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

Bibliography

• Denny FW Jr. The clinical impact of human respiratory virus infections. Am J Respir Crit Care Med 1995;152:S4-12
   Google Scholar
• Monto AS. Acute respiratory infection in children of developing countries: challenge of the 1990s. Rev Infect Dis 1989;11:498-505
   PubMedGoogle Scholar
• Melnick JL. Enteroviruses, polioviruses, coxsackieviruses, echoviruses, and newer enteroviruses. In: Virology, 3rd eds, 1996. p. 655-712
   Google Scholar
• 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. 823-56
   Google Scholar
• Holmes KV. SARS-associated coronavirus. N Eng J Med 2003;348:1948-51
   PubMed Web of Science ®Google Scholar
• Monto AS, Fendrick AM, Sarnes MW. Respiratory illness caused by Picornavirus infection: a review of clinical outcomes. Clin Ther 2001;23:1615-27
   PubMed Web of Science ®Google Scholar
• Peiris JS, Kuey KY, Osterhaus KD, The severe acute respiratory syndrome. N Eng J Med 2003;349:2431-41
   PubMed Web of Science ®Google Scholar
• Kuiken T, Fouchier RA, Schutten M, New discovered coronavirus as the primary cause of severe acute respiratory syndrome. Lancet 2003;362:263-70
   PubMed Web of Science ®Google Scholar
• Ksiazek TG, Erdman D, Goldsmith CS, A novel coronavirus associated with severe acute respiratory syndrome. N Eng J Med 2003;348:1953-66
   PubMed Web of Science ®Google Scholar
• Drosten C, Gunther S, Preiser W, Identification of a novel coronavirus in patients with severe acute respiratory syndrome. N Eng J Med 2003;348:1967-76
   PubMed Web of Science ®Google Scholar
• Kitamaru N, Semler BL, Rothberg PG, Primary structure, gene organization and polypeptide expression of poliovirus RNA. Nature 1981;291:547-53
   PubMed Web of Science ®Google Scholar
• 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;78:4887-91
   PubMed Web of Science ®Google Scholar
• Kaku Y, Sarai A, Murakami Y. Genetic reclassification of porcine enteroviruses. J Gen Virol 2001;82:417-24
   PubMed Web of Science ®Google Scholar
• 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;82:732-6
   PubMed Web of Science ®Google Scholar
• Chua BH, Mcminn PC, Lam SK, 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;82:2629-39
   PubMed Web of Science ®Google Scholar
• Shih SR, Ho MS, Lin KH, 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;68:127-36
   PubMed Web of Science ®Google Scholar
• Lindberg AM, Johansson S, Andersson A. Echovirus 5: infectious transcripts and complete nucleotide sequence from uncloned cDNA. Virus Res 1999;59:75-87
   PubMed Web of Science ®Google Scholar
• Heikkinen T, Jarvinen A. The common cold. Lancet 2003;361:51-9
   PubMed Web of Science ®Google Scholar
• Blomberg K, Lycke E, Ahlfors K, New enterovirus type associated with epidemic of aseptic meningitis and-or hand, foot, and mouse disease. Lancet 1974;2:112
   PubMed Web of Science ®Google Scholar
• Chang LY, Lin TY, Hsu KH, Clinical features and risk factors of pulmonary oedema after enterovirus-71-related hand, foot, and mouth disease. Lancet 1999;354:1682-6
   PubMed Web of Science ®Google Scholar
• Lum LC, Wong KT, Lam SK, Neurogenic pulmonary oedema and enterovirus 71 encephalomyelitis. Lancet 1998;352:1391
   PubMed Web of Science ®Google Scholar
• Lee CK, Kono K, Haas E, 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
   PubMed Web of Science ®Google Scholar
• Turner RB. The treatment of rhinovirus infections: progress and potential. Antiviral Res 2001;49:1-14
   PubMed Web of Science ®Google Scholar
• Rotbart HA, Hayden FG. Picornavirus infections: a primer for the practitioner. Arch Fam Med 2000;9:913-20
   PubMedGoogle Scholar
• Sperber SJ, Hayden FG. Chemotherapy of rhinovirus colds. Antimicrob Agents Chemother 1998;32:409-14
   Google Scholar
• McKinlay MA, Pevear DC, Rossmann MG. Treatment of the picornavirus common cold by inhibitors of viral uncoating and attachment. Annu Rev Microbiol 1992;46:635-54
   PubMed Web of Science ®Google Scholar
• Munoz FM, Galasso GJ, Gwaltney JM Jr, Current research on influenza and other respiratory viruses: II international symposium. Antiviral Res 2000;46:91-124
   PubMed Web of Science ®Google Scholar
• Diana GD, Pevear DC. Antipicornavirus drugs: current status. Antiviral Chem Chemother 1997;8:401-8
