Self-assembled methoxy poly(ethylene glycol)-cholesterol micelles for hydrophobic drug delivery

Journal of Pharmaceutical Sciences

Volumn 102, Issue 3, 2013, Pages 1054-1062

  Yu, Yiyi ^a   He, Yingju ^b   Xu, Bei ^a   He, Zhiyao ^a   Zhang, Ying ^c   Chen, Yan ^a   Yang, Yang ^b   Xie, Yongmei ^a   Zheng, Yu ^a   He, Gu ^a   He, Jun ^a   Song, Xiangrong ^a  

^a SICHUAN UNIVERSITY   (China)

^b SICHUAN UNIVERSITY   (China)

^c KUNMING MEDICAL UNIVERSITY   (China)

Author keywords

Calorimetry(DSC); Cholesterol; Cosolvent evaporation; Docetaxel; Hydrophobic drug; Methoxy poly(ethylene glycol); Micelle; Polymers; Stability; Targeted drug delivery

Indexed keywords

CHOLESTEROL DERIVATIVE; DOCETAXEL; MACROGOL; METHOXY POLY(ETHYLENE GLYCOL) CHOLESTEROL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BIOCOMPATIBILITY; CELL GROWTH; CHEMICAL COMPOSITION; DIFFERENTIAL SCANNING CALORIMETRY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG STABILITY; ENCAPSULATION; EVAPORATION; HUMAN; HUMAN CELL; HYDROPHOBICITY; IN VITRO STUDY; MICELLE; PARTICLE SIZE; PROCESS OPTIMIZATION; STORAGE; TRANSMISSION ELECTRON MICROSCOPY;

EID: 84878134524     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.23418     Document Type: Article

References (55)

