Design and synthesis of high-avidity tetravalent glycoclusters as probes for sambucus sieboldiana agglutinin and characterization of their binding properties

Bioconjugate Chemistry

Volumn 23, Issue 1, 2012, Pages 97-105

  Ogata, Makoto ^a   Yano, Megumi ^a   Umemura, Seiichiro ^a   Murata, Takeomi ^a   Park, Enoch Y ^a   Kobayashi, Yuka ^b   Asai, Tomohiro ^c   Oku, Naoto ^c   Nakamura, Naoki ^d   Matsuo, Ichiro ^d   Usui, Taichi ^a  

^a SHIZUOKA UNIVERSITY   (Japan)

^b J Oil Mills Inc   (Japan)

^c UNIVERSITY OF SHIZUOKA   (Japan)

^d GUNMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AGGREGATES; ANTIGEN-ANTIBODY REACTIONS; BINDING ENERGY; DYNAMIC LIGHT SCATTERING; ETHYLENE; ETHYLENE GLYCOL; PARTICLE SIZE; PRECIPITATION (CHEMICAL);

AS-LIGANDS; BINDING LECTIN; BINDING PROPERTIES; CARBOXY GROUPS; DOUBLE DIFFUSION; DYNAMIC LIGHT-SCATTERING; DYNAMIC-LIGHT SCATTERINGS; SIALIC ACIDS; STRONG INTERACTION; SYNTHESISED;

LIGANDS;

AGGLUTININ; SIALIC ACID DERIVATIVE;

ARTICLE; COMPLEX FORMATION; HEMAGGLUTINATION INHIBITION; LIGHT SCATTERING; NONHUMAN; PHYTOCHEMISTRY; PROTEIN CARBOHYDRATE INTERACTION; PROTEIN DETERMINATION; QUANTITATIVE ANALYSIS; SAMBUCUS; SAMBUCUS SIEBOLDIANA; STOICHIOMETRY;

SAMBUCUS SIEBOLDIANA;

EID: 84855918935     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200440e     Document Type: Article

References (40)

