Fluorescence polarization-based assay using N-glycan-conjugated quantum dots for screening in hemagglutinin blockers for influenza A viruses

Journal of Virological Methods

Volumn 187, Issue 2, 2013, Pages 390-394

  Okamatsu, Masatoshi ^a   Feng, Fei ^b   Ohyanagi, Tatsuya ^b   Nagahori, Noriko ^b   Someya, Kazuhiko ^c   Sakoda, Yoshihiro ^a   Miura, Nobuaki ^b   Nishimura, Shin Ichiro ^b   Kida, Hiroshi ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c DAIICHI SANKYO CO   (Japan)

Author keywords

Fluorescence polarization; Hemagglutinin; High throughput screening; Influenza virus; Quantum dot

Indexed keywords

ANTIVIRUS AGENT; GLYCAN; INFLUENZA VIRUS HEMAGGLUTININ; N GLYCAN; QUANTUM DOT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; COMPETITIVE INHIBITION; CONTROLLED STUDY; EXPERIMENTAL DESIGN; FEASIBILITY STUDY; FLUORESCENCE POLARIZATION; HIGH THROUGHPUT SCREENING; INFLUENZA VIRUS A; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN INTERACTION; SIALYLATION; VIRUS ATTACHMENT;

ANTIVIRAL AGENTS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; FLUORESCENCE POLARIZATION; HEMAGGLUTININ GLYCOPROTEINS, INFLUENZA VIRUS; HIGH-THROUGHPUT SCREENING ASSAYS; INFLUENZA A VIRUS; PROTEIN BINDING; QUANTUM DOTS; STAINING AND LABELING;

INFLUENZA A VIRUS; ORTHOMYXOVIRIDAE;

EID: 84872685302     PISSN: 01660934     EISSN: 18790984     Source Type: Journal    
DOI: 10.1016/j.jviromet.2012.11.004     Document Type: Article

References (29)

