Novel 3,4-disubstituted-Neu5Ac2en derivatives as probes to investigate flexibility of the influenza virus sialidase 150-loop

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 16, 2013, Pages 4820-4830

  Rudrawar, Santosh ^a   Dyason, Jeffrey C ^a   Maggioni, Andrea ^a   Thomson, Robin J ^a   Itzstein, Mark Von ^a  

^a GRIFFITH UNIVERSITY   (Australia)

Author keywords

150 loop; Influenza; Neu5Ac2en; Sialic acid; Sialidase

Indexed keywords

2 DEOXY 2,3 DEHYDRO N ACETYLNEURAMINIC ACID DERIVATIVE; 5 ACETAMIDO 2,6 ANHYDRO 3,4,5 TRIDEOXY 4 GUANIDINO 3 C [3' (4 TOLYL)PROP 2'ENYL] DEXTRO GLYCERO DEXTRO TALO NON 2 ENONIC ACID; 5 ACETAMIDO 4 AMINO 2,6 ANHYDRO 3,4,5 TRIDEOXY 3 C [3' (4 TOLYL)PROP 2' ENYL] DEXTRO GLYCERO DEXTRO GALACTO NON 2 ENONIC ACID; ANTIVIRUS AGENT; GUANIDINO 3 (4 TOLYL)ALLYL 2 DEOXY 2,3 DEHYDRO N ACETYLNEURAMINIC ACID DERIVATIVE; HYDROXYL GROUP; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS SIALIDASE; ZANAMIVIR;

ARTICLE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H2N2;

150-LOOP; INFLUENZA; NEU5AC2EN; SIALIC ACID; SIALIDASE;

MOLECULAR PROBES; N-ACETYLNEURAMINIC ACID; NEURAMINIDASE; ORTHOMYXOVIRIDAE; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; SIALIC ACIDS;

ORTHOMYXOVIRIDAE;

EID: 84880574055     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.05.054     Document Type: Article

References (40)

