The design and synthesis of potent inhibitors of hepatitis C virus NS3-4A proteinase

Antiviral Chemistry and Chemotherapy

Volumn 10, Issue 5, 1999, Pages 259-273

  Attwood, M R ^a   Bennett, J M ^a   Campbell, A D ^a   Canning, G G M ^a   Carr, M G ^a   Conway, E ^a   Dunsdon, R M ^a   Greening, J R ^a   Jones, P S ^a   Kay, P B ^a   Handa, B K ^a   Hurst, D N ^a   Jennings, N S ^a   Jordan, S ^a   Keech, E ^a   O'Brien, M A ^a   Overton, H A ^a   King Underwood, J ^a   Raynham, T M ^a   Stenson, K P ^a   Wilkinson, C S ^a   Wilkinson, T C I ^a   Wilson, F X ^a   more..

^a ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

Aldehydes; Boronic acids; Hepatitis C virus; Inhibitors; NS3; NS4a; Synthetic substrates

Indexed keywords

PROTEINASE; PROTEINASE INHIBITOR; SYNTHETIC PEPTIDE;

AMINO TERMINAL SEQUENCE; ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ESCHERICHIA COLI; HEPATITIS C; HEPATITIS C VIRUS; LIVER CELL CARCINOMA; LIVER CIRRHOSIS; NONHUMAN; NUCLEOTIDE SEQUENCE; OPEN READING FRAME; PRIORITY JOURNAL; VIRUS GENOME;

EID: 0032821515     PISSN: 09563202     EISSN: None     Source Type: Journal    
DOI: 10.1177/095632029901000505     Document Type: Article

References (26)

