Chemoenzymatic synthesis of artificial glycopolypeptides containing multivalent sialyloligosaccharides with a γ-polyglutamic acid backbone and their effect on inhibition of infection by influenza viruses

Ogata, Makoto; Murata, Takeomi; Murakami, Kouki; Suzuki, Takashi; Hidari, Kazuya I.P.J.; Suzuki, Yasuo; Usui, Taichi

doi:10.1016/j.bmc.2006.11.006

Cited by 69 publications

(88 citation statements)

References 35 publications

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“…22) Viral suspensions at 2 ml/well of a 96-well microtiter plate (black, flat-bottom, BD Falcon, U.S.A.) were preincubated for 30 min at 4°C with 1 ml of GH solution diluted at various concentrations. The enzymatic reaction was initiated by addition of 1 ml of a substrate, 2Ј-(4-methylumbelliferyl)-a-D-N-acetylneuraminic acid.…”

Section: Methodsmentioning

confidence: 99%

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Saha

Takahashi

Suzuki

2009

Biological & Pharmaceutical Bulletin

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Hesperidin, a flavonoid obtained from citrus fruits, is known to have multiple biological activities and antimicrobial activities for human viruses; however, hesperidin has very low solubility in water and the target molecule of hesperidin for influenza virus remains unknown. A water-soluble derivative of hesperidin, glucosyl hesperidin (GH), which was synthesized by regioselective transglycosylation with cyclodextrin glucanotransferase, has been reported to have biological activities that are as or stronger than those of hesperidin. To determine the inhibitory effect of GH on influenza A virus (IAV) infection, Madin-Darby canine kidney (MDCK) cells were treated with GH before, at the same time as, and after IAV inoculation. GH treatment before IAV inoculation had no effect on virus replication, whereas, treatment with GH at the same time as or after IAV inoculation induced distinct reduction in IAV replication. Inhibition analysis of GH against two surface glycoprotein spikes of IAV revealed that GH prevents IAV replication by inhibition of viral sialidase activity that is involved in the entry and release stages on IAV infection but not by receptor binding inhibition. GH had no cytotoxic effects on MDCK cells in a dose range of 0-25 mM. Our results provide useful information for the development of novel sialidase inhibitors for influenza prevention.

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Section: Methodsmentioning

confidence: 99%

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Saha

Takahashi

Suzuki

2009

Biological & Pharmaceutical Bulletin

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“…To conclude, synthetic linear trisaccharides terminating with ␣2,3 linkages were explored as inhibitory agents for IV HA (21,31,32). Our study suggests that these linear trisaccharides might not be a potent O-glycoform that mediates hemagglutinin interactions in human IV-H1N1 infections.…”

Section: Vol 84 2010 O-glycans Mediating the Nkp46 And IV H1n1 Intementioning

confidence: 91%

NKp46 O-Glycan Sequences That Are Involved in the Interaction with Hemagglutinin Type 1 of Influenza Virus

Mendelson

Tekoah

Zilka

et al. 2010

J Virol

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“…Figure 8 shows the results of double diffusion reactions using tetravalent glycosides 9-14 with WGA and ECA lectins. In general, precipitate is formed by the reaction between two specific high molecular weight compounds, such as lectin-glycoprotein and lectinpolysaccharide (Ogata et al, 2007;Zeng et al, 2000;Usui et al, 1981). Interestingly, sharp precipitin bands are seen between the central well with WGA and the surrounding wells containing tetravalent glycosides 10, 12 and 13 (Fig.…”

Section: Precipitation Analysismentioning

confidence: 97%

Molecular Design of Multivalent Glycosides Bearing GlcNAc, (GlcNAc)2 and LacNAc - Analysis of Cross-linking Activities with WGA and ECA Lectins

Ogata¹,

Misawa²,

Usui³

2011

Biosensors - Emerging Materials and Applications

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Chemoenzymatic synthesis of artificial glycopolypeptides containing multivalent sialyloligosaccharides with a γ-polyglutamic acid backbone and their effect on inhibition of infection by influenza viruses

Cited by 69 publications

References 35 publications

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

Glucosyl Hesperidin Prevents Influenza A Virus Replication <i>in Vitro</i> by Inhibition of Viral Sialidase

NKp46 O-Glycan Sequences That Are Involved in the Interaction with Hemagglutinin Type 1 of Influenza Virus

Molecular Design of Multivalent Glycosides Bearing GlcNAc, (GlcNAc)2 and LacNAc - Analysis of Cross-linking Activities with WGA and ECA Lectins

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