Picornaviral 3C protease inhibitors and the dual 3C protease/coronaviral 3C-like protease inhibitors

Expert Opinion on Therapeutic Patents

Volumn 20, Issue 1, 2010, Pages 59-71

  Liang, Po Huang ^a   Wang, Hui Min ^b  

^a INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

^b KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

Author keywords

3C protease; 3CL protease; Coronavirus; Inhibitor; Picornavirus; Rhinovirus

Indexed keywords

3C LIKE PROTEASE; 3C PROTEASE; ALDEHYDE DERIVATIVE; BENZAMIDE; BENZAMIDE DERIVATIVE; BENZENE DERIVATIVE; ESTER DERIVATIVE; GLUTAMINE DERIVATIVE; ISATIN DERIVATIVE; PEPTIDOMIMETIC AGENT; PLACEBO; PLECONARIL; PROTEINASE; PROTEINASE INHIBITOR; QUINONE DERIVATIVE; RUPINTRIVIR; S NITROSOTHIOL; TG 0204998; TG 0205221; TG 0205486; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; CLINICAL TRIAL; COMMON COLD; CORONAVIRUS; DRUG BINDING SITE; DRUG INDICATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; HUMAN; NAUSEA; NONHUMAN; PICORNAVIRUS; PICORNAVIRUS INFECTION; PROTEIN TARGETING; RESPIRATORY TRACT INFECTION; REVIEW; RHINOVIRUS; STRUCTURE ACTIVITY RELATION; TASTE DISORDER;

ANIMALS; ANTIVIRAL AGENTS; CORONAVIRUS; CORONAVIRUS INFECTIONS; CYSTEINE ENDOPEPTIDASES; DRUG DELIVERY SYSTEMS; DRUG DESIGN; HUMANS; PATENTS AS TOPIC; PICORNAVIRIDAE; PICORNAVIRIDAE INFECTIONS; PROTEASE INHIBITORS; VIRAL PROTEINS;

EID: 73649093410     PISSN: 13543776     EISSN: None     Source Type: Journal    
DOI: 10.1517/13543770903460323     Document Type: Review

References (81)

