Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 15, 2009, Pages 5465-5475

  Oka, Hiroyuki ^a   Onaga, Tomotsune ^a   Koyama, Tetsuo ^a   Guo, Chao Tan ^b,c,d   Suzuki, Yasuo ^b,c   Esumi, Yasuaki ^e   Hatano, Ken ^a   Terunuma, Daiyo ^a   Matsuoka, Koji ^a  

^a SAITAMA UNIVERSITY   (Japan)

^b CHUBU UNIVERSITY   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^d INSTITUTE OF MATERIA MEDICA   (China)

^e INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

Author keywords

Carbosilanes; Dendrimers; Glycoclusters; Hemagglutinin; Influenza virus; Sialic acid; Sialyl lactose

Indexed keywords

CARBOHYDRATE; CARBOSILANE; DENDRIMER; GLYCODENDRIMER; LACTATE DEHYDROGENASE; SIALIC ACID DERIVATIVE; SIALYLLACTOSE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VIRUS HEMAGGLUTININ;

ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; INFLUENZA; INFLUENZA VIRUS; INFLUENZA VIRUS A H1N1; INFLUENZA VIRUS A H3N2; MONOLAYER CULTURE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; DENDRIMERS; DOGS; ERYTHROCYTES; HEMAGGLUTINATION; HEMOLYSIS; HUMANS; INFLUENZA A VIRUS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA A VIRUS, H3N2 SUBTYPE; INFLUENZA, HUMAN; KIDNEY; LACTOSE; MOLECULAR STRUCTURE; N-ACETYLNEURAMINIC ACID; SILANES; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN INFLUENZA VIRUS; ORTHOMYXOVIRIDAE;

EID: 67651094099     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.06.035     Document Type: Article

References (38)

