3-(2-pyridyldithio)propionic acid hydrazide as a cross-linker in the formation of liposome-antibody conjugates

Bioconjugate Chemistry

Volumn 7, Issue 4, 1996, Pages 490-496

  Ansell, Steven M ^a   Tardi, Paul G ^a   Buchkowsky, Susan S ^a  

^a Inex Pharmaceuticals Corporation   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; DRUG DELIVERY; LIPOSOMES; SATURATED FATTY ACIDS;

AMINE MODIFICATION; ANTIBODY CONJUGATE; CROSSLINKER; DEPROTECTION; HYDRAZONE DERIVATIVE; IN-VITRO; MALEIMIDES; N-HYDROXYSUCCINIMIDE; NEW PROTOCOL; VITRO PROPERTIES;

PROPIONIC ACID;

ANIMALIA;

EID: 0030198445     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc960036+     Document Type: Article

References (22)

1. Heath, T. D., and Martin, F. J. (1986) The development and application of protein-liposome conjugation techniques. Chem. Phys. Lipids 40, 347-358.
2. Domen, P. L., Nevens, J. R., Mallia, K., Hermanson, G. T., and Klenk, D. C. (1990) Site directed immobilization of proteins. J. Chromatogr. 510, 293-302.
3. Chua, M. M., Fan, S. T., and Karush, F. (1984) Attachment of immunoglobulin to liposomal membrane via protein carbohydrate. Biochim. Biophys. Acta 800, 291-300.
4. Hansen, C. B., Kao, G. Y., Moase, E. H., Zalipsky, S., and Allen, T. M. (1995) Attachment of antibodies to sterically stabilized liposomes: evaluation, comparison and optimization of coupling procedures. Biochim. Biophys. Acta 1239, 133-144.
5. Parr, M. J., Ansell, S. M., Choi, L. S., and Cullis, P. R. (1994) Factors influencing the retention and chemical stability of poly(ethyleneglycol)-lipid conjugates incorporated into large unilamellar vesicles. Biochim. Biophys. Acta 1195, 21-30.
6. Hope, M. J., Bally, M. B., Webb, G., and Cullis, P. R. (1985) Production of large unilammelar vesicles by a rapid extrusion procedure. Characterization of size distribution, trapped volume and ability to maintain a membrane potential. Biochim. Biophys. Acta 812, 55-65.
7. Derksen, J. T. P., Morselt, H. W. M., and Scherphof, G. L. (1987) Processing of different liposome markers after in vitro uptake of immunoglobin-coated liposomes by rat liver macrophages. Biochim. Biophys. Acta 931, 33-40.
8. Hermanson, G. T., Mallia, A. K., and Smith, P. K. (1992) Immobilized Affinity Ligand Techniques, 230 pp, Academic Press, San Diego, CA.
9. Carlsson, J., Drevin, H., and Axén, R. (1978) Protein thiolation and reversible protein-protein conjugation. Biochem. J. 173, 723-737.
10. Harasym, T. O., Tardi, P., Longman, S. A., Ansell, S. M., Bally, M. B., Cullis, P. R., and Choi, L. S. L. (1995) Poly-(ethylene glycol)-modified phospholipids prevent aggregation during covalent conjugation of proteins to liposomes. Bioconjugate Chem. 6, 187-194.
11. Kondejewski, L. H., Kralovec, J. A., Blair, A. H., and Ghose, T. (1994) Synthesis and characterization of carbohydrate-linked murine monoclonal antibody K20-human serum albumin conjugates. Bioconjugate Chem. 5, 602-611.
12. Webb, M. S., Harasym, T. O., Masin, D., Bally, M. B., and Mayer, L. D. (1995) Sphingomyelin-cholesterol liposomes significantly enhance the pharmacokinetics and therapeutic properties of vincristine in murine and human tumour models. Br. J. Cancer 72, 896-904.
13. Zara, J. J., Wood, R. D., Bredehorst, R., and Vogel, C. H (1990) Site-specific heterobifunctional crosslinking reagents. World Intellectual Property Organization, International Publication WO 90/10621 (International Application PCT/US/ 01201).
14. Taylor, K. E., and Wu, Y. C. (1980) A thiolation reagent for cell surface carbohydrate. Biochem. Int. 4, 353-358.
15. Matthay, K. K., Heath, T. D., and Papahadjopoulos, D. (1984) Specific enhancement of drug delivery to AKR lymphoma by antibody-targeted small unilamellar vesicles. Cancer Res. 44, 1880-1886.
16. Aragonol, D., and Leserman, L. D. (1986) Immune clearance of liposomes inhibited by an anti-Fc receptor antibody in vivo. Proc. Natl. Acad. Sci. U.S.A. 83, 2699-2703.
17. Sutton, B. J., and Phillips, D. C. (1983) The three-dimensional structure of the carbohydrate within the Fc fragment of immunoglobin G. Biochem. Soc. Trans. 11, 130-132.
18. Deisenhofer, J. (1981) Crystallographic refinement and atomic models of human Fc fragment and its complex with fragment B of protein A form Staphylcoccus aureus at 2.9-and 2.8-Å resolution. Biochemistry 20, 2361-2370.
19. Nose, M., and Wigzell, H. (1983) Biological significance of carbohydrate chains on monoclonal antibodies. Proc. Natl. Acad. Sci. U.S.A. 80, 6632-6636.
20. Leatherbarrow, R., Rademacher, T., Dwek, R., Woof, J., Clark, A., Burton, D., Richardson, N., and Feinstein, A. (1985) Effector functions of a monoclonal aglycosylated mouse IgG2a: binding and activation of complement component C1 and interaction with human monocyte Fc receptor. Mol. Immunol. 22, 407-415.
21. Tao, M.-H., and Morrison, S. (1989) Studies of aglycosylated chimeric mouse-human IgG. Role of carbohydrates in the structure and effector functions mediated by the human IgG constant region. J. Immunol. 143, 2595-2601.
22. Klibanov, A. L., Maruyama, K., Beckerleg, A. M., Torchilin, V. P., and Huang, L. (1991) Activity of amphiphathic poly-(ethylene glycol) 5000 to prolong the circulation time of liposomes depends on the liposome size and is unfavourable for immunoliposome binding to target. Biochim. Biophys. Acta 1062, 142-148.