3′,5′ Di-o-trityluridine inhibits in vitro flavivirus replication

Antiviral Research

Volumn 98, Issue 2, 2013, Pages 242-247

  De Burghgraeve, Tine ^a   Selisko, Barbara ^b   Kaptein, Suzanne ^a   Chatelain, Grégory ^a   Leyssen, Pieter ^a   Debing, Yannick ^a   Jacobs, Michael ^c   Van Aerschot, Arthur ^a   Canard, Bruno ^b   Neyts, Johan ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^b AIX MARSEILLE UNIVERSITY   (France)

^c ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

Author keywords

Dengue virus; Flavivirus inhibitors; Tritylated nucleosides; Tritylated nucleosides.; Yellow fever virus

Indexed keywords

3',5' DI O TRITYLURIDINE; ANTIVIRUS AGENT; UNCLASSIFIED DRUG; 3',5'-DI-O-TRITYLURIDINE; DRUG DERIVATIVE; RNA DIRECTED RNA POLYMERASE; TRITYL DERIVATIVE; URIDINE; VIRUS PROTEIN;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOPATHOGENIC EFFECT; DENGUE VIRUS; FLAVIVIRUS; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; REPLICON; RNA REPLICATION; VIRUS INHIBITION; VIRUS REPLICATION; YELLOW FEVER FLAVIVIRUS; DENGUE; DOWN REGULATION; DRUG ANTAGONISM; DRUG EFFECT; DRUG SCREENING; GENETICS; HUMAN; METABOLISM; PHYSIOLOGY; VIROLOGY; YELLOW FEVER;

DENGUE VIRUS; FLAVIVIRIDAE; FLAVIVIRUS; POLYMERA; YELLOW FEVER VIRUS;

ANTIVIRAL AGENTS; DENGUE; DENGUE VIRUS; DOWN-REGULATION; DRUG EVALUATION, PRECLINICAL; HUMANS; RNA REPLICASE; TRITYL COMPOUNDS; URIDINE; VIRAL PROTEINS; VIRUS REPLICATION; YELLOW FEVER; YELLOW FEVER VIRUS;

EID: 84875981242     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2013.01.011     Document Type: Article

References (48)

