Sultam thiourea inhibition of West Nile virus

Antimicrobial Agents and Chemotherapy

Volumn 51, Issue 7, 2007, Pages 2642-2645

  Barklis, Eric ^a   Still, Amelia ^a   Sabri, Mohammad I ^a   Hirsch, Alec J ^a,b   Nikolich Zugich, Janko ^a,b   Brien, James ^a,b   Dhenub, Tenzin Choesang ^a   Scholz, Isabel ^a   Alfadhli, Ayna ^a  

^a OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

^b OREGON HEALTH AND SCIENCE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(1,1 DIOXIDO 2 PHENYL 1,4,2 DITHIAZOLIDIN 3 YLIDENE)BIS(PHENYLMETHYL)THIOUREA; (2,5 DIMETHYL 1,1 DIOXIDO 1,4,2 DITHIAZOLIDIN 3 YLIDENE)BIS(1 METHYLETHYL)THIOUREA; [1,1 DIOXIDO 2 (PHENYLMETHYL) 1,4,2 DITHIAZOLIDIN 3 YLIDENE]BIS(1 METHYLETHYL)THIOUREA; N' (1,1 DIOXIDO 2 PHENYL 1,4,2 DITHIAZOLIDIN 3 YLIDENE) N,N DIPHENYLTHIOUREA; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; GENE EXPRESSION; IC 50; NONHUMAN; PRIORITY JOURNAL; REAL TIME POLYMERASE CHAIN REACTION; REPLICON; REPORTER GENE; STRUCTURE ACTIVITY RELATION; VIRUS ASSEMBLY; VIRUS CELL INTERACTION; VIRUS INHIBITION; VIRUS REPLICATION; VIRUS TITRATION; WEST NILE FLAVIVIRUS;

ANIMALS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; REPLICON; RNA, VIRAL; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA; VERO CELLS; VIRUS REPLICATION; WEST NILE VIRUS;

EID: 34447271709     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.00007-07     Document Type: Article

References (39)

