Carrier-mediated delivery of 9-(2-phosphonylmethoxyethyl)adenine to parenchymal liver cells: A novel therapeutic approach for hepatitis B

Antimicrobial Agents and Chemotherapy

Volumn 44, Issue 3, 2000, Pages 477-483

  De Vrueh, Remco L A ^a   Rump, Erik T ^a   Van De Bilt, Erika ^a   Van Veghel, Richard ^a   Balzarini, Jan ^b   Biessen, Erik A L ^a   Van Berkel, Theo J C ^a   Bijsterbosch, Martin K ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ADEFOVIR; CHOLESTEROL OLEATE; DRUG CARRIER; HIGH DENSITY LIPOPROTEIN; LACTOSE; M PROTEIN; PHOSPHATIDYLCHOLINE; PRODRUG; TRITIUM;

ARTICLE; CELL FRACTIONATION; DRUG BINDING; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG STRUCTURE; DRUG UPTAKE; HEPATITIS B; HUMAN; LIVER PARENCHYMA; NONHUMAN; PH; PRIORITY JOURNAL;

ADENINE; ANIMALS; ANTIVIRAL AGENTS; CHROMATOGRAPHY; DRUG CARRIERS; HEPATITIS B; LIPOPROTEINS, HDL; LITHOCHOLIC ACID; LIVER; MALE; PHOSPHONIC ACIDS; PRODRUGS; RATS; RATS, WISTAR; TISSUE DISTRIBUTION; TRITIUM;

EID: 0034001854     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.44.3.477-483.2000     Document Type: Article

References (39)