1. Gueritte-Voegelein F, Guenard D, Lavelle F, Le Goff MT, Mangatal L, Potier P. 1991. Relationships between the structure of taxol analogues and their antimitotic activity. J Med Chem 34:992-998.
2. Bissery MC. 1995. Preclinical pharmacology of docetaxel. Eur J Cancer 31(Suppl 4):S1-S6.
3. Kintzel PE, Michaud LB, Lange MK. 2006. Docetaxel-associated epiphora. Pharmacotherapy 26:853-867.
4. Baker J, Ajani J, Scotté F, Winther D, Martin M, Aapro MS, von Minckwitz G. 2009. Docetaxel-related side effects and their management. Eur J Oncol Nurs 13:49-59.
5. Du W, Hong L, Yao T, Yang X, He Q, Yang B, Hu Y. 2007. Synthesis and evaluation of water-soluble docetaxel prodrugs-Docetaxel esters of malic acid. Bioorg Med Chem Lett 15:6323-6330.
6. Persohn E, Canta A, Schoepfer S, Traebert M, Mueller L, Gilardini A, Galbiati S, Nicolini G, Scuteri A, Lanzani F, Giussani G, Cavaletti G. 2005. Morphological and morphometric analysis of paclitaxel and docetaxel-induced peripheral neuropathy in rats. Eur J Cancer 41:1460-1466.
7. Engels FK, Mathot RA, Verweij J. 2007. Alternative drug formulations of docetaxel: A review. Anticancer Drugs 18:95-103.
8. Ernsting MJ, Tang W-L, MacCallum NW, Li S-D. 2012. Preclinical pharmacokinetic, biodistribution, and anti-cancer efficacy studies of a docetaxel-carboxymethylcellulose nanoparticle in mouse models. Biomaterials 33:1445-1454.
9. Liu Q, Li R, Zhu Z, Qian X, Guan W, Yu L, Yang M, Jiang X, Liu B. 2012. Enhanced antitumor efficacy, biodistribution and penetration of docetaxel-loaded biodegradable nanoparticles. Int J Pharm 430:350-358.
10. Ungaro F, Conte C, Ostacolo L, Maglio G, Barbieri A, Arra C, Misso G, Abbruzzese A, Caraglia M, Quaglia F. 2012. Core-shell biodegradable nanoassemblies for the passive targeting of docetaxel: Features, antiproliferative activity and in vivo toxicity. Nanomedicine 8:637-646.
11. Muthu MS, Kulkarni SA, Xiong J, Feng SS. 2011. Vitamin E TPGS coated liposomes enhanced cellular uptake and cytotoxicity of docetaxel in brain cancer cells. Int J Pharm 421:332-340.
12. Muthu MS, Kulkarni SA, Raju A, Feng SS. 2012. Theranostic liposomes of TPGS coating for targeted co-delivery of docetaxel and quantum dots. Biomaterials 33:3494-3501.
13. Qu G, Wu X, Yin L, Zhang C. 2012. N-octyl-O-sulfate chitosan-modified liposomes for delivery of docetaxel: Preparation, characterization, and pharmacokinetics. Biomed Pharmacother 66:46-51.
14. Lee SW, Yun MH, Jeong SW, In CH, Kim JY, Seo MH, Pai CM, Kim SO. 2011. Development of docetaxel-loaded intravenous formulation, Nanoxel-PM™ using polymer-based delivery system. J Control Release 155:262-271.
15. Zhang Y, Wang X, Wang J, Zhang X, Zhang Q. 2011. Octreotide-modified polymeric micelles as potential carriers for targeted docetaxel delivery to somatostatin receptor overexpressing tumor cells. Pharm Res 28:1167-1178.
16. Jun YJ, Jadhav VB, Min JH, Cui JX, Chae SW, Choi JM, Kim I-S, Choi S-J, Lee HJ, Sohn YS. 2012. Stable and efficient delivery of docetaxel by micelle-encapsulation using a tripodal cyclotriphosphazene amphiphile. Int J Pharm 422:374-380.
17. Koo AN, Min KH, Lee HJ, Lee S-U, Kim K, Chan Kwon I, Cho SH, Jeong SY, Lee SC. 2012. Tumor accumulation and antitumor efficacy of docetaxel-loaded core-shell-corona micelles with shell-specific redox-responsive cross-links. Biomaterials 33:1489-1499.
18. Leonhard V, Alasino RV, Bianco ID, Garro AG, Heredia V, Beltramo DM. 2012. Self-assembled micelles of monosialogangliosides as nanodelivery vehicles for taxanes. J Control Release 162:619-627.
19. Liu J, Zahedi P, Zeng F, Allen C. 2008. Nano-sized assemblies of a PEG-docetaxel conjugate as a formulation strategy for docetaxel. J Pharm Sci 97:3274-3290.
20. Wu Y, Ma Q, Song X, Zheng Y, Ren W, Zhang J, Ouyang L, Wu F, He G. 2012. Biocompatible poly(ethylene glycol)-poly(γ-cholesterol-l-glutamate) copolymers: Synthesis, characterization, and in vitro studies. J Polym Sci 50:4532-4537.
21. Gaucher G, Dufresne MH, Sant VP, Kang N, Maysinger D, Leroux JC. 2005. Block copolymer micelles: Preparation, characterization and application in drug delivery. J Control Release 109:169-188.
22. Wang X, Wang Y, Chen X, Wang J, Zhang X, Zhang Q. 2009. NGR-modified micelles enhance their interaction with CD13-overexpressing tumor and endothelial cells. J Control Release 139:56-62.
23. Mi Y, Liu Y, Feng S-S. 2011. Formulation of docetaxel by folic acid-conjugated d-α-tocopheryl polyethylene glycol succinate 2000 (Vitamin E TPGS2k) micelles for targeted and synergistic chemotherapy. Biomaterials 32:4058-4066.
24. Yang DB, Zhu JB, Huang ZJ, Ren HX, Zheng ZJ. 2008. Synthesis and application of poly(ethylene glycol)-cholesterol (Chol-PEGm) conjugates in physicochemical characterization of nonionic surfactant vesicles. Colloids Surf B Biointerfaces 63:192-199.
25. He ZY, Zheng X, Wu XH, Song XR, He G, Wu WF, Yu S, Mao SJ, Wei YQ. 2010. Development of glycyrrhetinic acid-modified stealth cationic liposomes for gene delivery. Int J Pharm 397:147-154.
26. Xu J-P, Ji J, Chen W-D, Shen J-C. 2005. Biomimetic amphiphiles for polymeric micellar carrier system. Key Eng Mater 288-289:465-468.
27. Qian X, Lai J, Zhan S, Zhang J, Wang L, Tu K. 2008. Novel MePEG-Chol and MePEG-St mixed micellar systems for drug delivery: Preparation and characterization. Rare Metal Mat Eng 37:4.
28. Zhou Y, Briand V, Sharma N, Ahn S-k, Kasi R. 2009. Polymers comprising cholesterol: Synthesis, self-assembly, and applications. Materials 2:636-660.
