Specific targeting of a lipophilic prodrug of iododeoxyuridine to parenchymal liver cells using lactosylated reconstituted high density lipoprotein particles

Biochemical Pharmacology

Volumn 52, Issue 1, 1996, Pages 113-121

  Bijsterbosch, Martin K ^a   Van De Bilt, Hendrika ^a   Van Berkel, Theo J C ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

antivirals; asialoglycoprotein receptor; hepatitis B; parenchymal liver cells; reconstituted lipoproteins; selective drug delivery

Indexed keywords

ANTIVIRUS AGENT; ASIALOFETUIN; CHOLESTEROL; CHOLESTEROL OLEATE; DIOLEOYL IDOXURIDINE; DRUG CARRIER; HIGH DENSITY LIPOPROTEIN; IDOXURIDINE; LACTOSE; PHOSPHATIDYLCHOLINE; PRODRUG; RADIOISOTOPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CELL FRACTIONATION; CELL ISOLATION; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG TARGETING; DRUG TISSUE LEVEL; DRUG UPTAKE; INTRAVENOUS DRUG ADMINISTRATION; KUPFFER CELL; LIPOPHILICITY; LIVER CELL; LIVER PARENCHYMA; LYSOSOME; MALE; NONHUMAN; PRIORITY JOURNAL; PROTEIN MODIFICATION; RAT; TISSUE SPECIFICITY;

EID: 0029952026     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(96)00170-0     Document Type: Article

References (37)

