Oligosaccharides and peptide displayed on an amphiphilic polymer enable solid phase assay of hapten specific antibodies

Bioconjugate Chemistry

Volumn 25, Issue 4, 2014, Pages 685-697

  Bundle, David R ^a   Tam, Pui Hang ^a   Tran, Huu Anh ^a   Paszkiewicz, Eugenia ^a   Cartmell, Jonathan ^a   Sadowska, Joanna M ^a   Sarkar, Susmita ^a   Joe, Maju ^a   Kitov, Pavel I ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; ACRYLIC MONOMERS; ANTIBODIES; CONJUGATED POLYMERS; ETHYLENE; PEPTIDES; POLYVINYL ACETATES; SYNTHESIS (CHEMICAL); T-CELLS;

AMPHIPHILIC POLYMERS; CLICK CHEMISTRY; DEACETYLATION; GLYCANS; N-VINYL-2-PYRROLIDONE; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; SOLID PHASIS; SOLID-PHASE; SYNTHESISED; VINYL ACETATES;

POLYSACCHARIDES;

1 VINYL 2 PYRROLIDINONE; ALKYNE; AMINO ACID; AMPHOPHILE; ANTIBODY; AZIDE; CARBOHYDRATE; COPOLYMER; COPOVIDONE; GLYCOCONJUGATE; HAPTEN; HEXASACCHARIDE; OLIGOSACCHARIDE; PEPTIDE; POLYMER; TRISACCHARIDE; UNCLASSIFIED DRUG; VINYL ACETATE; POLY(VINYLPYRROLIDONE-CO-VINYL-ACETATE); PYRROLIDINE DERIVATIVE; SURFACTANT; VINYL DERIVATIVE;

ADSORPTION KINETICS; ANIMAL EXPERIMENT; ANTIGEN BINDING; ARTICLE; ASSAY; CANDIDA ALBICANS; CARBOXY TERMINAL SEQUENCE; CLICK CHEMISTRY; CONJUGATE; CONTROLLED STUDY; DEACETYLATION; DEGRADATION; ENZYME LINKED IMMUNOSORBENT ASSAY; IMMUNOASSAY; MOUSE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; POLYMERIZATION; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER POLYMERIZATION; SOLID; SQUARATE CHEMISTRY; SYNTHESIS; T LYMPHOCYTE; ADSORPTION; ANTIBODY SPECIFICITY; CHEMISTRY; CONFORMATION; IMMUNOLOGY; RECYCLING;

ADSORPTION; ANTIBODIES; ANTIBODY SPECIFICITY; CANDIDA ALBICANS; CLICK CHEMISTRY; ENZYME-LINKED IMMUNOSORBENT ASSAY; EQUIPMENT REUSE; HAPTENS; MOLECULAR CONFORMATION; MYCOBACTERIUM TUBERCULOSIS; OLIGOSACCHARIDES; PEPTIDES; POLYMERS; PYRROLIDINES; SURFACE-ACTIVE AGENTS; VINYL COMPOUNDS;

EID: 84899009730     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc400486w     Document Type: Article

References (35)

