In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease

Antimicrobial Agents and Chemotherapy

Volumn 43, Issue 10, 1999, Pages 2444-2450

  Patick, A K ^a   Binford, S L ^a   Brothers, M A ^a   Jackson, R L ^a   Ford, C E ^a   Diem, M D ^a   Maldonado, F ^a   Dragovich, P S ^a   Zhou, R ^a   Prins, T J ^a   Fuhrman, S A ^a   Meador, J W ^a   Zalman, L S ^a   Matthews, D A ^a   Worland, S T ^a  

^a AGOURON PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MUCIN; OROSOMUCOID; PROTEINASE INHIBITOR; RUPINTRIVIR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; COXSACKIE VIRUS; DRUG CYTOTOXICITY; DRUG EFFICACY; DRUG INHIBITION; DRUG STRUCTURE; DRUG TARGETING; ECHO VIRUS; ENTEROVIRUS; HUMAN; HUMAN CELL; HUMAN RHINOVIRUS; NONHUMAN; PRIORITY JOURNAL; VIRUS REPLICATION;

EID: 0032870120     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.43.10.2444     Document Type: Article

References (55)

1. Andries, K., B. Dewindt, J. Snoeks, R. Willebrords, K. Van Eemeren, R. Stokbroekx, and P. A. J. Janssen. 1992. In vitro activity of pirodavir (R77975), a substituted phenoxy-pyridazinamine with broad-spectrum antipicornaviral activity. Antimicrob. Agents Chemother. 36:100-107.
2. Andries, K., B. Dewindt, J. Snoeks, L. Wouters, H. Moereels, P. J. Lewi, and P. A. J. Janssen. 1990. Two groups of rhinoviruses revealed by a panel of antiviral compounds present sequence divergence and differential pathogenicity. J. Virol. 64:1117-1123.
3. Arruda, E., and F. G. Hayden. 1995. Clinical studies of antiviral agents for picornaviral infections, p. 321-355. In D. J. Jeffries and E. De Clerq (ed.), Antiviral chemotherapy. John Wiley & Sons, Ltd., Chichester, N.Y.
4. Bilello, J. A., P. A. Bilello, M. Prichard, T. Robins, and G. L. Drusano. 1995. Reduction of the in vitro activity of A77003, an inhibitor of human immunodeficiency virus protease, by human serum alpha-1 acid glycoprotein. J. Infect. Dis. 171:546-551.
5. Carrasco, L. 1994. Picornavirus inhibitors. Pharmacol. Ther. 64:119-128.
6. Cheah, K.-C., L. E.-C. Leong, and A. G. Porter. 1990. Site-directed mutagenesis suggests close functional relationship between a human rhinovirus 3C cysteine protease and cellular trypsin-like serine proleases. J. Biol. Chem. 265:7180-7187.
7. Couch, R. B. 1990. Rhinoviruses, p. 607-629. In B. N. Fields and D. M. Knipe (ed.), Virology, Raven Press, New York, N.Y.
8. Dahllund, L., L. Nissinen, T. Pulli, V. P. Hyttinen, G. Stanway, and T. Hyypia. 1995. The genome of echovirus 11. Virus Res. 35:215-222.
9. Diana, G. D., and D. C. Pevear. 1997. Antipicornavirus drugs: current status. Antiviral Chem. Chemother. 8:401-408.
10. Dougherty, W. G., and B. L. Semler. 1993. Expression of virus-encoded proteinases: functional and structural similarities with cellular enzymes. Microbiol. Rev. 57:781-822.
11. Dragovich, P. S., T. J. Prins, R. Zhou, S. A. Fuhrman, A. K. Patick, D. A. Matthews, C. E. Ford, J. W. Meador III, R. A. Ferre, and S. T. Worland. 1999. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics. J. Med. Chem. 42:1203-1212.