1. Dam, T. K. and Brewer, C. F. (2010) Multivalent lectin-carbohydrate interactions: energetics and mechanisms of binding Adv. Carbohydr. Chem. Biochem. 63, 139-164
2. Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., and Marth, J., Eds. (1999) Essentials of Glycobiology, Cold Spring Harbor Laboratory Press, Cold Spring Harbor.
3. Bhattacharyya, L., Fant, J., Lonn, H., and Brewer, C. F. (1990) Binding and precipitating activities of Lotus tetragonolobus isolectins with L-fucosyl oligosaccharides. Formation of unique homogeneous cross-linked lattices observed by electron microscopy Biochemistry 29, 7523-7530 (Pubitemid 20251804)
4. Dam, T. K., Gerken, T. A., and Brewer, C. F. (2009) Thermodynamics of multivalent carbohydrate-lectin cross-linking interactions: Importance of Entropy in the bind and jump mechanism Biochemistry 48, 3822-3827
5. Gupta, D., Kaltner, H., Dong, X., Gabius, H.-J., and Brewer, C. F. (1996) Comparative cross-linking activities of lactose-specific plant and animal lectins and a natural lactose-binding immunoglobulin G fraction from human serum with asialofetuin Glycobiology 6, 843-849 (Pubitemid 27016391)
6. Dam, T. K., Roy, R., Pagé, D., and Brewer, C. F. (2002) Thermodynamic binding parameters of individual epitopes of multivalent carbohydrates to concanavalin A as determined by "reverse" isothermal titration microcalorimetry Biochemistry 41, 1359-1363 (Pubitemid 34083791)
7. Mann, D. A., Kanai, M., Maly, D. J., and Kiessling, L. L. (1998) Probing low affinity and multivalent interactions with surface Plasmon resonance: Ligands for concanavalin A J. Am. Chem. Soc. 120, 10575-10582 (Pubitemid 28498799)
8. Chabre, Y. M. and Roy, R. (2010) Design and creativity in synthesis of multivalent neoglycoconjugates Adv. Carbohydr. Chem. Biochem. 63, 165-393
9. Jayaraman, N. (2009) Multivalent ligand presentation as a central concept to study intricate carbohydrate-protein interactions Chem. Soc. Rev 38, 3463-3483
10. Mammen, M., Choi, S.-K., and Whitesides, G. M. (1998) Polyvalent interactions in biological system: Implications for design and use of multivalent ligands and inhibitors Angew. Chem., Int. Ed. 37, 2754-2794 (Pubitemid 29008561)
11. Roy, R. (2003) A decade of glycodendrimer chemistry Trends Glycosci. Glycotechnol. 15, 291-310 (Pubitemid 38071814)
12. Lindhorst, T. K. (2002) Artificial multivalent sugar ligands to understand and manipulate carbohydrate-protein interactions Top. Curr. Chem. 218, 201-232
13. Houseman, B. T. and Mrksich, M. (2002) Model systems for studying polyvalent carbohydrate binding interactions Top. Curr. Chem. 218, 1-44
14. Lundquist, J. L. and Toone, E. J. (2002) The cluster glycoside effect Chem. Rev. 102, 555-578 (Pubitemid 35377623)
15. Chabre, Y. M. and Roy, R. (2008) Recent trends in glycodendrimer syntheses and applications Curr. Top. Med. Chem. 8, 1237-1285
16. Chebre, Y. M. and Roy, R. (2009) in The Sugar Code: Fundamentals of Glycosciences (Gabius, H.-J., Ed.) pp 53-70, Wiley-VCH, Weinheim.
17. Lee, Y. C., Townsend, R. R., Hardy, M. R., Lönngren, J., Arnarp, J., Haraldsson, M., and Lönn, H. (1983) Binding of synthetic oligosaccharides to the hepatic Gal/GalNAc lectin J. Biol. Chem. 258, 199-202
18. Bertozzi, C. R. and Kiessling, L. L. (2001) Chemical glycobiology Science 291, 2357-2364 (Pubitemid 32231790)
19. Lindhorst, T. L. and Kieburg, C. (1996) Glycocoating of oligovalent amines: Synthesis of thiourea-bridged cluster glycosides from glycosyl lsothiocyanates Angew. Chem., Int. Ed. 35, 1953-1956
20. Murthy, B. N., Sinha, S., Surolia, A., Indi, S. S., and Jayaraman, N. (2008) SPR and ITC determination of the kinetics and the thermodynamics of bivalent versus monovalent sugar ligand-lectin interactions Glycoconj. J. 25, 313-321 (Pubitemid 351432854)
21. Cecioni, S., Lalor, R., Blanchard, B., Praly, J., Imberty, A., Matthews, S. E., and Vidal, S. (2009) Achieving high affinity towards a bacterial lectin through multivalent topological isomers of calix[4]arene glycoconjugates Chem. - Eur. J. 15, 13232-13240
22. Marra, A., Moni, L., Pazzi, D., Corallini, A., Bridi, D., and Dondoni, A. (2008) Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses Org. Biomol. Chem. 6, 1396-1409 (Pubitemid 351469858)
23. Aoi, K., Itoh, K., and Okada, M. (1995) Globular carbohydrate macromolecules "Sugar Balls". 1. Synthesis of novel sugar-persubstituted poly(amino amine) dendrimers Macromolecules 28, 5391-5393
