Sustained liver targeting and improved antiproliferative effect of doxorubicin liposomes modified with galactosylated lipid and PEG-lipid

AAPS PharmSciTech

Volumn 11, Issue 2, 2010, Pages 870-877

  Wang, Shaoning ^a   Xu, Hui ^a   Xu, Jinghua ^a   Zhang, Ying ^a   Liu, Yingchun ^a   Deng, Yi Hui ^a   Chen, Dawei ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Antitumor; Cleavable PEG lipid; Doxorubicin; Galactosylated lipsomes; Sustained liver targeting

Indexed keywords

[(5 CHOLESTEN 3BETA YL) 4 OXO 4 [2 (LACTOBIONYL AMIDO)ETHYLAMIDO]BUTANOATE]; AMMONIUM SULFATE; CHOLESTEROL DERIVATIVE; DOXORUBICIN; LIPOSOME; MACROGOL 2000; UNCLASSIFIED DRUG; ANTINEOPLASTIC ANTIBIOTIC; DELAYED RELEASE FORMULATION; GALACTOSE; LIPID; MACROGOL DERIVATIVE;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CELLULAR DISTRIBUTION; CONTROLLED STUDY; DRUG FORMULATION; DRUG TARGETING; FEMALE; IN VIVO STUDY; LIVER CELL; MOUSE; NONHUMAN; PARTICLE SIZE; PRIORITY JOURNAL; TUMOR VOLUME; ADMINISTRATION AND DOSAGE; ANIMAL; CARCINOMA, HEPATOCELLULAR; CELL PROLIFERATION; CHEMISTRY; DELAYED RELEASE FORMULATION; DRUG EFFECTS; LIVER; LIVER NEOPLASMS; METABOLIC CLEARANCE RATE; METABOLISM; PATHOLOGY; PHARMACOKINETICS; PROCEDURES; SYNTHESIS; TISSUE DISTRIBUTION; TUMOR CELL LINE;

ANIMALS; ANTIBIOTICS, ANTINEOPLASTIC; CARCINOMA, HEPATOCELLULAR; CELL LINE, TUMOR; CELL PROLIFERATION; DELAYED-ACTION PREPARATIONS; DOXORUBICIN; DRUG COMPOUNDING; GALACTOSE; LIPIDS; LIPOSOMES; LIVER; LIVER NEOPLASMS; METABOLIC CLEARANCE RATE; MICE; POLYETHYLENE GLYCOLS; TISSUE DISTRIBUTION;

EID: 77954819567     PISSN: None     EISSN: 15309932     Source Type: Journal    
DOI: 10.1208/s12249-010-9450-8     Document Type: Article

References (33)