12. 1 lactam moieties as L-glutamine replacements. J. Med. Chem. 42:1213-1224.
13. Dragovich, P. S., S. E. Webber, R. E. Babine, S. A. Fuhrman, A. K. Patick, D. A. Matthews, C. A. Lee, S. H. Reich, T. J. Prins, J. T. Marakovits, E. S. Littlefield, R. Zhou, J. Tikhe, C. E. Ford, M. Wallace, J. W. Meador III, R. A. Ferre, E. L. Brown, S. L. Binford, J. E. V. Harr, D. M. DeLisle, and S. T. Worland. 1998. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 1. Michael acceptor structure-activity studies. J. Med. Chem. 41:2806-2818.
14. Dragovich, P. S., S. E. Webber, R. E. Babine, S. A. Fuhrman, A. K. Patick, D. A. Matthews, S. H. Reich, J. T. Marakovits, T. J. Prins, R. Zhou, J. Tikhe, E. S. Littlefield, T. M. Bleckman, M. Wallace, T. Little, C. E. Ford, J. W. Meador III, R. A. Ferre, E. L. Brown, S. L. Binford, D. M. DeLisle, and S. T. Worland. 1998. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 2. Peptide structure-activity studies. J. Med. Chem. 41:2819-2834.
15. Dragovich, P. S., R. Zhou, D. J. Skalitzky, S. A. Fuhrman, A. K. Patick, C. E. Ford, J. W. Meador III, and S. T. Worland. 1999. Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. 1. Optimization of tripeptides incorporating N-terminal amides. Bioorg. Med. Chem. Lett. 7: 589-598.
16. Duechler, M., T. Skern, W. Sommergruber, C. Neubauer, P. Gruendler, I. Fogy, D. Blaas, and E. Kuechler. 1987. Evolutionary relationships within the human rhinovirus genus: comparison of serotypes 89, 2, and 14. Proc. Natl. Acad. Sci. USA 84:2605-2609.
17. Fromtling, R. A., and J. Castañer. 1997. VP-63843 pleconaril WIN-63843. Drugs Future 22:40-44.
18. Hammerle, T., C. U. T. Hellen, and E. Wimmer. 1991. Site-directed mutagenesis of the putative catalytic triad of poliovirus 3C proteinase. J. Biol. Chem. 266:5412-5416.
19. Heinz, B. A., J. Tang, J. M. Labus, F. W. Chadwell, S. W. Kaldor, and M. Hammond. 1996. Simple in vitro translation assay to analyze inhibitors of rhinovirus proteases. Antimicrob. Agents Chemother. 40:267-270.
20. Hughes, P. J., C. North, C. H. Jellis, P. D. Minor, and G. Stanway. 1988. The nucleotide sequence of human rhinovirus 1B: molecular relationships within the rhinovirus genus, J. Gen. Virol. 69:49-50.
21. Hughes, P. J., C. North, P. D. Minor, and G. Stanway. 1989. The complete nucleotide sequence of coxsackievirus A21. J. Gen. Virol. 70:2943-2952.
22. Kaldor, S. W., M. Hammond, B. A. Dressman, J. M. Labus, F. W. Chadwell, A. D. Kline, and B. A. Heinz. 1995. Glutamine-derived aldehydes for the inhibition of human rhinovirus 3C protease. Bioorg. Med. Chem. Lett. 5:2021-2026.
23. Kay, J., and B. M. Dunn. 1990. Viral proteinases: weakness in strength. Biochim. Biophys. Acta 1048:1-18.
24. Kean, K. M., M. T. Howell, S. Grünert, M. Girard, and R. J. Jackson. 1993. Substitution mutations at the putative catalytic triad of the poliovirus 3C protease have differential effects on cleavage at different sites. Virology 194:360-364.
25. Kean, K. M., N. L. Teterina, D. Marc, and M. Girard. 1991. Analysis of putative active site residues of the poliovirus 3C protease. Virology 181:609-619.
