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. 1983 Jul 25;11(14):4947–4956. doi: 10.1093/nar/11.14.4947

Preferential binding of the chemical carcinogen N-hydroxy-2-aminofluorene to B-DNA as compared to Z-DNA.

P Rio, M Leng
PMCID: PMC326098  PMID: 6878038

Abstract

The reaction between the chemical carcinogen N-hydroxy-2-aminofluorene and poly (dG-dC) . poly (dG-dC) (B-form), poly (dG-m5dC) . poly (dG-m5dC) (B-or Z-form), poly(dG-br5dC) . poly (dG-br5dC) (Z-form) has been studied. The carcinogen binds covalently to B-DNA but does not bind significantly to Z-DNA. These results are discussed as related to the accessibility, the electrostatic potential and the dynamic structure of DNA. The accessibility and the electrostatic potential of DNA do not explain the difference in reactivity of the carcinogen since a related carcinogen N-acetoxy-N-acetyl-2-aminofluorene binds equally well to both B and Z-DNA. On the other hand, poly (dG-dC) . poly(dG-dC) and poly (dG-br5dC) . poly(dG-br5dC), in presence of ethidium bromide binds equally well to N-hydroxy-2-aminofluorene. It is suggested that the very low binding of this carcinogen to Z-DNA as compared to B-DNA is due to differences in the dynamic structures of these two forms of DNA.