1. Denny FW Jr. The clinical impact of human respiratory virus infections. Am J Respir Crit Care Med 1995;152:S4-12
2. Monto AS. Acute respiratory infection in children of developing countries: challenge of the 1990s. Rev Infect Dis 1989;11:498-505
3. Melnick JL. Enteroviruses, polioviruses, coxsackieviruses, echoviruses, and newer enteroviruses. In: Virology, 3rd eds, 1996. p. 655-712
4. Siddell SG, Ziebuhr J, Snijder EJ. Coronaviruses, toroviruses, and arteriviruses. In: Mahy BW, Ter Meulen V, editors. Topley and Wilson's microbiology and microbial infections: Volume 1. Hodder Arnold, London, 2005. p. 823-856
5. Holmes KV. SARS-associated coronavirus. N Eng J Med 2003;348:1948-1951
6. Monto AS, Fendrick AM, Sarnes MW. Respiratory illness caused by Picornavirus infection: a review of clinical outcomes. Clin Ther 2001;23:1615-1627
7. Peiris JS, Kuey KY, Osterhaus KD, et al. The severe acute respiratory syndrome. N Eng J Med 2003;349:2431-2441
8. Kuiken T, Fouchier RA, Schutten M, et al. New discovered coronavirus as the primary cause of severe acute respiratory syndrome. Lancet 2003;362:263-270
9. Ksiazek TG, Erdman D, Goldsmith CS, et al. A novel coronavirus associated with severe acute respiratory syndrome. N Eng J Med 2003;348:1953-1966
10. Drosten C, Gunther S, Preiser W, et al. Identification of a novel coronavirus in patients with severe acute respiratory syndrome. N Eng J Med 2003;348:1967-1976 (Pubitemid 36569985)
11. Kitamaru N, Semler BL, Rothberg PG, et al. Primary structure, gene organization and polypeptide expression of poliovirus RNA. Nature 1981;291:547-553
12. Racaniello VR, Baltimore D. Molecular cloning of poliovirus cDNA and determination of the complete nucleotide sequence of the viral genome. Proc Natl Acad Sci USA 1981;78:4887-4891
13. Kaku Y, Sarai A, Murakami Y. Genetic reclassification of porcine enteroviruses. J Gen Virol 2001;82:417-424
14. Callahan PL, Mizutani S, Colonno RJ. Molecular cloning and complete sequence determination of RNA genome of human rhinovirus type 14. Proc Natl Acad Sci USA 1985;82:732-736
15. Chua BH, Mcminn PC, Lam SK, et al. Comparison of the complete nucleotide sequences of echovirus 7 strain UMMC and the prototype (Wallace) strain demonstrates significant genetic drift over time. J Gen Virol 2001;82:2629-2639
16. Shih SR, Ho MS, Lin KH, et al. Genetic analysis of enterovirus 71 isolated from fatal and non-fatal cases of hand, foot and mouth disease during an epidemic in Taiwan, 1998. Virus Res 2000;68:127-136
17. Lindberg AM, Johansson S, Andersson A. Echovirus 5: infectious transcripts and complete nucleotide sequence from uncloned cDNA. Virus Res 1999;59:75-87
18. Heikkinen T, Jarvinen A. The common cold. Lancet 2003;361:51-59
19. Blomberg K, Lycke E, Ahlfors K, et al. New enterovirus type associated with epidemic of aseptic meningitis and-or hand, foot, and mouse disease. Lancet 1974;2:112
20. Chang LY, Lin TY, Hsu KH, et al. Clinical features and risk factors of pulmonary oedema after enterovirus-71-related hand, foot, and mouth disease. Lancet 1999;354:1682-1686
21. Lum LC, Wong KT, Lam SK, et al. Neurogenic pulmonary oedema and enterovirus 71 encephalomyelitis. Lancet 1998;352:1391
22. Lee CK, Kono K, Haas E, et al. Characterization of an infectious cDNA copy of the genome of a naturally occurring, avirulent coxsackievirus B3 clinical isolate. J Gen Virol 2005;86:197-210
23. Turner RB. The treatment of rhinovirus infections: progress and potential. Antiviral Res 2001;49:1-14u
24. Rotbart HA, Hayden FG. Picornavirus infections: a primer for the practitioner. Arch Fam Med 2000;9:913-920
25. Sperber SJ, Hayden FG. Chemotherapy of rhinovirus colds. Antimicrob Agents Chemother 1998;32:409-414
26. McKinlay MA, Pevear DC, Rossmann MG. Treatment of the picornavirus common cold by inhibitors of viral uncoating and attachment. Annu Rev Microbiol 1992;46:635-654
27. Munoz FM, Galasso GJ, Gwaltney JM Jr, et al. Current research on influenza and other respiratory viruses: II international symposium. Antiviral Res 2000;46:91-124
