Unsaturated N-acetyl-D-glucosaminuronic acid glycosides as inhibitors of influenza virus sialidase

Glycoconjugate Journal

Volumn 23, Issue 1-2, 2006, Pages 127-133

  Mann, Maretta C ^a   Islam, Tasneem ^a   Dyason, Jeffrey C ^a   Florio, Pas ^b   Trower, Carolyn J ^a,b   Thomson, Robin J ^a   Von Itzstein, Mark ^a  

^a GRIFFITH UNIVERSITY   (Australia)

^b MONASH UNIVERSITY   (Australia)

Author keywords

Influenza virus; Inhibitors; Sialic acids; Sialidase; Sialylmimetics

Indexed keywords

ANTIINFLUENZA AGENT; ANTIVIRUS AGENT; CARBOHYDRATE N ACETYLGLUCOSAMINE; N ACETYL DEXTRO GLUCOSAMINURONIC ACID GLYCOSIDE; N ACETYLNEURAMINIC ACID; SIALIDASE; SIALIDASE INHIBITOR; SIALYLMIMETIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; INFLUENZA; INFLUENZA VIRUS; NONHUMAN; PRIORITY JOURNAL; VIRUS INHIBITION;

ENZYME INHIBITORS; GLYCOSIDES; MODELS, MOLECULAR; MOLECULAR MIMICRY; NEURAMINIDASE; PROTEIN CONFORMATION; URONIC ACIDS;

ORTHOMYXOVIRIDAE;

EID: 33645458687     PISSN: 02820080     EISSN: 15734986     Source Type: Journal    
DOI: 10.1007/s10719-006-5445-9     Document Type: Article

References (20)

1. Abbott, A.: What's in the medicine cabinet. Nature 435, 407-409 (2005)
2. Wilson, J.C., von Itzstein, M.: Recent strategies in the search for new anti-influenza therapies. Current Drug Targets 4, 389-408 (2003)
3. Thomson, R.J., von Itzstein, M.: N-Acetylneuraminic acid derivatives and mimetics as anti-influenza agents, In Carbohydrate-based Drug Discovery, edited by Wong C-H (Wiley-VCH, Weinheim, 2003) Vol. 2, pp. 831-862
4. Dyason, J.C., Wilson, J.C., von Itzstein, M.: Sialidases: Targets for rational drug design, In Computational Medicinal Chemistry and Drug Discovery, edited by Bultinck, P., De Winter, H., Langenaeker, W. and Tollenaere, J. (Dekker Inc, New York, 2004) pp. 727-745
5. Roberts, N.A.: Anti-influenza drugs and neuraminidase inhibitors. Progress Drug Res. 56, 197-236 (2001)
6. McCullers, J.A.: Antiviral therapy of influenza. Expert Opin. Investig. Drugs 14, 305-312, (2005)
7. 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 10, 40-44 (1993) and references within
8. 4-β-D-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition. Bioorg. Med. Chem. Lett. 9, 2065-2068 (1999)
9. Mann, M.C., Thomson, R.J., von Itzstein, M.: An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors. Bioorg. Med. Chem. Lett. 14, 5555-5558 (2004)
10. Smith, P.W., Robinson, J.E., Evans, D.N., Sollis, S.L., Howes, P.D., Trivedi, N., Bethell, R.C.: Sialidase Inhibitors Related to Zanamivir: Synthesis and Biological Evaluation of 4H-Pyran 6-Ether and Ketone. Bioorg. Med. Chem. Lett. 9, 601-604 (1999)
11. Chong, A.K.J., Pegg, M.S., von Itzstein, M.: Influenza virus sialidase: Effect of calcium on steady-state kinetic parameters. Biochim. Biophys. Acta. 1077, 65-71 (1991)
12. Potier, M., Mameli, L., Belisle, M., Dallaire, L., Melançon, S.B.: Fluorometric assay of neuraminidase with a sodium (4-methylumbelliferyl-alpha- D-N-acetylneuraminate) substrate. Anal. Biochem. 94, 287-296 (1979)
13. Tiralongo, J., Abo, A., Danylec, B., Gerardy-Schahn, R., von Itzstein, M.: A High-Throughput Assay for Rat Liver Golgi and Saccharomyces cerevisiae-Expressed Murine CMP-N-Acetylneuraminic Acid Transport Proteins. Anal. Biochem. 285, 21-32 (2000)
14. Accelrys, InsightII (Accelrys Inc, San Diego)
15. Smith, B.J., Colman, P.M., von Itzstein, M., Danylec, B., Varghese, J.N.: Analysis of inhibitor binding in influenza virus neuraminidase. Prot. Sci. 10, 689-696 (2001)
16. Varghese, J.N., Smith, P.W., Sollis, S.L., Blick, T.J., Sahasrabudhe, A., McKimm-Breschkin, J.L., Colman, P.M.: Drug design against a shifting target: A structural basis for resistance to inhibitors in a variant of influenza virus neuraminidase. Structure 6, 735-746 (1998)
17. Sanner, M.F., Python: A programming language for software integration and development. J. Mol. Graph. Model. 17, 57-61 (1999)
18. Morris, G.M., Goodsell, D.S., Halliday, R.S., Huey, R., Hart, W.E., Belew, R.K., Olson, A.J.: Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J. Comput. Chem. 19, 1639-1662 (1998)
19. Taylor, N.R., Cleasby, A., Singh, O., Skarzynski, T., Wonacott, A.J., Smith, P.W., Sollis, S.L., Howes, P.D., Cherry, P.C., Bethell, R., Colman, P., Varghese, J.: Dihydropyrancarboxamides related to zanamivir: A new series of inhibitors of influenza virus sialidases. 2. Crystallographic and molecular modeling study of complexes of 4-amino-4H-pyran-6-carboxamides and sialidase from influenza virus types A and B. J. Med. Chem. 41, 798-807 (1998)
20. Florio, P., Thomson, R.J., Smith, B., Colman, P.M., von Itzstein, M., (unpublished data)