26. Kong, J.-S., S. Venkatraman, K. Furness, S. Nimkar, T. A. Shepherd, Q. M. Wang, J. Aube, and R. P. J. Hanzlik. 1998. Synthesis and evaluation of peptidyl Michael acceptors that inactivate human rhinovirus 3C protease and inhibit virus replication. J. Med. Chem. 41:2579-2587.
27. Kräusslich, H.-G., and E. Wimmer. 1988. Viral proteinases. Annu. Rev. Biochem. 57:701-754.
28. Lazdins, J. K., J. Mestan, G. Goutte, M. R. Walker, G. Bold, H. G. Capraro, and T. Klimkait. 1997. In vitro effect of alpha-acid glycoprotein on the anti-human immunodeficiency virus (HIV) activity of the protease inhibitor CGP 61755: a comparative study with other relevant HIV protease inhibitors. J. Infect. Dis. 175:1063-1070.
29. Lee, W. M., W. Wang, and R. R. Rueckert. 1995. Complete sequence of the RNA genome of human rhinovirus 16, a clinically useful common cold virus belonging to the ICAM-1 receptor group. Virus Genes 9:177-181.
30. Lentner, C. (ed.), 1984. Geigy scientific tables, p. 142. Ciba-Geigy Ltd., Basel, Switzerland.
31. Lindberg, A. M., P. O. Stalhandske, and U. Pettersson. 1987. Genome of coxsackievirus B3. Virology 156:50-63.
32. Livingston, D. J., S. Pazhanisamy, D. J. T. Porter, J. A. Partaledis, R. D. Tung, and G. R. Painter. 1995. Weak binding of VX-478 to human plasma proteins and implications for anti-human immunodeficiency virus therapy. J. Infect. Dis. 172:1238-1245.
33. Lorin, M. L, P. F. Gaerlin, and I. D. Mandel. 1972. Quantitative composition of nasal secretions in normal subjects. J. Clin. Med. 80:275-281.
34. Marom, Z., J. Shelhamer, and M. Kaliner. 1984. Nasal mucus secretion. Ear Nose Throat J. 63:36-37.
35. Matthews, D. A., P. S. Dragovich, S. E. Webber, S. A. Fuhrman, A. K. Patick, L. S. Zalman, T. Hendrickson, T. J. Prins, J. T. Marakovits, R. Zhou, J. Tikhe, C. E. Ford, J. W. Meador, R. A. Ferre, E. L. Brown, S. L. Binford, M. A. Brothers, D. M. DeLisle, and S. T. Worland. Structure-assisted design of mechanism based irreversible inhibitors of human rhinovirus 3C protease with potent antiviral activity against multiple rhinovirus serotypes. Proc. Natl. Acad. Sci. USA, in press.
36. Matthews, D. A., W. W. Smith, R. A. Ferre, B. Condon, G. Budahazi, W. Sisson, J. E. Villafranca, C. A. Janson, H. E. McElroy, C. L. Gribskov, and S. Worland. 1994. Structure of human rhinovirus 3C protease reveals a trypsin-like polypeptide fold, RNA-binding site, and means for cleaving precursor polyprotein. Cell 77:761-771.
37. McKinlay, M. A., D. C. Pevear, and M. G. Rossmann. 1992. Treatment of the picornavirus common cold by inhibitors of viral uncoating and attachment. Annu. Rev. Microbiol. 46:635-654.
38. Meador, J. W., III, H. Ngo, C. E. Ford, A. K. Palick, R. A. Ferre, D. A. Matthews, and S. T. Worland. 1998. PCR amplification and determination of the RNA sequences for the P3 coding region of human rhinoviral serotypes. Antivir. Res. 37:A72.
39. Melnick, J. L. 1990. Enteroviruses: polioviruses, coxsackieviruses, echoviruses, and newer enteroviruses, p. 549-605. In B. N. Fields and D. M. Knipe (ed.), Virology. Raven Press, New York, N.Y.
