Glycosilated Macromolecular Conjugates of Antiviral Drugs with a Polyaspartamide

References

• Alexander, G.J., Fagan, E.A. and Hegarty, J.E. (1987) “Controlled trial of acyclovir in chronic hepatitis B virus infection”, J. Med. Virol. 21, 81– 87.
   PubMed Web of Science ®Google Scholar
• Ashwell, G. and Harford, J. (1982) “Carbohydrate-specific receptors of the liver”, Annu. Rev. Biochem. 51, 531– 554.
   PubMed Web of Science ®Google Scholar
• Ashwell, G. and Morell, A.G. (1974) “The role of surface carbohydrates in the hepatic recognition and transport of circulating glycoproteins”, Adv. Enzymol. Relat. Areas Mol. Biol. 41, 99– 128.
   PubMedGoogle Scholar
• Caliceti, P., Quarta, S.M., Veronese, F.M., Cavallaro, G., Pedone, E. and Giammona, G. (2001) “Synthesis and biopharmaceutical character- isation of new poly(hydroxyaspartamide)copolymers as drug carriers”, Biochim. Biophys. Acta 1528, 177– 186.
   PubMed Web of Science ®Google Scholar
• Cascio, G. (1957) “Pharmacological action of N-(4-methylbenzene- sulfonyl)-N1-butylurea on the pigeon. I. Changes of blood glucose & hepatic glycogen in relation to dose”, Boll. Soc. Ital. Biol. Sper. 33, 1007– 1011.
   PubMedGoogle Scholar
• Cavallaro, G., Pitarresi, G., Licciardi, M. and Giammona, G. (2001) “Polimeric pro-drug for release of an antitumoral agent by specific enzymes”, Bioconjug. Chem. 12, 143– 151.
   PubMed Web of Science ®Google Scholar
• Chachoua, A., Dieterich, D., Krasinski, K., Greene, J., Laubenstein, L., Wernz, J., Buhles, W. and Koretz, S. (1987) “9-(1,3-Dihydroxy-2- propoxymethyl)guanine (Ganciclovir) in the treatment of cytomegalovirus gastrointestinal disease with the acquired immuno- deficiency syndrome”, Ann. Intern. Med. 107, 133– 137.
   PubMed Web of Science ®Google Scholar
• Colla, L., De Clercq, E., Busson, R. and Vanderhaeghe, H. (1983) “Synthesis and antiviral activity of water soluble esters of Acyclovir 9-[(2-hydroxyethoxy)methyl]guanine”, J. Med. Chem. 26, 602– 604.
   PubMed Web of Science ®Google Scholar
• Dragsten, P.R., Mitchell, D.B., Covert, G. and Baker, T. (1987) “Drug delivery using vesicles targeted to the hepatic asialoglycoprotein receptors”, Biochem. Biophys. Acta 926, 270– 279.
   PubMed Web of Science ®Google Scholar
• Fallon, R.J. and Schwartz, A.L. (1989) “Receptors mediated delivery of drugs to hepatocytes”, Adv. Drug Deliv. Rev. 4, 49– 63.
   Google Scholar
• Fan-Havard, P., Nahata, M.C. and Brady, M.T. (1989) “Ganciclovir—a review of pharmacology, therapeutic efficacy and potential use for treatment of congenital cytomegalovirus infections”, J. Clin. Pharm. Ther. 75, 329– 340.
   Google Scholar
• Faulds, D. and Heel, R.C. (1990) “Ganciclovir. A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in cytomegalovirus infections”, Drugs 39, 597– 638.
   PubMed Web of Science ®Google Scholar
• Franssen, E.J.F., Jansen, R.W., Vaalburg, M. and Meijer, D.K.F. (1993) “Hepatic and intrahepatic targeting of an anti-inflammatory agent with human serum albumin and neoglycoproteins as carrier molecules”, Biochem. Pharmacol. 45, 1215– 1226.
   PubMed Web of Science ®Google Scholar
• Giammona, G., Carlisi, B. and Palazzo, S. (1987) “Reaction of a, b-poly (N-hydroxyethyl)-DL-aspartamide with derivatives of carboxylic acid”, J. Polym. Chem. 25, 2813– 2818.
   Web of Science ®Google Scholar
• Giammona, G., Carlisi, B., Pitarresi, G. and Fontana, G. (1991) “Hydrophilic and hydrophobic derivatives of antiinflammatory agents such Alclofenac, Ketoprofen and Ibuprofen”, J. Bioact. Compat. Polym. 6, 129– 141.
