Preparation and evaluation of galactosylated vesicular carrier for hepatic targeting of silibinin

References

• Berg T, Boman D. (1973). Distribution of lysosomal enzymes between parenchymal and Kupffer cells of rat liver. Biochim Biophys Acta, 321:585–96.
   PubMed Web of Science ®Google Scholar
• Sinha J, Das N, Basu MK. (2000). Targeting of glycoside-grafted liposomes to specific hepatocellular sites. J Surf Sci Technol, 16:200–9.
   Google Scholar
• Murao A, Nishikawa M, Managit C, Wong J, Kawakami S, Yamashita F, Hashida M. (2002). Targeting efficiency of galactosylated liposomes to hepatocytes in vivo: Effect of lipid composition. Pharm Res, 19(12):1808–14.
   PubMed Web of Science ®Google Scholar
• Hara T, Ishihara H, Aramaki Y, Tsuchiya S. (1988). Specific uptake of asialofetuin-labeled liposomes by isolated hepatocytes. Int J Pharm, 42:69–75.
   Google Scholar
• Tsuchiya S, Aramaki Y, Hara T, Hoshi K, Okada A. (1986). Preparation and disposition of asialofetuin labeled liposomes. Biopharm Drug Dispos, 7:549–8.
   PubMed Web of Science ®Google Scholar
• Wu J, Liu P, Zhu JL, Maddukuri S, Zern MA. (1998). Increased liver uptake of liposomes and improved targeting efficacy by labeling with asialofetuin in rodents. Hepatology, 27:772–8.
   PubMed Web of Science ®Google Scholar
• Spanjer HH, Scherphof GL. (1983). Targeting of lactosylceramide-containing liposomes to hepatocytes in vivo. Biochim Biophys Acta, 734:40–7.
   PubMed Web of Science ®Google Scholar
• Ghosh PC, Bachhawat BK. (1991). Targeting of liposomes to hepatocytes. Targeted Diagn Ther, 4:87–103.
   PubMedGoogle Scholar
• Murahashi N, Ishihara H, Sasaki A, Sakagami M, Hamana H. (1997). Hepatic accumulation of glutamic acid branched neogalactosyllipid modified liposomes. Biol Pharm Bull, 20:259–66.
   PubMed Web of Science ®Google Scholar
• Kawakami S, Yamashita F, Nishikawa M, Takakura Y, Hashida M. (1998). Asialoglycoprotein receptor-mediated gene transfer using novel galactosylated cationic liposomes. Biochem Biophys Res Commun, 252:78–83.
   PubMed Web of Science ®Google Scholar
• Kawakami S, Fumoto S, Nishikawa M, Yamashita F, Hashida M. (2000). In vivo gene delivery to the liver using novel galactosylated cationic liposomes. Pharm Res, 17:306–13.
   PubMed Web of Science ®Google Scholar
• Kawakami S, Wong J, Sato A, Hattori Y, Yamashita F, Hashida M. (2000). Biodistribution characteristics of mannosylated, fucosylated and galactosylated liposomes in mice. Biochim Biophys Acta, 1524:258–65.
   PubMed Web of Science ®Google Scholar
• Nag A, Ghosh PC. (1999). Assessment of targeting potential of galactosylated and mannosylated sterically stabilized liposomes to different cell types of mouse liver. J Drug Target, 6:427–38.
   PubMed Web of Science ®Google Scholar
• Yamamoto M, Ichinose K, Ishii N, Khoji T, Akiyoshi K, Moriguchi N, . (2000). Utility of liposomes coated with polysaccharide bearing 1-amino-lactose as targeting chemotherapy for AH66 hepatoma cells. Oncol Rep, 7:107–11.
   PubMed Web of Science ®Google Scholar
• Hattori Y, Kawakami S, Yamashita F, Hashida M. (2000). Controlled biodistribution of galactosylated liposomes and incorporated probucol in hepatocyte-selective drug targeting. J Control Release, 69:369–77.
