Conservation of amino acids in human rhinovirus 3C protease correlates with broad-spectrum antiviral activity of rupintrivir, a novel human rhinovirus 3C protease inhibitor

Antimicrobial Agents and Chemotherapy

Volumn 49, Issue 2, 2005, Pages 619-626

  Binford, S L ^a   Maldonado, F ^a   Brothers, M A ^a   Weady, P T ^a   Zalman, L S ^a   Meador III, J W ^a   Matthews, D A ^a   Patick, A K ^a  

^a PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; PROTEINASE; PROTEINASE INHIBITOR; RUPINTRIVIR;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; ENZYME BINDING; ENZYME MECHANISM; GENETIC CONSERVATION; HUMAN RHINOVIRUS; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; SEQUENCE ANALYSIS; VIRUS ISOLATION; VIRUS STRAIN;

AMINO ACIDS; ANTIVIRAL AGENTS; CONSERVED SEQUENCE; CYSTEINE ENDOPEPTIDASES; HELA CELLS; HUMANS; ISOXAZOLES; MOLECULAR SEQUENCE DATA; PROTEASE INHIBITORS; PYRROLIDINONES; REVERSE TRANSCRIPTASE POLYMERASE CHAIN REACTION; RHINOVIRUS; RNA, VIRAL; VIRAL PROTEINS;

EID: 12944268369     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.49.2.619-626.2005     Document Type: Article

References (69)

