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Volumn 53, Issue 2, 2010, Pages 778-786

Antiviral potential and molecular insight into neuraminidase inhibiting diarylheptanoids from Alpinia katsumadai

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; KATSUMADAIN A; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS SIALIDASE;

EID: 77249115238     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901440f     Document Type: Article
Times cited : (118)

References (53)
  • 2
    • 36749056771 scopus 로고    scopus 로고
    • The war against influenza: Discovery and development of sialidase inhibitors
    • von Itzstein, M. The war against influenza: discovery and development of sialidase inhibitors. Nat. Rev. Drug Discovery 2007, 6, 967-974.
    • (2007) Nat. Rev. Drug Discovery , vol.6 , pp. 967-974
    • von Itzstein, M.1
  • 3
    • 25444501243 scopus 로고    scopus 로고
    • Neuraminidase inhibitors for influenza
    • Moscona, A. Neuraminidase inhibitors for influenza. N. Engl. J. Med. 2005, 353, 1363-1373.
    • (2005) N. Engl. J. Med , vol.353 , pp. 1363-1373
    • Moscona, A.1
  • 4
    • 7644241814 scopus 로고    scopus 로고
    • Neuraminidase is important for the initiation of influenza virus infection in human airway epithelium
    • Matrosovich,M. N.; Matrosovich, T. Y.; Gray, T.; Roberts, N. A.; Klenk, H.-D. Neuraminidase is important for the initiation of influenza virus infection in human airway epithelium. J. Virol. 2004, 78, 12665-12667.
    • (2004) J. Virol , vol.78 , pp. 12665-12667
    • Matrosovich, M.N.1    Matrosovich, T.Y.2    Gray, T.3    Roberts, N.A.4    Klenk, H.-D.5
  • 5
    • 0026603612 scopus 로고
    • Emergence and transmission of influenza A viruses resistant to amantadine and rimantadine
    • Hayden, F. G.; Hay, A. J. Emergence and transmission of influenza A viruses resistant to amantadine and rimantadine. Curr. Top. Microbiol. Immunol. 1992, 176, 119-130.
    • (1992) Curr. Top. Microbiol. Immunol , vol.176 , pp. 119-130
    • Hayden, F.G.1    Hay, A.J.2
  • 6
    • 0028883441 scopus 로고
    • Prolonged shedding of amantadine-resistant influenza A viruses by immunodeficient patients: Detection by polymerase chain reaction-restriction analysis
    • Klimov, A. I.; Rocha, E.; Hayden, F. G.; Shult, P. A.; Roumillat, L. F.; Cox, N. J. Prolonged shedding of amantadine-resistant influenza A viruses by immunodeficient patients: Detection by polymerase chain reaction-restriction analysis. J. Infect. Dis. 1995, 172, 1352-1355.
    • (1995) J. Infect. Dis , vol.172 , pp. 1352-1355
    • Klimov, A.I.1    Rocha, E.2    Hayden, F.G.3    Shult, P.A.4    Roumillat, L.F.5    Cox, N.J.6
  • 7
    • 0037560121 scopus 로고    scopus 로고
    • High frequency of resistant viruses harboring different mutations in amantadine-treated children with influenza
    • Shiraishi, K.; Mitamura, K.; Sakai-Tagawa, Y.; Goto, H.; Sugaya, N.; Kawaoka, Y. High frequency of resistant viruses harboring different mutations in amantadine-treated children with influenza. J. Infect. Dis. 2003, 188, 57-61.
    • (2003) J. Infect. Dis , vol.188 , pp. 57-61
    • Shiraishi, K.1    Mitamura, K.2    Sakai-Tagawa, Y.3    Goto, H.4    Sugaya, N.5    Kawaoka, Y.6
  • 9
    • 46049095460 scopus 로고    scopus 로고
    • Emergence and phylogenetic relationships of amantadine-resistant human H3N2 influenza A viruses in Germany in the season 2005/2006
    • Schmidtke, M.; Bauer, K.; Ludwig, N.; Wutzler, P. Emergence and phylogenetic relationships of amantadine-resistant human H3N2 influenza A viruses in Germany in the season 2005/2006. Int. J. Antimicrob. Agents 2008, 32, 192-195.
    • (2008) Int. J. Antimicrob. Agents , vol.32 , pp. 192-195
    • Schmidtke, M.1    Bauer, K.2    Ludwig, N.3    Wutzler, P.4
  • 10
    • 67349177735 scopus 로고    scopus 로고
    • The origin and global emergence of adamantane resistant A/H3N2 influenza viruses
    • Nelson Martha, I.; Simonsen, L.; Viboud, C.; Miller Mark, A.; Holmes Edward, C. The origin and global emergence of adamantane resistant A/H3N2 influenza viruses. Virology 2009, 388, 270-278.
