Highly potent and selective inhibition of bovine viral diarrhea virus replication by γ-carboline derivatives

Antiviral Research

Volumn 88, Issue 3, 2010, Pages 263-268

  Salim, Mohammed T A ^a   Goto, Yukinori ^a,d   Hamasaki, Takayuki ^a   Okamoto, Mika ^a   Aoyama, Hiroshi ^b   Hashimoto, Yuichi ^b   Musiu, Simone ^c   Paeshuyse, Jan ^c   Neyts, Johan ^c   Froeyen, Matheus ^c   Herdewijn, Piet ^c   Baba, Masanori ^a  

^a KAGOSHIMA UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^d OSAKA UNIVERSITY   (Japan)

Author keywords

BVDV; Carboline; Drug resistance; Flavivirus; HCV; RNA polymerase

Indexed keywords

GAMMA CARBOLINE DERIVATIVE; RNA DIRECTED RNA POLYMERASE; VIRUS RNA;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; BOVINE DIARRHEA VIRUS; CRYSTAL STRUCTURE; DRUG CYTOTOXICITY; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; REVERSE TRANSCRIPTION POLYMERASE CHAIN REACTION; RNA SYNTHESIS; VIRUS INHIBITION; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; BOVINE VIRUS DIARRHEA-MUCOSAL DISEASE; CARBOLINES; CATTLE; CELL LINE; DIARRHEA VIRUSES, BOVINE VIRAL; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; RNA REPLICASE; RNA, VIRAL; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; VIRUS REPLICATION;

BOVINE VIRAL DIARRHEA VIRUS 1; FLAVIVIRUS; HEPATITIS C VIRUS;

EID: 78650241146     PISSN: 01663542     EISSN: 18729096     Source Type: Journal    
DOI: 10.1016/j.antiviral.2010.09.013     Document Type: Article

References (28)