   Web of Science ®Google Scholar
• Giammona, G., Carlisi, B., Pitarresi, G., Cavallaro, G. and Turco Liveri, V. (1992) “Water-soluble copolymers of an antiviral agent: synthesis and their interaction with biomembrane model”, J. Control. Rel. 22, 197– 204.
   Web of Science ®Google Scholar
• Giammona, G., Pugliesi, G., Cavallaro, G., Spadaro, A. and Pitarresi, G. (1995) “Chemical stability and bioavailability of Acyclovir coupled to a,b-poly(N-hydroxyethyl)-DL-aspartamide”, J. Control. Rel. 33, 261– 271.
   Web of Science ®Google Scholar
• Giammona, G., Cavallaro, G., Fontana, G., De Guidi, G. and Giuffrida, S. (1996) “Macromolecular pro-drug of Diflunisal. II. Investigations of in vitro release and of photochemical behaviour”, Eur. J. Pharm. Sci. 4, 273– 282.
   Web of Science ®Google Scholar
• Giammona, G., Cavallaro, G., Fontana, G., Pitarresi, G. and Carlisi, B. (1998) “Coupling of the antiviral agent zidovudine to polyaspart- amide and in vitro drug release”, J. Control. Rel. 54, 321– 331.
   PubMed Web of Science ®Google Scholar
• Greene, T.W. and Wuts, P.G.M. (1991) Protective Groups in Organic Synthesis, 2nd Ed. (Wiley, New York). Harbison, M.A., De Girolami, P.C. and Hammer, S.M. (1988) “Ganciclovir therapy of severe cytomegalovirus infections in solid organ transplant recipients”, Transplantation 46, 82–88.
   Google Scholar
• Hashida, M., Nishikawa, M., Yamashita, F. and Takakura, Y. (2001) “Cell-specific delivery of genes with glycosylated carriers”, Adv. Drug Deliv. Rev. 52, 187– 196.
   PubMed Web of Science ®Google Scholar
• Jansen, R.W., Molema, G., Ching, T.L., Oosting, R., Harms, G., Moolenaar, F., et al. (1991) “Hepatic endocytosis of various types of mannose- terminated albumins. What is important, sugar recognition, net charge or the combination of these features”, J. Biol. Chem. 266, 3343– 3348.
   PubMed Web of Science ®Google Scholar
• Kawakami, S., Wong, J., Sato, A., Hattori, Y., Yamashita, F. and Hashida, M. (2000) “Biodisitribution characterisitics of manno- sylated, fucosylated and glycosylated liposomes in mice”, BBA 1524, 258– 265.
   PubMed Web of Science ®Google Scholar
• Kawakami, S., Yamashita, F., Nishida, K., Nakamura, J. and Hashida, M. (2002) “Glycosylated cationic liposomes for cell-selective gene delivery”, Crit. Rev. Ther. Drug Carrier Syst. 19, 171– 190.
   PubMed Web of Science ®Google Scholar
• Korba, B.E. and Boyd, M.R. (1996) “Penciclovir is a selective inhibitor of hepatitis B virus replication in cultured human hepatoblastoma cells”, Antimicrob. Agents Chemother. 40, 1282– 1284.
   PubMed Web of Science ®Google Scholar
• Kotler, D.P., Culpepper-Morgan, J.A., Tierney, A.R. and Klein, E.B. (1986) “Treatment of disseminated cytomegalovirus infection with 9-(1,3 dihydroxy-2-propoxymethyl)guanine: evidence of prolonged survival in patients with the acquired immunodeficienty sindrome”, AIDS Res. 2, 299– 308.
   PubMedGoogle Scholar
• Luscombe, C., Pedersen, J., Uren, E. and Locarnini, S. (1996) “Long- term ganciclovir chemotherapy for congenital duck hepatitis B virus infection in vivo. Effect on intrahepatic-viral DNA, RNA and protein expression”, Hepatology 24, 766– 773.
   PubMed Web of Science ®Google Scholar
• Mahato, R.I., Takemura, S., Akamatsu, K., Nishikawa, M., Takakura, Y. and Hashida, M. (1997) “Physical and disposition characterisitics of antisense oligonucleotides complexed with glycosylated poly(L-lysine)”, Biochem. Pharmacol. 53, 887– 895.
   PubMed Web of Science ®Google Scholar
• Martin, J.C., Tippie, M.A., McGee, D.P.C. and Verheyden, J.P.H. (1987) “Synthesis and antiviral activity of various esters of 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine”, J. Pharm. Sci. 76, 180– 184.