29. Li J, He Z, Yu S, Li S, Ma Q, Yu Y, Zhang J, Li R, Zheng Y, He G, Song X. 2012. Micelles based on methoxy poly(ethylene glycol)-cholesterol conjugate for controlled and targeted drug delivery of a poorly water soluble drug. J Biomed Nanotechnol 8:809-817.
30. Kataoka K, Harada A, Nagasaki Y. 2001. Block copolymer micelles for drug delivery: Design, characterization and biological significance. Adv Drug Deliv Rev 47:113-131.
31. Kwon GS, Naito M, Yokoyama M, Okano T, Sakurai Y, Kataoka K. 1995. Physical entrapment of adriamycin in AB block copolymer micelles. Pharm Res 12:192-195.
32. Kataoka K, Matsumoto T, Yokoyama M, Okano T, Sakurai Y, Fukushima S, Okamoto K, Kwon GS. 2000. Doxorubicin-loaded poly(ethylene glycol)-poly(beta-benzyl-l-aspartate) copolymer micelles: Their pharmaceutical characteristics and biological significance. J Control Release 64:143-153.
33. Lavasanifar A, Samuel J, Kwon GS. 2001. Micelles self-assembled from poly(ethylene oxide)-block-poly(N-hexyl stearate l-aspartamide) by a solvent evaporation method: Effect on the solubilization and haemolytic activity of amphotericin B. J Control Release 77:155-160.
34. Aliabadi HM, Lavasanifar A. 2006. Polymeric micelles for drug delivery. Expert Opin Drug Deliv 3:139-162.
35. Kim SY, Shin IG, Lee YM, Cho CS, Sung YK. 1998. Methoxy poly(ethylene glycol) and epsilon-caprolactone amphiphilic block copolymeric micelle containing indomethacin. II. Micelle formation and drug release behaviours. J Control Release 51:13-22.
36. Jette KK, Law D, Schmitt EA, Kwon GS. 2004. Preparation and drug loading of poly(ethylene glycol)-block-poly(epsilon-caprolactone) micelles through the evaporation of a cosolvent azeotrope. Pharm Res 21:1184-1191.
37. Shuai X, Ai H, Nasongkla N, Kim S, Gao J. 2004. Micellar carriers based on block copolymers of poly(epsilon-caprolactone) and poly(ethylene glycol) for doxorubicin delivery. J Control Release 98:415-426.
38. Shuai X, Merdan T, Schaper AK, Xi F, Kissel T. 2004. Core-cross-linked polymeric micelles as paclitaxel carriers. Bioconjug Chem 15:441-448.
39. Ahlin P, Kristl J, Kristl A, Vrecer F. 2002. Investigation of polymeric nanoparticles as carriers of enalaprilat for oral administration. Int J Pharm 239:113-120.
40. Harada Y, Yamamoto T, Sakai M, Saiki T, Kawano K, Maitani Y, Yokoyama M. 2011. Effects of organic solvents on drug incorporation into polymeric carriers and morphological analyses of drug-incorporated polymeric micelles. Int J Pharm 404:271-280.
41. Johnson BK, Prud homme RK. 2003. Flash Nanoprecipitation of organic actives and block copolymers using a confined impinging jets mixer. Aust J Chem 56:1021-1024.
42. Johnson BK, Prud'homme RK. 2003. Mechanism for rapid self-assembly of block copolymer nanoparticles. Phys Rev Lett 91:118302.
43. Vangeyte P, Gautier S, Jérôme R. 2004. About the methods of preparation of poly(ethylene oxide)-b-poly(ε-caprolactone) nanoparticles in water: Analysis by dynamic light scattering. Colloids Surf A Physicochem Eng Aspects 242:203-211.
44. Zhang X, Jackson JK, Burt HM. 1996. Development of amphiphilic diblock copolymers as micellar carriers of taxol. Int J Pharm 132:195-206.
45. Le Garrec D, 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.
46. Huh KM, Lee SC, Cho YW, Lee J, Jeong JH, Park K. 2005. Hydrotropic polymer micelle system for delivery of paclitaxel. J Control Release 101:59-68.
47. le Garrec D, Gori S, Karkan D, Luo L, Lessard DG, Smith D, Ranger M, Yessine MA, Leroux JC. 2005. Preparation, characterization, cytotoxicity and biodistribution of docetaxel-loaded polymeric micelle formulations. J Drug Delivery Sci Technol 15:115-120.
48. Park EK, Kim SY, Lee SB, Lee YM. 2005. Folate-conjugated methoxy poly(ethylene glycol)/poly(epsilon-caprolactone) amphiphilic block copolymeric micelles for tumor-targeted drug delivery. J Control Release 109:158-168.
49. Forrest ML, Yanez JA, Remsberg CM, Ohgami Y, Kwon GS, Davies NM. 2008. Paclitaxel prodrugs with sustained release and high solubility in poly(ethylene glycol)-b-poly(epsilon-caprolactone) micelle nanocarriers: Pharmacokinetic disposition, tolerability, and cytotoxicity. Pharm Res 25:194-206.
50. Liggins RT, Hunter WL, Burt HM. 1997. Solid-state characterization of paclitaxel. J Pharm Sci 86:1458-1463.
51. Alipour S, Montaseri H, Tafaghodi M. 2010. Preparation and characterization of biodegradable paclitaxel loaded alginate microparticles for pulmonary delivery. Colloids Surf B Biointerfaces 81:521-529.
52. Gill KK, Nazzal S, Kaddoumi A. 2011. Paclitaxel loaded PEG(5000)-DSPE micelles as pulmonary delivery platform: Formulation characterization, tissue distribution, plasma pharmacokinetics, and toxicological evaluation. Eur J Pharm Biopharm 79:276-284.
53. Mu L, Feng SS. 2001. Fabrication, characterization and in vitro release of paclitaxel (Taxol) loaded poly (lactic-co-glycolic acid) microspheres prepared by spray drying technique with lipid/cholesterol emulsifiers. J Control Release 76:239-254.
54. Gaber NN, Darwis Y, Peh K-K, Tan YT-F. 2006. Characterization of polymeric micelles for pulmonary delivery of beclomethasone dipropionate. J Nanosci Nanotechnol 6:3095-3101.
55. Ostacolo L, Marra M, Ungaro F, Zappavigna S, Maglio G, Quaglia F, Abbruzzese A, Caraglia M. 2010. In vitro anticancer activity of docetaxel-loaded micelles based on poly(ethylene oxide)-poly(epsilon-caprolactone) block copolymers: Do nanocarrier properties have a role? J Control Release 148:255-263.