Self-assembly and characterization of Pluronic P105 micelles for liver-targeted delivery of silybin

References

• Ahuja N, Katare OP, Singh B. (2007). Studies on dissolution enhancement and mathematical modeling of drug release of a poorly water soluble drug using water-soluble carriers. Eur J Pharm Biopharm, 65, 26–38.
   PubMed Web of Science ®Google Scholar
• Aliabadi HM, Lavasanifar A. (2006). Polymeric micelles for drug delivery. Exp Opin Drug Deliv, 3, 139–162.
   PubMedGoogle Scholar
• Ammazzalorso A, Amoroso A, Bettoni G, De Filippis B, Giampietro L, Pierini M, Tricca ML. (2002). Asymmetric synthesis of (S)-ibuprofen by esterification with amides of (S)-lactic acid as chiral auxiliaries: experimental and theoretical results. Tetrahedron Lett, 43, 4325–4238.
   Web of Science ®Google Scholar
• Batrakova EV, Dorodnych TY, Klinskii EY, Kliushnenkova EN, Shemchukova OB, Goncharova ON, Arjakov SA, Alakhov VY, Kabanov AV. (1996). Anthracycline antibiotics non-covalently incorporated into the block copolymer micelles: in vivo evaluation of anticancer activity. Br J Cancer, 74, 1545–1552.
   PubMed Web of Science ®Google Scholar
• Batrakova EV, Kelly DL, Li S, Li Y, Yang Z, Xiao L, Alakhova DY, Sherman S, Alakhov VY, Kabanov AV. (2006). Alteration of genomic responses to doxorubicin and prevention of MDR in breast cancer cells by a polymer excipient: Pluronic P85. Mol Pharm, 3, 113–123.
   PubMed Web of Science ®Google Scholar
• Booth C, Attwood D. (2000). Effects of block architecture and composition on the association properties of poly(oxyalkylene) copolymers in aqueous solution. Macromol Rap Comm, 21, 501–527.
   Web of Science ®Google Scholar
• Booth C, Attwood D, Price C. (2006). Self-association of block copoly(oxyalkylene)s in aqueous solution. Effects of composition, block length and block architecture. Phys Chem Chem Phys, 8, 3612–3622.
   PubMed Web of Science ®Google Scholar
• Bromberg LE, Ron ES. (1998). Temperature-responsive gels and thermogelling polymer matrices for protein and peptide delivery. Adv Drug Deliv Rev, 31, 197–221.
   PubMed Web of Science ®Google Scholar
• Calmès M, Escale F, Rolland M, Martinez J. (2003). Diastereoselective esterification of (±)-N-trifluoroacetyl pipecolic acid using (S)-α-methyl pantolactone: synthesis of (S)-N-Boc pipecolic acid and (S)-N-Boc-2-piperidinemethanol. Tetrahedron Asymmetry, 14, 1685–1689.
   Web of Science ®Google Scholar
• Cao Y, Rodriguez A, Vacanti M, Ibarra C, Arevalo C, Vacanti CA. (1998). Comparative study of the use of poly(glycolic acid), calcium alginate and pluronics in the engineering of autologous porcine cartilage. J Biomater Sci Polym Ed, 9, 475–487.
   PubMed Web of Science ®Google Scholar
• Crothers M, Zhou Z, Ricardo NM, Yang Z, Taboada P, Chaibundit C, Attwood D, Booth C. (2005). Solubilisation in aqueous micellar solutions of block copoly(oxyalkylene)s. Int J Pharm, 293, 91–100.
   PubMed Web of Science ®Google Scholar
• Croy SR, Kwon GS. (2006). Polymeric micelles for drug delivery. Curr Pharm Design, 12, 4669–4684.
   PubMed Web of Science ®Google Scholar
• Gallo D, Giacomelli S, Ferlini C, Raspaglio G, Apollonio P, Prislei S, Riva A, Morazzoni P, Bombardelli E, Scambia G. (2003). Antitumour activity of the silybin–phosphatidylcholine complex, IdB 1016, against human ovarian cancer. Eur J Cancer, 39, 2403–2410.
   PubMed Web of Science ®Google Scholar
• Gao Z, Fain HD, Rapoport N. (2004). Ultrasound-enhanced tumor targeting of polymeric micellar drug carriers. Mol Pharm, 1, 317–330.
   PubMed Web of Science ®Google Scholar
• Garrec DLe, Gori S, Luo L, Lessard D, Smith DC, Yessine MA, Ranger M, Leroux JC. (2004). Poly(N-vinylpyrrolidone)-block-poly(d,l-lactide) as a new polymeric solubilizer for hydrophobic anticancer drugs: in vitro and in vivo evaluation. J Control Release, 99, 83–101.