1. World Health Organisation, Influenza: WHO - Fact sheet N 211: < http://www.who.int/mediacentre/factsheets/fs211/en/ >.
2. C.J.L. Murray, A.D. Lopez, B. Chin, D. Feehan, and K.H. Hill Lancet 368 2006 2211
3. K.G. Nicholson, J.M. Wood, and M. Zambon Lancet 362 2003 1733
4. R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel Nature 443 2006 45
5. R. Wagner, M. Matrosovich, and H.-D. Klenk Rev. Med. Virol. 12 2002 159
6. M. von Itzstein Nat. Rev. Drug Disc. 6 2007 967
7. M. von Itzstein, W.-Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T.V. Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.J. Hotham, J.M. Cameron, and C.R. Penn Nature 363 1993 418
8. C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, and R.C. Stevens J. Am. Chem. Soc. 119 1997 681
9. M. Wang, J. Qi, Y. Liu, C.J. Vavricka, Y. Wu, Q. Li, and G.F. Gao J. Virol. 85 2011 8431
10. R.E. Amaro, X. Cheng, I. Ivanov, D. Xu, and J.A. McCammon J. Am. Chem. Soc. 131 2009 4702
11. P.M. Colman Protein Sci. 3 1994 1687
12. C.J. Vavricka, Q. Li, Y. Wu, J. Qi, M. Wang, Y. Liu, F. Gao, J. Liu, E. Feng, J. He, J. Wang, H. Liu, H. Jiang, and G. Gao F PLoS Pathog. 7 2011 e1002249 10.1371/journal.ppat.1002249
13. Q. Li, J. Qi, W. Zhang, C.J. Vavricka, Y. Shi, J. Wei, E. Feng, J. Shen, J. Chen, D. Liu, J. He, J. Yan, H. Liu, H. Jiang, M. Teng, X. Li, and G.F. Gao Nat. Struct. Mol. Biol. 17 2010 1266
14. R.E. Amaro, R.V. Swift, L. Votapka, W.W. Li, R.C. Walker, and R.M. Bush Nat. Commun. 2 2011 388 10.1038/ncomms1390
15. A.T. García-Sosa, S. Sild, and U. Maran J. Chem. Inf. Model. 48 2008 2074
16. S. Rudrawar, J.C. Dyason, M.-A. Rameix-Welti, F.J. Rose, P.S. Kerry, R.J.M. Russell, S. van der Werf, R.J. Thomson, N. Naffakh, and M. von Itzstein Nat. Commun. 1 2010 113 10.1038/ncomms1114
17. S. Rudrawar, P.S. Kerry, M.-A. Rameix-Welti, A. Maggioni, J.C. Dyason, F.J. Rose, S. van der Werf, R.J. Thomson, N. Naffakh, R.J.M. Russell, S. van der Werf, and M. von Itzstein Org. Biomol. Chem. 10 2012 8628
18. W.-H. Wen, S.-Y. Wang, K.-C. Tsai, Y.-S.E. Cheng, A.-S. Yang, J.-M. Fang, and C.-H. Wong Bioorg. Med. Chem. 18 2010 4074
19. S. Mohan, S. McAtamney, T. Haselhorst, M. von Itzstein, and B.M. Pinto J. Med. Chem. 53 2010 7377
20. D. Ye, W.-J. Shin, N. Li, W. Tang, E. Feng, J. Li, P.-L. He, J.-P. Zuo, H. Kim, K.-Y. Nam, W. Zhu, B.-L. Seong, K.T. No, H. Jiang, and H. Liu Eur. J. Med. Chem. 54 2012 764
21. M. von Itzstein, J.C. Dyason, S.W. Oliver, H.F. White, W.-Y. Wu, G.B. Kok, and M.S. Pegg J. Med. Chem. 39 1996 388
22. S. Rudrawar, M. Pascolutti, B. Bhatt, R.J. Thomson, and M. von Itzstein Tetrahedron Lett. 54 2013 1198
23. K. Okamoto, T. Kondo, and T. Goto Bull. Chem. Soc. Jpn. 60 1987 631
24. H. Paulsen, and P. Matschulat Liebigs Ann. Chem. 1991 487
25. R.H. Grubbs, and S. Chang Tetrahedron 54 1998 4413
26. S.J. Connon, and S. Blechert Angew. Chem., Int. Ed. 42 2003 1900
27. E. Schreiner, E. Zbiral, R.G. Kleineidam, and R. Schauer Liebigs Ann. Chem. 1991 129
28. M. Chandler, M.J. Bamford, R. Conroy, B. Lamont, B. Patel, V.K. Patel, I.P. Steeples, R. Storer, N.G. Weir, M. Wright, and C. Williamson J. Chem. Soc., Perkin Trans 1 1995 1173
29. J. Scheigetz, R. Zamboni, M.A. Bernstein, and B. Roy Org. Prep. Proced. Int. 27 1995 637
30. A.S. Thompson, G.R. Humphrey, A.M. DeMarco, D.J. Mathre, and E.J.J. Grabowski J. Org. Chem. 58 1993 5886
31. M. von Itzstein, W.-Y. Wu, and B. Jin Carbohydrate Res. 259 1994 301
32. P.W. Smith, S.L. Sollis, P.D. Howes, P.C. Cherry, I.D. Starkey, K.N. Cobley, H. Weston, J. Scicinski, A. Merritt, A. Whittington, P. Wyatt, N. Taylor, D. Green, R. Bethell, S. Madar, R.J. Fenton, P.J. Morley, T. Pateman, and A. Beresford J. Med. Chem. 41 1998 787
33. D.M. Andrews, P.C. Cherry, D.C. Humber, P.S. Jones, S.P. Keeling, P.F. Martin, C.D. Shaw, and S. Swanson Eur. J. Med. Chem. 34 1999 563
34. von Itzstein, L. M.; Wu, W.-Y.; Phan, T. V.; Danylec, B.; Jin, B. (Biota Scientific Management Pty Ltd), 1991, WO 91/16320.
35. G.B. Kok, and M. von Itzstein Carbohydrate Res. 302 1997 237
36. S.-I. Murahashi, Y. Taniguchi, Y. Imada, and Y. Tanigawa J. Org. Chem. 54 1989 3292
37. J.N. Varghese, V.C. Epa, and P.M. Colman Protein Sci. 4 1995 1081
38. N.Yu. Kulikova, A.M. Shpirt, and L.O. Kononov Synthesis 24 2006 4113
39. A.K.J. Chong, M.S. Pegg, and M. von Itzstein Biochim. Biophys. Acta 1077 1991 65
40. M. Potier, L. Mameli, M. Bélisle, L. Dallaire, and S.B. Melançon Anal. Biochem. 94 1979 287