Lipase-catalyzed Synthesis of 6-O-acyl-D-galactose Ester for Surface Modification of Cantharidin Liposomal Nanoparticles
|
摘要
[Objectives] To prepare and characterize a novel liver targeted drug carrier. [Methods] 6-O-acyl-D-galactose esters were enzymatically synthesized as a targeting molecule and incorporated into liposomes to prepare liposomal nanoparticles surface-modified with galactose. [Results] Liposomes were characterized by morphology, particle distribution size, zeta potential and encapsulating efficiency of drugs. [Conclusions] This novel approach for the liposomes surface-modifed with galactose by enzymatic synthesis is expected to provide potential application as drug carrier for active targeted delivery to hepatocytes.
[Objectives] To prepare and characterize a novel liver targeted drug carrier. [Methods] 6-O-acyl-D-galactose esters were enzymatically synthesized as a targeting molecule and incorporated into liposomes to prepare liposomal nanoparticles surface-modified with galactose. [Results] Liposomes were characterized by morphology, particle distribution size, zeta potential and encapsulating efficiency of drugs. [Conclusions] This novel approach for the liposomes surface-modifed with galactose by enzymatic synthesis is expected to provide potential application as drug carrier for active targeted delivery to hepatocytes.
[Objectives] To prepare and characterize a novel liver targeted drug carrier. [Methods] 6-O-acyl-D-galactose esters were enzymatically synthesized as a targeting molecule and incorporated into liposomes to prepare liposomal nanoparticles surface-modified with galactose. [Results] Liposomes were characterized by morphology, particle distribution size, zeta potential and encapsulating efficiency of drugs. [Conclusions] This novel approach for the liposomes surface-modifed with galactose by enzymatic synthesis is expected to provide potential application as drug carrier for active targeted delivery to hepatocytes.
引文
[1] FABIENNE D,OLIVIER F,VERONIQUE P.To exploit the tumor microenvironment:Passive and active tumor targeting of nanocarriers for anti-cancer drug delivery[J].Journal of Controlled Release,2010,148(2):135-146.
[2] ARUN KL,GREISH K,JUN F,et al.Exploiting the enhanced permeability and retention effect for tumor targeting[J].Drug Discovery Today,2006,11(17-18):812-818.
[3] DAN P,JEFFREY MK,SEUNGPYO H,et al.Nanocarriers as an emerging platform for cancer therapy[J].Nature Nanotechnology,2007,2(12):751-760.
[4] GUNASEELAN S,GUNASEELAN K,DESHMUKH M,et al.Surface modifications of nanocarriers for effective intracellular delivery of anti-HIV drugs[J].Advanced Drug Delivery Reviews,2010,62(4):518-531,2010.
[5] MAMIDYALA S,DUTTA S,CHRUNYK B,et al.Glycomimetic ligands for the human asialoglycoprotein receptor[J].Journal of the American Chemical Society,2012,134(4):1978-1981.
[6] MEIE M,BIDER M,MALASHKEVICH V,et al.Crystal structure of the carbohydrate recognition domain of the H1 subunit of the asialoglycoprotein receptor[J].Journal of Molecular Biology,2000,300(4):857-865.
[7] YOSHIE M,HIROSHI S,WAN JP,et al.Modified ethanol injection method for liposomes containing β-sitosterol β-D-glucoside[J].Journal of Liposome Research,2001,11(1):115-125.
[8] WANG S,DENG Y,XU H,et al.Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin[J].European Journal of Pharmaceutics and Biopharmaceutics,2006,62(1):32-38.
[9] BRANNON-PEPPAS L,BLANCHETTE JO.Nanoparticle and targeted systems for cancer therapy[J].Advanced Drug Delivery Reviews,2004,56(11):1649-1659.
[10] NOBS L,BUCHEGGER F,GURNY R,et al.Current methods for attaching targeting ligands to liposomes and nanoparticles[J].Journal of Pharmaceutical Sciences,2004,93(8):1980-1992.
[11] FATOUMA SH,BENOIT F,FRANCIS S.Targeted liposomes:Convenient coupling of ligands to preformed vesicles using click chemistry[J].Bioconjugate Chemistry,2006,17(3):849-854.
[12] GUO BH,CHENG Y,LIN YP,et al.Preparation and characterization of galactose-modified liposomes by a nonaqueous enzymatic reaction[J].Journal of Liposome Research,2011,21(3):255-260.
[13] CHENG Y,WU W,ZHANG D,et al.Enzyme-catalyzed synthesis of ASGPR ligand-targeted modifier in non-aqueous medium[J].Acta Pharmaceutica Sinica,2010,45(9):1134-1138.