   PubMed Web of Science ®Google Scholar
• Managit C, Kawakami S, Nishikawa M, Yamashita F, Hashida M. (2003). Targeted and sustained drug delivery using PEGylated galactosylated liposomes. Int J Pharm, 266:77–84.
   PubMed Web of Science ®Google Scholar
• Wang S, Deng Y, Xu H, Wu H, Qiu Y, Chen D. (2006). Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin. Eur J Pharm Biopharm, 62:32–8.
   PubMed Web of Science ®Google Scholar
• Han JH, Oh YK, Kim DS, Kim CK. (1999). Enhanced hepatocyte uptake and liver targeting of methotrexate using galactosylated albumin as a carrier. Int J Pharm, 188:39–47.
   PubMed Web of Science ®Google Scholar
• Kawakami S, Munakata C, Fumoto S, Yamashita F, Hashida M. (2001). Novel galactosylated liposomes for hepatocyte-selective targeting of lipophilic drugs. J Pharm Sci, 90:105–13.
   PubMed Web of Science ®Google Scholar
• Behari JR, Nihal M. (2000). Galactosylated liposomes as carriers for targeting meso-2,3-dimercaptosuccinic acid to cadmium storage sites in cadmium exposed mice. Ind Health, 38:408–12.
   PubMed Web of Science ®Google Scholar
• Mandal AK, Das N. (2005). Sugar coated liposomal flavonoid: A unique formulation in combating carbontetrachloride induced hepatic oxidative damage. J Drug Target, 13(5):305–15.
   PubMed Web of Science ®Google Scholar
• Flora K, Hahn M, Rosen H, Benner K. (1998). Milk thistle (Silybum marianum) for the therapy of liver diseases. Am J Gastroenterol, 93:139–43.
   PubMed Web of Science ®Google Scholar
• Valenzuela A, Garrido A. (1994). Biochemical bases of the pharmacological action of the flavonoid silymarin and its structural isomer silibinin. Biol Res, 27:105–12.
   PubMed Web of Science ®Google Scholar
• Morazzoni P, Bombardelli E. (1999). Silybum marianum (Carduus marianus). Fitoterapia, 66:3–42.
   Google Scholar
• Skottová N, Krěcman V. (1998). Dietary silymarin improves removal of low density lipoproteins by the perfused rat liver. Acta Univ Palacki Olomuc Fac Med, 141:39–40.
   PubMedGoogle Scholar
• Skottová N, Krěcman V, Šimánek V. (1999). Activities of silymarin and its flavonolignans upon low density lipoprotein oxidizability in vitro. Phytother Res, 13:535–7.
   PubMed Web of Science ®Google Scholar
• Basaga H, Poli G, Tekkaya C, Aras I. (1997). Free radical scavenging and antioxidative properties of ‘silibin’ complexes on microsomal lipid peroxidation. Cell Biochem Funct, 15:27–33.
   PubMed Web of Science ®Google Scholar
• Skottová N, Krěcman V, Váňa P, Chmela Z, Ulrichová J, Šimánek V. (2000). Effect of silymarin and silibinin-phosphatidylcholine complex on plasma and lipoprotein cholesterol, and oxidation of LDL in rats fed on high cholesterol diet supplemented with currant oil. Acta Univ Palacki Olomuc Fac Med, 144:55–8.
   Google Scholar
• El-Samaligy MS, Afifi NN, Mahmoud EA. (2006). Evaluation of hybrid liposomes-encapsulated silymarin regarding physical stability and in vivo performance. Int J Pharm, 319:121–9.
   PubMed Web of Science ®Google Scholar
• Ghosh P, Bachawat BK. (1980). Grafting of different glycosides on the surface of liposomes and its effect on tissue distribution of I-labelled globulin encapsulated liposomes. Biochim. Biophys Acta, 632:562–72.
