleic Acids Res. 1981 Mar 11;9(5):1241–1250. doi: 10.1093/nar/9.5.1241. [DOI] [PMC free article] [PubMed] [Google Scholar]
  24. Santella R. M., Grunberger D., Broyde S., Hingerty B. E. Z-DNA conformation of N-2-acetylaminofluorene modified poly(dG-dC).poly(dG-dC) determined by reactivity with anti cytidine antibodies and minimized potential energy calculations. Nucleic Acids Res. 1981 Oct 24;9(20):5459–5467. doi: 10.1093/nar/9.20.5459. [DOI] [PMC free article] [PubMed] [Google Scholar]
  25. Santella R. M., Grunberger D., Weinstein I. B., Rich A. Induction of the Z conformation in poly(dG-dC).poly(dG-dC) by binding of N-2-acetylaminofluorene to guanine residues. Proc Natl Acad Sci U S A. 1981 Mar;78(3):1451–1455. doi: 10.1073/pnas.78.3.1451. [DOI] [PMC free article] [PubMed] [Google Scholar]
  26. 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]

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

RESOURCES