1. Babu Y.S., Chand P., Bantia S., Kotian P., Dehghani A., El-Kattan Y., Lin T.H., Hutchison T.L., Elliott A.J., Parker C.D., Ananth S.L., Horn L.L., Laver G.W., Montgomery J.A. BCX-1812 (RWJ-270201): discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design. J. Med. Chem. 2000, 43:3482-3486.
2. Crich D., Li W. O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring. J. Org. Chem. 2007, 72:2387-2391.
3. Dell A., Lee J.J., Pang P.C., Parry S., Smith M.S., Tissort B., Morris H.R., Panico M., Haslam S.M. Glycomics and mass spectrometry. Glycoscience, Chemistry and Chemical Biology 2008, Springer-Verlag, Berlin, Heidelberg, pp. 2191-2217. B.O. Fraser-Reid, K. Tatsuta, J. Thiem (Eds.).
4. Feng F., Miura N., Isoda N., Sakoda Y., Okamatsu M., Kida H., Nishimura S.I. Novel trivalent anti-influenza reagent. Bioorg. Med. Chem. Lett. 2010, 20:3772-3776.
5. Freyssinet J.M., Lewis B.A., Holbrook J.J., Shore J.D. Protein-protein interactions in blood clotting. The use of polarization of fluorescence to measure the dissociation of plasma factor XIIIa. Biochem. J. 1978, 169:403-410.
6. Gamblin S.J., Haire L.F., Russell R.J., Stevens D.J., Xiao B., Ha Y., Vasisht N., Steinhauer D.A., Daniels R.S., Elliot A., Wiley D.C., Skehel J.J. The structure and receptor binding properties of the 1918 influenza hemagglutinin. Science 2004, 303:1838-1842.
7. Gubareva L.V. Molecular mechanisms of influenza virus resistance to neuraminidase inhibitors. Virus Res. 2004, 103:199-203.
8. 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.
9. Holmlin R.E., Chen X., Chapman R.G., Takayama S., Whitesides G.M. Zwitterionic SAMs that resist nonspecific adsorption of protein from aqueous buffer. Langmuir 2001, 17:2841-2850.
10. Kida H., Yanagawa R. Isolation and characterization of influenza A viruses from wild free-flying ducks in Hokkaido, Japan. Zentralbl. Bakteriol. Orig. A 1979, 244:135-143.
11. Luo G., Torri A., Harte W.E., Danetz S., Cianci C., Tiley L., Day S., Mullaney D., Yu K.L., Ouellet C., Dextraze P., Meanwell N., Colonno R., Krystal M. Molecular mechanism underlying the action of a novel fusion inhibitor of influenza A virus. J. Virol. 1997, 71:4062-4070.
12. Matrosovich M.N., Mochalova L.V., Marinina V.P., Byramova N.E., Bovin N.V. Synthetic polymeric sialoside inhibitors of influenza virus receptor-binding activity. FEBS Lett. 1990, 272:209-212.
13. Mochalova L.V., Tuzikov A.B., Marinina V.P., Gambaryan A.S., Byramova N.E., Bovin N.V., Matrosovich M.N. Synthetic polymeric inhibitors of influenza virus receptor-binding activity suppress virus replication. Antiviral Res. 1994, 23:179-190.
14. Nagahori N., Abe M., Nishimura S.I. Structural and functional glycosphingolipidomics by glycoblotting with an aminooxy-functionalized gold nanoparticle. Biochemistry 2009, 48:583-594.
15. Ng E.S., Yang F., Kameyama A., Palcic M.M., Hindsgaul O., Schriemer D.C. High-throughput screening for enzyme inhibitors using frontal affinity chromatography with liquid chromatography and mass spectrometry. Anal. Chem. 2005, 77:6125-6133.
16. Nikolovska-Coleska Z., Wang R., Fang X., Pan H., Tomita Y., Li P., Roller P.P., Krajewski K., Saito N.G., Stuckey J.A., Wang S. Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization. Anal. Biochem. 2004, 332:261-273.
17. Nishimura S.I., Niikura K., Kurogochi M., Matsushita T., Fumoto M., Hinou H., Kamitani R., Nakagawa H., Deguchi K., Miura N., Monde K., Kondo H. High-throughput protein glycomics: combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry. Angew. Chem. Int. Ed. 2005, 44:91-96.
18. Ogata M., Hidari K.I., Kozaki W., Murata T., Hiratake J., Park E.Y., Suzuki T., Usui T. Molecular design of spacer-N-linked sialoglycopolypeptide as polymeric inhibitors against influenza virus infection. Biomacromolecules 2009, 10:1894-1903.
19. Ohta T., Miura N., Fujitani N., Nakajima F., Niikura K., Sadamoto R., Guo C.T., Suzuki T., Suzuki Y., Monde K., Nishimura S.I. Glycotentacles: synthesis of cyclic glycopeptides, toward a tailored blocker of influenza virus hemagglutinin. Angew. Chem. Int. Ed. Engl. 2003, 42:5186-5189.
20. Ohyanagi T., Nagahori N., Shimawaki K., Hinou H., Yamashita T., Sasaki A., Jin T., Iwanaga T., Kinjo M., Nishimura S.I. Importance of sialic acid residues illuminated by live animal imaging using phosphorylcholine self-assembled monolayer-coated quantum dots. J. Am. Chem. Soc. 2011, 133:12507-12517.
21. Perrin F. Polarisation de la lumière de fluorescence. Vie moyenne des molécules dans l'etat excité. J. Phys. Radium 1926, 7:390-401.
22. Sauter N.K., Hanson J.E., Glick G.D., Brown J.H., Crowther R.L., Park S., Skehel J.J., Wiley D.C. Binding of influenza virus hemagglutinin to analogs of its cell-surface receptor, sialic acid: analysis by proton nuclear magnetic resonance spectroscopy and X-ray crystallography. Biochemistry 1992, 31:9609-9621.
23. Schuck P. Use of surface plasmon resonance to probe the equilibrium and dynamic aspects of interactions between biological macromolecules. Annu. Rev. Biophys. Biomol. Struct. 1997, 26:541-566.
24. Sever J.L. Application of a microtechnique to viral serological investigations. J. Immunol. 1962, 88:320-329.
25. Shuker S.B., Hajduk P.J., Meadows R.P., Fesik S.W. Discovering high-affinity ligands for proteins: SAR by NMR. Science 1996, 274:1531-1534.
26. Sigurskjold B.W. Exact analysis of competition ligand binding by displacement isothermal titration calorimetry. Anal. Biochem. 2000, 277:260-266.
27. Weinhold E.G., Knowles J.R. Design and evaluation of a tightly binding fluorescent ligand for influenza A hemagglutinin. J. Am. Chem. Soc. 1992, 114:9270-9275.
28. Yamashita M., Tomozawa T., Kakuta M., Tokumitsu A., Nasu H., Kubo S. CS-8958, a prodrug of the new neuraminidase inhibitor R-125489, shows long-acting anti-influenza virus activity. Antimicrob. Agents Chemother. 2009, 53:186-192.
29. Yoshimoto J., Kakui M., Iwasaki H., Fujiwara T., Sugimoto H., Hattori N. Identification of a novel HA conformational change inhibitor of human influenza virus. Arch. Virol. 1999, 144:865-878.