24. Oka, H., Onaga, T., Koyama, T., Guo, C.-T., Suzuki, Y., Esumi, Y., Hatano, K., Terunuma, D., and Matsuoka, K. (2009) Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses Bioorg. Med. Chem. 17, 5465-5475
25. Luczkowiak, J., Sattin, S., Sutkeviciute, I., Reina, J. J., Sánchez-Navarro, M., Thépaut, M., Martinez-Prats, L., Daghetti, A., Fieschi, F., Delgado, R., Bernardi, A., and Rojo, J. (2011) Pseudosaccharide functionalized dendrimers as potent inhibitors of DC-SIGN dependent ebola pseudotyped viral infection Bioconjugate Chem. 22, 1354-1365
26. Xue, C., Velayudham, S., Johnson, S., Saha, R., Smith, A., Brewer, W., Murthy, P., Bagley, S. T., and Liu, H. (2009) Highly water-soluble, fluorescent, conjugated fluorine-based glycopolymers with poly(ethylene glycol)-tethered spacers for sensitive detection of Escherichia coli Chem. - Eur. J. 15, 2289-2295
27. Miyachi, A., Dohi, H., Neri, P., Mori, H., Uzawa, H., Seto, Y., and Nishida, Y. (2009) Multivalent galacto -trehaloses: Design, synthesis, and biological evaluation under the concept of carbohydrate modules Biomacromolecules 10, 1846-1853
28. Masaka, R., Ogata, M., Misawa, Y., Yano, M., Hashimoto, C., Murata, T., Kawagishi, H., and Usui, T. (2010) Molecular design of N-linked tetravalent glycosides bearing N -acetylglucosamine, N, N′ -diacetylchitobiose and N -acetyllactosamine: Analysis of cross-linking activities with WGA and ECA lectins Bioorg. Med. Chem. 18, 621-629
29. Cecioni, S., Faure, S., Darbost, U., Bonnamour, I., Parrot-Lopez, H., Roy, O., Taillefumier, C., Wimmerová, M., Praly, J.-P., Imberty, A., and Vidal, S. (2011) Selectivity among two lectins: Probing the effect of topology, multivalency and flexibility of "Clicked" multivalent glycoclusters Chem. - Eur. J. 17, 2149-2159
30. Shibuya, N., Tazaki, K., Song, Z., Tarr, G. E., Goldstein, I. J., and Peumans, W. J. (1989) A comparative study of bark lectins from three elderberry (Sambucus) species J. Biochem. (Tokyo) 106, 1098-1103 (Pubitemid 20010128)
31. Kaku, H., Tanaka, Y., Tazaki, K., Minami, E., Mizuno, H., and Shibuya, N. (1996) Sialylated oligosaccharide-specific plant lectin from Japanese elderberry (Sambucus sieboldiana) bark tissue has a homologous structure to type II ribosome-inactivating proteins, ricin and abrin J. Biol. Chem. 271, 1480-1485
32. Tazaki, K. and Shibuya, N. (1989) Purification and partial characterization of a lectin from the bark of Japanese elderberry (Sambucus sieboldiana) Plant Cell Physiol. 30, 899-903
33. Kaku, H. and Shibuya, N. (1992) Preparation of a stable subunit of Japanese elderberry (Sambucus sieboldiana) bark lectin and its application for the study of cell surface carbohydrates by flow cytometry FEBS Lett. 306, 176-180
34. Kaku, H., Mori, Y., Goldstein, I. J., and Shibuya, N. (1993) Monomeric, monovalent derivative of Maackia amurensis leukoagglutinin J. Biol. Chem. 268, 13237-13241
35. Ogata, M., Hidari, K. I.-P.J., Murata, T., Shimada, S., Kozaki, W., Park, E. Y., Suzuki, T., and Usui, T. (2009) Chemoenzymatic synthesis of sialoglycopolypeptides as glycomimetics to block infection by avian and human influenza virus Bioconjugate Chem. 20, 538-549
36. Kato, T., Murata, T., Usui, T., and Park, E. Y. (2003) Improvement of GFPuv-β3GnT2 fusion protein production by suppressing protease in baculovirus expression system Biosci. Biotechnol. Biochem. 67, 2388-2395 (Pubitemid 39251641)
37. Ogata, M., Nakajima, M., Kato, T., Obara, T., Yagi, H., Kato, K., Usui, T., and Park, E. Y. (2009) Synthesis of sialoglycopolypeptide for potentially blocking influenza virus infection using a rat α2,6-sialyltransferase expressed in BmNPV bacmid-injected silkworm larvae BMC Biotechnol. 9 (54) 1-13
38. Misawa, Y., Akimoto, T., Amarume, S., Murata, T., and Usui, T. (2008) Enzymatic synthesis of spacer-linked divalent glycosides carrying N -acetylglucosamine and N -acetyllactosamine: Analysis of cross-linking activities with WGA J. Biochem. (Tokyo) 143, 21-30 (Pubitemid 351197720)
39. Green, E. D., Adelt, G., and Baenziger, J. U. (1988) The asparagines-linked oligosaccharides on bovine fetuin J. Biol. Chem. 263, 18253-18268
40. Zeng, X., Nakaaki, Y., Murata, T., and Usui, T. (2000) Chemoenzymatic synthesis of glycopolypeptides carrying α-Neu5Ac-(2→3)-β-D-Gal- (1→3)-α-D-GalNAc, β-D-Gal-(1→3)-α-D-GalNAc, and related compounds and analysis of their specific interactions with lectins Arch. Biochem. Biophys. 383, 28-37