   PubMed Web of Science ®Google Scholar
• Gazak R, Walterova D, Kren V. (2007). Silybin and silymarin—new and emerging application in medicine. Curr Med Chem, 14, 315–338.
   PubMed Web of Science ®Google Scholar
• Grindel JM, Jaworski T, Piraner O, Emanuele RM, Balasubramanian M. (2002). Distribution, metabolism, and excretion of a novel surface-active agent, purified poloxamer 188, in rats, dogs, and humans. J Pharm Sci, 91, 1936–1947.
   PubMed Web of Science ®Google Scholar
• Hammad MA, Muller BW. (1998). Solubility and stability of clonazepam in mixed micelles. Int J Pharm, 169, 55–64.
   Web of Science ®Google Scholar
• Han LM, Guo J, Zhang LJ, Wang QS, Fang XL. (2006). Pharmacokinetics and biodistribution of polymeric micelles of paclitaxel with Pluronic P123. Acta Pharmacol Sin, 27, 747–753.
   PubMed Web of Science ®Google Scholar
• Ilium L, Davis SS. (1984). The organ uptake of intravenously administered colloidal particles can be altered using a non-ionic surfactant (poloxamer 338). FEBS Lett, 167, 79–92.
   PubMed Web of Science ®Google Scholar
• Illum L, Davis SS, Mtiller RH, Mak E, West P. (1987). The organ distribution and circulation time of intravenously injected colloidal carriers sterically stabilized with a block copolymer-poloxamine 908. Life Sci, 40, 367–374.
   PubMed Web of Science ®Google Scholar
• Kabanov AV, Alkhov VY. (2002). Pluronic block copolymers in drug delivery: from micellar nanocontainers to biological response modifiers. Crit Rev Therap Drug Carrier Syst, 19, 1–72.
   PubMed Web of Science ®Google Scholar
• Kabanov AV, Ckekhonin VP, Alakhov VY, Batrakova EV, Lebedev AS, Melik-Nubarov NS, Arzhakov SA, Levashov AV, Morozov GV, Severin ES, Kabanov VA. (1989). The neuroleptic activity of haloperidol increases after its solubilization in surfactant micelles. FEBS Lett, 258, 343–345.
   PubMed Web of Science ®Google Scholar
• Kalyanasundaram K, Thomas JK. (1977). Environmental effects on vibronic band intensities in pyrene monomer fluorescence and their application in studies of micellar systems. J Am Chem Soc, 99, 2039–2044.
   Web of Science ®Google Scholar
• Kamruzzaman Selima KM, Haa Y-S, Kima S-J, Chang Y, Kim TJ, Ho Lee G, Kang IK. (2007). Surface modification of magnetite nanoparticles using lactobionic acid and their interaction with hepatocytes. Biomaterials, 28, 710–716.
   PubMed Web of Science ®Google Scholar
• Kawano K, Nakamura K, Hayashi K, Nagai T, Takayama K, Maitani Y. (2002). Liver targeting liposomes containing beta-sitosterol glucoside with regard to penetration-enhancing effect on HepG2 cells. Biol Pharm Bull, 25, 766–770.
   PubMed Web of Science ®Google Scholar
• Kibbe AH. (2000). Handbook of Pharmaceutical Excipients ( pp. 386–388). Washington, DC: American Pharmaceutical Association.
   Google Scholar
• Kren V, Walterova D. (2005). Silybin and silymarin—new effects and applications. Biomedicine, 149, 29–41.
   Google Scholar
• Kwon GS. (2003). Polymeric micelles for delivery of poorly water-soluble compounds. Crit Rev Therap Drug Carrier Syst, 20, 357–403.
   PubMed Web of Science ®Google Scholar
• Lee HJ, Ahn BN, Paik WH, Shim CK, Lee MG. (1996). Inverse targeting of reticuloendothelial system-rich organs after intravenous administration of adriamycin-loaded neutral proliposomes containing poloxamer 407 to rats. Int J Pharm, 131, 91–96.
   Web of Science ®Google Scholar
• Lee J, Cho EC, Cho K. (2004). Incorporation and release behavior of hydrophobic drug in functionalized poly(d,l-lactide)-block–poly(ethylene oxide) micelles. J Control Release, 94, 323–335.
   PubMed Web of Science ®Google Scholar
• Lee MJ, Lee MH, Shim C-K. (1995). Inverse targeting of drugs to reticuloendothelial system-rich organs by lipid microemulsion emulsified with poloxamer 338. Int J Pharm, 113, 175–187.