    • (2009) Virology , vol.388 , pp. 270-278
    • Nelson Martha, I.1    Simonsen, L.2    Viboud, C.3    Miller Mark, A.4    Holmes Edward, C.5
  • 12
    • 34247626313 scopus 로고    scopus 로고
    • The emergence of adamantane resistance in influenza A(H1) viruses in Australia and regionally in 2006
    • Barr, I. G.; Hurt, A. C.; Deed, N.; Iannello, P.; Tomasov, C.; Komadina, N. The emergence of adamantane resistance in influenza A(H1) viruses in Australia and regionally in 2006. Antivir. Res. 2007, 75, 173-176.
    • (2007) Antivir. Res , vol.75 , pp. 173-176
    • Barr, I.G.1    Hurt, A.C.2    Deed, N.3    Iannello, P.4    Tomasov, C.5    Komadina, N.6
  • 13
    • 33747283747 scopus 로고    scopus 로고
    • Amantadine resistance among porcine H1N1, H1N2, and H3N2 influenzaAviruses isolated in Germany between 1981 and 2001
    • Schmidtke, M.; Zell, R.; Bauer, K.; Krumbholz, A.; Schrader, C.; Suess, J.; Wutzler, P. Amantadine resistance among porcine H1N1, H1N2, and H3N2 influenzaAviruses isolated in Germany between 1981 and 2001. Intervirology 2006, 49, 286-293.
    • (2006) Intervirology , vol.49 , pp. 286-293
    • Schmidtke, M.1    Zell, R.2    Bauer, K.3    Krumbholz, A.4    Schrader, C.5    Suess, J.6    Wutzler, P.7
  • 15
    • 33747156960 scopus 로고    scopus 로고
    • Antivirals for influenza: Historical perspectives and lessons learned
    • Hayden, F. G. Antivirals for influenza: Historical perspectives and lessons learned. Antivir. Res. 2006, 71, 372-378.
    • (2006) Antivir. Res , vol.71 , pp. 372-378
    • Hayden, F.G.1
  • 16
    • 62049086175 scopus 로고    scopus 로고
    • Different neuraminidase inhibitor susceptibilities of human H1N1, H1N2, and H3N2 influenza A viruses isolated in Germany from 2001 to 2005/2006
    • Bauer, K.; Richter, M.; Wutzler, P.; Schmidtke, M. Different neuraminidase inhibitor susceptibilities of human H1N1, H1N2, and H3N2 influenza A viruses isolated in Germany from 2001 to 2005/2006. Antivir. Res. 2009, 82, 34-41.
    • (2009) Antivir. Res , vol.82 , pp. 34-41
    • Bauer, K.1    Richter, M.2    Wutzler, P.3    Schmidtke, M.4
  • 18
    • 61849118968 scopus 로고    scopus 로고
    • Global transmission of oseltamivir-resistant influenza
    • Moscona, A. Global transmission of oseltamivir-resistant influenza. N. Engl. J. Med. 2009, 360, 953-956.
    • (2009) N. Engl. J. Med , vol.360 , pp. 953-956
    • Moscona, A.1
  • 19
    • 62149112223 scopus 로고    scopus 로고
    • The evolution of influenza resistance and treatment
    • Weinstock, D. M.; Zuccotti, G. The evolution of influenza resistance and treatment. JAMA, J. Am. Med. Assoc. 2009, 301, 1066-1069.