1. Angelastro MR, Mehdi S, Burkhart JP, Peet NP & Bey P (1990) α-Diketone and α-keto ester derivatives of N-protected amino acids and peptides as novel inhibitors of cysteine and serine proteinases. Journal of Medicinal Chemistry 33:11-13.
2. Attwood MR, Hurst DN, Jones PS, Kay PB, Raynham TM & Wilson FX (1998) Preparation of antiviral peptide derivatives. WO 9822496.
3. Bartenschlager R (1997) Molecular targets in inhibition of hepatitis C virus replication. Antiviral Chemistry & Chemotherapy 8: 281-301 and references cited therein.
4. Bartenschlager R, Ahlborn-Laake L, Mous J & Jacobsen H (1993) Nonstructural protein 3 of the hepatitis C virus encodes a serine type proteinase required for cleavage at the NS3/4 and NS4/5 junctions. Journal of Virology 67:3835-3844.
5. Edwards PD & Bernstein PR (1994) Synthetic inhibitors of Elastase. Medicinal Research Reviews 14:127-194 and references cited therein.
6. Fehrentz J-A & Castro B (1983) An efficient synthesis of optically active α-(1-butoxycarbonylamino)-aldehydes from α-amino acids. Synthesis 676-678.
7. Gallinari P, Bennan D, Nardi C, Brunett M, Tomei L, Steinkuhler C & De Francesco R (1998) Multiple enzymatic activities associated with the recombinant NS3 protein of hepatitis C virus. Journal of Virology 72:6758-6769.
8. Grakoui A, Wychowski C, Lin C, Feinstone SM & Rice CM (1993) Expression and identification of hepatitis C virus polyprotein cleavage products. Journal of Virology 67:1385-1395.
9. Greer J (1981) Comparative model-building of the mammalian serine proteases. Journal of Molecular Biology 153:1027-1042.
10. Greer J (1990) Comparative modelling methods: application to the family of the mammalian serine proteases. Proteins: structure, function and genetics. 7:317-334.
11. Houghton M (1996) Hepatitis C viruses. In Fields Virology, pp., 1035-1051. Edited by BN Fields, DM Knipe, PM Chanock, JL Melnick, TP Monath, B Roizman & SE Straus. Philadelphia: Lippincott-Raven.
12. Ingallinella P, Altamura S, Bianchi E, Taliani M, Ingenito R, Cortese R, De Francesco R, Steinkuhler C & Pessi A (1998) Potent peptide inhibitors of human hepatitis C NS3 protease are obtained by optimising the cleavage products. Biochemistry 37:8906-8914.
13. Kettner CA & Shenvi AB (1984) Inhibition of the serine proteases Leukocyte Elastase, Pancreatic Elastase, Cathepsin G and Chymotrypsin by peptide boronic acids. Journal of Biological Chemistry 259:15106-15112.
14. Kettner C, Mersinger L & Knabb R (1990) The selective inhibition of Thrombin by peptides of boroarginine. Journal of Biological Chemistry 265:18289-18293.
15. Kim JL, Morgenstern KA, Lin C, Fox T, Dwyer MD, Landro JA, Chambers SP, Markland W, Lepre CA, O'Malley ET, Harbeson SL, Rice CM, Murcko MA, Caron, PR & Rice CM (1996) Crystal structure of the hepatitis C virus NS3 protease domain complexed with a synthetic NS4A cofactor peptide. Cell 87:343-355.
16. Kinder DH, Elstad CA, Meadows GG & Ames MM (1992) Antimetastatic activity of boro-amino acid analog protease inhibitors against B16BL6 melanoma in vivo. Invasion Metastasis 12:309-319.
17. Kwong AD (1997) Hepatitis C virus NS3/4A protease. Current Opinions in Injections Diseases 10:485-490.
18. Leatherbarrow, RJ (1987) Enzfitter: A non-linear regression data analysis program for the IBM-PC. Elsevier Biosoft: Cambridge.
19. Llinas-Brunet M, Bailey M, Deziel R, Fazal G, Gorys V, Goulet S, Halmos T, Maurice R, Poirier M, Poupart MA, Rancourt J, Thibeault D, Wernic D & Lamarre D (1998) Studies on the C-terminal of hexapeptide inhibitors of the Hepatitis C Virus serine protease. Bioorganic and Medicinal Chemistry Letters. 8:2719-24.
20. Love RA, Parge HE, Wickersham JA, Hostomsky Z, Habuka N, Moomaw, EW, Adachi T & Hostomska Z (1996) The crystal structure of hepatitis C virus NS3 proteinase reveals a trypsin-like fold and a structural zinc binding site. Cell 87:331-342.
21. Matteson DS (1989) α-Halo boronic esters: intermediates for stereodirected synthesis. Chemical Reviews 89:1535-1551 and references cites therein.
22. Nahm S & Weinreb SM (1981) N-Methoxy-N-methylamides as effective acylating agents. Tetrahedron Letters 22:3815-3818.
23. Navia MA, McKeever BM, Springer JP, Lin T-Y, Williams HR, Fluder EM, Dorn CP & Hoogsteen K (1989) Structure of human neutrophil elastase in complex with a peptide chloromethyl ketone inhibitor at 1.84-Å resolution. Proceedings of the National Academy of Sciences, USA 86:7-11.
24. Roberts NA, Martin JA, Kinchington D, Broadhurst AV, Craig C, Duncan IB, Galpin SA, Handa BK, Kay J, Kröhn A, Lambert RW, Merrett JH, Mills JS, Parkes KEB, Redshaw S, Ritchie AJ, Taylor DL, Thomas GJ & Machin PJ (1990) Rational design of peptide-based HIV proteinase inhibitors. Science 248:358-248.
25. Yan Y, Li Y, Munshi S, Sardana V, Cole JL, Sardana M, Steinkuehler C, Tomei L, De Francesco R, Kuo LC & Chen Z (1998) Complex of NS3 protease and NS4A peptide of BK strain hepatitis C virus: a 2.2 Å resolution structure in a hexagonal crystal form. Protein Science 7:837-847.
26. Zhang R, Durkin J, Windsor WT, McNemar C, Ramanthan L & Le Hung V (1997) Probing the substrate specificity of hepatitis C virus NS3 serine protease by using synthetic peptides. Journal of Virology 71:6208-6213.