Abstract
Literature reports have described the covalent coupling of the primary amine-containing anticancer drug, adriamycin, to polymeric supports through the amine group on the drug. These reports also have described drug mechanism studies with the immobilized adriamycin, where the release of the drug would undermine the validity of the conclusions. In the present paper, detailed experimental conditions are given for preparation of nonwater-soluble particles of polyvinyl alcohol by crosslinking water-soluble polyvinyl alcohol with 1,4-benzenedi-carboxaldehyde, and for activation with cyanuric chloride and covalent attachment of adriamycin. The expected stability of this drug-support linkage against hydrolytic cleavage is compared mechanistically to that expected for less stable coupling through a carbamate linkage or for less stable coupling via an azomethine link.
Similar content being viewed by others
References
Wingard, Jr., L. B. (1983),Biochem. Pharmacol. 32, 2647.
Venter, J. C. (1982),Pharmacological Rev. 34, 153.
Wingard, Jr., L.B. (1983),Fed. Proc. 42, 271.
Strosberg, A. D. (1984) inReceptor Purification Procedures, Venter, J. C. and Harrison, L. C., eds., Liss, New York, pp. 1–13.
Sigel, E., Mamalaki, C., and Barnard, E. A. (1982),FEBS Lett. 147, 45.
Taguchi, J-I. and Kuriyama, J-I. (1984),Brain Res. 323, 219.
Shen, W-C. and Ryser, H.J-P. (1981),Proc. Natl. Acad. Sci. USA 78, 7589.
Tirrell, D. A., Donaruma, L. G., and Turek, A. B., eds. (1985),Macromolecules As Drugs and As Carriers for Biologically Active Materials, NY Acad. Sci., New York.
Arcamone, F. (1984),Med. Res. Reviews 4, 153.
Wheeler, C., Rader, R., and Kessel, D. (1982),Biochem. Pharmacol. 31, 2691.
Siegfried, J. A., Kennedy, K. A., Sartorelli, A. C., and Tritton, T. R. (1983),J. Biol. Chem. 258, 339.
Meyers, C., Gianni, L., Zweier, J., Muindi, J., Sinha, B. K., and Eliot, H. (1986),Fed. Proc. 45, 2792.
Haidle, C. W. and McKinney, S. H. (1986),Cancer Biochem. Biophys. 8, 327.
Tewey, K. M., Rowe, T. C., Yang, L., Halligan, B. D., and Liu, L. F. (1984),Science 226, 499.
Wingard, Jr., L. B., Tritton, T. R., and Egler, K. A. (1985),Cancer Res. 45, 3529.
Tokes, Z. A., Rogers, K. E., and Rembaum, A. (1982),Proc. Natl. Acad. Sci. USA 79, 2026.
Tritton, T. R., and Yee, G. (1982),Science 217, 248.
Rogers, K. E., Forssen, E. A., and Tokes, Z. A. (1982),Dev. Oncol. 10, 282.
Goldberg, E. P., Terry, R. W., and Levy, M. (1981),Org. Coat. Plast. Chem. 49, 132.
Tokes, Z. A. and Ross, K. L. (1984),Stud. Biophys. 104, 161.
Manecke, G. and Vogt, H. G. (1976),Makromolekielare Chemie 177, 725.
Abuchowski, A., Van Es, T., Palczuk, N. C., and Davis, F. F. (1977),J. Biol. Chem. 252, 3578.
Kay, G. and Lilly, M. D. (1970),Biochim. Biophys. Acta 198, 276.
Smith III, N. L., and Lenhoff, H. M. (1974),Anal. Biochem. 61, 392.
Bouma, J., Beijnen, J. H., Bult, A., and Underberg, W. J. (1986),Pharm. Weekbl. (Sci.) 8, 109.
Beijmem, J. H., Van der Houwen, O.A., and Underberg, W. J. (1986),Intern. J. Pharmaceu. 32, 123.
Monsan, P., Buzo, G., and Mazarguil, H. (1975),Biochimie 57, 1281.
Wilchek, M. and Miron, T. (1982),Biochem. Intern. 4, 629.
Johnson, D., Mendicino, J., Cormier, M., and Travis, J. (1974),Fed. Proc. 33, 1502.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Wingard, L.B., Narasimhan, K. Immobilization of a primary amine-containing drug, adriamycin. Appl Biochem Biotechnol 19, 117–127 (1988). https://doi.org/10.1007/BF02921477
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02921477