1. Barnett, E.D.,2007.Yellow fever:epidemiology and prevention.Clin.Infect.Dis.44, 850-856.
2. Barnett E.D. Yellow fever: epidemiology and prevention. Clin. Infect. Dis. 2007, 44:850-856.
3. Blank, H.U.,Pfleiderer, W.,1967.Pyrimidine XXI:Zur synthese des ersten definierten 20.30.50-trio-O-trityl-ribonucleosids. Tetrahedron Lett.8,869-870.
4. Blank H.U., Pfleiderer W. Pyrimidine XXI: Zur synthese des ersten definierten 2'.3'.5'-trio-O-trityl-ribonucleosids. Tetrahedron Lett. 1967, 8:869-870.
5. Bollati, M.,Alvarez, K.,Assenberg, R.,Baronti, C.,Canard, B.,et al.,2010.Structure and functionality inflavivirusNS-proteins:perspectives for drug design. Antiviral Res. 87,125-148.
6. Bollati M., Alvarez K., Assenberg R., Baronti C., Canard B., et al. Structure and functionality in flavivirus NS-proteins: perspectives for drug design. Antiviral Res. 2010, 87:125-148.
7. Charlier, N.,Molenkamp, R.,Leyssen, P.,Paeshuyse, J.,Drosten, C.,et al.,2004. Exchanging the yellow fever virus envelope proteins with modoc virus prM and E proteins results inachimeric virus that isneuroinvasive inSCID mice.J.Virol. 78, 7418-7426.
8. Charlier N., Molenkamp R., Leyssen P., Paeshuyse J., Drosten C., et al. Exchanging the yellow fever virus envelope proteins with modoc virus prM and E proteins results in a chimeric virus that is neuroinvasive in SCID mice. J. Virol. 2004, 78:7418-7426.
9. De Palma, A.M.,Heggermont, W.,Leyssen, P.,Purstinger, G.,Wimmer, E.,et al.,2007. Anti-enterovirus activity and structure-activity relationship ofaseries of2,6- dihalophenyl-substituted 1H,3H-thiazolo[3,4-a]benzimidazoles. Biochem. Biophys. Res.Commun.353,628-632.
10. De Palma A.M., Heggermont W., Leyssen P., Purstinger G., Wimmer E., et al. Anti-enterovirus activity and structure-activity relationship of a series of 2,6-dihalophenyl-substituted 1H,3H-thiazolo[3,4-a]benzimidazoles. Biochem. Biophys. Res. Commun. 2007, 353:628-632.
11. Gould, E.A., Solomon, T.,2008.Pathogenic flaviviruses.Lancet 371,500-509.
12. Gould E.A., Solomon T. Pathogenic flaviviruses. Lancet 2008, 371:500-509.
13. Halstead, S.B.,Porterfield, J.S.,O'Rourke, E.J.,1980.Enhancement ofdengue virus infection in monocytes byflavivirusantisera.Am.J.Trop.Med.Hyg.29,638- 642.
14. Halstead S.B., Porterfield J.S., O'Rourke E.J. Enhancement of dengue virus infection in monocytes by flavivirus antisera. Am. J. Trop. Med. Hyg. 1980, 29:638-642.
15. Jones, M.,Davidson, A.,Hibbert, L.,Gruenwald, P.,Schlaak, J.,etal.,2005.Dengue virus inhibits alpha interferon signaling byreducing STAT2 expression.J.Virol. 79, 5414-5420.
16. Jones M., Davidson A., Hibbert L., Gruenwald P., Schlaak J., et al. Dengue virus inhibits alpha interferon signaling by reducing STAT2 expression. J. Virol. 2005, 79:5414-5420.
17. Julander, J.G.,Shafer, K.,Smee, D.F.,Morrey, J.D.,Furuta, Y.,2009.Activity ofT-705 in a hamster model ofyellow fever virus infection incomparison with that ofa chemically related compound, T-1106.Antimicrob.Agents Chemother.53,202- 209.
18. Julander J.G., Shafer K., Smee D.F., Morrey J.D., Furuta Y. Activity of T-705 in a hamster model of yellow fever virus infection in comparison with that of a chemically related compound, T-1106. Antimicrob. Agents Chemother. 2009, 53:202-209.
19. Kaptein, S.J.,DeBurghgraeve, T.,Froeyen, M.,Pastorino, B.,Alen, M.M.,et al.,2010.A derivate of the antibiotic doxorubicin isaselective inhibitor ofdengue and yellow fever virus replication invitro.Antimicrob.Agents Chemother.54, 5269-5280.
20. Kaptein S.J., De Burghgraeve T., Froeyen M., Pastorino B., Alen M.M., et al. A derivate of the antibiotic doxorubicin is a selective inhibitor of dengue and yellow fever virus replication in vitro. Antimicrob. Agents Chemother. 2010, 54:5269-5280.
21. Latour, D.R.,Jekle, A.,Javanbakht, H.,Henningsen, R.,Gee, P.,et al.,2010. Biochemical characterization ofthe inhibition ofthe dengue virus RNA polymerase by beta- D-20-ethynyl-7-deaza-adenosine triphosphate. Antiviral Res. 87,213-222.
22. Latour D.R., Jekle A., Javanbakht H., Henningsen R., Gee P., et al. Biochemical characterization of the inhibition of the dengue virus RNA polymerase by beta-d-2'-ethynyl-7-deaza-adenosine triphosphate. Antiviral Res. 2010, 87:213-222.