   Web of Science ®Google Scholar
• Li C. (2002). Poly(l-glutamic acid)-anticancer drug conjugates. Adv Drug Deliv Rev, 54, 695–713.
   PubMed Web of Science ®Google Scholar
• Litzinger DC, Buiting AMJ, Rooijen NV, Huang L. (1994). Effect of liposome size on the circulation time and intraorgan distribution of amphipathic poly(ethylene glycol)-containing liposomes. Biochim Biophys Acta, 1190, 99–107.
   PubMed Web of Science ®Google Scholar
• Maeda H, Matsumura Y. (1989). Tumoritropic and lymphotropic principles of macromolecular drugs. Crit Rev Ther Drug Carr Syst, 6, 193–210.
   PubMed Web of Science ®Google Scholar
• Maitani Y, Kawano K, Yamada K, Nagai T, Takayama K. (2001). Efficiency of liposomes surface-modified with soybean-derived sterylglucoside as a liver targeting carrier in HepG2 cells. J Control Release, 75, 381–389.
   PubMed Web of Science ®Google Scholar
• Mi F-L, Yu S-H, Peng C-K, Sungd H-W, Shyue S-S, Liangd H-F, Huangf M-F, Wange C-C. (2006). Synthesis and characterization of a novel glycoconjugated macromolecule. Polymer, 47, 4348–4358.
   Web of Science ®Google Scholar
• Nagarajan R. (1999). Solubilization of hydrocarbons and resulting aggregate shape transitions in aqueous solutions of Pluronic (PEO-PPO-PEO) block copolymers. Colloids Surf B Biointerfaces, 16, 55–72.
   Web of Science ®Google Scholar
• Nagarajan R, Ganesh K. (1996). Comparison of solubilization of hydrocarbons in (PEO-PPO) diblock versus (PEO-PPO-PEO) triblock copolymer micelles. J Colloid Interface Sci, 184, 489–499.
   PubMed Web of Science ®Google Scholar
• Park EK, Lee SB, Lee YM. (2005a). Preparation and characterization of methoxy poly(ethylene glycol)/poly(e-caprolactone) amphiphilic block copolymeric nanospheres for tumor-specific folate-mediated targeting of anticancer drugs. Biomaterials, 26, 1053–1061.
   PubMed Web of Science ®Google Scholar
• Park EK, Kim SY, Lee SB, Lee YM. (2005b). Folate-conjugated methoxy poly(ethylene glycol)/poly([var epsilon]-caprolactone) amphiphilic block copolymeric micelles for tumor-targeted drug delivery. J Control Release, 109, 158–168.
   PubMed Web of Science ®Google Scholar
• Pec EA, Wout ZG, Johnston TP. (1992). Biological activity of urease formulated in poloxamer 407 after intraperitoneal injection in the rat. J Pharm Sci, 81, 626–630.
   PubMed Web of Science ®Google Scholar
• Rapoport N. (1999). Stabilization and activation of Pluronic micelles for tumor-targeted drug delivery. Colloids Surf B Biointerfaces, 16, 93–111.
   Web of Science ®Google Scholar
• Rapoport N, Herron J, Pitt WG, Pitina L. (1999). Micellar delivery of doxorubicin and its paramagnetic analog, ruboxyl, to HL-60: effect of micelle structure and ultrasound on the intracellular drug uptake. J Control Release, 58, 153–162.
   PubMed Web of Science ®Google Scholar
• Rapoport N, Marin A, Christensen D. (2002a). Ultrasound activated micellar drug delivery. Drug Deliv Syst Sci, 2, 37–46.
   Google Scholar
• Rapoport N, Marin A, Luo Y, Prestwich GD, Muniruzzaman MD. (2002b). Intracellular uptake and trafficking of Pluronic micelles in drug-sensitive and MDR cells: effect on the intracellular drug localization. J Pharm Sci, 91, 157–170.
   PubMed Web of Science ®Google Scholar
• Reeve L. (1997). The poloxamers: their chemistry and medical applications. In: Domb A, Kost Y, Wiseman D, eds. Handbook of Biodegradable Polymers, Drug Targeting and Delivery (Vol. 7, pp. 231–249). London: Harwood Academic Publishers.
   Google Scholar
• Rekatas CJ, Mai SM, Crothers M, Quinn M, Collett JH, Attwood D, Heatley F, Martini L, Booth C. (2001). The effect of hydrophobe chemical structure and chain length on the solubilization of griseofulvin in aqueous micellar solutions of block copoly(oxyalkylene)s. Phys Chem Chem Phys, 3, 4769–4773.