1. Andeweg, A. C., T. M. Bestebroer, M. Huybreghs, T. G. Kimman, and J. C. De Jong. 1999. Improved detection of rhinoviruses in clinical samples by using a newly developed nested reverse transcription-PCR assay. J. Clin. Microbiol. 37:524-530.
2. Andries, K., B. Dewindt, J. Snoeks, L. Wouters, H. Moereels, P. J. Lewi, and P. A. 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. Arruda, E., A. Pitkaranta, T. J. Witek, Jr., C. A. Doyle, and F. G. Hayden. 1997. Frequency and natural history of rhinovirus infections in adults during autumn. J. Clin. Microbiol. 35:2864-2868.
5. Blomqvist, S., C. Savolainen, L. Raman, M. Roivainen, and T. Hovi. 2002. Human rhinovirus 87 and enterovirus 68 represent a unique serotype with rhinovirus and enterovirus features. J. Clin. Microbiol. 40:4218-4223.
6. Brown, B. A., and M. A. Pallansch. 1995. Complete nucleotide sequence of enterovirus 71 is distinct from poliovirus. Virus Res. 39:195-205.
7. Chang, K. H., P. Auvinen, T. Hyypiä, and G. Stanway. 1989. The nucleotide sequence of coxsackievirus A9; implications for receptor binding and enterovirus classification. J. Gen. Virol. 70:3269-3280.
8. Couch, R. B. 2001. Rhinoviruses, p. 777-797. In D. M. Knipe, P. M. Howley, D. E. Griffin, R. A. Lamb, M. A. Martin, B. Roizman, and S. E. Straus (ed.), Fields virology, 4th ed. Lippincott Williams & Wilkins, Philadelphia, Pa.
9. Dahllund, L., L. Nissinen, T. Pulli, V. P. Hyttinen, G. Stanway, and T. Hyypiä. 1995. The genome of echovirus 11. Virus Res. 35:215-222.
10. 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.
11. 1 lactam moieties as L-glutamine replacements. J. Med. Chem. 42:1213-1224.
12. 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.
13. 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.
14. 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. 7:589-598.
15. 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.
16. Fleischer, R., and K. Laessig. 2003. Safety and efficacy evaluation of pleconaril for treatment of the common cold. Clin. Infect. Dis. 37:1722.
17. Fromtling, R. A., and J. Castañer. 1997. VP-63843 pleconaril WIN-63843. Drugs Future 22:40-44.
18. Gwaltney, J. M., Jr., B. Winther, J. T. Patrie, and J. O. Hendley. 2002. Combined antiviral-antimediator treatment for the common cold. J. Infect. Dis. 186:147-154.
19. Hayden, F. G., K. Andries, and P. A. Janssen. 1992. Safety and efficacy of intranasal pirodavir (R77975) in experimental rhinovirus infection. Antimicrob. Agents Chemother. 36:727-732.
20. Hayden, F. G., T. Coats, K. Kim, H. A. Hassman, M. M. Blatter, B. Zhang, and S. Liu. 2002. Oral pleconaril treatment of picornavirus-associated viral respiratory illness in adults: efficacy and tolerability in phase II clinical trials. Antivir. Ther. 7:53-65.
21. Hayden, F. G., and J. M. Gwaltney, Jr. 1984. Intranasal interferon-alpha 2 treatment of experimental rhinoviral colds. J. Infect. Dis. 150:174-180.
22. Hayden, F. G., G. J. Hipskind, D. H. Woerner, G. F. Eisen, M. Janssens, P. A. Janssen, and K. Andries. 1995. Intranasal pirodavir (R77,975) treatment of rhinovirus colds. Antimicrob. Agents Chemother. 39:290-294.
23. Hayden, F. G., D. L. Kaiser, and J. K. Albrecht. 1988. Intranasal recombinant alfa-2b interferon treatment of naturally occurring common colds. Antimicrob. Agents Chemother. 32:224-230.
24. Hayden, F. G., D. T. Herrington, T. L. Coats, K. Kim, E. C. Cooper, S. A. Vilano, S. Liu, S. Hudson, D. C. Pevear, M. Collett, M. McKinlay, and the Pleconaril Respiratory Infection Study Group. 2003. Efficacy and safety of oral pleconaril for treatment of colds due to picornaviruses in adults: results of 2 double-blind, randomized, placebo-controlled trials. Clin. Infect. Dis. 36:1523-1532.
25. Hayden, F. G., R. B. Turner, J. M. Gwaltney, K. Chi-Burris, M. Gersten, P. Hsyu, A. K. Patick, G. J. Smith III, and L. S. Zalman. 2003. Phase II, randomized, double-blind, placebo-controlled studies of rupintrivir nasal spray 2-percent suspension for prevention and treatment of experimentally induced rhinovirus colds in healthy volunteers. Antimicrob. Agents Chemother. 47:3907-3916.
26. Horsnell, C., R. E. Gama, P. J. Hughes, and G. Stanway. 1995. Molecular relationships between 21 rhinovirus serotypes. J. Gen. Virol. 76:2549-2555.
27. Hovi, T., J. Nokso-Koivisto, S. Blomqvist, C. Savolainen, R. Raty, P. Lukkari, and T. Kilpi. 2001. Phylogenetic analysis of human rhinoviruses calls for revision of taxonomy and sequence based strain identification, abstr. LBI. Abstr. 4th Int. Symp. Influenza Other Respir. Viruses, 29 November to 2 December, 2001, Curacao, Netherlands Antilles.
28. 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. Virology. 69:49-50.
29. 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.
30. Hughes, P. J., D. M. A. Evans, P. D. Minor, G. C. Schild, J. W. Almond, and G. Stanway. 1986. The nucleotide sequence of a type 3 poliovirus isolated during a recent outbreak of poliomyelitis in Finland. J. Gen. Virol. 67:2093-2102.
31. Iizuka, N., S. Kuge, and A. Nomoto. 1987. Complete nucleotide sequence of the genome of coxsackievirus B1. Virology 156:64-73.
32. Ishiko, H., N. Takeda, K, Miyamura, N. Kato, M. Tanimura, K. H. Lin, M. Yin-Murphy, J. S. Tam, G. F. Mu, and S. Yamazaki. 1992. Phylogenic analysis of a coxsackievirus A24 variant: the most recent worldwide pandemic was caused by progenies of a virus prevalent around 1981. Virology 187:748-759.
33. Jenkins, O., J. D. Booth, P. D. Minor, and J. W. Almond. 1987. The complete nucleotide sequence of coxsackievirus B4 and its comparison to other members of the Picornaviridae. J. Gen. Virol. 68:1835-1848.
34. Kaiser, L., C. E. Crump, and F. G. Hayden. 2000. In vitro activity of pleconaril and AG7088 against selected serotypes and clinical isolates of human rhinoviruses. Antivir. Res. 47:215-220.