    • (2009) JAMA, J. Am. Med. Assoc , vol.301 , pp. 1066-1069
    • Weinstock, D.M.1    Zuccotti, G.2
  • 21
    • 69149093400 scopus 로고    scopus 로고
    • Itoh, Y, Shinya, K, Kiso, M, Watanabe, T, Sakoda, Y, Hatta, M, Muramoto, Y, Tamura, D, Sakai-Tagawa, Y, Noda, T, Sakabe, S, Imai, M, Hatta, Y, Watanabe, S, Li, C, Yamada, S, Fujii, K, Murakami, S, Imai, H, Kakugawa, S, Ito, M, Takano, R, Iwatsuki-Horimoto, K, Shimojima, M, Horimoto, T, Goto, H, Takahashi, K, Makino, A, Ishigaki, H, Nakayama, M, Okamatsu, M, Takahashi, K, Warshauer, D, Shult, P. A, Saito, R, Suzuki, H, Furuta, Y, Yamashita, M, Mitamura, K, Nakano, K, Nakamura, M, Brockman-Schneider, R, Mitamura, H, Yamazaki, M, Sugaya, N, Suresh, M, Ozawa, M, Neumann, G, Gern, J, Kida, H, Ogasawara, K, Kawaoka, Y. In vitro and in vivo characterization of new swine-origin H1N1 influenza viruses. Nature (London) 2009, 460, 1021-1025
    • Itoh, Y.; Shinya, K.; Kiso, M.; Watanabe, T.; Sakoda, Y.; Hatta, M.; Muramoto, Y.; Tamura, D.; Sakai-Tagawa, Y.; Noda, T.; Sakabe, S.; Imai, M.; Hatta, Y.; Watanabe, S.; Li, C.; Yamada, S.; Fujii, K.; Murakami, S.; Imai, H.; Kakugawa, S.; Ito, M.; Takano, R.; Iwatsuki-Horimoto, K.; Shimojima, M.; Horimoto, T.; Goto, H.; Takahashi, K.; Makino, A.; Ishigaki, H.; Nakayama, M.; Okamatsu, M.; Takahashi, K.; Warshauer, D.; Shult, P. A.; Saito, R.; Suzuki, H.; Furuta, Y.; Yamashita, M.; Mitamura, K.; Nakano, K.; Nakamura, M.; Brockman-Schneider, R.; Mitamura, H.; Yamazaki, M.; Sugaya, N.; Suresh, M.; Ozawa, M.; Neumann, G.; Gern, J.; Kida, H.; Ogasawara, K.; Kawaoka, Y. In vitro and in vivo characterization of new swine-origin H1N1 influenza viruses. Nature (London) 2009, 460, 1021-1025.
  • 22
    • 30344479474 scopus 로고    scopus 로고
    • Neuraminidase as a target for drugs for the treatment of influenza
    • Liu, A.-L.; Wang, Y.-T.; Du, G.-H. Neuraminidase as a target for drugs for the treatment of influenza. Drugs Future 2005, 30, 799-806.
    • (2005) Drugs Future , vol.30 , pp. 799-806
    • Liu, A.-L.1    Wang, Y.-T.2    Du, G.-H.3
  • 24
    • 0018844023 scopus 로고
    • The synthesis of 4-methylumbelliferyl alphaketoside of N-acetylneuraminic acid and its use in a fluorometric assay for neuraminidase
    • Myers, R. W.; Lee, R. T.; Lee, Y. C.; Thomas, G. H.; Reynolds, L. W.; Uchida, Y. The synthesis of 4-methylumbelliferyl alphaketoside of N-acetylneuraminic acid and its use in a fluorometric assay for neuraminidase. Anal. Biochem. 1980, 101, 166-174.
    • (1980) Anal. Biochem , vol.101 , pp. 166-174
    • Myers, R.W.1    Lee, R.T.2    Lee, Y.C.3    Thomas, G.H.4    Reynolds, L.W.5    Uchida, Y.6
  • 26
    • 77249083736 scopus 로고    scopus 로고
    • Wang, Z, Huang, W, Li, Y. Antiviral activity of extracts from Alpinia. Canadian Patent CN 16988472005, 2005
    • Wang, Z.; Huang, W.; Li, Y. Antiviral activity of extracts from Alpinia. Canadian Patent CN 16988472005, 2005.
  • 27
    • 77249178289 scopus 로고    scopus 로고
    • Manufacture of traditional Chinese medicine with antiviral, anti-inflammatory, and detoxicating effects
    • Canadian Patent CN 18401472006
    • Wu, J. Manufacture of traditional Chinese medicine with antiviral, anti-inflammatory, and detoxicating effects. Canadian Patent CN 18401472006, 2006.
    • (2006)
    • Wu, J.1
  • 28
    • 77249139767 scopus 로고    scopus 로고
    • Topical chinese medicinal preparation with good antiviral effect
    • Canadian Patent CN 1012191962008
    • Wang, X.; Wang, L. Topical chinese medicinal preparation with good antiviral effect. Canadian Patent CN 1012191962008, 2008.
    • (2008)
    • Wang, X.1    Wang, L.2
  • 32
    • 47349084839 scopus 로고    scopus 로고
    • Suksamrarn, A.; Ponglikitmongkol, M.; Wongkrajang, K.; Chindaduang, A.; Kittidanairak, S.; Jankam, A.; Yingyongnarongkul, B.-e.; Kittipanumat, N.; Chokchaisiri, R.; Khetkam, P.; Piyachaturawat, P. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: isolation, chemical modification and estrogenic activity evaluation. Bioorg. Med. Chem. 2008, 16, 6891-6902.