1. Gambillara, V. (2012) The conception and production of conjugate vaccines using recombinant DNA technology BioPharm. Int. 25, 28-32
2. Guttormsen, H. K., Paoletti, L. C., Mansfield, K. G., Jachymek, W., Jennings, H. J., and Kasper, D. L. (2008) Rational chemical design of the carbohydrate in a glycoconjugate vaccine enhances IgM-to-IgG switching Proc. Natl. Acad. Sci. U. S. A. 105, 5903-5908
3. Safari, D., Dekker, H. A., Joosten, J. A., Michalik, D., de Souza, A. C., Adamo, R., Lahmann, M., Sundgren, A., Oscarson, S., Kamerling, J. P., and Snippe, H. (2008) Identification of the smallest structure capable of evoking opsonophagocytic antibodies against Streptococcus pneumoniae type 14 Infect. Immun. 76, 4615-4623
4. Martin, C. E., Broecker, F., Oberli, M. A., Komor, J., Mattner, J., Anish, C., and Seeberger, P. H. (2013) Immunological evaluation of a synthetic Clostridium difficile oligosaccharide conjugate vaccine candidate and identification of a minimal epitope J. Am. Chem. Soc. 35, 9713-9722
5. Anish, C., Schumann, B., Pereira, C. L., and Seeberger, P. H. (2014) Chemical biology approaches to designing defined carbohydrate vaccines Chem. Biol. 21, 38-50
6. Lipinski, T., Wu, X., Sadowska, J. M., Kreiter, E., Yasui, Y., Cheriaparambil, S., Rennie, R., and Bundle, D. R. (2012) A trisaccharide conjugate vaccine induces high titer Î-mannan specific antibodies that aid clearance of Candida albicans in immunocompromised rabbits Vaccine 30, 6263-6269
7. Ragupathi, G., Koide, F., Livingston, P. O., Cho, Y. S., Endo, A., Wan, Q., Spassova, M. K., Keding, S. J., Allen, J., Ouerfelli, O., Wilson, R. M., and Danishefsky, S. J. (2006) Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: a synthetic route to anticancer vaccine candidates J. Am. Chem. Soc. 128, 2715-2725
8. Lakshminarayanan, V., Thompson, P., Wolfert, M. A., Buskas, T., Bradley, J. M., Pathangey, L. B., Madsen, C. S., Cohen, P. A., Gendler, S. J., and Boons, G.-J. (2012) Immune recognition of tumor-associated mucin MUC1 is achieved by a fully synthetic aberrantly glycosylated MUC1 tripartite vaccine Proc. Natl. Acad. Sci. U.S.A. 109, 261-266
9. Bundle, D. R., Nycholat, C., Costello, C., Rennie, R., and Lipinski, T. (2012) Design of a Candida albicans disaccharide conjugate vaccine by reverse engineering a protective monoclonal antibody ACS Chem. Biol. 7, 1754-1763
10. Wu, X. and Bundle, D. R. (2005) Synthesis of glycoconjugate vaccines for Candida albicans using novel linker methodology J. Org. Chem. 70, 7381-7388
11. Miller, J. M., Mesaros, N., van der Wielen, M., and Baine, Y. (2011) Conjugate meningococcal vaccines development: GSK biologicals experience Advances in Preventive Medicine 2011, 1-17
12. Goldblatt, D. (2000) Conjugate vaccines Clin. Exp. Immunol. 119, 1-3
13. Hong, S. W., Lee, B. S., Park, S. J., Jeon, H. R., Moon, K. Y., Kang, M. H., Park, S. H., Choi, S. U., Song, W. H., Lee, J., and Choi, Y. W. (2011) Solid dispersion formulations of megastrol acetate with copovidone for enhanced dissolution and oral bioavailability Arch. Pharmacal. Res. 34, 127-135
14. Kitov, P. I., Kotsuchibashi, Y., Paszkiewicz, E., Wilhelm, D., Narain, R., and Bundle, D. R. (2013) Poly(n-vinyl-2-pyrrolidone-co-vinyl alcohol) as a versatile amphiphilic polymeric scaffold for multivalent probes Org. Lett. 15, 5190-5193
15. Han, Y., Kanbe, T., Cherniak, R., and Cutler, J. E. (1997) Biochemical characterization of Candida albicans epitopes that can elicit protective and nonprotective antibodies Infect. Immun. 65, 4100-4107
16. Han, Y., Riesselman, M. H., and Cutler, J. E. (2000) Protection against candidiasis by an Immunoglobulin G3 (IgG3) monoclonal antibody specific for the same mannotriose as an IgM protective antibody Infect. Immun. 68, 1649-1654