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Selected References

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

  1. Behe M., Felsenfeld G. Effects of methylation on a synthetic polynucleotide: the B--Z transition in poly(dG-m5dC).poly(dG-m5dC). Proc Natl Acad Sci U S A. 1981 Mar;78(3):1619–1623. doi: 10.1073/pnas.78.3.1619. [DOI] [PMC free article] [PubMed] [Google Scholar]
  2. Corbin S., Lavery R., Pullman B. The molecular electrostatic potential and steric accessibility of double-helical A-RNA. Biochim Biophys Acta. 1982 Jul 30;698(1):86–92. doi: 10.1016/0167-4781(82)90188-9. [DOI] [PubMed] [Google Scholar]
  3. Fuchs R. P. Arylamidation and arylation by the carcinogen N-2-fluorenylacetamide: a sensitive and rapid radiochemical assay. Anal Biochem. 1978 Dec;91(2):663–673. doi: 10.1016/0003-2697(78)90553-5. [DOI] [PubMed] [Google Scholar]
  4. 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]
  5. Hartmann B., Pilet J., Ptak M., Ramstein J., Malfoy B., Leng M. The B reversible Z transition of poly(dI-br5dC).poly(dI-br5dC). A quantitative description of the Z form dynamic structure. Nucleic Acids Res. 1982 May 25;10(10):3261–3277. doi: 10.1093/nar/10.10.3261. [DOI] [PMC free article] [PubMed] [Google Scholar]
  6. Kadlubar F. F., Miller J. A., Miller E. C. Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res. 1977 Mar;37(3):805–814. [PubMed] [Google Scholar]
  7. Kapuler A. M., Michelson A. M. The reaction of the carcinogen N-acetoxy-2-acetyl-aminofluorene with DNA and other polynucleotides and its stereochemical implications. Biochim Biophys Acta. 1971 Mar 25;232(3):436–450. doi: 10.1016/0005-2787(71)90598-3. [DOI] [PubMed] [Google Scholar]
  8. Kriek E., Miller J. A., Juhl U., Miller E. C. 8-(N-2-fluorenylacetamido)guanosine, an arylamidation reaction product of guanosine and the carcinogen N-acetoxy-N-2-fluorenylacetamide in neutral solution. Biochemistry. 1967 Jan;6(1):177–182. doi: 10.1021/bi00853a029. [DOI] [PubMed] [Google Scholar]
  9. Kriek E., Westra J. G. Structural identification of the pyrimidine derivatives formed from N-(deoxyguanosin-8-yl)-2-aminofluorene in aqueous solution at alkaline pH. Carcinogenesis. 1980 Jun;1(6):459–468. doi: 10.1093/carcin/1.6.459. [DOI] [PubMed] [Google Scholar]
  10. Lavery R., Pullman B., Corbin S. The molecular electrostatic potential and steric accessibility of poly (dA-dT). poly (dA-dT) in various conformations: B-DNA, D-DNA and 'alternating-B' DNA. Nucleic Acids Res. 1981 Dec 11;9(23):6539–6552. doi: 10.1093/nar/9.23.6539. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Lemeunier F., Derbin C., Malfoy B., Leng M., Taillandier E. Identification of left-handed Z-DNA by indirect immunofluorescence in polytene chromosomes of Chironomus thummi thummi. Exp Cell Res. 1982 Oct;141(2):508–513. doi: 10.1016/0014-4827(82)90245-2. [DOI] [PubMed] [Google Scholar]
  12. Leng M., Hartmann B., Malfoy B., Pilet J., Ramstein J., Sage E. Interactions between nucleic acids and antibodies to Z-DNA. Cold Spring Harb Symp Quant Biol. 1983;47(Pt 1):163–170. doi: 10.1101/sqb.1983.047.01.021. [DOI] [PubMed] [Google Scholar]
  13. 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]
  14. Lipps H. J., Nordheim A., Lafer E. M., Ammermann D., Stollar B. D., Rich A. Antibodies against Z DNA react with the macronucleus but not the micronucleus of the hypotrichous ciliate stylonychia mytilus. Cell. 1983 Feb;32(2):435–441. doi: 10.1016/0092-8674(83)90463-4. [DOI] [PubMed] [Google Scholar]
  15. Malfoy B., Rousseau N., Leng M. Interaction between antibodies to Z-form deoxyribonucleic acid and double-stranded polynucleotides. Biochemistry. 1982 Oct 26;21(22):5463–5467. doi: 10.1021/bi00265a013. [DOI] [PubMed] [Google Scholar]
  16. Morgenegg G., Celio M. R., Malfoy B., Leng M., Kuenzle C. C. Z-DNA immunoreactivity in rat tissues. Nature. 1983 Jun 9;303(5917):540–543. doi: 10.1038/303540a0. [DOI] [PubMed] [Google Scholar]
  17. Nordheim A., Pardue M. L., Lafer E. M., Möller A., Stollar B. D., Rich A. Antibodies to left-handed Z-DNA bind to interband regions of Drosophila polytene chromosomes. Nature. 1981 Dec 3;294(5840):417–422. doi: 10.1038/294417a0. [DOI] [PubMed] [Google Scholar]
  18. Pilet J., Leng M. Comparison of poly(dG-dC).poly(dG-dC) conformations in oriented films and in solution. Proc Natl Acad Sci U S A. 1982 Jan;79(1):26–30. doi: 10.1073/pnas.79.1.26. [DOI] [PMC free article] [PubMed] [Google Scholar]
  19. Pohl F. M., Jovin T. M., Baehr W., Holbrook J. J. Ethidium bromide as a cooperative effector of a DNA structure. Proc Natl Acad Sci U S A. 1972 Dec;69(12):3805–3809. doi: 10.1073/pnas.69.12.3805. [DOI] [PMC free article] [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. 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]
  22. Rio P., Bazgar S., Leng M. Detection of N-hydroxy-2-acetylaminofluorene-DNA adducts in rat liver measured by radioimmunoassay. Carcinogenesis. 1982;3(2):225–227. doi: 10.1093/carcin/3.2.225. [DOI] [PubMed] [Google Scholar]
  23. 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]
  24. Santella R. M., Grunberger D., Nordheim A., Rich A. N-2-Acetylaminofluorene modification of poly(dG-m5dC) . poly(dG-m5dC) induces the Z-DNA conformation. Biochem Biophys Res Commun. 1982 Jun 30;106(4):1226–1232. doi: 10.1016/0006-291x(82)91243-8. [DOI] [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. Santella R. M., Kriek E., Grunberger D. Circular dichroism and proton magnetic resonance studies of dApdG modified with 2-aminofluorene and 2-acetylaminofluorene. Carcinogenesis. 1980;1(11):897–902. doi: 10.1093/carcin/1.11.897. [DOI] [PubMed] [Google Scholar]
  27. Spodheim-Maurizot M., Malfoy B., Saint-Ruf G. Reactivity of B and Z-DNA towards N-acetoxy-2-acetylaminofluorene. Nucleic Acids Res. 1982 Jul 24;10(14):4423–4430. doi: 10.1093/nar/10.14.4423. [DOI] [PMC free article] [PubMed] [Google Scholar]
  28. Spodheim-Maurizot M., Saint-Ruf G., Leng M. Conformational changes induced in DNA by in vitro reaction with N-hydroxy-N-2-aminofluorene. Nucleic Acids Res. 1979 Apr;6(4):1683–1694. doi: 10.1093/nar/6.4.1683. [DOI] [PMC free article] [PubMed] [Google Scholar]
  29. Teitelbaum H., Englander S. W. Open states in native polynucleotides. I. Hydrogen-exchange study of adenine-containing double helices. J Mol Biol. 1975 Feb 15;92(1):55–78. doi: 10.1016/0022-2836(75)90091-1. [DOI] [PubMed] [Google Scholar]
  30. Teitelbaum H., Englander S. W. Open states in native polynucleotides. II. Hydrogen-exchange study of cytosine-containing double helices. J Mol Biol. 1975 Feb 15;92(1):79–92. doi: 10.1016/0022-2836(75)90092-3. [DOI] [PubMed] [Google Scholar]
  31. 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]

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