    • Suksamrarn, A.; Ponglikitmongkol, M.; Wongkrajang, K.; Chindaduang, A.; Kittidanairak, S.; Jankam, A.; Yingyongnarongkul, B.-e.; Kittipanumat, N.; Chokchaisiri, R.; Khetkam, P.; Piyachaturawat, P. Diarylheptanoids, new phytoestrogens from the rhizomes of Curcuma comosa: isolation, chemical modification and estrogenic activity evaluation. Bioorg. Med. Chem. 2008, 16, 6891-6902.
  • 34
    • 34250303103 scopus 로고    scopus 로고
    • Neuraminidase inhibitor susceptibility of porcine H3N2 influenza Aviruses isolated in Germany between 1982 and 1999
    • Bauer, K.; Schrader, C.; Suess, J.; Wutzler, P.; Schmidtke, M. Neuraminidase inhibitor susceptibility of porcine H3N2 influenza Aviruses isolated in Germany between 1982 and 1999. Antivir. Res. 2007, 75, 219-226.
    • (2007) Antivir. Res , vol.75 , pp. 219-226
    • Bauer, K.1    Schrader, C.2    Suess, J.3    Wutzler, P.4    Schmidtke, M.5
  • 36
    • 67949124553 scopus 로고    scopus 로고
    • Amaro, R. E.; Cheng, X. L.; Ivanov, I.; Xu, D.; McCammon, J. A. Characterizing Loop Dynamics and Ligand Recognition in Human-and Avian-Type Influenza Neuraminidases via Generalized Born Molecular Dynamics and End-Point Free Energy Calculations. J. Am. Chem. Soc. 2009, 131, 4702-4709.
    • Amaro, R. E.; Cheng, X. L.; Ivanov, I.; Xu, D.; McCammon, J. A. Characterizing Loop Dynamics and Ligand Recognition in Human-and Avian-Type Influenza Neuraminidases via Generalized Born Molecular Dynamics and End-Point Free Energy Calculations. J. Am. Chem. Soc. 2009, 131, 4702-4709.
  • 38
    • 46849105028 scopus 로고    scopus 로고
    • Ensemble-based virtual screening reveals potential novel antiviral compounds for avian influenza neuraminidase
    • Cheng, L. S.; Amaro, R. E.; Xu, D.; Li, W. W.; Arzberger, P. W.; McCammon, J. A. Ensemble-based virtual screening reveals potential novel antiviral compounds for avian influenza neuraminidase. J. Med. Chem. 2008, 51, 3878-3894.
    • (2008) J. Med. Chem , vol.51 , pp. 3878-3894
    • Cheng, L.S.1    Amaro, R.E.2    Xu, D.3    Li, W.W.4    Arzberger, P.W.5    McCammon, J.A.6
  • 39
    • 84986522918 scopus 로고
    • ICM - a new method for protein modeling and design: Applications to docking and structure prediction from the distorted native conformation
    • Abagyan, R.; Totrov, M.; Kuznetsov, D. ICM - a new method for protein modeling and design: applications to docking and structure prediction from the distorted native conformation. J. Comput. Chem. 1994, 15, 488-506.
    • (1994) J. Comput. Chem , vol.15 , pp. 488-506
    • Abagyan, R.1    Totrov, M.2    Kuznetsov, D.3
  • 40
    • 65649103683 scopus 로고    scopus 로고
    • A Novel Small-Molecule Inhibitor of the Avian Influenza H5N1 Virus Determined through Computational Screening against the Neuraminidase
    • An, J. H.; Lee, D. C. W.; Law, A. H. Y.; Yang, C. L. H.; Poon, L. L. M.; Lau, A. S. Y.; Jones, S. J. M. A Novel Small-Molecule Inhibitor of the Avian Influenza H5N1 Virus Determined through Computational Screening against the Neuraminidase. J. Med. Chem. 2009, 52, 2667-2672.
    • (2009) J. Med. Chem , vol.52 , pp. 2667-2672
    • An, J.H.1    Lee, D.C.W.2    Law, A.H.Y.3    Yang, C.L.H.4    Poon, L.L.M.5    Lau, A.S.Y.6    Jones, S.J.M.7
  • 41
    • 0031552362 scopus 로고    scopus 로고
    • Development and validation of a genetic algorithm for flexible docking
    • Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
    • (1997) J. Mol. Biol , vol.267 , pp. 727-748
    • Jones, G.1    Willett, P.2    Glen, R.C.3    Leach, A.R.4    Taylor, R.5
  • 45
    • 0035997940 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity and antiviral activity ofN,N′-bis-5- nitropyrimidyl derivatives of dispirotripiperazine
    • Schmidtke, M.; Riabova, O.; Dahse, H. M.; Stelzner, A.; Makarov, V. Synthesis, cytotoxicity and antiviral activity ofN,N′-bis-5- nitropyrimidyl derivatives of dispirotripiperazine. Antivir. Res. 2002, 55, 117-127.