1. Abbenante, G., and D. Fairlie. 2005. Protease inhibitors in the clinic. Med. Chem. 1:71-104.
2. Alfadhli, A., Z. Love, B. Arvidson, J. Seeds, J. Willey, and E. Barklis. 2001. Hantavirus nucleocapsid protein oligomerization. J. Virol. 75:2019-2023.
3. Anonymous. 2003. Tricyclic lactam and sultam derivatives as histone deacetylase inhibitors. Expert Opin. Ther. Pat. 13:387-391.
4. Arvidson, B., J. Seeds, M. Webb, L. Finlay, and E. Barklis. 2003. Analysis of the retrovirus capsid interdomain linker region. Virology 308:166-177.
5. Baker, D. C., and B. Jiang. March 2002. Sultams: solid phase and other synthesis of anti-HIV compounds and compositions. U.S. patent 6,353,112 B1.
6. Barltrop, J., T. Owen, A. Cory, and J. Cory. 1991. 5-(3carboxymethoxyphenyl)-2-(4,5-dimethylthiazolyl)-3-(4-sulfophenyl) tetrazolium, inner salt (MTS) and related analogs of 3-(4,5-dimethylthiazolyl)- 2,5-diphenyltetrazolium bromide (mTT) reducing to purple water-soluble formazans as cell-viability indicators. Bioorg. Med. Chem. Lett. 1:611.
7. Borowski, P., M. Lang, A. Haag, H. Schmitz, J. Choe, H.-M. Chen, and R. Hosmane. 2002. Characterization of imidazo(4,5-d)pyridazine nucleosides as modulators of unwinding reaction mediated by West Nile virus nucleoside triphosphatase/helicase: evidence for activity on the level of substrate and/or enzyme. Antimicrob. Agents Chemother. 46:1231-1239.
8. Briese, T., W. Glass, and W. I. Lipkin. 2000. Detection of West Nile virus sequences in cerebrospinal fluid. Lancet 355:1614-1615.
9. Brinton, M. 2002. The molecular biology of West Nile virus. Annu. Rev. Microbiol. 56:371-402.
10. Centers for Disease Control and Prevention. 1999. Outbreak of West Nile-like viral encephalitis - New York. Morb. Mortal. Wkly. Rep. 48:25-28.
11. Centers for Disease Control and Prevention. 2002. Provisional surveillance summary of the West Nile virus epidemic - United States, January-November 2002. Morb. Mortal. Wkly. Rep. 51:1129-1133.
12. Centers for Disease Control and Prevention. 2005. West Nile virus. Centers for Disease Control and Prevention, Atlanta, GA. http://www.cdc.gov/ ncidod/dvbid/westnile/index.html.
13. Chambers, T., C. Hahn, R. Galler, and C. Rice. 1990. Flavivirus genome organization, expression, and replication. Annu. Rev. Microbiol. 44:649-688.
14. Cherney, R., R. Mo, D. Meyer, K. Hardman, R. Liu, M. Covington, M. Qian, Z. Wasserman, D. Christ, J. Trzaskos, R. Newton, and C. Decicco. 2004. Sultam hydroxamates as novel matrix metalloproteinase inhibitors. J. Med. Chem. 47:2981-2983.
15. Courageot, M.-P., M.-P. Frenkiel, C. Duarte Dos Santos, V. Deubel, and P. Despres. 2000. α-Glucosidase inhibitors reduce dengue virus production by affecting the initial steps of virion morphogenesis in the endoplasmic reticulum. J. Virol. 74:564-572.
16. Dayam, R., J. Deng, and N. Neamati. 2006. HIV-1 integrase inhibitors: 2003-2004 update. Med. Res. Rev. 26:271-309.
17. Diamond, M., M. Zachariah, and E. Harris. 2002. Mycophenolic acid inhibits dengue virus infection by preventing replication of viral RNA. Virology 304:211-221.
18. Hansen, M., L. Jelinek, S. Whiting, and E. Barklis. 1990. Transport and assembly of Gag proteins into Moloney murine leukemia virus. J. Virol. 64:5306-5316.
19. Hirsch, A., G. Medigeshi, H. Meyers, V. DeFilippis, K. Fruh, T. Briese, W. I. Lipkin, and J. Nelson. 2005. The Src family kinase c-Yes is required for maturation of West Nile virus particles. J. Virol. 79:11943-11951.
20. Hong, Z., and C. Cameron. 2002. Pleiotropic mechanisms of ribavirin antiviral activities. Prog. Drug Res. 59:41-69.
21. Inagaki, M. 2003. Studies on the new antiarthritic drug candidate S-2474. Yakugaku Zasshi 123:323-330.
22. Inagaki, M., T. Tsuri, H. Jyoyama, T. Ono, K. Yamada, M. Kobayashi, Y. Hori, A. Arimura, K. Yasui, K. Ohno, S. Kakudo, K. Koizumi, R. Suzuki, S. Kawai, M. Kato, and S. Matsumoto. 2000. Novel antiarthritic agents with 1,2-isothiazolidine-1,1-dioxide (gamma-sultam) skeleton: cytokine suppressive dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase. J. Med. Chem. 43:2040-2048.
23. Jones, T. A., G. Blaug, M. Hansen, and E. Barklis. 1990. Assembly of Gag-β-galactosidase proteins into retrovirus particles. J. Virol. 64:2265-2279.
24. Jordan, I., T. Briese, N. Fischer, J. Lau, and W. I. Lipkin. 2000. Ribavirin inhibits West Nile virus replication and cytopathic effect in neural cells. J. Infect. Dis. 182:1214-1217.
25. Kimura-Kuroda, J., and K. Yasui. 1988. Protection of mice against Japanese encephalitis virus by passive administration with monoclonal antibodies. J. Immunol. 141:3606-3610.
26. Leung, D., K. Schroder, H. White, N.-X. Fang, M. Stoermer, G. Abbenante, J. Martin, P. Young, and D. Fairlie. 2001. Activity of recombinant dengue 2 virus NS3 protease in the presence of a truncated NS2B cofactor, small peptide substrates, and inhibitors. J. Biol. Chem. 276:45762-45771.
27. Leyssen, P., J. Balzarini, E. De Clercq, and J. Neyts. 2005. The predominant mechanism by which ribavirin exerts its antiviral activity in vitro against flaviviruses and paramyxoviruses is mediated by inhibition of IMP dehydrogenase. J. Virol. 79:1943-1947.
28. Linden, H., and J. Goerdeler. 1977. Ring opening cycloadditions. 5. Reaction of iminodithiazoles with sulfenes in 5-membered sultams. Tetrahedron Lett. 20:1729-1732.
29. Morrey, J., D. Smee, R. Sidwell, and C. Tseng. 2002. Identification of active antiviral compounds against a New York isolate of the West Nile virus. Antivir. Res. 55:107-116.
30. Ni, H., N. Burns, G. Chang, M. Zhang, M. Wills, D. Trent, P. Sanders, and A. Barrett. 1994. Comparison of nucleotide and deduced amino acid sequence of the 5′ non-coding region and structural protein genes of the wild-type Japanese encephalitis virus strain SA14 and its attenuated vaccine derivatives. J. Gen. Virol. 75:1505-1510.
31. Page, M. 2004. Beta-sultams - mechanism of reactions and use as inhibitors of serine proteases. Acc. Chem. Res. 37:297-303.
32. Puig-Basagoiti, F., M. Tilgner, B. Forshey, S. Philpott, N. Espina, D. Wentworth, S. Goebel, P. Masters, B. Falgout, P. Ren, D. Ferguson, and P.-Y. Shi. 2006. Triaryl pyrazoline compound inhibits flavivirus RNA replication. Antimicrob. Agents Chemother. 50:1320-1329.
33. Rossi, S., Q. Zhao, V. O'Donnell, and P. Mason. 2005. Adaptation of West Nile virus replicons to cells in culture and use of replicon-bearing cells to probe antiviral action. Virology 331:457-470.
34. Scholz, I., B. Arvidson, D. Huseby, and E. Barklis. 2005. Virus particle core defects caused by mutations in the human immunodeficiency virus capsid N-terminal domain. J. Virol. 79:1470-1479.
35. Shimoni, Z., M. Niven, S. Pitlick, and S. Bulvik. 2001. Treatment of West Nile virus encephalitis with intravenous immunoglobulin. Emerg. Infect. Dis. 7:759.
36. Whitby, K., T. Pierson, B. Geiss, K. Lane, M. Engel, Y. Zhou, R. Doms, and M. Diamond. 2005. Castanospermine, a potent inhibitor of dengue virus infection in vitro and in vivo. 1. Virol. 79:8698-8706.
37. World Health Organization. 2002. Immunization vaccines and biologicals: Japanese encephalitis. World Health Organization, Geneva, Switzerland. http://www.who.int/vaccines-disease/diseases/je.shtml.
38. Wu, S.-F., C.-J. Lee, C.-L. Liao, R. Dwek, N. Zitzmann, and Y.-L. Lin. 2002. Antiviral effects of an iminosugar derivative on flavivirus infections. J. Virol. 76:3596-3604.
39. Zhang, N., H. Chen, V. Koch, H. Schmitz, M. Minczuk, P. Stepien, A. Fattom, R. Naso, K. Kalicharran, P. Borowski, and R. Hosmane. 2003. Potent inhibition of NTPase/helicase of the West Nile virus by ring-expanded ("fat") nucleoside analogues. J. Med. Chem. 46:4776-4789.