28. Diana GD, Pevear DC. Antipicornavirus drugs: current status. Antiviral Chem Chemother 1997;8:401-408
29. McKinlay MA. Recent advances in the treatment of rhinovirus infections. Curr Opin Pharmacol 2001;1:477-481
30. Krausslich HG, Wimmer E. Viral proteinases. Annu Rev Biochem 1988;57:701-754
31. Anderson J, Schiffer C, Lee SK, et al. Viral protease inhibitors. Handb Exp Pharmacol 2009;189:85-110
32. Leong LE, Cornell CT, Semler BL. Processing determinants and functions of cleavage products of picornavirus proteins. In: Semler BL, Wimmer E, editors, Molecular biology of picornaviruses. ASM Press, Washington, DC; 2002. p. 187-197
33. Mason PW, Grubman MJ, Baxt B. Molecular basis of pathogenesis of FMDV. Virus Res 2003;91:9-32
34. Lee CK, Wimmer E. Proteolytic processing of poliovirus polyprotein: elimination of 2Apro-mediated, alternative cleavage of polypeptide 3CD by in vitro mutagenesis. Virology 1988;166:405-414
35. Miyashita K, Okunishi J, Utsumi R, et al. Cleavage specificity of coxsackievirus 3C proteinase for peptide substrate (2): Importance of the P2 and P4 residues. Biosci Biotechnol Biochem 1996;60:1528-1529
36. Knott JA, Orr DC, Montgomery DS, et al. The expression and purification of human rhinovirus protease 3C. Eur J Biochem 1989;182:547-555
37. Sommergruber W, Zorn M, Blaas D, et al. Polypeptide 2A of human rhinovirus type 2: identification as a protease and characterization by mutational analysis. Virology 1989;169:68-77
38. Witherell G. AG-7088 Pfizer. Curr Opin Investig Drugs 2000;1:297-302
39. Binford SL, Maldonado F, Brothers MA, et al. Conservation of amino acids in human rhinovirus 3C protease correlates with broad-spectrum antiviral activity of rupintrivir, a novel human rhinovirus 3C protease inhibitor. Antimicrob Agents Chemother 2005;49:619-626 (Pubitemid 40175671)
40. Binford SL, Weady PT, Maldonado F, et al. In vitro resistance study of rupintrivir, a novel inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother 2007;51:4366-4373
41. Bradburne AF, Bynoe ML, Tyrrell DA. Effects of a "new" human respiratory virus in volunteers. Br Med J 1967;3:767-769
42. Woo PC, Lau SK, chu CM, et al. Characterization and complete genome sequence of a novel coronavirus, coronavirus HKU1, from patients with pneumonia. J Virol 2005;79:884-895
43. van der Hoek L, Pyrc K, Berkhout B. Human coronavirus NL63, a new respiratory virus. FEMS Microbiol Rev 2006;30:760-773
44. Anand K, Ziebuhr J, Wadhwani P, et al. Coronavirus main proteinase (3CLpro) structure: basis for design of anti-SARS drugs. Science 2003;300:1763-1767
45. Shie JJ, Fang JM, Kuo TH, et al. Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic alpha,beta-unsaturated esters. Bioorg Med Chem Lett 2005;13:5240-5252
46. Lall MS, Jain RP, Vederas JC. Inhibitors of 3C cysteine proteinases from Picornaviridae. Curr Top Med Chem 2004;4:1239-1253
47. Dragovich PS, Webber SE, Babine RE, et al. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 1. Michael acceptor structure-activity studies. J Med Chem 1998 41:2806-2818
48. Dragovich PS, Webber SE, Babine RE, et al. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 2. Peptide structure-activity studies. J Med Chem 1998;41:2819-2834
49. Dragovich PS, Prins TJ, Zhou R, et al. 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 1999;42:1203-1212 (Pubitemid 29181143)
50. Dragovich PS, Prins TJ, Zhou R, et al. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements. J Med Chem 1999;42:1213-1224 (Pubitemid 29181144)
51. Dragovich PS, Prins TJ, Zhou R, et al. Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3Cpro inhibitors. 8. pharmacological optimization of orally bioavailable 2-pyridone-containing peptidomimetics. J Med Chem 2003;46:4572-4585
52. Kaiser L, Crump CE, Hayden FG, et al. In vitro activity of pleconaril and AG7088 against selected serotypes and clinical isolates of human rhinoviruses. Antiviral Res 2000;47:215-220
