Skip to main content
PMC home page
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1981 Jan 24;9(2):365–373. doi: 10.1093/nar/9.2.365

Transcriptional errors and ambiguity resulting from the presence of 1,N6-ethenoadenosine or 3,N4-ethenocytidine in polyribonucleotides.

S Spengler, B Singer
PMCID: PMC326698  PMID: 7208355

Abstract

1,N6-Ethenoadenosine (epsilon A) and 3,N4-Ethenocytidine (epsilon C) in copolymers with unmodified nucleosides were transcribed using DNA-dependent RNA polymerase in the presence of Mn2+. Nearest neighbor analysis of the products showed that epsilon A directed incorporation of A much greater than U greater than C while epsilon C directed the incorporation of U greater than or equal to A much greater than C Neither directed G into the complementary polymer. Such misincorporations resulting from epsilon A and epsilon C, compounds that are formed in vivo by the carcinogen vinyl chloride, may have a biological role as promutagens.

Full text

PDF
365

Selected References

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

  1. Barbin A., Brésil H., Croisy A., Jacquignon P., Malaveille C., Montesano R., Bartsch H. Liver-microsome-mediated formation of alkylating agents from vinyl bromide and vinyl chloride. Biochem Biophys Res Commun. 1975 Nov 17;67(2):596–603. doi: 10.1016/0006-291x(75)90854-2. [DOI] [PubMed] [Google Scholar]
  2. Barrio J. R., Secrist J. A., 3rd, Leonard N. J. Fluorescent adenosine and cytidine derivatives. Biochem Biophys Res Commun. 1972 Jan 31;46(2):597–604. doi: 10.1016/s0006-291x(72)80181-5. [DOI] [PubMed] [Google Scholar]
  3. Bartsch H., Montesano R. Mutagenic and carcinogenic effects of vinyl chloride. Mutat Res. 1975;32(2):93–114. doi: 10.1016/0165-1110(75)90001-9. [DOI] [PubMed] [Google Scholar]
  4. Biernat J., Ciesiołka J., Górnicki P., Adamiak R. W., Kryzosiak W. J., Wiewiórowski M. New observations concerning the chloroacetaldehyde reaction with some tRNA constituents. Stable intermediates, kinetics and selectivity of the reaction. Nucleic Acids Res. 1978 Mar;5(3):789–804. doi: 10.1093/nar/5.3.789. [DOI] [PMC free article] [PubMed] [Google Scholar]
  5. Bodell W. J., Singer B. Influence of hydrogen bonding in DNA and polynucleotides on reaction of nitrogens and oxygens toward ethylnitrosourea. Biochemistry. 1979 Jun 26;18(13):2860–2863. doi: 10.1021/bi00580a029. [DOI] [PubMed] [Google Scholar]
  6. Green T., Hathway D. E. Interactions of vinyl chloride with rat-liver DNA in vivo. Chem Biol Interact. 1978 Sep;22(2-3):211–224. doi: 10.1016/0009-2797(78)90126-6. [DOI] [PubMed] [Google Scholar]
  7. Janik B., Sommer R. G., Kotick M. P., Wilson D. P., Erickson J. Synthesis and properties of poly (1,N-6-ethenoadenylic acid) and poly (3,N-4-ethenocytidylic acid). Physiol Chem Phys. 1973;5(1):27–36. [PubMed] [Google Scholar]
  8. Kimura K., Nakanishi M., Yamamoto T., Tsuboi M. A correlation between the secondary structure of DNA and the reactivity of adenine residues with chloroacetaldehyde. J Biochem. 1977 Jun;81(6):1699–1703. doi: 10.1093/oxfordjournals.jbchem.a131629. [DOI] [PubMed] [Google Scholar]
  9. Kröger M., Singer B. Ambiguity and transcriptional errors as a result of methylation of N-1 of purines and N-3 of pyrimidines. Biochemistry. 1979 Aug 7;18(16):3493–3500. doi: 10.1021/bi00583a009. [DOI] [PubMed] [Google Scholar]
  10. Ledneva R. K., Razjivin A. P., Kost A. A., Bogdanov A. A. Interaction of tobacco mosaic virus protein with synthetic polynucleotides containing a fluorescent label: optical properties of poly(A,epsilonA) and poly(C,epsilonC) copolymers and energy migration from the tryptophan to 1,N6-ethenoadenine or 3,N4-ethenocytosine residues in RNP. Nucleic Acids Res. 1978 Nov;5(11):4225–4243. doi: 10.1093/nar/5.11.4225. [DOI] [PMC free article] [PubMed] [Google Scholar]