35. King, A. M. Q., F. Brown, P. Christian, T. Hovi, T. Hyypiä, N. J. Knowles, S. M. Lemon, P. D. Minor, A. C. Palmenberg, T. Skern, and G. Stanway. 2000. Picornaviridae, p. 657-678. In M. H. V. van Regenmortel, C. M. Fauquet, D. H. L. Bishop, E. B. Carsten, M. K. Estes, S. M. Lemon, J. Maniloff, M. A. Mayo, D. J. McGeoch, C. R. Pringle, and R. B. Wickner (ed.), Virus taxonomy: classification and nomenclature of viruses. Seventh Report of the International Committee for the Taxonomy of Viruses. Academic Press, San Diego, Calif.
36. Kraus, W., H. Zimmermann, H. J. Eggers, and B. Neson-Salz. 1995. Infectious cDNA clones of echovirus 12 and a variant resistant against the uncoating inhibitor rhodanine differ in seven amino acids. J. Virol. 69:5853-5858.
37. Ledford, R. M., N. R. Patel, T. M. Demenczuk, A. Watanyar, T. Herbertz, M. S. Collett, and D. C. Pevear. 2004. VP1 sequencing of all human rhinovirus serotypes: insights into genus phylogeny and susceptibility to antiviral capsid-binding compounds. J. Virol. 78:3663-3674.
38. 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.
39. Lindberg, A. M., P. O. Stalhandske, and U. Pettersson. 1987. Genome of coxsackievirus B3. Virology 156:50-63.
40. Makela, M. J., T. Puhakka, O. Ruuskanen, M. Leinonen, P. Saikku, M. Kimpimaki, S. Blomqvist, T. Hyypiä, and P. Arstila. 1998. Viruses and bacteria in the etiology of the common cold. J. Clin. Microbiol. 36:539-542.
41. Matthews, D. A., P. S. Dragovich, S. E. Webber, S. A. Fuhrman, A. K. Patick, L. S. Zalman, T. F. Hendrickson, R. A. Love, T. J. Prins, J. T. Marakovits, R. Zhou, J. Tikhe, C. E. Ford, J. W. Meador III, R. A. Ferre, E. L. Brown, S. L. Binford, M. A. Brothers, D. M. DeLisle, and S. T. Worland. 1999. 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 96:11000-11007.
42. 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.
43. Mori, J., and J. P. Clewley. 1994. Polymerase chain reaction and sequencing for typing rhinovirus RNA. J. Med. Virol. 44:323-329.
44. Nomoto, A., T. Omata, H. Toyoda, S. Kuge, H. Horie, Y. Kataoka, Y. Genba, Y. Nakano, and N. Imura. 1982. Complete nucleotide sequence of the attenuated poliovirus Sabin 1 strain genome. Proc. Natl. Acad. Sci. USA 79:5793-5797.
45. Ostroff, R., A. Ettinger, H. La, M. Rihanek, L. Zalman, J. Meador III, A. K. Patick, S. Worland, and B. Polisky. 2001. Rapid multiserotype detection of human rhinoviruses on optically coated silicon surfaces. J. Clin. Virol. 21: 105-117.
46. Patick, A. K., S. L. Binford, M. A. Brothers, R. L. Jackson, C. E. Ford, M. D. Diem, F. Maldonado, P. S. Dragovich, R. Zhou, T. J. Prins, S. A. Fuhrman, J. W. Meador III, L. S. Zalman, D. A. Matthews and S. T., Worland. 1999. Antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob. Agents Chemother. 43:2444-2450.
47. Patick, A. K., and K. Potts. 1998. Protease inhibitors as antiviral agents. Clin. Microbiol. Rev. 11:614-627.
48. Pitkaranta, A., and F. G. Hayden. 1998. Rhinoviruses:important respiratory pathogens. Ann. Med. 30:529-537.
49. Poyry, T., T. Hyypiä, C. Horsnell, L. Kinnunen, T. Hovi, and G. Stanway. 1994. Molecular analysis of coxsackievirus A16 reveals a new genetic group of enteroviruses. Virology 202:982-987.
50. Righthand, V. F., and T. E. Gratsch. 1994. Construction of a recombinant cDNA of echovirus 6 that established a persistent in vitro infection. Virology 201:341-348.
51. Rodrigo, M. J., and J. Dopazo. 1995. Evolutionary analysis of the picornavirus family. J. Mol. Evol. 40:362-371.
52. Rotbart, H. A. 2002. Treatment of picornavirus infections. Antivir. Res. 53:83-98.
53. Rotbart, H. A., and A. D. Webster. 2001. Treatment of potentially life-threatening enterovirus infections with pleconaril. Clin. Infect. Dis. 32:228-235.
54. 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.
55. Savolainen, C., S. Blomqvist, M. N. Mulders, and T. Hovi. 2002. Genetic clustering of all 102 human rhinovirus prototype strains: serotype 87 is close to human enterovirus 70. J. Gen. Virol. 83:333-342.
56. Scudiero, D. A., R. H. Shoemaker, K. D. Paull, A. Monks, S. Tierney, T. H. Nofziger, M. J. Currens, D. Seniff, and M. R. Boyd. 1988. XTT evaluation of a soluble tetrazolium/formazan assay for cell growth and drug sensitivity in culture using human and other tumor cell lines. Cancer Res. 48:4827-4833.
57. 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.
58. 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.
59. Toyoda, H., M. Kohara, Y. Kataoka, T. Suganuma, T. Omata, N. Imura, and A. Nomoto. 1984, Complete nucleotide sequences of all three poliovirus serotype genomes. Implication for genetic relationship, gene function and antigenic determinants. J. Mol. Biol. 174:561-585.
60. Wallace, A. C., R. A. Laskowski, and J. M. Thornton. 1995. LIGPLOT: a program to generate schematic diagrams of protein-ligand interactions. Protein Eng. 8:127-134.
61. 1 glutamine isosteric replacements. J. Med. Chem. 41:2786-2805.
62. 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.
63. 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.
64. Zalman, L. S., M. A. Brothers, P. S. Dragovich, R. Zhou, T. J. Prins, S. T. Worland, and A. K. Patick. 2000. Inhibition of human rhinovirus-induced cytokine production by AG7088, a human rhinovirus 3C protease inhibitor. Antimicrob. Agents Chemother. 44:1236-1241.
65. Zell, R. H., E. Birch-Hirschfeld, U. Fortmuller, A. Henke, and A. Stelzner. Unpublished data.
66. Zell, R. H. 1997. Unpublished data.
67. Zell, R. H. 1999. Unpublished data.
68. Zhang, G., G. Wilsden, N. J. Knowles, and J. W. McCauley. 1993. Complete nucleotide sequence of a coxsackie B5 virus and its relationship to swine vesicular disease virus. J. Gen. Virol. 74:845-853.
69. Zimmermann, H., H. J. Eggers, and B. Nelson-Salz. 1996. Molecular cloning and sequence determination of the complete genome of the virulent echovirus 9 strain Barty. Virus Genes 12:149-154.