1. Aoyama H., Sako K., Sato S., Nakamura M., Miyachi H., Goto Y., Olamoto M., Baba M., Hashimoto Y. Polymethylated γ-carbolines with potent anti-bovine viral diarrhea virus (BVDV) activity. Heterocycles 2009, 77:779-785.
2. Baba C., Yanagida K., Kanzaki T., Baba M. Colorimetric lactate dehydrogenase (LDH) assay for evaluation of antiviral activity against bovine viral diarrhea virus (BVDV) in vitro. Antiviral Chem. Chemother. 2005, 16:33-39.
3. Baginski S.G., Pevear D.C., Seipel M., Sun S.C., Benetatos C.A., Chunduru S.K., Rice C.M., Collett M.S. Mechanism of action of a pestivirus antiviral compound. Proc. Natl. Acad. Sci. U.S.A. 2000, 97:7981-7986.
4. Buckwold V.E., Beer B.E., Donis R.O. Bovine viral diarrhea virus as a surrogate model of hepatitis C virus for the evaluation of antiviral agents. Antiviral Res. 2003, 60:1-15.
5. Chang J., Wang L., Ma D., Qu X., Guo H., Xu X., Mason P.M., Bourne N., Moriarty R., Gu B., Guo J.T., Block T.M. Novel imino sugar derivatives demonstrate potent antiviral activity against flaviviruses. Antimicrob. Agents Chemother. 2009, 53:1501-1508.
6. Choi K.H., Groarke J.M., Young D.C., Kuhn R.J., Smith J.L., Pevear D.C., Rossmann M.G. The structure of the RNA-dependent RNA polymerase from bovine viral diarrhea virus establishes the role of GTP in de novo initiation. Proc. Natl. Acad. Sci. U.S.A. 2004, 101:4425-4430.
7. Houe H. Economic impact of BVDV infection in dairies. Biologicals 2003, 31:137-143.
8. Ishii N., Watashi K., Hishiki T., Goto K., Inoue D., Hijikata M., Wakita T., Kato N., Shimotohno K. Diverse effects of cyclosporine on hepatitis C virus strain replication. J. Virol. 2006, 80:4510-4520.
9. Kalaycioglu A.T. Bovine viral diarrhoea virus (BVDV) diversity and vaccination. A review. Vet. Q. 2007, 29:60-67.
10. Kobrak A., Weber E.L. Bovine diarrhea virus: an update. Rev. Argent. Microbiol. 1997, 29:47-61.
11. Luscombe C.A., Huang Z., Murray M.G., Miller M., Wilkinson J., Ewart G.D. A novel Hepatitis C virus p7 ion channel inhibitor BIT225, inhibits bovine viral diarrhea virus in vitro and shows synergism with recombinant interferon-α-2b and nucleoside analogues. Antiviral Res. 2010, 86:144-153.
12. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang C., Hendrickson T., Still W.C. An integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 1990, 11:440-467.
13. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olsen A.J. Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 1998, 19:1639-1662.
14. Nam J.H., Bukh J., Purcell R.H., Emerson S.U. High-level expression of hepatitis C virus (HCV) structural proteins by a chimeric HCV/BVDV genome propagated as a BVDV pseudotype. J. Virol. Methods 2001, 97:113-123.
15. Okamoto M., Sakai M., Goto Y., Salim M.T.A., Baba C., Goto K., Watashi K., Shimotohno K., Baba M. Anti-bovine viral diarrhea virus and hepatitis C virus activity of the cyclooxygenase inhibitor SC-560. Antiviral Chem. Chemother. 2009, 20:47-54.
16. Paeshuyse J., Leyssen P., Mabery E., Boddeker N., Vrancken R., Froeyen M., Ansari I.H., Dutartre H., Rozenski J., Gil L.H., Letellier C., Lanford R., Canard B., Koenen F., Kerkhofs P., Donis R.O., Herdewijn P., Watson J., De Clercq E., Puerstinger G., Neyts J. A novel, highly selective inhibitor of pestivirus replication that targets the viral RNA-dependent RNA polymerase. J. Virol. 2006, 80:149-160.
17. Paeshuyse J., Chezal J.M., Froeyen M., Leyssen P., Dutartre H., Vrancken R., Canard B., Letellier C., Li T., Mittendorfer H., Koenen F., Kerkhofs P., De Clercq E., Herdewijn P., Puerstinger G., Gueiffier A., Chavignon O., Teulade J.C., Neyts J. The imidazopyrrolopyridine analogue AG110 is a novel, highly selective inhibitor of pestiviruses that targets the viral RNA-dependent RNA polymerase at a hot spot for inhibition of viral replication. J. Virol. 2007, 81:11046-11053.
18. Paeshuyse J., Letellier C., Froeyen M., Dutartre H., Vrancken R., Canard B., De Clercq E., Gueiffier A., Teulade J.C., Herdewijn P., Puerstinger G., Koenen F., Kerkhofs P., Baraldi P.G., Neyts J. A pyrazolotriazolopyrimidinamine inhibitor of bovine viral diarrhea virus replication that targets the viral RNA-dependent RNA polymerase. Antiviral Res. 2009, 82:141-147.
19. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., Ferrin T.E. UCSF chimera - a visualization system for exploratory research and analysis. J. Comput. Chem. 2004, 25:1605-1612.
20. Sako K., Aoyama H., Sato S., Hashimoto Y., Baba M. γ-Carboline derivatives with anti-bovine viral diarrhea virus (BVDV) activity. Bioorg. Med. Chem. 2008, 16:3780-3790.
21. Salim M.T.A., Okamoto M., Hosoda S., Aoyama H., Hashimoto Y., Baba M. Anti-bovine viral diarrhea virus activity of novel diphenylmethane derivatives. Antiviral Chem. Chemother. 2010, 20:193-200.
22. Schuettelkopf A.W., van Aalten D.M.F. PRODRG - a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr. D60 2010, 1355-1363.
23. Tabarrini O., Manfroni G., Fravolini A., Cecchetti V., Sabatini S., De Clercq E., Rozenski J., Canard B., Dutartre H., Paeshuyse J., Neyts J. Synthesis and anti-BVDV activity of acridones as new potential antiviral agents. J. Med. Chem. 2006, 49:2621-2627.
24. van Oirschot J.T., Bruschke C.J., van Rijn P.A. Vaccination of cattle against bovine viral diarrhoea. Vet. Microbiol. 1999, 64:169-183.
25. Vliegen I., Paeshuyse J., De Burghgraeve T., Lehman L.S., Paulson M., Shih I.H., Mabery E., Boddeker N., De Clercq E., Reiser H., Oare D., Lee W.A., Zhong W., Bondy S., Pürstinger G., Neyts J. Substituted imidazopyridines as potent inhibitors of HCV replication. J. Hepatol. 2009, 50:999-1009.
26. Watashi K., Hijikata M., Hosaka M., Yamaji M., Shimotohno K. Cyclosporine A suppresses replication of hepatitis C virus genome in cultured hepatocytes. Hepatology 2003, 38:1282-1288.
27. Wallace A.C., Laskowski R.A., Thornton J.M. LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Prot. Eng. 1995, 8:127-134.
28. Yanagida K., Baba C., Baba M. Inhibition of bovine viral diarrhea virus (BVDV) by mizoribine: synergistic effect of combination with interferon-α. Antiviral Res. 2004, 64:195-201.