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Glycobiology, 2002, Vol. 12, No. 3 183-190
© 2002 Oxford University Press

An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses

Chao-Tan Guo2, Xue-Long Sun3, Osamu Kanie1,3,4, Kennedy Francis Shortridge5, Takashi Suzuki2, Daisei Miyamoto2, Kazuya I.-P. Jwa Hidari2, Chi-Huey Wong1,3,6 and Yasuo Suzuki1,2

2Department of Biochemistry, University of Shizuoka School of Pharmaceutical Sciences, 52-1 Yada, Shizuoka-shi 422–8526, Japan; 3Institute of Physical and Chemical Research (RIKEN), 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan; 4Advanced Techno-Bioscience Department, Mitsubishi Kagaku Institute of Life Sciences (MITILS), 11 Minamiooya, Machida-shi 194-8511, Tokyo, Japan; 5Department of Microbiology, University of Hong Kong, Queen Mary Hospital, Hong Kong; and 6Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA

The compound Neu5Ac3{alpha}F-DSPE (4), in which the C-3 position was modified with an axial fluorine atom, inhibited the catalytic hydrolysis of influenza virus sialidase and the binding activity of hemagglutinin. The inhibitory activities to sialidases were independent of virus isolates examined. With the positive results obtained for inhibition of hemagglutination and hemolysis induced by A/Aichi/2/68 virus, the inhibitory effect of Neu5Ac3{alpha}F-DSPE (4) against MDCK cells was examined, and it was found that 4 inhibits the viral infection with IC50 value of 5.6 µM based on the cytopathic effects. The experimental results indicate that compound 4 not only inhibits the attachment of virus to the cell surface receptor but also disturbs the release of the progeny viruses from infected cells by inhibiting both hemagglutinin and sialidase of the influenza viruses. The study suggested that the compound is a new class of bifunctional drug candidates for the future chemotherapy of influenza.

1 To whom correspondence should be addressed


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