A study of the active site of influenza virus sialidase: An approach to the rational design of novel anti-influenza drugs

Journal of Medicinal Chemistry

Volumn 39, Issue 2, 1996, Pages 388-391

  Von Itzstein, Mark ^a,b   Dyason, Jeffrey C ^a   Oliver, Stuart W ^a   White, Hume F ^a   Wu, Wen Yang ^a   Kok, Gaik B ^a   Pegg, Michael S ^a  

^a MONASH UNIVERSITY   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; SIALIDASE; SIALIDASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; CRYSTAL STRUCTURE; DRUG BINDING; DRUG DESIGN; ENZYME ACTIVE SITE; ENZYME INHIBITION; INFLUENZA; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTIVIRAL AGENTS; BINDING SITES; COMPUTER SIMULATION; DRUG DESIGN; MOLECULAR PROBES; NEURAMINIDASE; ORTHOMYXOVIRIDAE; PROTEIN CONFORMATION;

EID: 0030044141     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950294c     Document Type: Article

References (20)

1. Drzeniek, R. Viral and Bacterial Neuraminidases. Curr. Top. Microbiol. Immunol. 1972, 59, 35-74.
2. Chong, A. K. J.; Pegg, M. S.; von Itzstein, M. Influenza Virus Sialidase: Effect of Calcium on Steady-state Kinetic Parameters. Biochim. Biophys. Acta 1991, 1077, 65-71.
3. Chong, A. K. J.; Pegg, M. S.; von Itzstein, M. Characterization of an Ionisable Group Involved in Binding and Catalysis by Sialidase from Influenza Virus. Biochem. Int. 1991, 24, 165-171.
4. Chong, A. K. J.; Pegg, M. S.; Taylor, N. R.; von Itzstein, M. Evidence for a Sialosyl Cation Transition-state Complex in the Reaction of Sialidase from Influenza Virus. Eur. J. Biochem. 1992, 207, 335-343.
5. Palese, P.; Jobita, K.; Ueda, M.; Compans, R. W. Characterization of Temperature Sensitive Influenza Virus Mutants Defective in Neuraminidase. Virology 1974, 61, 397-410.
6. Varghese, J. H.; Colman, P. M. The Three-dimensional Structure of the Neuraminidase of Influenza Virus A/Tokyo/3/67 at 2.2 Å Resolution. J. Mol. Biol. 1991, 221, 473-486.
7. Bossart-Whitaker, P.; Carson, M.; Babu, Y. S.; Smith, C. D.; Laver, W. G.; Air, G. M. Three-dimensional Structure of Influenza A N9 Neuraminidase and Its Complex with the Inhibitor 2-Deoxy-2,3-Dehydro-N-Acetyl Neuraminic Acid. J. Mol. Biol. 1993, 232, 1069-1083.
8. Burmeister, W. P.; Ruigrok, R. W. H.; Cusack, S. The 2.2 Å Resolution Crystal Structure of Influenza B Neuraminidase and its Complex with Sialic Acid. EMBO J. 1991, 11, 49-56.
9. Varghese, J. N.; McKimm-Breschkin, J.; Caldwell, J. B.; Kortt, A. A.; Colman, P. M. The Structure of the Complex between Influenza Virus Neuraminidase and Sialic Acid, the Viral Receptor. Proteins 1992, 14, 327-32.
10. Colman, P. M. Neuraminidase: Enzyme and Antigen. In The Influenza Viruses; Krug, R. M., Ed.; Plenum: New York, 1989; pp 175-218.
11. Goodford, P. J. A Computational Procedure for Determining Energetically Favorable Binding Sites on Biologically Important Macromolecules. J. Med. Chem. 1985, 28, 849-857.
12. von Itzstein, M.; Wu, W. Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Van Phan, T.; Smythe, M.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; Penn, C. R. Rational Design of Potent Sialidase-based Inhibitors of Influenza Virus Replication. Nature 1993, 363, 418-423.
13. von Itzstein, M.; Wu, W. Y.; Jin, B. The Synthesis of 2,3-didehydro-2,4-dideoxy-4-guanidinyl-N-acetylneuraminic acid: a potent influenza virus Sialidase inhibitor. Carbohydr. Res. 1994, 259, 301-305.
14. Taylor, N. R.; von Itzstein, M. Molecular Modeling Studies on Ligand Binding to Sialidase from Influenza Virus and the Mechanism of Catalysis. J. Med. Chem. 1994, 37, 616-624.
15. Holzer, C. T.; von Itzstein, M.; Jin, B.; Pegg, M. S.; Stewart, W. P.; Wu, W. Y. Inhibition of Sialidases from Viral, Bacterial, and Mammalian Sources by Analogues of 2-Deoxy-2,3-didehydro-N-acetylneuraminic acid Modified at the C-4 Position. Glycoconjugate J. 1993, 10, 40-44.
16. Goodford, P. J. Personal communication.
17. Pegg, M. S.; von Itzstein, M. Slow-Binding Inhibition of Sialidase from Influenza Virus. Biochem. Mol. Biol. Int. 1994, 32, 851-858.
18. von Itzstein, M.; Jin, B.; Wu, W. Y.; Chandler, M. A convenient method for the introduction of nitrogen and sulfur at C-4 on a sialic acid analogue. Carbohydr. Res. 1993, 244, 181-185.
19. von Itzstein, M.; Wu, W. Y.; Van Phan, T.; Danylec, B.; Jin, B. International Patent Appl. WO9116320-A92.10.31 (9147), 1991; Chem. Abstr. 1991, 117, 49151y.
20. White, C. L.; Janakiraman, M. N.; Laver, W. G.; Philippon, C.; Vasella, A.; Air, G. M.; Luo, M. A Sialic Acid-derived Phosphonate analog inhibits different strains of Influenza virus Neuraminidase with different efficiencies. J. Mol. Biol. 1995, 245, 623-634.