Activation of soluble polysaccharides with 1-cyano-4- dimethylaminopyridinium tetrafluoroborate (CDAP) for use in protein- polysaccharide conjugate vaccines and immunological reagents. II. Selective crosslinking of proteins to CDAP-activated polysaccharides

Vaccine

Volumn 18, Issue 13, 2000, Pages 1273-1281

  Shafer, Douglas E ^a   Toll, Barbara ^a   Schuman, Richard F ^a   Nelson, Brett L ^a   Mond, James J ^b   Lees, Andrew ^a,b  

^a Virion Systems Inc   (United States)

^b UNIFORMED SERVICES UNIVERSITY OF THE HEALTH SCIENCES   (United States)

Author keywords

1 cyano 4 dimethylaminopyridinium tetrafluoroborate (CDAP); Conjugate vaccines; Hydrazides

Indexed keywords

1 CYANO 4 DIMETHYLAMINOPYRIDINIUM TETRAFLUOROBORATE; BACTERIAL POLYSACCHARIDE; HYDRAZIDE; PNEUMOCOCCUS VACCINE; PYRIDINIUM DERIVATIVE; TETANUS TOXOID; UNCLASSIFIED DRUG;

ANIMAL MODEL; ANTIBODY TITER; ARTICLE; CROSS LINKING; IMMUNIZATION; IMMUNOGENICITY; MOUSE; NONHUMAN; PH; PRIORITY JOURNAL; VACCINATION;

AMINES; ANIMALS; CROSS-LINKING REAGENTS; HAPTENS; HYDRAZONES; HYDROGEN-ION CONCENTRATION; MICE; MICE, INBRED BALB C; NITRILES; POLYSACCHARIDES, BACTERIAL; PROTEINS; PYRIDINIUM COMPOUNDS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; VACCINES, CONJUGATE;

EID: 0033987024     PISSN: 0264410X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0264-410X(99)00370-9     Document Type: Article

References (19)

1. Lees A., Nelson B.L., Mond J.J. Activation of soluble polysaccharides with 1-cyano-4-dimethylaminopyridinium tetrafluoroborate for use in protein-polysaccharide conjugate vaccines and immunological reagents. Vaccine. 14:1996;190-198.
2. Konadu E.J., Shiloach J., Bryla D.A., Robbins J.B., Szu S.C. Synthesis, characterization and immunological properties in mice of conjugates composed of detoxified lipopolysaccharide of Salmonella paratyphi A bound to tetanus toxoid with emphasis on the role of O-acetyls. Infect. Immun. 64:1996;2709-2715.
3. Akkoyunlu M., Melhus A., Capiau C., Van Opstal O., Forsgren A. The acylated form of protein D of Haemophilus influenzae is more immunogenic than the nonacylated form and elicits an adjuvant effect when it is used as a carrier conjugated to polyribosyl ribitol phosphate. Infect. Immun. 65:1997;5010-5016.
4. Masssen A., Thielen T.P.G.M., Moller W. Synthesis and application of two reagents for the introduction of sulfhydryl groups into proteins. Eur. J. Biochem. 134:1993;327-330.
5. Qi X.-Y., Keyhani N.O., Lee Y.C. Spectrophotometric determination of hydrazine, hydrazides and their mixtures with trinitrobenzenesulfonic acid. Anal. Biochem. 175:1988;139-144.
6. Ellman G.L. Tissue sulfhydryl groups. Arch. Biochem Biophys. 82:1959;70-77.
7. Monsigny M., Petit C., Roche A.C. Colorimetric determination of neutral sugars by a resorcinol sulfuric acid micromethod. Anal. Chem. 175:1988;525-530.
8. King T.P., Zhao S.W., Lam T. Preparation of protein conjugates via intermolecular hydrazone linkage. Biochemistry. 25:1986;5774-5779.
9. Inman J.K. Thymus-independent antigens: The preparation of covalent, hapten-Ficoll conjugates. J. Immunol. 114:1975;704-709.
10. Poos G.I., Kleis J., Cain C.K. 2-Alkoxy-2-imidazolines and related compounds. J. Org. Chem. 24:1959;645-646.
11. Dick W.E. Jr., Beurret M. Glycoconjugates of bacterial carbohydrate antigens. Cruse J.M., Lewis R.E. Jr. Conjugate vaccines. 1989;48-114 Karger, Basel.
12. Jensen K.A., Due M., Holm A., Wentrup C. Alkyl cyanates. VI. Chemical reactions of alkyl cyanates. Acta Chem. Scand. 20:1966;2091-2106.
13. Wilchek M., Miron T. Stable high capacity and non charged agarose derivatves for immobilization of biologically active compounds and for affinity chromatography. Mol. Cell Biochem. 4:1974;181-187.
14. Hermanson G.T. Bioconjugate techniques. 1996;Academic Press, New York.
15. Jost R., Miron T., Wilchek M. The mode of adsorption of proteins to aliphatic and aromatic amines coupled to cyanogen bromide-activated agarose. Biochim. Biophys. Acta. 362:1974;75-82.
16. Zara J.J., Wood R.D., Boon P., Kim C.-H., Pomato N., Bredehorst R., Vogel C.-W. A carbohydrate-directed heterobifunctional crosslinking reagent for the synthesis of immunoconjugates. Anal. Biochem. 194:1991;156-162.
17. Heimgartner U., Kozulic B., Mosbach K. Reversible and irreversible cross-linking of immunoglobulin heavy chains through their carbohydrate residues. Biochem. J. 267:1990;585-591.
18. Bernatowicz M.S., Matsueda G.R. Preparation of peptide-protein immunogens using N-succinimidyl bromoacetate as a heterobifunctional crosslinking reagent. Anal. Biochem. 155:1986;95-102.
19. Schneerson R., Barrera O., Sutton A., Robbins J.B. Preparation, characterization and immunogenicity of Haemophilus influenzae type b polysaccharide-protein conjugates. J. Exp. Med. 152:1980;361-376.