    • (2002) Antivir. Res , vol.55 , pp. 117-127
    • Schmidtke, M.1    Riabova, O.2    Dahse, H.M.3    Stelzner, A.4    Makarov, V.5
  • 46
    • 3242886771 scopus 로고    scopus 로고
    • PDB2PQR: An automated pipeline for the setup of Poisson-Boltzmann electrostatics calculations
    • Dolinsky, T. J.; Nielsen, J. E.; McCammon, J. A.; Baker, N. A. PDB2PQR: an automated pipeline for the setup of Poisson-Boltzmann electrostatics calculations. Nucleic Acids Res. 2004, 32, W665-W667.
    • (2004) Nucleic Acids Res , vol.32
    • Dolinsky, T.J.1    Nielsen, J.E.2    McCammon, J.A.3    Baker, N.A.4
  • 47
    • 34547559704 scopus 로고    scopus 로고
    • PDB2PQR: Expanding and upgrading automated preparation of biomolecular structures for molecular simulations
    • Dolinsky, T. J.; Czodrowski, P.; Li, H.; Nielsen, J. E.; Jensen, J. H.; Klebe, G.; Baker, N. A. PDB2PQR: expanding and upgrading automated preparation of biomolecular structures for molecular simulations. Nucleic Acids Res. 2007, 35, W522-W525.
    • (2007) Nucleic Acids Res , vol.35
    • Dolinsky, T.J.1    Czodrowski, P.2    Li, H.3    Nielsen, J.E.4    Jensen, J.H.5    Klebe, G.6    Baker, N.A.7
  • 49
    • 36649006642 scopus 로고    scopus 로고
    • Clustering molecular dynamics trajectories: 1. Characterizing the performance of different clustering algorithms
    • Shao, J. Y.; Tanner, S. W.; Thompson, N.; Cheatham, T. E. Clustering molecular dynamics trajectories: 1. Characterizing the performance of different clustering algorithms. J. Chem. Theory Comput. 2007, 3, 2312-2334.
    • (2007) J. Chem. Theory Comput , vol.3 , pp. 2312-2334
    • Shao, J.Y.1    Tanner, S.W.2    Thompson, N.3    Cheatham, T.E.4
  • 50
    • 31444452744 scopus 로고
    • Automatic generation of 3D atomic coordinates for organic molecules
    • Gasteiger, J.; Rudolph, C.; Sadowski, J. Automatic generation of 3D atomic coordinates for organic molecules. Tetrahedron Comput. Methodol. 1990, 3, 537-547.
    • (1990) Tetrahedron Comput. Methodol , vol.3 , pp. 537-547
    • Gasteiger, J.1    Rudolph, C.2    Sadowski, J.3
  • 51
    • 0026729637 scopus 로고
    • Gasteiger, J.The generation of 3Dmodels of host-guest complexes
    • Sadowski, J.;Rudolph,C.;Gasteiger, J.The generation of 3Dmodels of host-guest complexes. Anal. Chim. Acta 1992, 265, 233-241.
    • (1992) Anal. Chim. Acta , vol.265 , pp. 233-241
    • Sadowski, J.1    Rudolph, C.2
  • 52
    • 0028466540 scopus 로고
    • Comparison of Automatic Three-Dimensional Model Builders Using 639 X-ray Structures
    • Sadowski, J.; Gasteiger, J.; Klebe, G. Comparison of Automatic Three-Dimensional Model Builders Using 639 X-ray Structures. J. Chem. Inf. Comput. Sci. 1994, 34, 1000-1008.
    • (1994) J. Chem. Inf. Comput. Sci , vol.34 , pp. 1000-1008
    • Sadowski, J.1    Gasteiger, J.2    Klebe, G.3
  • 53
    • 77249118812 scopus 로고    scopus 로고
    • DeLano, W. L. The PyMOL Molecular Graphics System, version 1.0; DeLano Scientific: Palo Alto, CA, 2002
    • DeLano, W. L. The PyMOL Molecular Graphics System, version 1.0; DeLano Scientific: Palo Alto, CA, 2002.


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