S-Linked sialyloligosaccharides bearing liposomes and micelles as influenza virus inhibitors

作者: Hsien-Wei Yeh , Tzung-Sheng Lin , Hsiao-Wen Wang , Hou-Wen Cheng , Der-Zen Liu

DOI: 10.1039/C5OB01376C

关键词: Virus inhibitorsVirusPhospholipidHemagglutination assayLiposomeMolecular biologyMicelleH1N1 influenzaChemistryCell culture

摘要: An efficient, homogeneous synthesis of phospholipid conjugation S-Neu5Acα2-6Galβ1-4GluNAcβ1-3 (3) and its 6-sulphate analogue 4 has been developed. The self-assembled micelles liposomes these trisaccharides formed in solution were found to be inhibitors interfering with the entry H1N1 influenza virus into MDCK cells. Compound 3 bearing a liposome micelle displayed superior inhibitory activity than 6-sulfate congener both neutralization assay hemagglutination inhibition assay.

参考文章(42)
Bryan Ja, The serologic diagnosis of viral infection. An update. Archives of Pathology & Laboratory Medicine. ,vol. 111, pp. 1015- 1023 ,(1987)
R.N. Knibbs, S.E. Osborne, G.D. Glick, I.J. Goldstein, Binding determinants of the sialic acid-specific lectin from the slug Limax flavus. Journal of Biological Chemistry. ,vol. 268, pp. 18524- 18531 ,(1993) , 10.1016/S0021-9258(17)46659-2
N Shibuya, I J Goldstein, W F Broekaert, M Nsimba-Lubaki, B Peeters, W J Peumans, The elderberry (Sambucus nigra L.) bark lectin recognizes the Neu5Ac(alpha 2-6)Gal/GalNAc sequence. Journal of Biological Chemistry. ,vol. 262, pp. 1596- 1601 ,(1987) , 10.1016/S0021-9258(19)75677-4
Xiu-Jing Zheng, Fan Yang, Mingwei Zheng, Chang-Xin Huo, Ye Zhang, Xin-Shan Ye, Improvement of the immune efficacy of carbohydrate vaccines by chemical modification on the GM3 antigen Organic and Biomolecular Chemistry. ,vol. 13, pp. 6399- 6406 ,(2015) , 10.1039/C5OB00405E
E. J. Corey, A. Venkateswarlu, Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives Journal of the American Chemical Society. ,vol. 94, pp. 6190- 6191 ,(1972) , 10.1021/JA00772A043
Ming-Han Hsieh, Jung-Tung Hung, Ya-Wen Liw, Yin-Jen Lu, Chi-Huey Wong, Alice L. Yu, Pi-Hui Liang, Synthesis and evaluation of acyl-chain- and galactose-6''-modified analogues of α-GalCer for NKT cell activation. ChemBioChem. ,vol. 13, pp. 1689- 1697 ,(2012) , 10.1002/CBIC.201200004
Teruhiko Matsubara, Ai Onishi, Tomomi Saito, Aki Shimada, Hiroki Inoue, Takao Taki, Kyosuke Nagata, Yoshio Okahata, Toshinori Sato, Sialic acid-mimic peptides as hemagglutinin inhibitors for anti-influenza therapy. Journal of Medicinal Chemistry. ,vol. 53, pp. 4441- 4449 ,(2010) , 10.1021/JM1002183
Irina Carlescu, Dan Scutaru, Marcel Popa, Constantin V Uglea, None, Synthetic sialic-acid-containing polyvalent antiviral inhibitors Medicinal Chemistry Research. ,vol. 18, pp. 477- 494 ,(2009) , 10.1007/S00044-008-9139-7
James Stevens, Ola Blixt, Laurel Glaser, Jeffery K. Taubenberger, Peter Palese, James C. Paulson, Ian A. Wilson, Glycan Microarray Analysis of the Hemagglutinins from Modern and Pandemic Influenza Viruses Reveals Different Receptor Specificities Journal of Molecular Biology. ,vol. 355, pp. 1143- 1155 ,(2006) , 10.1016/J.JMB.2005.11.002