1. Aduma, P., M. C. Connelly, R. V. Srinivas, and A. Fridland. 1995. Metabolic diversity and antiviral activities of acyclic nucleoside phosphonates. Mol. Pharmacol. 47:816-822.
2. Annaert, P., J. Van Gelder, L. Naesens, E. De Clercq, G. Van den Mooter, R. Kinget, and P. Augustijns. 1998. Carrier mechanisms involved in the transepithelial transport of bis(POM)-PMEA and its metabolites across Caco-2 monolayers. Pharm. Res. 15:1168-1173.
3. Ashwell, G., and J. Harford. 1982. Carbohydrate-specific receptors of the liver. Ann. Rev. Biochem. 51:531-554.
4. Balzarini, J., Z. Hao, P. Herdewijn, D. G. Johns, and E. De Clercq. 1991 Intracellular metabolism and mechanism of anti-retrovirus action of 9-(2-phosphonylmethoxyethyl)adenine, a potent anti-human immunodeficiency virus compound. Proc. Natl. Acad. Sci. USA 88:1499-1503.
5. Balzarini, J., S. Hatse, L. Naesens, and E. De Clercq. 1998. Selection and characterization of murine leukemia L1210 cells with high-level resistance to the cytostatic activity of the acyclic nucleoside phosphonate 9-(2-phosphonylmethoxyethyl)adenine (PMEA). Biochim. Biophys. Acta 1402:29-38.
6. Beasley, R. P. 1988. Hepatitis B virus. The major etiology of hepatocellular carcinoma. Cancer 61:1942-1956.
7. Biessen, E. A., H. F. Bakkeren, D. M. Beuting, J. Kuiper, and T. J. Van Berkel. 1994. 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.
8. Bijsterbosch, M. K., A. M. Duursma, J. M. Bouma, and M. Gruber. 1981. The plasma volume of the Wistar rat in relation to the body weight. Experientia 37:381-382.
9. Bijsterbosch, M. K., and T. J. Van Berkel. 1991. Lactosylated high density lipoprotein: a potential carrier for the site-specific delivery of drugs to parenchymal liver cells. Mol. Pharmacol. 41:404-411.
10. Bijsterbosch, M. K., L. J. Smeijsters, and T. J. Van Berkel. 1998. Disposition of the acyclic nucleoside phosphonate (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine. Antimicrob. Agents Chemother. 42:1146-1150.
11. Bischofberger, N., M. J. Hitchcock, M. S. Chen, D. B. Barkhimer, K. C. Cundy, K. M. Kent, S. A. Lacy, W. A. Lee, Z. H. Li, D. B. Mendel, D. F. Smee, and J. L. Smith. 1994. 1-[((S)-2-Hydroxy-2-oxo-1,4,2-dioxaphosphorinan-5-yl)methyl] cytosine, an intracellular prodrug for (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl)cytosine with improved therapeutic index in vivo. Antimicrob. Agents Chemother. 38:2387-2391.
12. Caster, W. O., A. B. Simon, and W. D. Armstrong. 1955. Evans Blue space in tissues of the rat. Am. J. Physiol. 183:317-321.
13. Cihlar, T., I. Rosenberg, I. Votruba, and A. Holy. 1995 Transport of 9-(2-phosphonomethoxyethyl)adenine across plasma membrane of HeLa S3 cells is protein mediated. Antimicrob. Agents Chemother. 39:117-124.
14. Connelly, M. C., B. L. Robbins, and A. Fridland. 1993. Mechanism of uptake of the phosphonate analog (S)-1-(3-hydroxy-2-phosphonylmethoxypropyl) cytosine (HPMPC) in Vero cells. Biochem. Pharmacol. 46:1053-1057.
15. Cundy, K. C., J. A. Fishback, J.-P. Shaw, M. L. Lee, K. F. Soike, G. C. Visor, and W. A. Lee. 1994. Oral bioavailability of the antiretroviral agent 9-(2-phosphonylmethoxyethyl)adenine (PMEA) from three formulations of prodrug Bis(pivaloyloxymethyl)-PMEA in fasted male cynomolgus monkeys. Pharm. Res. 11:839-843.
16. Cundy, K. C., B. G. Petty, J. Flaherty, P. E. Fisher, M. A. Polis, M. Wachsman, P. S. Lietman, J. P. Lalezari, M. J. Hitchcock, and H. S. Jaffe. 1995. Clinical pharmacokinetics of cidofovir in human immunodeficiency virus-infected patients. Antimicrob. Agents Chemother. 39:1247-1252.
17. De Duve, C., B. C. Pressman, R. Gianetto, R. Wattiaux, and F. Appelmans. 1955. Tissue fractionation studies. 6. Intracellular distribution patterns of enzymes in rat liver tissue. Biochem. J. 60:604-617.
18. De Vrueh, R. L., E. T. Rump, L. A. Sliedregt, E. A. Biessen, T. J. Van Berkel, and M. K. Bijsterbosch. 1999. Synthesis of a lipophilic prodrug of 9-(2-phosphonylmethoxyethyl)adenine (PMEA) and its incorporation into a hepatocyte-specific lipidic carrier. Pharm. Res. 16:1179-1185.
19. Hoard, D. E., and D. G. Ott. 1965. Conversion of mono and oligodeoxyribonucleotides to 5′-triphosphates. J. Am. Chem. Soc. 87:1785-1788.