17. Johnson, M. A. and Bundle, D. R. (2013) Designing a new antifungal glycoconjugate vaccine Chem. Soc. Rev. 42, 4327-4344
18. Dang, A.-T., Johnson, M. A., and Bundle, D. R. (2012) Synthesis of a Candida albicans tetrasaccharide spanning the Î1,2-mannan phosphodiester α-mannan junction Org. Biomol. Chem. 10, 8348-8360
19. Xin, H., Dziadek, S., Bundle, D. R., and Cutler, J. (2008) Synthetic glycopeptide vaccines combining Î-mannan and peptide epitopes induce protection against candidiasis Proc. Natl. Acad. Sci. U.S.A. 105, 13526-13531
20. Xin, H., Cartmell, J., Bailey, J. J., Dziadek, S., Bundle, D. R., and Cutler, J. E. (2012) Self-adjuvanting glycopeptide conjugate vaccine against disseminated candidiasis PLoS One 7, e35106
21. Gadikota, R. R., Callam, C. S., Appelmelk, B. J., and Lowary, T. L. (2003) Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan appropriately functionalized for neoglycoconjugate preparation J. Carbohydr. Chem. 22, 459-480
22. Murase, T., Zheng, R. B., Joe, M., Bai, Y., Marcus, S. L., Lowary, T. L., and Ng, K. K. S. (2009) Structural insights into antibody recognition of mycobacterial polysaccharides J. Mol. Biol. 392, 381-392
23. Crich, D., Banerjee, A., and Yao, Q. (2004) Direct chemical synthesis of the Î-D-mannans: the Î-(1â†?2) and Î- (1â†?4) series J. Am. Chem. Soc. 126, 14930-14934
24. Crich, D. and Smith, M. (2001) 1-Benzenesulfinyl piperidine/ trifluoromethanesulfonic anhydride: a potent combination of shelf-stable reagents for the low-temperature conversion of thioglycosides to glycosyl triflates and for the formation of diverse glycosidic linkages J. Am. Chem. Soc. 123, 9015-9020
25. Mukherjee, C., Ranta, K., Savolainen, J., and Leino, R. (2012) Synthesis and immunological screening of b -linked mono- and divalent mannosides Eur. J. Org. Chem. 2957-2968
26. Rao, Y., Venot, A., Swayze, E. E., Griffey, R. H., and Boons, G.-J. (2006) Trisaccharide mimetics of the aminoglycoside antibiotic neomycin Org. Biomol. Chem. 4, 1328-1337
27. Seo, T. S, Bai, X., Ruparel, H., Li, Z., Turro, N. J., and Ju, J. (2004) Photocleavable fluorescent nucleotides for DNA sequencing on a chip constructed by site-specific coupling chemistry Proc. Natl. Acad. Sci. U.S.A. 101, 5488-5493
28. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: copper(I)-catalyzed regioselective â€ligation†of azides and terminal alkynes Angew. Chem., Int. Ed. Engl. 41, 2596-2599
29. Tornoe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides J. Org. Chem. 67, 3057-3064
30. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., and Finn, M. G. (2003) Bioconjugation by copper(I)-catalyzed azidealkyne [3 + 2] cycloaddition J. Am. Chem. Soc. 125, 3192-3193
31. Sen Gupta, S., Kuzelka, J., Singh, P., Lewis, W. G., Manchester, M., and Finn, M. G. (2005) Accelerated bioorthogonal conjugation: A practical method for the Ligation of diverse functional molecules to a polyvalent virus scaffold Bioconjugate Chem. 16, 1572-1579
32. Dasgupta, S., Kitov, P. I., Sadowska, J. M., and Bundle, D. R. (2014) Discovery of Shiga toxin type 2 inhibitors by on-plategeneration and screening of a focused library Angew. Chem., Int. Ed. Engl. 10.1002/anie.201309436
33. Baunoch, D. A., Das, P., Browning, M. E., and Hari, V. (1992) R-ELISA: Repeated use of antgen coated plates for ELISA and its application for testing of antibodies to HIV and other pathogens BioTechniques 12, 412-417
34. Simoney, N., Labrousse, H., Ternynck, T., and Lagrange, P. H. (1996) Recycling ELISA plates for the serological diagnosis of tuberculosis using a Mycobacterium tuberculosis -specific glycolipid antigen J. Immunol. Methods 199, 101-105
35. Bemiller, J. N. (1967) Acid-catalyzed hydrolysis of glycosides Adv. Carbohydr. Chem. 22, 25-108