Inhibition of herpesvirus replication by 5-substituted 4′- thiopyrimidine nucleosides

Antimicrobial Agents and Chemotherapy

Volumn 53, Issue 12, 2009, Pages 5251-5258

  Prichard, Mark N ^a   Quenelle, Debra C ^a   Hartline, Caroll B ^a   Harden, Emma A ^a   Jefferson, Geraldine ^a   Frederick, Samuel L ^a   Daily, Shannon L ^a   Whitley, Richard J ^a   Tiwari, Kamal N ^b   Maddry, Joseph A ^b   Secrist III, John A ^b   Kern, Earl R ^a  

^a UNIVERSITY OF ALABAMA SCHOOL OF MEDICINE   (United States)

^b SOUTHERN RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 DEOXY 4 THIO BETA DEXTRO RIBOFURANOSYL) 5 BROMOCYTOSINE; 1 (2 DEOXY 4 THIO BETA DEXTRO RIBOFURANOSYL) 5 BROMOURACIL; 1 (2 DEOXY 4 THIO BETA DEXTRO RIBOFURANOSYL) 5 IODOURACIL; 1 (2 DEOXY 4 THIO BETA DEXTRO RIBOFURANOSYL) 5 TRIFLUOROMETHYLURACIL; 1 (4 THIO BETA DEXTRO ARABINOFURANOSYL) CYTOSINE; 1 (4 THIO BETA DEXTRO ARABINOFURANOSYL) FLUCYTOSINE; 4' THIOTHYMIDINE; ACICLOVIR; ANTIVIRUS AGENT; CIDOFOVIR; DNA POLYMERASE; FOSCARNET; GANCICLOVIR; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; VIRUS DNA;

ANIMAL EXPERIMENT; ANTIVIRAL ACTIVITY; ANTIVIRAL RESISTANCE; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; EPSTEIN BARR VIRUS; FEMALE; GENE MUTATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HERPES VIRUS; HERPES VIRUS INFECTION; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HUMAN CYTOMEGALOVIRUS; HUMAN HERPESVIRUS 6; HUMAN HERPESVIRUS 8; IN VITRO STUDY; IN VIVO STUDY; MORTALITY; MOUSE; NEWBORN; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROGNOSIS; SKIN FIBROBLAST; SURVIVAL; VARICELLA ZOSTER VIRUS; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; CELL PROLIFERATION; CELLS, CULTURED; DNA-DIRECTED DNA POLYMERASE; DRUG RESISTANCE, VIRAL; FLUORESCENT ANTIBODY TECHNIQUE, INDIRECT; HERPESVIRIDAE; HERPESVIRIDAE INFECTIONS; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; HERPESVIRUS 6, HUMAN; HERPESVIRUS 8, HUMAN; HUMANS; MICE; MICE, INBRED BALB C; MICROSCOPY, FLUORESCENCE; MOLECULAR STRUCTURE; PYRIMIDINE NUCLEOSIDES; VIRAL PROTEINS; VIRUS REPLICATION;

EID: 71249092151     PISSN: 00664804     EISSN: 10986596     Source Type: Journal    
DOI: 10.1128/AAC.00417-09     Document Type: Article

References (36)