   Web of Science ®Google Scholar
• McKinlay MA. Recent advances in the treatment of rhinovirus infections. Curr Opin Pharmacol 2001;1:477-81
   PubMedGoogle Scholar
• Krausslich HG, Wimmer E. Viral proteinases. Annu Rev Biochem 1988;57:701-54
   PubMed Web of Science ®Google Scholar
• Anderson J, Schiffer C, Lee SK, Viral protease inhibitors. Handb Exp Pharmacol 2009;189:85-110
   PubMedGoogle Scholar
• 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. 187-97
   Google Scholar
• Mason PW, Grubman MJ, Baxt B. Molecular basis of pathogenesis of FMDV. Virus Res 2003;91:9-32
   PubMed Web of Science ®Google Scholar
• Lee CK, Wimmer E. Proteolytic processing of poliovirus polyprotein: elimination of 2Apro-mediated, alternative cleavage of polypeptide 3CD by in vitro mutagenesis. Virology 1988;166:405-14
   PubMed Web of Science ®Google Scholar
• Miyashita K, Okunishi J, Utsumi R, Cleavage specificity of coxsackievirus 3C proteinase for peptide substrate (2): Importance of the P2 and P4 residues. Biosci Biotechnol Biochem 1996;60:1528-9
   PubMed Web of Science ®Google Scholar
• Knott JA, Orr DC, Montgomery DS, The expression and purification of human rhinovirus protease 3C. Eur J Biochem 1989;182:547-55
   PubMedGoogle Scholar
• Sommergruber W, Zorn M, Blaas D, Polypeptide 2A of human rhinovirus type 2: identification as a protease and characterization by mutational analysis. Virology 1989;169:68-77
   PubMed Web of Science ®Google Scholar
• Witherell G. AG-7088 Pfizer. Curr Opin Investig Drugs 2000;1:297-302
   PubMedGoogle Scholar
• Binford SL, Maldonado F, Brothers MA, 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;49:619-26
   PubMed Web of Science ®Google Scholar
• Binford SL, Weady PT, Maldonado F, In vitro resistance study of rupintrivir, a novel inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother 2007;51:4366-73
   PubMed Web of Science ®Google Scholar
• Bradburne AF, Bynoe ML, Tyrrell DA. Effects of a “new” human respiratory virus in volunteers. Br Med J 1967;3:767-9
   PubMed Web of Science ®Google Scholar
• Woo PC, Lau SK, chu CM, Characterization and complete genome sequence of a novel coronavirus, coronavirus HKU1, from patients with pneumonia. J Virol 2005;79:884-95
   PubMed Web of Science ®Google Scholar
• van der Hoek L, Pyrc K, Berkhout B. Human coronavirus NL63, a new respiratory virus. FEMS Microbiol Rev 2006;30:760-73
   PubMed Web of Science ®Google Scholar
• Anand K, Ziebuhr J, Wadhwani P, Coronavirus main proteinase (3CLpro) structure: basis for design of anti-SARS drugs. Science 2003;300:1763-7
   PubMed Web of Science ®Google Scholar
• Shie JJ, Fang JM, Kuo TH, Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic alpha,beta-unsaturated esters. Bioorg Med Chem Lett 2005;13:5240-52
   Google Scholar
• Lall MS, Jain RP, Vederas JC. Inhibitors of 3C cysteine proteinases from Picornaviridae. Curr Top Med Chem 2004;4:1239-53
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Webber SE, Babine RE, Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 1. Michael acceptor structure-activity studies. J Med Chem 1998 41:2806-18
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Webber SE, Babine RE, Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 2. Peptide structure-activity studies. J Med Chem 1998;41:2819-34
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Prins TJ, Zhou R, 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;42:1203-12
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Prins TJ, Zhou R, 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;42:1213-24
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Prins TJ, Zhou R, 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;46:4572-85
   PubMed Web of Science ®Google Scholar
• Kaiser L, Crump CE, Hayden FG, In vitro activity of pleconaril and AG7088 against selected serotypes and clinical isolates of human rhinoviruses. Antiviral Res 2000;47:215-20
   PubMed Web of Science ®Google Scholar
• Schmidt AC, Couch RB, Galasso GJ, Current research on respiratory viral infections: Third International Symposium. Antiviral Res 2001;50:157-96
   PubMed Web of Science ®Google Scholar
• Agouron Pharmaceuticals, Inc. Use of csaids in rhinovirus infection. WO0114329; 2001
   Google Scholar