[14] WU W,CHENG Y,GUO B,et al.Pharmacokinetics of liver-targeted docetaxel liposomes modified with 6-O-acyl-D-galactose esters in rabbits[J].Biomedical Reports,2014,2(4):545-548.
[15] SOARES C,CASTRO H,MORAES F,et al.Characterization and utilization of Candida rugosa lipase immobilized on controlled pore silica[J].Applied Biochemistry and Biotechnology,1999,79(3):745-757.
[16] PONS M,FOMDADA M,ESTELRICH J.Liposomes obtained by the ethanol injection method[J].International Journal of Pharmaceutics,1993,95(1):51-56.
[17] YIN YM,CUI FD,MU CF,et al.Docetaxel microemulsion for enhanced oral bioavailability:Preparation and in vitro and in vivo evaluation[J].Journal of Controlled Release,2009,140(2):86-94.
[2] ARUN KL,GREISH K,JUN F,et al.Exploiting the enhanced permeability and retention effect for tumor targeting[J].Drug Discovery Today,2006,11(17-18):812-818.
[3] DAN P,JEFFREY MK,SEUNGPYO H,et al.Nanocarriers as an emerging platform for cancer therapy[J].Nature Nanotechnology,2007,2(12):751-760.
[4] GUNASEELAN S,GUNASEELAN K,DESHMUKH M,et al.Surface modifications of nanocarriers for effective intracellular delivery of anti-HIV drugs[J].Advanced Drug Delivery Reviews,2010,62(4):518-531,2010.
[5] MAMIDYALA S,DUTTA S,CHRUNYK B,et al.Glycomimetic ligands for the human asialoglycoprotein receptor[J].Journal of the American Chemical Society,2012,134(4):1978-1981.
[6] MEIE M,BIDER M,MALASHKEVICH V,et al.Crystal structure of the carbohydrate recognition domain of the H1 subunit of the asialoglycoprotein receptor[J].Journal of Molecular Biology,2000,300(4):857-865.
[7] YOSHIE M,HIROSHI S,WAN JP,et al.Modified ethanol injection method for liposomes containing β-sitosterol β-D-glucoside[J].Journal of Liposome Research,2001,11(1):115-125.
[8] WANG S,DENG Y,XU H,et al.Synthesis of a novel galactosylated lipid and its application to the hepatocyte-selective targeting of liposomal doxorubicin[J].European Journal of Pharmaceutics and Biopharmaceutics,2006,62(1):32-38.
[9] BRANNON-PEPPAS L,BLANCHETTE JO.Nanoparticle and targeted systems for cancer therapy[J].Advanced Drug Delivery Reviews,2004,56(11):1649-1659.
[10] NOBS L,BUCHEGGER F,GURNY R,et al.Current methods for attaching targeting ligands to liposomes and nanoparticles[J].Journal of Pharmaceutical Sciences,2004,93(8):1980-1992.
[11] FATOUMA SH,BENOIT F,FRANCIS S.Targeted liposomes:Convenient coupling of ligands to preformed vesicles using click chemistry[J].Bioconjugate Chemistry,2006,17(3):849-854.
[12] GUO BH,CHENG Y,LIN YP,et al.Preparation and characterization of galactose-modified liposomes by a nonaqueous enzymatic reaction[J].Journal of Liposome Research,2011,21(3):255-260.
[13] CHENG Y,WU W,ZHANG D,et al.Enzyme-catalyzed synthesis of ASGPR ligand-targeted modifier in non-aqueous medium[J].Acta Pharmaceutica Sinica,2010,45(9):1134-1138.
[14] WU W,CHENG Y,GUO B,et al.Pharmacokinetics of liver-targeted docetaxel liposomes modified with 6-O-acyl-D-galactose esters in rabbits[J].Biomedical Reports,2014,2(4):545-548.
[15] SOARES C,CASTRO H,MORAES F,et al.Characterization and utilization of Candida rugosa lipase immobilized on controlled pore silica[J].Applied Biochemistry and Biotechnology,1999,79(3):745-757.
[16] PONS M,FOMDADA M,ESTELRICH J.Liposomes obtained by the ethanol injection method[J].International Journal of Pharmaceutics,1993,95(1):51-56.
[17] YIN YM,CUI FD,MU CF,et al.Docetaxel microemulsion for enhanced oral bioavailability:Preparation and in vitro and in vivo evaluation[J].Journal of Controlled Release,2009,140(2):86-94.