Heteroaromatic ester inhibitors of hepatitis A virus 3C proteinase: Evaluation of mode of action

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 10, 2008, Pages 5761-5777

  Huitema, Carly ^a   Zhang, Jianmin ^b   Yin, Jiang ^b   James, Michael N G ^b   Vederas, John C ^b   Eltis, Lindsay D ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

Antiviral; Cysteine proteinase; Halopyridinyl ester; Picornavirus

Indexed keywords

5 CHLOROPYRIDIN 3 YL 3 (FURAN 2 YL)ACRYLATE; 5 CHLOROPYRIDIN 3 YL 4 CHLORO 2 HYDROXYBENZOATE; ANTIVIRUS AGENT; AROMATIC COMPOUND; ESTER DERIVATIVE; FURAN; PROTEINASE INHIBITOR; PYRIDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; HEPATITIS A VIRUS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; MOLECULAR MODEL; NONHUMAN; PROTEIN DEGRADATION;

CYSTEINE ENDOPEPTIDASES; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTERS; HETEROCYCLIC COMPOUNDS; HYDROCARBONS, AROMATIC; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

HEPATITIS A VIRUS; PICORNAVIRIDAE;

EID: 43749121582     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.03.059     Document Type: Article

References (24)

1. Tong L. Chem. Rev. 102 (2002) 4609
2. Allaire M., Chernaia M.M., Malcolm B.A., and James M.N. Nature 369 (1994) 72
3. Bergmann E.M., Mosimann S.C., Chernaia M.M., Malcolm B.A., and James M.N. J. Virol. 71 (1997) 2436
4. Yin J., Bergmann E.M., Cherney M.M., Lall M.S., Jain R.P., Vederas J.C., and James M.N. J. Mol. Biol. 354 (2005) 854
5. Mosimann S.C., Cherney M.M., Sia S., Plotch S., and James M.N. J. Mol. Biol. 273 (1997) 1032
6. Matthews D.A., Smith W.W., Ferre R.A., Condon B., Budahazi G., Sisson W., Villafranca J.E., Janson C.A., McElroy H.E., Gribskov C.L., et al. Cell 77 (1994) 761
7. Birtley J.R., Knox S.R., Jaulent A.M., Brick P., Leatherbarrow R.J., and Curry S. J. Biol. Chem. 280 (2005) 11520
8. Shi J., Wei Z., and Song J. J. Biol. Chem. 279 (2004) 24765
9. Yang H., Yang M., Ding Y., Liu Y., Lou Z., Zhou Z., Sun L., Mo L., Ye S., Pang H., Gao G.F., Anand K., Bartlam M., Hilgenfeld R., and Rao Z. PNAS 100 (2003) 13190
10. Malcolm B.A., Lowe C., Shechosky S., McKay R.T., Yang C.C., Shah V.J., Simon R.J., Vederas J.C., and Santi D.V. Biochemistry 34 (1995) 8172
11. Morris T.S., Frormann S., Shechosky S., Lowe C., Lall M.S., Gauss-Muller V., Purcell R.H., Emerson S.U., Vederas J.C., and Malcolm B.A. Bioorg. Med. Chem. 5 (1997) 797
12. Ramtohul Y.K., James M.N.G., and Vederas J.C. J. Org. Chem. 67 (2002) 3169
13. Yin J., Cherney M.M., Bergmann E.M., Zhang J., Huitema C., Pettersson H., Eltis L.D., Vederas J.C., and James M.N. J. Mol. Biol. 361 (2006) 673
14. Jain R.P., and Vederas J.C. Bioorg. Med. Chem. Lett. 14 (2004) 3655
15. Lall M.S., Ramtohul Y.K., James M.N.G., and Vederas J.C. J. Org. Chem. 67 (2002) 1536
16. Blanchard J.E., Elowe N.H., Huitema C., Fortin P.D., Cechetto J.D., Eltis L.D., and Brown E.D. Chem. Biol. 11 (2004) 1445
17. Zhang J., Pettersson H.I., Huitema C., Niu C., Yin J., James M.N., Eltis L.D., and Vederas J.C. J. Med. Chem. 50 (2007) 1850
18. Seah S.Y., Labbe G., Nerdinger S., Johnson M.R., Snieckus V., and Eltis L.D. J. Biol. Chem. 275 (2000) 15701
19. Jewell D.A., Swietnicki W., Dunn B.M., and Malcolm B.A. Biochemistry 31 (1992) 7862
20. Malcolm B.A., Chin S.M., Jewell D.A., Stratton-Thomas J.R., Thudium K.B., Ralston R., and Rosenberg S. Biochemistry 31 (1992) 3358
21. Niu C., Yin J., Zhang J., Vederas J.C., and James M.N. Bioorg. Med. Chem. 16 (2007) 293
22. Lee T.W., Cherney M.M., Huitema C., Liu J., James K.E., Powers J.C., Eltis L.D., and James M.N. J. Mol. Biol. 353 (2005) 1137
23. Liu Y., Kati W., Chen C.M., Tripathi R., Molla A., and Kohlbrenner W. Anal. Biochem. 267 (1999) 331
24. Cornish-Bowden A. Analysis of Enzyme Kinetic Data (1995), Oxford University Press, Oxford, New York