Abstract
3'-Deoxycytidine 5'-triphosphate and 3'-deoxyuridine 5'-triphosphate were synthesized starting from cordycepin in good yield. The inhibitory effects of these nucleotides were examined in comparison with that of cordycepin 5'-triphosphate (3'-dATP) using purified DNA-dependent RNA polymerases I and II from Dictyostelium discoideum cells. Both nucleotide analogues strongly and competitively inhibited the incorporations of CTP and UTP into RNA by the RNA polymerases. The Km and Ki values for CTP and 3'-dCTP were 6.3 micro M and 3.0 micro M, respectively, and those for UTP and 3'-dUTP were 6.3 micro M and 2.0 micro M, respectively. These two analogues will be useful in studies at the molecular level on the relationship of template and substrate in RNA synthesis with chromatin, isolated nuclei or permeable cells, because they do not have any effect on poly (rA) synthesis.
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Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Abelson H. T., Penman S. Messenger RNA formation: resistance to inhibition by 3'-deoxycytidine. Biochim Biophys Acta. 1972 Aug 16;277(1):129–133. doi: 10.1016/0005-2787(72)90359-0. [DOI] [PubMed] [Google Scholar]
- HOARD D. E., OTT D. G. CONVERSION OF MONO- AND OLIGODEOXYRIBONUCLEOTIDES TO 5-TRIPHOSPHATES. J Am Chem Soc. 1965 Apr 20;87:1785–1788. doi: 10.1021/ja01086a031. [DOI] [PubMed] [Google Scholar]
- Horowitz B., Goldfinger B. A., Marmur J. Effect of cordycepin triphosphate on the nuclear DNA-dependent RNA polymerases and poly(A) polymerase from the yeast, Saccharomyces cerevisiae. Arch Biochem Biophys. 1976 Jan;172(1):143–148. doi: 10.1016/0003-9861(76)90059-x. [DOI] [PubMed] [Google Scholar]
- Lindell T. J., Weinberg F., Morris P. W., Roeder R. G., Rutter W. J. Specific inhibition of nuclear RNA polymerase II by alpha-amanitin. Science. 1970 Oct 23;170(3956):447–449. doi: 10.1126/science.170.3956.447. [DOI] [PubMed] [Google Scholar]
- Litman R. M. A deoxyribonucleic acid polymerase from Micrococcus luteus (Micrococcus lysodeikticus) isolated on deoxyribonucleic acid-cellulose. J Biol Chem. 1968 Dec 10;243(23):6222–6233. [PubMed] [Google Scholar]
- Matsukage A., Ono K., Ohashi A., Takahashi T., Nakayama C., Saneyoshi M. Inhibitory effect of 1-beta-D-arabinofuranosylthymine 5'-triphosphate and 1-beta-D-arabinofuranosylcytosine 5'-triphosphate on DNA polymerases from murine cells and oncornavirus. Cancer Res. 1978 Sep;38(9):3076–3079. [PubMed] [Google Scholar]
- Mendecki J., Lee S. Y., Brawerman G. Characteristics of the polyadenylic acid segment associated with messenger ribonucleic acid in mouse sarcoma 180 ascites cells. Biochemistry. 1972 Feb 29;11(5):792–798. doi: 10.1021/bi00755a018. [DOI] [PubMed] [Google Scholar]
- Mutsukage A., Takahashi T., Nakayama C., Saneyoshi M. Inhibition of mouse myeloma DNA polymerase alpha by 5-triphosphates of 1-beta-D-arabinofuranosylthymine and 1-beta-D-arabinofuranosylcytosine. J Biochem. 1978 May;83(5):1511–1515. doi: 10.1093/oxfordjournals.jbchem.a132061. [DOI] [PubMed] [Google Scholar]
- Ono K., Ohashi A., Yamamoto A., Matsukage A., Takahasi T., Saneyoshi M., Ueda T. Inhibitory effects of 9-beta-D-arabinofuranosylguanine 5'-triphosphate and 9-beta-D-arabinofuranosyladenine 5'-triphosphate on DNA polymerases from murine cells and oncornavirus. Cancer Res. 1979 Nov;39(11):4673–4680. [PubMed] [Google Scholar]
- ROTTMAN F., GUARINO A. J. THE INHIBITION OF PHOSPHORIBOSYL-PYROPHOSPHATE AMIDOTRANSFERASE ACTIVITY BY CORDYCEPIN MONOPHOSPHATE. Biochim Biophys Acta. 1964 Sep 18;89:465–472. doi: 10.1016/0926-6569(64)90072-0. [DOI] [PubMed] [Google Scholar]
- Rose K. M., Bell L. E., Jacob S. T. Specific inhibition of chromatin-associated poly(A) synthesis in vitro by cordycepin 5'-triphosphate. Nature. 1977 May 12;267(5607):178–180. doi: 10.1038/267178a0. [DOI] [PubMed] [Google Scholar]
- Saneyoshi M., Morozumi M., Kodama K., Machida H., Kuninaka A., Yoshino H. Synthetic nucleosides and nucleotides. XVI. Synthesis and biological evaluations of a series of 1-beta-D-arabinofuranosylcytosine 5'-alkyl or arylphosphates. Chem Pharm Bull (Tokyo) 1980 Oct;28(10):2915–2923. doi: 10.1248/cpb.28.2915. [DOI] [PubMed] [Google Scholar]
- Takiya S., Takoh Y., Iwabuchi M. Template specificity of DNA-dependent RNA polymerase I and II for synthetic polynucleotides during development of the cellular slime mold Dictyostelium discoideum. J Biochem. 1980 May;87(5):1501–1509. doi: 10.1093/oxfordjournals.jbchem.a132891. [DOI] [PubMed] [Google Scholar]
- Yagura T., Yanagisawa M., Iwabuchi M. Evidence for two alpha-amanitin-resistant RNA polymerases in vegetative amoebae of Dictyostelium discoideum. Biochem Biophys Res Commun. 1976 Jan 12;68(1):183–189. doi: 10.1016/0006-291x(76)90027-9. [DOI] [PubMed] [Google Scholar]