1. Ashwell G, Harford J. Carbohydrate-specific receptors of the liver. Annu Rev Biochem. 1982;51:531-54.
2. Wu J, Nantz MH, Zern MA. Targeting hepatocytes for drug and gene delivery: emerging novel approaches and application. Front Biosci. 2002;7: d717-25.
3. Mandal AK, Das S, Basu MK, Chakrabarti RN, Das N. Hepatoprotective activity of liposomal flavonoid against arsenite-induced liver fibrosis. Pharmacol Exp Ther. 2007;320:994-1001.
4. Sato A, Takagi M, Shimamoto A, Kawakami S, Hashida M. Small interfering RNA delivery to the liver by intravenous administration of galactosylated cationic liposomes in mice. Biomaterials. 2007;28:1434-42.
5. Managit C, Kawakami S, Yamashita F, Hashida M. Effect of galactose density on asialoglycoprotein receptor-mediated uptake of galactosylated liposomes. J Pharm Sci. 2005;94:2266-75.
6. Murao A, Nishikawa M, Managit C, Wong J, Kawakami S, Yamashita F, et al. Targeting efficiency of galactosylated liposomes to hepatocytes in vivo: effect of lipid composition. Pharm Res. 2002;19:1808-14.
7. Wang SN, Deng YH, Xu H, Wu HB, Qiu YK, Chen DW. Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin. Eur J Pharm Biopharm. 2006;62:32-8.
8. Levy G. Targeted drug delivery-some pharmacokinetic considerations. Pharm Res. 1987;4:3-4.
9. Takino T, Koreeda N, Nomura T, Sakaeda T, Yamashita F, Takakura Y, et al. Control of plasma cholesterol-lowering action of probucol with various lipid carrier systems. Biol Pharm Bull. 1998;21:492-7.
10. Torchilin VP, Omelyanenko VG, Papisov MI, Bogdanov Jr AA, Trubetskoy VS, Herron JN, et al. Poly (ethylene glycol) on the liposome surface: on the mechanism of polymer-coated liposome longevity. Biochim Biophys Acta. 1994;1195:11-20.
11. Woodle MC, Lasic DD. Sterically stabilized liposomes. Biochim Biophys Acta. 1992;1113:171-99.
12. Maruyama K. PEG-immunoliposome. Biosci Rep. 2002;22:251-6.
13. Gosselin MA, Lee RJ. Folate receptor-targeted liposomes as vectors for therapeutic agents. Biotechnol Annu Rev. 2002;8:103-31.
14. Cattel L, Ceruti M, Dosio F. From conventional to stealth liposomes: a new frontier in cancer chemotherapy. Tumori. 2003;89:237-49.
15. Shimada K, Kamps JA, Regts J, Ikeda K, Shiozawa T, Hirota S, et al. Biodistribution of liposomes containing synthetic galactoseterminated diacylglyceryl-poly (ethyleneglycol). Biochim Biophys Acta. 1997;1326:329-41.
16. Gabizon A, Shmeeda H, Horowitz AT, Zalipsky S. Tumor cell targeting of liposome-entrapped drugs with phospholipid-anchored folic acid-PEG conjugates. Adv Drug Deliv Rev. 2004;56:1177-92.
17. Terada T, Iwai M, Kawakami S, Yamashita F, Hashida M. Novel PEG-matrix metalloproteinase-2 cleavable peptide-lipid containing galactosylated liposomes for hepatocellular carcinoma-selective targeting. J Control Release. 2006;111:333-42.
18. Xu H, Deng Y, Chen D, Hong W, Lu Y, Dong X. Esterasecatalyzed dePEGylation of pH-sensitive vesicles modified with cleavable PEG-lipid derivatives. J Control Release. 2008;130:238-45.
19. Lasic DD, Frederick PM, Stuart M C A, Barenholz Y, McIntosh TJ. Gelation of liposome interior: a novel method for drug encapsulation. FEBS Lett. 1992;312:255-8.
20. Mayer LD, Tai LC, Ko DS, Masin D, Ginsberg RS, Cullis PR, et al. Influence of vesicle size, lipid composition, and drug-to-lipid ratio on the biological activity of liposomal doxorubicin in mice. Cancer Res. 1989;49:5922-30.
21. Gupta PK, Hung CT. Quantitative evaluation of targeted drug delivery systems. Int J Pharm. 1989;56:217-26.
22. Valle JW, Dangoor A, Beech J, Sherlock DJ, Lee SM, Scarffe JH, et al. Treatment of inoperable hepatocellular carcinoma with pegylated liposomal doxorubicin (PLD): results of a phase II study. Br J Cancer. 2005;92:628-30.
23. Lind PA, Naucler G, Holm A, Gubanski M, Svensson C. Efficacy of pegylated liposomal doxorubicin in patients with advanced hepatocellular carcinoma. Acta Oncol. 2007;46:230-3.
24. Hopewel JW, Duncan R, Wilding D, Chakrabarti K. Preclinical evaluation of the cardiotoxicity of PK2: a novel HPMA copolymerdoxorubicin-galactosamine conjugate antitumour agent. Hum Exp Toxicol. 2001;20:461-70.
25. Fiume L, Baglioni M, Bolondi L, Farina C, Di Stefano G. Doxorubicin coupled to lactosaminated human albumin: a hepatocellular carcinoma targeted drug. Drug Discov Today. 2008;13:1002-9.
26. Managit C, Kawakami S, Nishikawa M, Yamashita F, Hashida M. Targeted and sustained drug delivery using PEGylated galactosylated liposomes. Int J Pharm. 2003;266:77-84.
27. D'Souza AJ, Topp EM. Release from polymeric prodrugs: linkages and their degradation. J Pharm Sci. 2004;93:1962-79.
28. Lee BS, Yuan X, Xu Q, McLafferty FS, Petersen BA, Collette JC, et al. Stimuli-responsive antioxidant nanoprodrugs of NSAIDs. Int J Pharm. 2009;372:112-4.
29. Virgolini I, Müller C, Klepetko W, Angelberger P, Bergmann H, O'Grady J, et al. Decreased hepatic function in patients with hepatoma or liver metastasis monitored by a hepatocyte specific galactosylated radioligand. Br J Cancer. 1990;61:937-41.
30. Gabizon A, Martin F. Polyethylene glycol-coated (pegylated) liposomal doxorubicin. Rationale for use in solid tumours. Drugs. 1997;54(S4):15-21.
31. Wu NZ, Da D, Rudoll TL, Needham D, Whorton AR, Dewhirst MW. Increased microvascular permeability contributes to preferential accumulation of stealth liposomes in tumor tissue. Cancer Res. 1993;53:3765-70.
32. Park JW, Hong K, Kirpotin DB, Meyer O, Papahadjopoulos D, Benz CC. Anti-HER2 immunoliposomes for targeted therapy of human tumors. Cancer Lett. 1997;118:153-60.
33. Kirpotin DB, Drummond DC, Shao Y, Shalaby MR, Hong K, Nielsen UB, et al. Antibody targeting of long-circulating lipidic nanoparticles does not increase tumor localization but does increase internalization in animal models. Cancer Res. 2006;66:6732-40.