20. Holy, A., and I. Rosenberg. 1987. Synthesis of 9-(2-phosphonylmethoxyethyl)adenine and related compounds. Collect. Czech. Chem. Commun. 52: 2801-2809.
21. Honkoop, P., H. G. Niesters, R. A. De Man, A. D. Osterhaus, and S. W. Schalm. 1997. Lamivudine resistance in immunocompetent chronic hepatitis B. J. Hepatol. 26:1393-1395.
22. Kolb-Bachofen, V., J. Schlepper-schafer, W. Vogell, and H. Kolb. 1982. Electronmicroscopic evidence for a asialoglycoprotein receptor on Kupffer cells: localization of lectin-mediated endocytosis. Cell 29:859-866.
23. Lai, C. L., C. K. Ching, K. M. Tung, E. Li, J. Young, A. Hill, C. Y. Wong, J. Dent, and P. C. Wu. 1997. Lamivudine is effective in surpressing hepatitis B virus DNA in Chinese hepatitis B surface antigen carriers: a placebo-controlled trial. Hepatology 25:241-244.
24. Ling, R., D. Multimer, M. Ahmed, E. H. Boxall, E. Elias, G. M. Dusheiko, and T. J. Harrison. 1996. Selection of mutations in the hepatitis B virus polymerase during therapy of transplant recipients with lamivudine. Hepatology 24:711-713.
25. Lowry, O. H., N. J. Rosebrough, A. L. Farr, and R. J. Randall. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193:265-275.
26. Myers, B. M., P. S. Tietz, J. E. Tarara, and N. F. LaRusso. 1995. Dynamic measurements of the acute and chronic effects of lysosomotropic agents on hepatocyte lysosomal pH using flow cytometry. Hepatology 22:1519-1526.
27. Naesens, L., J. Balzarini, and E. De Clercq. 1992. Pharmacokinetics in mice of the anti-retrovirus agent 9-(2-phosphonylmethoxyethyl)adenine. Drug Metab. Dispos. 20:747-752.
28. Nagelkerke, J. F., K. P. Barto, and T. J. Van Berkel. 1983. In vivo and in vitro uptake and degradation of acetylated low density lipoprotein by rat liver endothelial, Kupffer and parenchymal liver cells. J. Biol. Chem. 263:12221-12227.
29. Nicoll, A. J., D. L. Colledge, J. J. Toole, P. W. Angus, R. A. Smallwood, and S. A. Locarnini. 1998. Inhibition of duck hepatitis B virus replication by 9-(2-phosphonylmethoxyethyl)adenine, an acyclic phosphonate nucleoside analogue. Antimicrob. Agents Chemother. 42:3130-3135.
30. Pisoni, R. L., and J. G. Thoene. 1989. Detection and characterization of a nucleoside transport system in human fibroblast lysosomes. J. Biol. Chem. 264:4850-4856.
31. Pittman, R. C., C. K. Glass, D. Atkinson, and D. M. Small. 1987. Synthetic high density lipoprotein particles. J. Biol. Chem. 262:2435-2442.
32. Rensen, P. C., R. L. De Vrueh, and T. J. Van Berkel. 1996. Targeting hepatitis B therapy to the liver: clinical pharmacokinetic considerations. Clin. Pharmacokinet. 31:131-155.
33. Schouten, D., M. van der Kooij, J. Muller, M. N. Pieters, M. K. Bijsterbosch, and T. J. Van Berkel. 1993. Development of lipoprotein-like lipid particles for drug targeting: neo-high density lipoproteins. Mol. Pharmacol. 44:486-492.
34. Shaw, J.-P., M. S. Louie, V. V. Krishnamurthy, M. N. Arimilli, R. J. Jones, A. M. Bidgood, W. A. Lee, and K. C. Cundy. 1997. Pharmacokinetics and metabolism of selected prodrugs of PMEA in rats. Drug Metab. Dispos. 25:362-366.
35. Smeijsters, L. J., H. Nieuwenhuijs, R. C. Hermsen, G. M. Dorrestein, F. F. Franssen, and J. P. Overdulve. 1996. Antimalarial and toxic effects of the acyclic nucleoside phosphonate (S)-9-(3-hydroxy-2-phosphonylmethoxypropyl)adenine in Plasmodium berghei-infected mice. Antimicrob. Agents Chemother. 40:1584-1588.
36. Van Berkel, T. J., C. J. Dekker, J. K. Kruijt, and H. G. Van Eijk. 1987. The interaction in vivo of transferrin and asialotransferrin with liver cells. Biochem. J. 243:715-722.
37. Wong, D. K., A. M. Cheung, K. O'Rourke, C. D. Naylor, A. S. Detsky, and J. Heathcote. 1993. Effect of alpha-interferon treatment in patients with hepatitis B e antigen-positive chronic hepatitis B. Ann. Intern. Med. 119: 312-323.
38. Xiong, X., C. Flores, J. J. Toole, and C. S. Gibbs. 1998. Mutations in hepatitis B DNA polymerase associated with resistance to lamivudine do not confer resistance to adefovir in vitro. Hepatology 28:1669-1673.
39. Yokota, T., S. Mochizuki, K. Konno, S. Mori, S. Shigeta, and E. De Clercq. 1991. Inhibitory effects of selected antiviral compounds on human hepatitis B virus DNA synthesis. Antimicrob. Agents Chemother. 35:394-397.