1. Bidanset, D. J., J. R. Beadle, W. B. Wan, K. Y. Hostetler, and E. R. Kern. 2004. Oral activity of ether lipid ester prodrugs of cidofovir against experimental human cytomegalovirus infection. J. Infect. Dis. 190:499-503.
2. Black, M. E., and D. E. Hruby. 1992. Site-directed mutagenesis of a conserved domain in vaccinia virus thymidine kinase. Evidence for a potential role in magnesium binding. J. Biol. Chem. 267:6801-6806.
3. Buller, R. M., G. Owens, J. Schriewer, L. Melman, J. R. Beadle, and K. Y. Hostetler. 2004. Efficacy of oral active ether lipid analogs of cidofovir in a lethal mousepox model. Virology 318:474-481.
4. Ciesla, S. L., J. Trahan, W. B. Wan, J. R. Beadle, K. A. Aldern, G. R. Painter, and K. Y. Hostetler. 2003. Esterification of cidofovir with alkoxyalkanols increases oral bioavailability and diminishes drug accumulation in kidney. Antivir. Res. 59:163-171.
5. De Clercq, E. 2007. The design of drugs for HIV and HCV. Nat. Rev. Drug Discov. 6:1001-1018.
6. De Clercq, E., and A. Holy. 2005. Acyclic nucleoside phosphonates: a key class of antiviral drugs. Nat. Rev. Drug Discov. 4:928-940.
7. Erlich, K. S., J. Mills, P. Chatis, G. J. Mertz, D. F. Busch, S. E. Follansbee, R. M. Grant, and C. S. Crumpacker. 1989. Acyclovir-resistant herpes simplex virus infections in patients with the acquired immunodeficiency syndrome. N. Engl. J. Med. 320:293-296.
8. Fan, X., X. Zhang, L. Zhou, K. A. Keith, M. N. Prichard, E. R. Kern, and P. F. Torrence. 2006. Toward orthopoxvirus countermeasures: a novel heteromorphic nucleoside of unusual structure. J. Med. Chem. 49:4052-4054.
9. Ferir, G., S. Kaptein, J. Neyts, and E. De Clercq. 2008. Antiviral treatment of chronic hepatitis B virus infections: the past, the present and the future. Rev. Med. Virol. 18:19-34.
10. Fischer, P. H., M. A. Weddle, and R. D. Mossie. 1983. Modulation of the metabolism and cytotoxicity of iododeoxyuridine by 5′-amino-5′- deoxythymidine. Mol. Pharmacol. 23:709-716.
11. Gilbert, C., J. Bestman-Smith, and G. Boivin. 2002. Resistance of herpesviruses to antiviral drugs: clinical impacts and molecular mechanisms. Drug Resist. Updat. 5:88-114.
12. Gill, R. B., S. L. Frederick, C. B. Hartline, S. Chou, and M. N. Prichard. 2009. Conserved retinoblastoma protein-binding motif in human cytomegalovirus UL97 kinase minimally impacts viral replication but affects susceptibility to maribavir. Virol. J. 6:9.
13. Hartline, C. B., K. M. Gustin, W. B. Wan, S. L. Ciesla, J. R. Beadle, K. Y. Hostetler, and E. R. Kern. 2005. Ether lipid-ester prodrugs of acyclic nucleoside phosphonates: activity against adenovirus replication in vitro. J. Infect. Dis. 191:396-399.
14. Hartline, C. B., E. A. Harden, S. L. Williams-Aziz, N. L. Kushner, R. J. Brideau, and E. R. Kern. 2005. Inhibition of herpesvirus replication by a series of 4-oxodihydroquinolines with viral polymerase activity. Antivir. Res. 65:97-105.
15. Hruby, D. E., R. A. Maki, D. B. Miller, and L. A. Ball. 1983. Fine structure analysis and nucleotide sequence of the vaccinia virus thymidine kinase gene. Proc. Natl. Acad. Sci. USA 80:3411-3415.
16. Jamieson, A. T., and J. H. Subak-Sharpe. 1974. Biochemical studies on the herpes simplex virus-specified deoxypyrimidine kinase activity. J. Gen. Virol. 24:481-492.
17. Kern, E. R., D. J. Collins, W. B. Wan, J. R. Beadle, K. Y. Hostetler, and D. C. Quenelle. 2004. Oral treatment of murine cytomegalovirus infections with ether lipid esters of cidofovir. Antimicrob. Agents Chemother. 48:3516-3522.
18. Kern, E. R., C. Hartline, E. Harden, K. Keith, N. Rodriguez, J. R. Beadle, and K. Y. Hostetler. 2002. Enhanced inhibition of orthopoxvirus replication in vitro by alkoxyalkyl esters of cidofovir and cyclic cidofovir. Antimicrob. Agents Chemother. 46:991-995.
19. Kern, E. R., M. N. Prichard, D. C. Quenelle, K. A. Keith, K. N. Tiwari, J. A. Maddry, and J. A. Secrist III. 2009. Activities of certain 5-substituted 4′- thiopyrimidine nucleosides against orthopoxvirus infections. Antimicrob. Agents Chemother. 53:572-579.