53. Schmidt AC, Couch RB, Galasso GJ, et al. Current research on respiratory viral infections: Third International Symposium. Antiviral Res 2001;50:157-196
54. Agouron Pharmaceuticals, Inc. Use of csaids in rhinovirus infection. WO0114329; 2001
55. Patick AK, Binford SL, Brothers MA, et al. In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother 1999;43:2444-2450
56. Agouron Pharmaceuticals, Inc. Efficient methods for the preparation of rhinovirus protease inhibitors, key intermediates and a continuous membrane reactor useful for preparing the same. US20030064429A1; 2003
57. Lee ES, Lee WG, Yun SH, et al. Development of potent inhibitors of the coxsackievirus 3C protease. Biochem Biophys Chem Commun 2007;358:7-11
58. Webber SE, Okano K, Little TL, et al. Tripeptide aldehyde inhibitors of human rhinovirus 3C protease: design, synthesis, biological evaluation, and cocrystal structure solution of P1 glutamine isosteric replacements. J Med Chem 1998;41:2786-2805
59. Dragovich PS, Zhou R, Webber SE, et al. Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors. Bioorg Med Chem Lett 2000;10:45-48
60. Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis. WO0110894; 2001
61. Dragovich PS, Webber SE, Prins TJ, et al. Structure-based design of irreversible, tripeptidyl human rhinovirus 3C protease inhibitors containing N-methyl amino acids. Bioorg Med Chem Lett 1999;9:2189-2194
62. Kuo CJ, Shie JJ, Fang JM, et al. Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents. Bioorg Med Chem 2008;16:7388-7398
63. Agouron Pharmaceuticals, Inc. Substituted benzamide inhibitors of rhinovirus 3c protease. WO0078708; 2000
64. Eli Lilly & Co. Anti-picornaviral agents. US5821331; 1998
65. Xian M, Wang QM, Chen X, et al. S-nitrosothiols as novel, reversible inhibitors of human rhinovirus 3C protease. Bioorg Med Chem Lett 2000;10:2097-2100
66. Cytoclonal pharmaceutics, Inc. Anti-viral compounds. US6888033B1; 2005
67. Maugeri C, Alisi MA, Apicella C, et al. New anti-viral drugs for the treatment of the common cold. Bioorg Med Chem 2008;16:3091-3107
68. Webber SE, Tikhe J, Worland ST, et al. Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease. J Med Chem 1996;39:5072-5082
69. Mitsubishi Chemical Industries Co. Cysteine protease inhibitors. WO02076939; 2002
70. Im I, Lee ES, Choi SJ, et al. Structure-activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors. Bioorg Med Chem Lett 2009;19:3632-3636
71. Yang S, Chen SJ, Hsu MF, et al. Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor. J Med Chem 2006;49:4971-4980
72. Kuo CJ, Liu HG, Lo YK, et al. Individual and common inhibitors of coronavirus and picornavirus main proteases. FEBS Lett 2009;583:549-555
73. Lee CC, Kuo CJ, Ko TP, et al. Structural basis of inhibition specificities of 3C and 3C-like proteases by zinc-coordinating and peptidomimetic compounds. J Biol Chem 2009;284:7646-7655
74. Matthews DA, Dragovich PS, Webber SE, et al. 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 1999;96:11000-11007
75. Yang H, Yang M, Ding Y, et al. The crystal strcture of severe acute respiratory syndrome virus main protease and its complex with an inhibitor. Proc Natl Acad Sci USA 2003;100:13190-13195
76. Hsu MF, Kuo CJ, Chang KT, et al. Mechanism of the maturation process of SARS-CoV 3CL protease. J Biol Chem 2005;280:31257-31266
77. Yang H, Xie W, Xue X, et al. Design of wide-spectrum inhibitors targeting coronavirus main proteases. PLoS Biol 2005;3:e324
78. De Palma AM, Vliegen I, De Clercq E, et al. Selective inhibitors of picornavirus replication. Med Res Rev 2008;28:823-884
79. Liang PH. Characterization and inhibition of SARS-coronavirus main protease. Curr Top Med Chem 2006;6:361-376
80. Wang HM, Liang PH. Pharmacophores and biological activities of severe acute respiratory syndrome viral protease inhibitors. Expert Opin Ther Pat 2007;17:533-546
81. Tong TR. Therapies for coronaviruses. Part 2: inhibitors of intracellular life cycle. Expert Opin Ther Pat 2009;19:415-431