Abstract
The affinities of the monophosphates of 2'-fluoro-5-iodo-1-beta-D-arabinofuranosyluracil and its 5-methyl analog for cellular thymidylate kinase were two or more orders of magnitude greater than for the thymidine-thymidylate kinases from herpes simplex virus types 1 and 2. In contrast, the monophosphate of (E)-5-(2-bromovinyl)-2'-deoxyuridine was found to have a higher affinity for the viral enzymes than for the cellular enzyme.
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Selected References
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- Ashton W. T., Karkas J. D., Field A. K., Tolman R. L. Activation by thymidine kinase and potent antiherpetic activity of 2'-nor-2'-deoxyguanosine (2'NDG). Biochem Biophys Res Commun. 1982 Oct 29;108(4):1716–1721. doi: 10.1016/s0006-291x(82)80109-5. [DOI] [PubMed] [Google Scholar]
- Chen M. S., Chang P. K., Prusoff W. H. Photochemical studies and ultraviolet sensitization of Escherichia coli thymidylate kinase by various halogenated substrate analogs. J Biol Chem. 1976 Nov 10;251(21):6555–6561. [PMC free article] [PubMed] [Google Scholar]
- Chen M. S., Prusoff W. H. Association of thymidylate kinase activity with pyrimidine deoxyribonucleoside kinase induced by herpes simplex virus. J Biol Chem. 1978 Mar 10;253(5):1325–1327. [PubMed] [Google Scholar]
- Chen M. S., Walker J., Prusoff W. H. Kinetic studies of herpes simplex virus type 1-encoded thymidine and thymidylate kinase, a multifunctional enzyme. J Biol Chem. 1979 Nov 10;254(21):10747–10753. [PubMed] [Google Scholar]
- Cheng Y. C., Dutschman G., Fox J. J., Watanabe K. A., Machida H. Differential activity of potential antiviral nucleoside analogs on herpes simplex virus-induced and human cellular thymidine kinases. Antimicrob Agents Chemother. 1981 Sep;20(3):420–423. doi: 10.1128/aac.20.3.420. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Cheng Y. C., Ostrander M. Deoxythymidine kinase induced in HeLa TK- cells by herpes simplex virus type I and type II. II. Purification and characterization. J Biol Chem. 1976 May 10;251(9):2605–2610. [PubMed] [Google Scholar]
- De Clercq E., Descamps J., De Somer P., Barr P. J., Jones A. S., Walker R. T. (E)-5-(2-Bromovinyl)-2'-deoxyuridine: a potent and selective anti-herpes agent. Proc Natl Acad Sci U S A. 1979 Jun;76(6):2947–2951. doi: 10.1073/pnas.76.6.2947. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Elion G. B., Furman P. A., Fyfe J. A., de Miranda P., Beauchamp L., Schaeffer H. J. Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl) guanine. Proc Natl Acad Sci U S A. 1977 Dec;74(12):5716–5720. doi: 10.1073/pnas.74.12.5716. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Frank K. B., Chiou J. F., Cheng Y. C. Interaction of herpes simplex virus-induced DNA polymerase with 9-(1,3-dihydroxy-2-propoxymethyl)guanine triphosphate. J Biol Chem. 1984 Feb 10;259(3):1566–1569. [PubMed] [Google Scholar]
- Furman P. A., St Clair M. H., Fyfe J. A., Rideout J. L., Keller P. M., Elion G. B. Inhibition of herpes simplex virus-induced DNA polymerase activity and viral DNA replication by 9-(2-hydroxyethoxymethyl)guanine and its triphosphate. J Virol. 1979 Oct;32(1):72–77. doi: 10.1128/jvi.32.1.72-77.1979. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Fyfe J. A. Differential phosphorylation of (E)-5-(2-bromovinyl)-2'-deoxyuridine monophosphate by thymidylate kinases from herpes simplex viruses types 1 and 2 and varicella zoster virus. Mol Pharmacol. 1982 Mar;21(2):432–437. [PubMed] [Google Scholar]
- Grant A. J., Feinberg A., Chou T. C., Watanabe K. A., Fox J. J., Philips F. S. Incorporation of metabolites of 2'-fluoro-5-iodo-1-beta-D-arabinofuranosylcytosine into deoxyribonucleic acid of neoplastic and normal mammalian tissues. Biochem Pharmacol. 1982 Mar 15;31(6):1103–1108. doi: 10.1016/0006-2952(82)90349-5. [DOI] [PubMed] [Google Scholar]
- Lopez C., Watanabe K. A., Fox J. J. 2'-fluoro-5-iodo-aracytosine, a potent and selective anti-herpesvirus agent. Antimicrob Agents Chemother. 1980 May;17(5):803–806. doi: 10.1128/aac.17.5.803. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Miller W. H., Miller R. L. Phosphorylation of acyclovir (acycloguanosine) monophosphate by GMP kinase. J Biol Chem. 1980 Aug 10;255(15):7204–7207. [PubMed] [Google Scholar]
- Schinazi R. F., Peters J., Sokol M. K., Nahmias A. J. Therapeutic activities of 1-(2-fluoro-2-deoxy-beta-D-arabinofuranosyl)-5-iodocytosine and -thymine alone and in combination with acyclovir and vidarabine in mice infected intracerebrally with herpes simplex virus. Antimicrob Agents Chemother. 1983 Jul;24(1):95–103. doi: 10.1128/aac.24.1.95. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Smith K. O., Galloway K. S., Kennell W. L., Ogilvie K. K., Radatus B. K. A new nucleoside analog, 9-[[2-hydroxy-1-(hydroxymethyl)ethoxyl]methyl]guanine, highly active in vitro against herpes simplex virus types 1 and 2. Antimicrob Agents Chemother. 1982 Jul;22(1):55–61. doi: 10.1128/aac.22.1.55. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Trousdale M. D., Nesburn A. B., Su T. L., Lopez C., Watanabe K. A., Fox J. J. Activity of 1-(2'-fluoro-2'-deoxy-beta-D-arabinofuranosyl)thymine against herpes simplex virus in cell cultures and rabbit eyes. Antimicrob Agents Chemother. 1983 Jun;23(6):808–813. doi: 10.1128/aac.23.6.808. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Watanabe K. A., Reichman U., Hirota K., Lopez C., Fox J. J. Nucleosides. 110. Synthesis and antiherpes virus activity of some 2'-fluoro-2'-deoxyarabinofuranosylpyrimidine nucleosides. J Med Chem. 1979 Jan;22(1):21–24. doi: 10.1021/jm00187a005. [DOI] [PubMed] [Google Scholar]
- Yoshikawa M., Kato T., Takenishi T. A novel method for phosphorylation of nucleosides to 5'-nucleotides. Tetrahedron Lett. 1967 Dec;50:5065–5068. doi: 10.1016/s0040-4039(01)89915-9. [DOI] [PubMed] [Google Scholar]