   Web of Science ®Google Scholar
• Saito Y, Sato T. (1998). Effects of inorganic salts on solubilization of estriol in an aqueous solution of poly(ethylene oxide)/poly(propyleneoxide)/poly(ethylene oxide) triblock copolymer. Drug Dev Ind Pharm, 24, 385–388.
   PubMed Web of Science ®Google Scholar
• Saito Y, Kondo Y, Abe M. (1994). Solubilization behavior of estriol in an aqueous solution of pluronic L-64 as a function of concentration and temperature. Chem Pharm Bull, 42, 1348–1350.
   Web of Science ®Google Scholar
• Seow WY, Xue JM, Yang YY. (2007). Targeted and intracellular delivery of paclitaxel using multi-functional polymeric micelles. Biomaterials, 28, 1730–1740.
   PubMed Web of Science ®Google Scholar
• Sharma G, Singh RP, Chan DC, Agarwal R. (2003). Silibinin induces growth inhibition and apoptotic cell death in human lung carcinoma cells. Anticancer Res, 23, 2649–2655.
   PubMed Web of Science ®Google Scholar
• Shuai X, Ai H, Nasongkla N, Kim S, Gao J. (2004). Micellar carriers based on block copolymers of poly([varepsilon]-caprolactone) and poly(ethylene glycol) for doxorubicin delivery. J Control Release, 98, 415–426.
   PubMed Web of Science ®Google Scholar
• Singh RP, Agarwal R. (2004). Prostate cancer prevention by silibinin. Curr Cancer Drug Targets, 4, 1–11.
   PubMed Web of Science ®Google Scholar
• Sosnik A, Sefton MV. (2005). Semi-synthetic collagen/poloxamine matrices for tissue engineering applications. Biomaterials, 26, 7425–7435.
   PubMed Web of Science ®Google Scholar
• Strickley RG. (2004). Solubilizing excipients in oral and injectable formulations. Pharm Res, 21, 201–230.
   PubMed Web of Science ®Google Scholar
• Sylvain C, Wagner A, Mioskowski C. (1999). An efficient procedure for the esterification of nitroacetic acid: application to the preparation of Merrifield resin-bound nitroacetate. Tetrahedron Lett, 40, 875–878.
   Web of Science ®Google Scholar
• Taboada P, Velasquez G, Barbosa S, Castelletto V, Nixon SK, Yang Z, Heatley F, Hamley IW, Ashford M, Mosquera V, Attwood D, Booth C. (2005). Block copolymers of ethylene oxide and phenyl glycidyl ether: micellization, gelation, and drug solubilization. Langmuir, 21, 5263–5271.
   PubMed Web of Science ®Google Scholar
• Taboada P, Velasquez G, Barbosa S, Yang Z, Nixon SK, Zhou Z, Heatley F, Ashford M, Mosquera V, Attwood D, Booth C. (2006). Micellization and drug solubilization in aqueous solutions of a diblock copolymer of ethylene oxide and phenyl glycidyl ether. Langmuir, 22, 7465–7470.
   PubMed Web of Science ®Google Scholar
• Tae HK, In KP, Jae WN. (2004). Galactosylated chitosan/DNA nanoparticles prepared using water-soluble chitosan as a gene carrier. Biomaterials, 25, 3783–3792.
   PubMed Web of Science ®Google Scholar
• Yang KW, Li XR, Yang ZL, Li PZ, Wang F, Liu Y. (2008). Novel polyion complex micelles for liver-targeted delivery of diammonium glycyrrhizinate: in vitro and in vivo characterization. J Biomed Mater Res A, 87, 140–148.
   Google Scholar
• Yokoyama M, Fukushima S, Uehara R, Okamoto K, Kataoka K, Sakurai Y, Okano T. (1998). Characterization of physical entrapment and chemical conjugation of adriamycin in polymeric micelles and their design for in vivo delivery to a solid tumor. J Control Release, 50, 79–92.
   PubMed Web of Science ®Google Scholar
• Yoo HS, Park TG. (2004). Folate receptor targeted biodegradable polymeric doxorubicin micelles. J Control Release, 96, 273–283.
   PubMed Web of Science ®Google Scholar
• Zhang Y, Qi XR, Gao Y, Wei L, Maitani Y, Nagai T. (2007). Mechanisms of co-modified liver-targeting liposomes as gene delivery carriers based on cellular uptake and antigens inhibition effect. J Control Release, 117, 281–290.
   PubMed Web of Science ®Google Scholar