40. Otto, M. J., M. P. Fox, M. J. Fancher, M. F. Kuhrt, G. D. Diana, and M. A. McKinlay. 1985. In vitro activity of WIN 51711, a new broad-spectrum antipicornavirus drug. Antimicrob. Agents Chemother. 27:883-886.
41. Patick, A., and K. Potts. 1998. Protease inhibitors as antiviral agents. Clin. Microbiol. Rev. 11:614-627.
42. Patow, C. A., J. Shelhamer, Z. Marom, C. Logun, and M. Kaliner. 1984. Analysis of human nasal mucous glycoproteins. Am. J. Otolaryngol. 5:334-343.
43. Platts-Mills, T. A. 1979. Local production of IgG, IgA, and IgE antibodies in grass pollen hay fever. J. Immunol. 12:2218-2225.
44. Rueckert, R. R. 1990. Picornaviridae and their replication, p. 507-548. In B. N. Fields and D. M. Knipe (ed.), Virology. Raven Press, New York, N.Y.
45. Ryan, M. D., O. Jenkins, P. J. Hughes, A. Brown, N. J. Knowles, D. Booth, P. D. Minor, and J. W. Almond. 1990. The complete nucleotide sequence of enterovirus type 70: relationships with other members of the picornaviridae. J. Gen. Virol. 71:2291-2299.
46. Schorn, D., and M. Hochestrasser. 1979. Biochemical investigations of nasal secretions. Acta Otorhinolaryngol. Belgica 33:603-606.
47. Shepherd, T. A., G. A. Cox, E. McKinney, J. Tang, M. Wakulchik, R. E. Zimmerman, and E. C. Villarreal. 1996. Small peptidic aldehyde inhibitors of human rhinovirus 3C protease. Bioorg. Med. Chem. Lett. 6:2893-2896.
48. Skern, T., W. Sommergruber, D. Blaas, P. Gruendler, F. Fraundorfer, C. Pieler, I. Fogy, and E. Kuechler. 1985. Human rhinovirus 2: complete nucleotide sequence and proteolytic processing signals in the capsid protein region. Nucleic Acids Res. 13:2111-2126.
49. Stanway, G., P. J. Hughes, R. C. Mountford, P. D. Minor, and J. W. Almond. 1984. The complete nucleotide sequence of a common cold virus: human rhinovirus 14. Nucleic Acids Res. 12:7859-7875.
50. Uncapher, C. R., C. M. DeWitt, and R. J. Colonno. 1991. The major and minor group receptor families contain all but one human rhinovirus seratype. Virology 180:814-817.
51. Wang, Q. M., R. B. Johnson, L. N. Hungheim, J. D. Cohen, and E. C. Villarreal. 1998. Dual inhibition of human rhinovirus 2A and 3C proteases by homophthalimides. Antimicrob. Agents Chemother. 42:916-920.
52. Webber, S., J. Tikhe, S. T. Worland, S. A. Fuhrman, T. F. Hendrickson, D. A. Matthews, R. A. Love, A. K. Patick, J. W. Meador, R. A. Ferre, E. L. Brown, D. M. DeLisle, C. E. Ford, and S. L. Binford. 1996. Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease. J. Med. Chem. 39:5072-5082.
53. 1 glutamine isosteric replacements. J. Med. Chem. 41:2786-2805.
54. Weislow, O. S., R. Kiser, D. L. Fine, J. Bader, R. H. Shoemaker, and M. R. Boyd. 1989. New soluble-formazan assay for HIV-1 cytopathic effects: application to high-flux screening of synthetic and natural products for AIDS-antiviral activity. J. Natl. Cancer Inst. 81:577-586.
55. Werner, G., B. Rosenwirth, E. Bauer, J. M. Seifert, F. J. Werner, and J. Besemer. 1986. Molecular cloning and sequence determination of the genomic regions encoding protease and genome-linked protein of three picornaviruses. J. Virol. 57:1084-1093.