Coding and Conformational Properties of Oligonucleotides Modified with the Carcinogen N -2-Acetylaminofluorene
- 1 June 1970
- journal article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 66 (2) , 488-494
- https://doi.org/10.1073/pnas.66.2.488
Abstract
The present studies were undertaken to determine the mechanism by which attachment of the carcinogen N-2-acetylaminofluorene to guanosine residues in nucleic acids distors their structure and function. Oligonucleotides were modified with N-acetoxy-2-acetylaminofluorene, repurified, and their base compositions analyzed. Evidence is presented that acetylaminofluorene residues bound to guanosines in GpUpU, ApApG, or poly (U,G) inactivates their function in codon recognition. Circular dichroism spectra suggest that this is caused by gross conformational changes in these compounds involving both a rotation about the glycosidic bond of guanosine residues bearing N-2-acetylaminofluorene, as well as stacking interactions between the drug and bases adjacent to the substituted guanosine.Keywords
This publication has 12 references indexed in Scilit:
- Codon—anticodon pairing: The wobble hypothesisPublished by Elsevier ,2009
- Modifications of ribonucleic acid by chemical carcinogens. I. In vitro modification of transfer ribonucleic acid by N-acetoxy-2-acetylaminofluoreneBiochemistry, 1970
- A possible role of transfer RNA in the mechanism of carcinogenesis.1968
- Mutations and decreases in density of transforming DNA produced by derivatives of the carcinogens 2-acetyl-aminofluorene and N-methyl-4-aminoazobenzene.1968
- Difference in binding of 2-acetylaminofluorene to rat liver deoxyribonucleic acid and ribosomal ribonucleic acid in vivoBiochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, 1968
- Differential responses of DNA and RNA polymerase to modifications of the template rat liver DNA caused by action of the carcinogen acetylaminofluorene in vivo and in vitroBiochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, 1968
- ON SIGNIFICANCE AND MECHANISM OF BINDING OF 2-ACETYLAMINIMOFLUORENE AND N-HYDROXY-2-ACETYLAMINOFLUORENE TO RAT-LIVER RIBONUCLEIC ACID IN VIVO1967
- 8-(N-2-Fluorenylacetamido) guanosine, an Arylamidation Reaction Product of Guanosine and the Carcinogen N-Acetoxy-N-2-fluorenylacetamide in Neutral Solution*Biochemistry, 1967
- Nucleic Acid Guanine: Reaction with the Carcinogen N -Acetoxy-2-AcetylaminofluoreneScience, 1966
- BINDING OF 2-ACETYLAMINOFLUORENE TO RAT LIVER RIBONUCLEIC ACID IN VIVO1965