   PubMed Web of Science ®Google Scholar
• New RRC. (1990). Introduction and preparation of liposomes. In: New RRC, ed. Liposomes: A practical approach, Oxford: Oxford University Press, 1–32.
   Google Scholar
• Fry DW, White JC, Goldman ID. (1978). Rapid separation of low molecular weight solutes from liposomes without dilution. Anal Biochem, 90:809–15.
   PubMed Web of Science ®Google Scholar
• Maheshwari H, Agarwal R, Patil C, Katare OP. (2003). Preparation and pharmacological evaluation of silibinin liposomes. Arzneim-Forsch./Drug Res, 53:420–7.
   PubMed Web of Science ®Google Scholar
• Vyas SP, Katare YK, Mishra V, Sihorkar V. (2000). Ligand directed macrophage targeting of Amphotericin B loaded liposomes. Int J Pharm, 210:1–14.
   PubMed Web of Science ®Google Scholar
• Zhao A, Agrawal R. (1999). Tissue distribution of silibinin, the major active constituent of silymarin, in mice and its association with enhancement of phase II enzymes: Implications in cancer chemoprevention. Carcinogenesis, 20:2101–8.
   PubMed Web of Science ®Google Scholar
• Khatri K, Rawat A, Mahor S, Gupta PN, Vyas SP. (2005). Hepatitis B surface protein docked vesicular carrier for site specific delivery to liver. J Drug Target, 13(6):359–66.
   PubMed Web of Science ®Google Scholar
• Saraf S, Dixit VK. (1991). Hepatoprotective activity of Tridax procumbens – Part II. Fitoterapia, 11(6):534–6.
   Google Scholar
• Moribe K, Maruyama K, Iwatsuru M. (2000). Spectroscopic investigation of the molecular state of nystatin encapsulated in liposomes. Int J Pharm, 201:37–49.
   PubMed Web of Science ®Google Scholar
• Gabetta B, Bombardelli E, Pifferi G. (1988). Complexes of flavanolignans with phospholipids, preparation thereof and associated pharmaceutical compositions, US patent no. 4,764,508,16
   Google Scholar
• Comoglio A, Tomasi A, Malandrino S, Poli G, Albano E. (1995). Scavenging effect of silipide, a new silybin-phospholipid complex on ethanol-derived free radicals. Biochem Pharm, 50:1313–6.
   PubMed Web of Science ®Google Scholar
• Ahsan F, Rivas IP, Khan MA, Suarez AIT. (2002). Targeting to macrophages: Role of physicochemical properties of particulate carriers—liposomes and microspheres—on the phagocytosis by macrophages. J Control Release, 79:29–40.
   PubMed Web of Science ®Google Scholar
• Datta N, Mukherjee S, Das L, Das PK. (2003). Targeting of immunostimulatory DNA cures experimental visceral leishmaniasis through nitric oxide upregulation and T-cell activation. Eur J Immunol, 33:1508–18.
   PubMed Web of Science ®Google Scholar
• Pagano RE, Weinstein JN. (1978). Interactions of liposomes with mammalian cells. Ann Rev Biophys Bioeng, 7:435–68.
   PubMedGoogle Scholar
• Garcon N, Gregoriadis G, Taylor M, Summerfield J. (1988). Mannose-mediated targeted immunoadjuvant action of liposomes. Immunology, 64(4):743–5.
   PubMed Web of Science ®Google Scholar
• Medda S, Mukherjee S, Das N, Naskar K, Mahato SB, Basu MK. (1993). Sugar-coated liposomes: A novel delivery system for increased drug efficacy and reduced drug toxicity. Biotechnol Appl Biochem, 17:37–47.
   PubMed Web of Science ®Google Scholar
• Raay B, Medda S, Mukhopadhyay S, Basu MK. (1999). Targeting of piperine intercalated in mannose-coated liposomes in experimental leishmaniasis. Indian J Biochem Biophys, 36(4):248–51.
   PubMed Web of Science ®Google Scholar