  11. Lehrach H., Scheit K. H. Synthesis and properties of a new fluorescent polynucleotide, poly(1,N6-ethenoadenylic acid). Biochim Biophys Acta. 1973 Apr 21;308(7):28–34. doi: 10.1016/0005-2787(73)90118-4. [DOI] [PubMed] [Google Scholar]
  12. Ludlum D. B., Metha J. R., Steiner R. F., DeWitt J. Physical properties of poly (3,N4-ethenocytidylic acid). Biophys Chem. 1978 Jan;7(4):339–346. doi: 10.1016/0301-4622(78)85010-8. [DOI] [PubMed] [Google Scholar]
  13. McCann J., Simmon V., Streitwieser D., Ames B. N. Mutagenicity of chloroacetaldehyde, a possible metabolic product of 1,2-dichloroethane (ethylene dichloride), chloroethanol (ethylene chlorohydrin), vinyl chloride, and cyclophosphamide. Proc Natl Acad Sci U S A. 1975 Aug;72(8):3190–3193. doi: 10.1073/pnas.72.8.3190. [DOI] [PMC free article] [PubMed] [Google Scholar]
  14. Sattsangi P. D., Leonard N. J., Frihart C. R. 1,N2-ethenoguanine and N2,3-ethenoguanine. Synthesis and comparison of the electronic spectral properties of these linear and angular triheterocycles related to the Y bases. J Org Chem. 1977 Sep 30;42(20):3292–3296. doi: 10.1021/jo00440a020. [DOI] [PubMed] [Google Scholar]
  15. Singer B., Fraenkel-Conrat H., Kuśmierek J. T. Preparation and template activities of polynucleotides containing O2- and O4-alkyluridine. Proc Natl Acad Sci U S A. 1978 Apr;75(4):1722–1726. doi: 10.1073/pnas.75.4.1722. [DOI] [PMC free article] [PubMed] [Google Scholar]
  16. Singer B., Fraenkel-Conrat H. Messenger and template activities of chemically modified polynucleotides. Biochemistry. 1970 Sep 15;9(19):3694–3701. doi: 10.1021/bi00821a007. [DOI] [PubMed] [Google Scholar]
  17. Singer B., Kröger M. Isolation of polyribonucleotides using cellulose thin-layer plates. Anal Biochem. 1978 Oct 15;90(2):590–595. doi: 10.1016/0003-2697(78)90152-5. [DOI] [PubMed] [Google Scholar]
  18. Singer B., Kröger M. Participation of modified nucleosides in translation and transcription. Prog Nucleic Acid Res Mol Biol. 1979;23:151–194. doi: 10.1016/s0079-6603(08)60133-6. [DOI] [PubMed] [Google Scholar]
  19. Tolman G. L., Barrio J. R., Leonard N. J. Chloroacetaldehyde-modified dinucleoside phosphates. Dynamic fluorescence quenching and quenching due to intramolecular complexation. Biochemistry. 1974 Nov 19;13(24):4869–4878. doi: 10.1021/bi00721a001. [DOI] [PubMed] [Google Scholar]
  20. Wang A. H., Barrio J. R., Paul I. C. Crystal and molecular structure of 3,N4-ethenocytidine hydrochloride. A study of the dimensions and molecular interactions of the fluorescent epsilon-cytidine system. J Am Chem Soc. 1976 Nov 10;98(23):7401–7408. doi: 10.1021/ja00439a048. [DOI] [PubMed] [Google Scholar]
  21. Wang A. H., Dammann L. G., Barrio J. R., Paul I. C. The crystal and molecular structure of a derivative of 1,N6-ethenoadenosine hydrochloride. Dimensions and molecular interactions of the fluorescent epsilon-adenosine (epsilon-ado) system. J Am Chem Soc. 1974 Feb 20;96(4):1205–1212. doi: 10.1021/ja00811a038. [DOI] [PubMed] [Google Scholar]
  22. Zajdela F., Croisy A., Barbin A., Malaveille C., Tomatis L., Bartsch H. Carcinogenicity of chloroethylene oxide, an ultimate reactive metabolite of vinyl chloride, and bis(chloromethyl)ether after subcutaneous administration and in initiation-promotion experiments in mice. Cancer Res. 1980 Feb;40(2):352–356. [PubMed] [Google Scholar]

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

RESOURCES