1. Smith N.M., Bresee J.S., Shay D.K., Uyeki T.M., Cox N.J., and Strikas R.A. MMWR Recomm. Rep. 55 (2006) 1
2. Webster R.G., Bean W.J., Gorman O.T., Chambers T.M., and Kawaoka Y. Microbiol. Mol. Biol. Rev. 56 (1992) 152
3. von Itzstein M., Wu W.Y., Kok G.B., Pegg M.S., Dyason J.C., Jin B., Phan T.V., Smythe M.L., White H.F., Oliver S.W., Colman P.M., Varghese J.N., Ryan M.D., Woods J.M., Bethell R.C., Hotham V.J., Cameron J.M., and Penn C.R. Nature (London) 363 (1993) 418
4. Kim C.U., Lew W., Williams M.A., Liu H., Zhang L., Swaminathan S., Bischofberger N., Chen M.S., Mende D.B., Tai C.Y., Laver W.G., and Stevens R.C. J. Am. Chem. Soc. 119 (1997) 681
5. Collins P.J., Haire L.F., Lin Y.P., Liu J., Russell R.J., Walker P.A., Skehel J.J., Martin S.R., Hay A.J., and Gamblin S.J. Nature (London) 453 (2008) 1258
6. Wiely D.C., and Skehel J.J. Ann. Rev. Biochem. 56 (1987) 365
7. Lee Y.C., Townsend R.R., Hardy M.R., Lönngren J., Arnarp J., Haraldsson M., and Lönn H. J. Biol. Chem. 258 (1983) 199
8. Kamitakahara H., Suzuki T., Nishigori N., Suzuki Y., Kanie O., and Wong C.H. Angew. Chem., Int. Ed. 37 (1998) 1524
9. Roy R., Zanini D., Meunier S.J., and Romanowska A. J. Chem. Soc., Chem. Commun. (1993) 1869
10. Mitchell J.P., Roberts K.D., Langley J., Koentgen F., and Lamberta J.N. Bioorg. Med. Chem. Lett. 9 (1999) 2785
11. Gan Z., and Roy R. Can. J. Chem. 80 (2002) 908
12. Marra A., Moni L., Pazzi D., Corallini A., Bridi D., and Dondoni A. Org. Biomol. Chem. 6 (2008) 1396
13. Matsuura K., Kitakouji H., Sawada N., Ishida H., Kiso M., Kitajima K., and Kobayashi K. J. Am. Chem. Soc. 122 (2000) 7406
14. Furuike T., Aiba S., Suzuki T., Takahashi T., Suzuki Y., Yamada K., and Nishimura S.-I. J. Chem. Soc., Perkin Trans. 1 (2000) 3000
15. Nishikawa K., Matsuoka K., Kita E., Okabe N., Mizuguchi M., Hino K., Miyazawa S., Yamasaki C., Aoki J., Takashima S., Yamakawa Y., Nishijima M., Terunuma D., Kuzuhara H., and Natori Y. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 7669
16. Matsuoka K., Terabatake M., Saito Y., Hagihara C., Esumi Y., Terunuma D., and Kuzuhara H. Bull. Chem. Soc. Jpn. 71 (1998) 2709
17. Matsuoka K., Terabatake M., Umino A., Esumi Y., Hatano K., Terunuma D., and Kuzuhara H. Biomacromolecules 7 (2006) 2274
18. Matsuoka K., Terabatake M., Esumi Y., Hatano K., Terunuma D., and Kuzuhara H. Biomacromolecules 7 (2006) 2284
19. Yamada A., Hatano K., Koyama T., Matsuoka K., Esumi Y., and Terunuma D. Carbohydr. Res. 341 (2006) 467
20. Otsubo N., Ishida H., and Kiso M. Carbohydr. Res. 330 (2001) 1
21. Matsuoka K., Oka H., Koyama T., Esumi Y., and Terunuma D. Tetrahedron Lett. 42 (2001) 3327
22. Matsuoka K., Onaga T., Mori T., Sakamoto J.-I., Koyama T., Sakairi N., Hatano K., and Terunuma D. Tetrahedron Lett. 45 (2004) 9383
23. Kartha K.P.R., Kameyama A., Kiso M., and Hasegawa A. J. Carbohydr. Chem. 8 (1989) 145
24. Mayers R.W., Lee R.T., Lee Y.C., Thomas G.H., Reynolds L.W., and Uchida Y. Anal. Biochem. 101 (1980) 166
25. Marra A., and Sinay P. Carbohydr. Res. 19 (1989) 317
26. Hasegawa A., Nagahama T., Ohki H., and Kiso M. J. Carbohydr. Chem. 11 (1992) 699
27. Tietze L.F., and Gretzke D. Eur. J. Org. Chem. (1998) 1895
28. Sato T., Ishi M., Terabayashi T., Kawanishi Y., and Okahata Y. Chem. Lett. (1997) 669
29. Oka H., Onaga T., Koyama T., Guo C.-T., Suzuki Y., Esumi Y., Hatano K., Terunuma D., and Matsuoka K. Bioorg. Med. Chem. Lett. 18 (2008) 4405
30. Rogers G.N., and Paulson J.C. Virology 127 (1983) 361
31. Shinya K., Ebina M., Yamada S., Ono M., Kasai N., and Kawaoka Y. Nature (London) 440 (2006) 435
32. Sakamoto J.-I., Koyama T., Miyamoto D., Yingsakmongkon S., Hidari K.I.P.J., Jampangern W., Suzuki T., Suzuki Y., Esumi Y., Hatano K., Terunuma D., and Matsuoka K. Bioorg. Med. Chem. Lett. 17 (2007) 717
33. Sakamoto, J.-I.; Koyama, T.; Miyamoto, D.; Yingsakmongkon, S.; Hidari, K.I.P.J.; Jampangern, W.; Suzuki, T.; Suzuki, Y.; Esumi, Y.; Nakamura, T.; Hatano, K.; Terunuma, D.; Matsuoka, K. Bioorg. Med. Chem., doi:10.1016/j/bmc.2009.06.036.
34. Hasegawa A., Nakamura J., and Kiso M. J. Carbohydr. Chem. 5 (1986) 11
35. Suzuki Y., Matsunaga M., and Matsumoto M. J. Biol. Chem. 260 (1985) 1362
36. Suzuki Y., Suzuki T., and Matsumoto M. J. Biochem. (Tokyo) 93 (1983) 1621
37. Suzuki T., Sometani A., Yamazaki Y., Horiike G., Mizutani Y., Masuda H., Yamada M., Tahara H., Xu G.Y., Miyamoto D., Oku N., Okada S., Kiso M., Hasegawa A., Ito T., Kawaoka Y., and Suzuki Y. Biochem. J. 318 (1996) 389
38. Watanabe W., Sado K., Asawa S., Konno K., Yokota T., and Shigeta S. J. Virol. Methods 51 (1995) 185