23. Malet, H.,Masse, N.,Selisko, B.,Romette, J.L.,Alvarez, K.,et al.,2008.The flavivirus polymerase as atarget for drug discovery.Antiviral Res.80,23-35.
24. Malet H., Masse N., Selisko B., Romette J.L., Alvarez K., et al. The flavivirus polymerase as a target for drug discovery. Antiviral Res. 2008, 80:23-35.
25. Olsen, D.B.,Eldrup, A.B.,Bartholomew, L.,Bhat, B.,Bosserman, M.R.,et al.,2004.A7- deaza-adenosine analog isapotent and selective inhibitor ofhepatitis Cvirus replication with excellent pharmacokinetic properties.Antimicrob.Agents Chemother. 48,3944-3953.
26. Olsen D.B., Eldrup A.B., Bartholomew L., Bhat B., Bosserman M.R., et al. A 7-deaza-adenosine analog is a potent and selective inhibitor of hepatitis C virus replication with excellent pharmacokinetic properties. Antimicrob. Agents Chemother. 2004, 48:3944-3953.
27. Paeshuyse, J.,Kaul, A.,DeClercq, E.,Rosenwirth, B.,Dumont, J.M.,et al.,2006.The non-immunosuppressive cyclosporin DEBIO-025 is apotent inhibitor of hepatitis C virus replication invitro.Hepatology 43,761-770.
28. Paeshuyse J., Kaul A., De Clercq E., Rosenwirth B., Dumont J.M., et al. The non-immunosuppressive cyclosporin DEBIO-025 is a potent inhibitor of hepatitis C virus replication in vitro. Hepatology 2006, 43:761-770.
29. Perera, R.,Kuhn, R.J.,2008.Structural proteomics ofdengue virus.Curr.Opin. Microbiol. 11,369-377.
30. Perera R., Kuhn R.J. Structural proteomics of dengue virus. Curr. Opin. Microbiol. 2008, 11:369-377.
31. Schul, W.,Liu, W.,Xu, H.Y.,Flamand, M.,Vasudevan, S.G.,2007.Adengue fever viremia model in mice shows reduction inviral replication and suppression of the inflammatory response after treatment with antiviral drugs.J.Infect.Dis. 195, 665-674.
32. Schul W., Liu W., Xu H.Y., Flamand M., Vasudevan S.G. A dengue fever viremia model in mice shows reduction in viral replication and suppression of the inflammatory response after treatment with antiviral drugs. J. Infect. Dis. 2007, 195:665-674.
33. van Dijk, A.A.,Makeyev, E.V.,Bamford, D.H.,2004.Initiation ofviral RNA-dependent RNA polymerization. J.Gen.Virol.85,1077-1093.
34. van Dijk A.A., Makeyev E.V., Bamford D.H. Initiation of viral RNA-dependent RNA polymerization. J. Gen. Virol. 2004, 85:1077-1093.
35. Whitehead, S.S.,Blaney, J.E.,Durbin, A.P.,Murphy, B.R.,2007.Prospects for adengue virus vaccine. Nat.Rev.Microbiol.5,518-528.
36. Whitehead S.S., Blaney J.E., Durbin A.P., Murphy B.R. Prospects for a dengue virus vaccine. Nat. Rev. Microbiol. 2007, 5:518-528.
37. World Health Organisation,2009.Dengue.Guidelines for Diagnosis,Treatment, Prevention and Control - New Edition.Document WHO/HTM/NTD/DEN/ 2009.1 .
38. World Health Organisation, 2009. Dengue. Guidelines for Diagnosis, Treatment, Prevention and Control - New Edition. Document <>. http://WHO/HTM/NTD/DEN/2009.1.
39. World Health Organization,2001.Yellow Fever.Fact sheet no.100.
40. World Health Organization, 2001. Yellow Fever. Fact sheet no. 100.
41. Yin, Z.,Chen, Y.L.,Kondreddi, R.R.,Chan, W.L.,Wang, G.,et al.,2009a. Nsulfonylanthranilic acid derivatives as allosteric inhibitors of dengue viral RNA-dependent RNA polymerase.J.Med.Chem.52,7934-7937.
42. Yin Z., Chen Y.L., Kondreddi R.R., Chan W.L., Wang G., et al. N-sulfonylanthranilic acid derivatives as allosteric inhibitors of dengue viral RNA-dependent RNA polymerase. J. Med. Chem. 2009, 52:7934-7937.
43. Yin, Z.,Chen, Y.L.,Schul, W.,Wang, Q.Y.,Gu, F.,et al.,2009b.Anadenosine nucleoside inhibitor of dengue virus.Proc.Natl.Acad.Sci.USA 106,20435- 20439.
44. Yin Z., Chen Y.L., Schul W., Wang Q.Y., Gu F., et al. An adenosine nucleoside inhibitor of dengue virus. Proc. Natl. Acad. Sci. USA 2009, 106:20435-20439.
45. Yung, N.C.,Fox, J.J.,1961.Nucleosides.X.Anhydronucleosides and related compounds derived from 2', 5'-di-O-trityluridine.J.Am.Chem.Soc.83,3060- 3066.
46. Yung N.C., Fox J.J. Nucleosides. X. Anhydronucleosides and related compounds derived from 2', 5'-di-O-trityluridine. J. Am. Chem. Soc. 1961, 83:3060-3066.
47. Zemlicka, J.,1964.3',5'-Di-O-trityluridine.Collect.Czech.Chem.Commun.29, 1734-1735.
48. Žemlička J. 3',5'-Di-O-trityluridine. Collect. Czech. Chem. Commun. 1964, 29:1734-1735.