20. Lagoja, I. M., and E. De Clercq. 2008. Anti-influenza virus agents: synthesis and mode of action. Med. Res. Rev. 28:1-38.
21. Larder, B. A., Y. C. Cheng, and G. Darby. 1983. Characterization of abnormal thymidine kinases induced by drug-resistant strains of herpes simplex virus type 1. J. Gen. Virol. 64(Pt. 3):523-532.
22. Larder, B. A., D. Derse, Y. C. Cheng, and G. Darby. 1983. Properties of purified enzymes induced by pathogenic drug-resistant mutants of herpes simplex virus. Evidence for virus variants expressing normal DNA polymerase and altered thymidine kinase. J. Biol. Chem. 258:2027-2033.
23. Morfin, F., and D. Thouvenot. 2003. Herpes simplex virus resistance to antiviral drugs. J. Clin. Virol. 26:29-37.
24. Prichard, M. N., S. L. Daily, G. M. Jefferson, A. L. Perry, and E. R. Kern. 2007. A rapid DNA hybridization assay for the evaluation of antiviral compounds against Epstein-Barr virus. J. Virol. Methods 144:86-90.
25. Prichard, M. N., K. A. Keith, M. P. Johnson, E. A. Harden, A. McBrayer, M. Luo, S. Qiu, D. Chattopadhyay, X. Fan, P. F. Torrence, and E. R. Kern. 2007. Selective phosphorylation of antiviral drugs by vaccinia virus thymidine kinase. Antimicrob. Agents Chemother. 51:1795-1803.
26. Prichard, M. N., K. A. Keith, D. C. Quenelle, and E. R. Kern. 2006. Activity and mechanism of action of N-methanocarbathymidine against herpesvirus and orthopoxvirus infections. Antimicrob. Agents Chemother. 50:1336-1341.
27. Prichard, M. N., and C. Shipman, Jr. 1990. A three-dimensional model to analyze drug-drug interactions. Antivir. Res. 14:181-205.
28. Prichard, M. N., E. Sztul, S. L. Daily, A. L. Perry, S. L. Frederick, R. B. Gill, C. B. Hartline, D. N. Streblow, S. M. Varnum, R. D. Smith, and E. R. Kern. 2008. Human cytomegalovirus UL97 kinase activity is required for the hyperphosphorylation of retinoblastoma protein and inhibits the formation of nuclear aggresomes. J. Virol. 82:5054-5067.
29. Prichard, M. N., A. D. Williams, K. A. Keith, E. A. Harden, and E. R. Kern. 2006. Distinct thymidine kinases encoded by cowpox virus and herpes simplex virus contribute significantly to the differential antiviral activity of nucleoside analogs. Antivir. Res. 71:1-6.
30. Quenelle, D. C., D. J. Collins, and E. R. Kern. 2004. Cutaneous infections of mice with vaccinia or cowpox viruses and efficacy of cidofovir. Antivir. Res. 63:33-40.
31. Rahim, S. G., N. Trivedi, M. V. Bogunovic-Batchelor, G. W. Hardy, G. Mills, J. W. Selway, W. Snowden, E. Littler, P. L. Coe, I. Basnak, R. F. Whale, and R. T. Walker. 1996. Synthesis and anti-herpes virus activity of 2′-deoxy-4′- thiopyrimidine nucleosides. J. Med. Chem. 39:789-795.
32. Randhawa, P., N. A. Farasati, R. Shapiro, and K. Y. Hostetler. 2006. Ether lipid ester derivatives of cidofovir inhibit polyomavirus BK replication in vitro. Antimicrob. Agents Chemother. 50:1564-1566.
33. Secrist, J. A., III, K. N. Tiwari, J. M. Riordan, and J. A. Montgomery. 1991. Synthesis and biological activity of 2′-deoxy-4′-thio pyrimidine nucleosides. J. Med. Chem. 34:2361-2366.
34. Tiwari, K. N., A. T. Shortnacy-Fowler, L. Cappellacci, W. B. Parker, W. R. Waud, J. A. Montgomery, and J. A. Secrist III. 2000. Synthesis of 4′-thio-beta- D-arabinofuranosylcytosine (4′-thio-ara-C) and comparison of its anticancer activity with that of ara-C. Nucleosides Nucleotides Nucleic Acids 19:329-340.
35. Tiwari, K. N., A. T. Shortnacy-Fowler, L. Cappellacci, W. R. Waud, W. B. Parker, J. A. Montgomery, and J. A. Secrist III. 2000. Synthesis and structure activity relationships of 5-substituted-4′-thio-beta-D- arabinofuranosylcytosines. Nucleosides Nucleotides Nucleic Acids 19:2005-2017.
36. Williams-Aziz, S. L., C. B. Hartline, E. A. Harden, S. L. Daily, M. N. Prichard, N. L. Kushner, J. R. Beadle, W. B. Wan, K. Y. Hostetler, and E. R. Kern. 2005. Comparative activities of lipid esters of cidofovir and cyclic cidofovir against replication of herpesviruses in vitro. Antimicrob. Agents Chemother. 49:3724-3733.