• Patick AK, Binford SL, Brothers MA, In vitro antiviral activity of AG7088, a potent inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother 1999;43:2444-50
   PubMed Web of Science ®Google Scholar
• 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
   Google Scholar
• Lee ES, Lee WG, Yun SH, Development of potent inhibitors of the coxsackievirus 3C protease. Biochem Biophys Chem Commun 2007;358:7-11
   PubMed Web of Science ®Google Scholar
• Webber SE, Okano K, Little TL, 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;41:2786-805
   PubMed Web of Science ®Google Scholar
• Dragovich PS, Zhou R, Webber SE, Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors. Bioorg Med Chem Lett 2000;10:45-8
   PubMed Web of Science ®Google Scholar
• Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis. WO0110894; 2001
   Google Scholar
• Dragovich PS, Webber SE, Prins TJ, Structure-based design of irreversible, tripeptidyl human rhinovirus 3C protease inhibitors containing N-methyl amino acids. Bioorg Med Chem Lett 1999;9:2189-94
   PubMed Web of Science ®Google Scholar
• Kuo CJ, Shie JJ, Fang JM, Design, synthesis, and evaluation of 3C protease inhibitors as anti-enterovirus 71 agents. Bioorg Med Chem 2008;16:7388-98
   PubMed Web of Science ®Google Scholar
• Agouron Pharmaceuticals, Inc. Substituted benzamide inhibitors of rhinovirus 3c protease. WO0078708; 2000
   Google Scholar
• Eli Lilly & Co. Anti-picornaviral agents. US5821331; 1998
   Google Scholar
• Xian M, Wang QM, Chen X, S-nitrosothiols as novel, reversible inhibitors of human rhinovirus 3C protease. Bioorg Med Chem Lett 2000;10:2097-100
   PubMed Web of Science ®Google Scholar
• Cytoclonal pharmaceutics, Inc. Anti-viral compounds. US6888033B1; 2005
   Google Scholar
• Maugeri C, Alisi MA, Apicella C, New anti-viral drugs for the treatment of the common cold. Bioorg Med Chem 2008;16:3091-107
   PubMed Web of Science ®Google Scholar
• Webber SE, Tikhe J, Worland ST, Design, synthesis, and evaluation of nonpeptidic inhibitors of human rhinovirus 3C protease. J Med Chem 1996;39:5072-82
   PubMed Web of Science ®Google Scholar
• Mitsubishi Chemical Industries Co. Cysteine protease inhibitors. WO02076939; 2002
   Google Scholar
• Im I, Lee ES, Choi SJ, Structure-activity relationships of heteroaromatic esters as human rhinovirus 3C protease inhibitors. Bioorg Med Chem Lett 2009;19:3632-6
   PubMed Web of Science ®Google Scholar
• Yang S, Chen SJ, Hsu MF, Synthesis, crystal structure, structure–activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor. J Med Chem 2006;49:4971-80
   PubMed Web of Science ®Google Scholar
• Kuo CJ, Liu HG, Lo YK, Individual and common inhibitors of coronavirus and picornavirus main proteases. FEBS Lett 2009;583:549-55
   PubMed Web of Science ®Google Scholar
• Lee CC, Kuo CJ, Ko TP, Structural basis of inhibition specificities of 3C and 3C-like proteases by zinc-coordinating and peptidomimetic compounds. J Biol Chem 2009;284:7646-55
   PubMed Web of Science ®Google Scholar
• Matthews DA, Dragovich PS, Webber SE, 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;96:11000-7
   PubMed Web of Science ®Google Scholar
• Yang H, Yang M, Ding Y, The crystal strcture of severe acute respiratory syndrome virus main protease and its complex with an inhibitor. Proc Natl Acad Sci USA 2003;100:13190-5
   PubMed Web of Science ®Google Scholar
• Hsu MF, Kuo CJ, Chang KT, Mechanism of the maturation process of SARS-CoV 3CL protease. J Biol Chem 2005;280:31257-66
   PubMed Web of Science ®Google Scholar
• Yang H, Xie W, Xue X, Design of wide-spectrum inhibitors targeting coronavirus main proteases. PLoS Biol 2005;3:e324
   PubMed Web of Science ®Google Scholar
• De Palma AM, Vliegen I, De Clercq E, Selective inhibitors of picornavirus replication. Med Res Rev 2008;28:823-84
   PubMed Web of Science ®Google Scholar
• Liang PH. Characterization and inhibition of SARS-coronavirus main protease. Curr Top Med Chem 2006;6:361-76
   PubMed Web of Science ®Google Scholar
• Wang HM, Liang PH. Pharmacophores and biological activities of severe acute respiratory syndrome viral protease inhibitors. Expert Opin Ther Pat 2007;17:533-46
   Web of Science ®Google Scholar
• Tong TR. Therapies for coronaviruses. Part 2: inhibitors of intracellular life cycle. Expert Opin Ther Pat 2009;19:415-31
   PubMed Web of Science ®Google Scholar