   PubMed Web of Science ®Google Scholar
• Matthews, S.E., Pouton, C.W. and Threadgill, M.D. (1996) “Macro- molecular systems for chemotherapy and magnetic resonance imaging”, Adv. Drug Del. Rev. 18, 219– 267.
   Web of Science ®Google Scholar
• Mertens, T., Kock, J., Hampl, W., Schlicht, H.J., Tillmann, H.L., Oldhafer, K.J., Manns, M.P. and Arnold, R. (1996) “Reactivated fulminant hepatitis B virus replication after bone marrow transplantation: clinical course and possible treatment with ganciclovir”, J. Hepatol. 25, 968– 971.
   PubMed Web of Science ®Google Scholar
• Neufeld, E. and Ashwell, G. (1979) “Carbohydrate recognition systems for receptor-mediated pinocytosis”, In: Lennarz, W., ed., Biochem- istry of Glycoproteins and Proteoglycans (Plenum Press, New York), pp 241–266.
   Google Scholar
• O’Brien, J.J. and Campoli-Richards, D.M. (1989) “Acyclovir. An update review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy”, Drug 37, 233– 309.
   PubMed Web of Science ®Google Scholar
• Reed, E.C., Bowden, R.A., Dandliker, P.S. and Meyers, J.D. (1988) “Treatment of cytomegalovirus pneumonia with ganciclovir and intravenous cytomegalovirus immunoglobulin in patients with bone marrow transplants”, Ann. Intern. Med. 109, 783– 788.
   PubMed Web of Science ®Google Scholar
• Schaeffer, H.J., Beauchamp, L., De Miranda, P., Elion, G.B., Bouer, D.J. and Collins, P. (1978) “9-[(2-hydroxyethoxy)methyl]guanine activity against viruses of the herpes group”, Nature 272, 583– 585.
   PubMed Web of Science ®Google Scholar
• Seymour, L.W. (1994) “Soluble polymers for lectin-mediated drug delivery”, Adv. Drug Deliv. Rev. 14, 89– 111.
   Web of Science ®Google Scholar
• Seymour, L.W., Ulbrich, K., Wedge, S.R., Hume, I.C., Strohalm, J. and Duncan, R. (1991) “N-(2-hydroxy-propyl)methacrylamide copoly- mers targeted to hepatocytes galactose receptor: pharmacokinetics in DBA2 mice”, Br. J. Cancer 63, 859– 866.
   PubMed Web of Science ®Google Scholar
• Shaw, T., Amor, P., Civitico, G., Boyd, M. and Locarnini, S. (1994) “In vitro antiviral activity of penciclovir, a novel purine nucleoside, against duck hepatitis B virus”, Antimicrob. Agents Chemother. 38, 719– 723.
   PubMed Web of Science ®Google Scholar
• Song, Y., Onishi, H., Nagai, T. and Iguchi, S. (1993) “Conjugate of Mitomycin C with N-succinyl-chitosan: in vitro drug release properties, toxicity and antitumor activity”, Int. J. Pharm. 98, 121– 130.
   Web of Science ®Google Scholar
• Takakura, Y. and Hashida, M. (1996) “Macromolecular carrier systems for targeted drug delivery: pharmacokinetic considerations on biodistribution”, Pharm. Res. 13, 820– 831.
   PubMed Web of Science ®Google Scholar
• Wall, D.A., Wilson, G. and Hubbard, A.L. (1980) “The Galactose- specific recognition systems of mammalian liver: the route of ligand internalization in rat hepatocytes”, Cell 21, 79– 93.
   PubMed Web of Science ®Google Scholar
• Weller, I.V.D., Carreno, V., Fowler, M.J.F., Monjardino, J., Makinen, D., Thomas, H.C. and Sherlock, S. (1982) “Acyclovir inhibits hepatitis B virus replication in man”, Lancet 1, 273.
   PubMed Web of Science ®Google Scholar
• Wu, J., Nantz, M.H. and Zern, M.A. (2002) “Targeting hepatocytes for drug and gene delivery: emerging novel approaches and appli- cations”, Front. Biosci. 7, 717– 725.
   PubMed Web of Science ®Google Scholar
• Yoshiharu, Y., Tanka, T. and Iguchi, S. (1990) “Preparation and properties of a Mitomycin C-Albumin conjugate”, Chem. Pharm. Bull. 38, 2614– 2616.
   PubMed Web of Science ®Google Scholar
• Zoulim, F. and Trepo, C. (1994) “Nucleoside analogs in the treatment of chronic viral hepatitis. Efficiency and complications”, J. Hepatol. 21, 142– 144.
   PubMed Web of Science ®Google Scholar