1. Poznanski MJ and Juliano RL, Biological approaches to the controlled delivery of drugs: a critical review. Pharmacol Rev 36: 278-336, 1984.
2. Meijer DKF, Jansen RW and Molema G, Drug targeting systems for antiviral agents: options and limitations. Antiviral Res 18: 215-258, 1992.
3. Ashwell G and Harford J, Carbohydrate-specific receptors of the liver. Ann Rev Biochem 51: 531-554, 1982.
4. Spies M, The asialoglycoprotein receptor: a model for endocytic transport receptors. Biochemistry 29: 10009-10018, 1990.
5. Kolb-Bachofen V, Schlepper-Schafer J and Vogell W, Electronmicroscopic evidence for a asialoglycoprotein receptor on Kupffer cells: localization of lectin-mediated endocytosis. Cell 29: 859-866, 1982.
6. Biessen EAL, Bakkeren HF, Beuting DM, Kuiper J and van Berkel ThJC, Ligand size is a major determinant of high affinity binding of fucose- and galactose-exposing (lipo)proteins by the hepatic fucose receptor. Biochem J 299: 291-296, 1994.
7. Hoyle GW and Hill RL, Molecular cloning and sequencing of a cDNA for a carbohydrate binding receptor unique to rat Kupffer cells. J Biol Chem 263: 7487-7492, 1988.
8. Kuiper J, Bakkeren HF, Biessen EAL and van Berkel ThJC, Characterization of the interaction of galactose-exposing particles with rat Kupffer cells. Biochem J 299: 285-290, 1994.
9. Bijsterbosch MK, Ziere GJ and van Berkel ThJC, Lactosylated low density lipoprotein: a potential carrier for the site-specific delivery of drugs to Kupffer cells. Mol Pharmacol 36: 484-489, 1989.
10. Bijsterbosch MK and van Berkel ThJC, Lactosylated high density lipoprotein: a potential carrier for the site-specific delivery of drugs to parenchymal liver cells. Mol Pharmacol 41: 404-411, 1992.
11. Counsell RE and Pohland RC, Lipoproteins as potential site-specific delivery systems for diagnostic and therapeutic agents. J Med Chem 25: 1115-1120, 1982.
12. Samadi-Baboli M, Favre G, Canal P and Soula G, Low density lipoprotein for cytotoxic drug targeting: improved activity of elliptinium derivative against B16 melanoma in mice. Br J Cancer 68: 319-326, 1993.
13. Bijsterbosch MK and van Berkel ThJC, Native and modified lipoproteins as drug delivery systems. Adv Drug Delivery Rev 5: 231-251, 1990.
14. Firestone RA, Low density lipoprotein as a vehicle for targeting antitumor compounds to cancer cells. Bioconjugate Chem 5: 105-113, 1994.
15. Jansen RW, Kruijt JK, van Berkel ThJC and Meijer DKF, Coupling of the antiviral drug Ara-AMP to lactosaminated albumin leads to specific uptake in rat and human hepatocytes. Hepatology 18: 146-152, 1993.
16. Biessen EAL, Beuting DM, Vietsch H, Bijsterbosch MK and van Berkel ThJC, Specific targeting of the antiviral drug 5-iodo-2′-deoxyuridine to the parenchymal liver cell using lactosylated poly-L-lysine. J Hepatology 21: 806-815, 1994.
17. Ponzetto A, Fiume L, Foranzi B, Song SY, Busi C, Mattioli A, Spinelli C, Marinelli M, Smedile A, Chiaberge E, Bonini F, Gervasi GB, Rapicetta M and Verme G, Adenine arabinoside monophosphate and acyclovir monophosphate coupled to lactosaminated albumin reduce woodchuck hepatitis virus viremia at doses lower than do the unconjugated drugs. Hepatology 44: 16-24, 1991.
18. Schouten D, van der Kooij M, Muller J, Pieters MN, Bijsterbosch MK and van Berkel ThJC, Development of lipoprotein-like lipid particles for drug targeting: Neo-high density lipoproteins. Mol Pharmacol 44: 486-492, 1993.
19. Prusoff WH and Goz B, Potential mechanisms of action of antiviral agents. Fed Proc 32: 1679-1687, 1974.
20. Santos O, Pant KD, Blank EW and Ceriani RL, 5-lododeoxy-uridine increases the efficacy of the radioimmunotherapy of human tumors growing in nude mice. J Nucl Med 33: 1530-1534, 1992.
21. Bijsterbosch MK, Schouten D and van Berkel ThJC, Synthesis of the dioleoyl derivative of iododeoxyuridine and its incorporation into reconstituted high density lipoprotein particles. Biochemistry 33: 14073-14080, 1994.
22. Sinkula AA and Yalowski SH, Rationale for design of biologically reversible drug derivatives: Prodrugs. J Pharm Sci 64: 181-210, 1975.
23. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ, Protein measurement with the Folin phenol reagent. J Biol Chem 193: 265-275, 1951.
24. Spiro RG, Analysis of sugars found in glycoproteins. Meth Enzymol 8: 3-26, 1966.
25. Nagelkerke JF, Bakkeren HF, Kuipers HF, Vonk RJ and van Berkel ThJC, Hepatic processing of the cholesteryl ester from low density lipoprotein in the rat. J Biol Chem 261: 8908-8913, 1986.
26. Caster WO, Simons AB and Armstrong WD, Evans blue space in tissues of the rat. Am J Physiol 183: 317-321, 1955.
27. Nagelkerke JF, Barto KP and van Berkel ThJC, In vivo and in vitro uptake and degradation of acetylated low density lipoprotein by rat liver endothelial, Kupffer and parenchymal cells. J Biol Chem 263: 12221-12227, 1983.
28. De Duve C, Pressman BC, Gianetto R, Wattiaux R and Appelmans F, Tissue fractionation studies. 6. Intracellular distribution patterns of enzymes in rat liver tissue. Biochem J 60: 604-617, 1955.
29. Gray GR, The direct coupling of oligosaccharides to proteins and derivatized gels. Arch Biochem Biophys 163: 426-428, 1974.
30. Van Berkel ThJC, De Rijke Y and Kruijt JK, Different fate in vivo of oxidatively modified low density lipoprotein and acetylated low density lipoprotein in rats. J Biol Chem 266: 2282-2289, 1991.
31. Van Berkel ThJC, Dekker CJ, Kruijt JK and van Eijk HG, The interaction in vivo of transferrin and asialofetuin with liver cells. Biochem J 243: 715-722, 1987.
32. Bijsterbosch MK and van Berkel ThJC, Uptake of lactosylated low density lipoprotein by galactose-specific receptors in rat liver. Biochem J 270: 233-239, 1990.
33. Bijsterbosch MK, Bernini F, Bakkeren HF, Gotto Jr AM, Smith LC and van Berkel ThJC, Enhanced hepatic uptake and processing of cholesterol esters from LDL by specific lactosaminated Fab fragments. Arterioscler Thromb 11: 1806-1813, 1991.
34. Bijsterbosch MK, Bakkeren HF, Kempen HJM, Roelen HCPF, van Boom JH and van Berkel ThJC, A monogalactosylated cholesterol derivative that specifically induces uptake of LDL by the liver. Arterioscler Thromb 12: 1153-1160, 1992.
35. Holtzman E, Lysosomes. Plenum Press, New York and London, 1989.
36. Burton R, Eck CD and Lloyd JB, The permeability properties of rat liver lysosomes to nucleosides. Biochem Soc Trans 3: 1251-1253, 1975.
37. Wilcoxon F, Individual comparisons by ranking methods. Biom Bull 1: 80-83, 1945.