Skip to main content
NCBI home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1979 Feb;6(2):733–744. doi: 10.1093/nar/6.2.733

Reactivity of antibodies to guanosine modified by the carcinogen N-acetoxy-N-2-acetylaminofluorene.

M Guigues, M Leng
PMCID: PMC327724  PMID: 570700

Abstract

N-(guanosin-8-yl) acetylaminofluorene (Guo-AAF) was prepared by the reaction of N-acetoxy-N-2-acetylaminofluorene (AAAF) and guanosine. Antibodies to Guo-AAF were elicited in rabbits by immunization with bovine serum albumin-Guo-AAF conjugate. The antibodies were purified by affinity chromatography on a Sepharose-Guo-AAF column. The reactivity of these antibodies towards several ligands was studied by radioimmunoassay. The antibodies have the same affinity for double stranded DNA-AAF and single stranded DNA-AAF. Thus the geometry of the regions of DNA substituted by AAF residues is the same in native and denatured DNA. The affinity of the antibodies is smaller for DNA-AAF than for Guo-AAF. This can be due in part to the stacking of AAF residues with the adjacent bases as shown by the study of the interactions between the antibodies and AAF-oligonucleotides. The circular dichroism spectra of AAF-oligonucleotides bound to the antibodies are reported.

Full text

PDF
733

Selected References

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

  1. Achter E. K., Felsenfeld G. The conformation of single-strand polynucleotides in solution: sedimentation studies of apurinic acid. Biopolymers. 1971;10(9):1625–1634. doi: 10.1002/bip.360100916. [DOI] [PubMed] [Google Scholar]
  2. ERLANGER B. F., BEISER S. M. ANTIBODIES SPECIFIC FOR RIBONUCLEOSIDES AND RIBONUCLEOTIDES AND THEIR REACTION WITH DNA. Proc Natl Acad Sci U S A. 1964 Jul;52:68–74. doi: 10.1073/pnas.52.1.68. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Eisenberg H., Felsenfeld G. Studies of the temperature-dependent conformation and phase separation of polyriboadenylic acid solutions at neutral pH. J Mol Biol. 1967 Nov 28;30(1):17–37. doi: 10.1016/0022-2836(67)90240-9. [DOI] [PubMed] [Google Scholar]
  4. Grunberger D., Weinstein I. B. Modifications of ribonucleic acid by chemical carcinogens. 3. Template activity of polynucleotides modified by N-acetoxy-2-acetylamino-fluorene. J Biol Chem. 1971 Feb 25;246(4):1123–1128. [PubMed] [Google Scholar]
  5. Inners L. D., Felsenfeld G. Conformation of polyribouridylic acid in solution. J Mol Biol. 1970 Jun 14;50(2):373–389. doi: 10.1016/0022-2836(70)90199-3. [DOI] [PubMed] [Google Scholar]
  6. Kriek E. Carcinogenesis by aromatic amines. Biochim Biophys Acta. 1974 Sep 9;355(2):177–203. doi: 10.1016/0304-419x(74)90003-1. [DOI] [PubMed] [Google Scholar]
  7. 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]
  8. Lavayre J., Leng M. Purification and specificity of antibodies to adenosine. Biochimie. 1977;59(1):33–42. doi: 10.1016/s0300-9084(77)80083-7. [DOI] [PubMed] [Google Scholar]
  9. 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]
  10. Leng M., Drocourt J. L., Lavayre J., Guigues M., Michelson M. Etude d'anticorps anti-mononucléotides et anti-dinucléotides. C R Acad Sci Hebd Seances Acad Sci D. 1974 Apr 8;278(15):1979–1982. [PubMed] [Google Scholar]
  11. Leng M., Sage E., Fuchs R. P., Duane M. P. Antibodies to DNA modified by the carcinogen N-acetoxy-N-2-acetylaminofluorene. FEBS Lett. 1978 Aug 15;92(2):207–210. doi: 10.1016/0014-5793(78)80755-8. [DOI] [PubMed] [Google Scholar]
  12. 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]
  13. Poirier M. C., Yuspa S. H., Weinstein I. B., Blobstein S. Detection of carcinogen-DNA adducts by radiommunoassay. Nature. 1977 Nov 10;270(5633):186–188. doi: 10.1038/270186a0. [DOI] [PubMed] [Google Scholar]
  14. Sage E., Leng M. Purification and specificity of antibodies to inosine 5'-monophosphate. Biochimie. 1977;59(3):269–274. doi: 10.1016/s0300-9084(77)80143-0. [DOI] [PubMed] [Google Scholar]
  15. Warner C., Schumaker V. Detection of two species of antibody molecules with the same specificity. Biochem Biophys Res Commun. 1970 Oct 9;41(1):225–231. doi: 10.1016/0006-291x(70)90492-4. [DOI] [PubMed] [Google Scholar]

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

RESOURCES