Thermosensitive polymeric micelles for targeted drug delivery

Nanomedicine

Volumn 6, Issue 7, 2011, Pages 1245-1255

  Talelli, Marina ^a   Hennink, Wim E ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

cloud point; lower critical solution temperature; nanoparticle; Pluronics; poly(hydroxypropyl methacrylamide lactate); poly(N isopropylacrylamide); polymeric micelle; targeted drug delivery; thermosensitive

Indexed keywords

COPOLYMER; DOCETAXEL; DOXORUBICIN; DOXORUBICIN DERIVATIVE; GOLD NANOPARTICLE; METHOTREXATE; PACLITAXEL; POLOXAMER; POLY(ETHYLENE GLYCOL) B POLY(PROPYLENE OXIDE) B POLY(ETHYLENE GLYCOL); POLY(ETHYLENE GLYCOL) B POLY(SOLKETAL ACRYLATE); POLY(N ISOPROPYLACRYLAMIDE CO N ACRYLAMIDE) B POLY(DEXTRO LEVO LACTIDE); POLY(N ISOPROPYLACRYLAMIDE CO N HYDROXYMETHYLACRYLAMIDE) B POLY(METHYL METHACRYLATE); POLY(N ISOPROPYLACRYLAMIDE CO N,N DIMETHYLACRYLAMIDE CO 2 AMINOETHYL METHACRYLATE) B POLY(10 UNDECENOIC ACID); POLY(N ISOPROPYLACRYLAMIDE CO N,N DIMETHYLACRYLAMIDE) B POLY(DEXTRO LEVO LACTIDE); POLY(N ISOPROPYLACRYLAMIDE CO N,N DIMETHYLACRYLAMIDE) B POLY(EPSILON CAPROLACTONE); POLY(N ISOPROPYLACRYLAMIDE); POLY(N ISOPROPYLACRYLAMIDE) CO 2 HYDROXYETHYL METHACRYLATE MONOLACTATE; POLY(N ISOPROPYLACRYLAMIDE) CO N (2 HYDROXYPROPYL)METHACRYLAMIDE LACTATE; POLY[N (2 HYDROXYPROPYL)METHACRYLAMIDE LACTATE]; POLY[N ISOPROPYLACRYLAMIDE CO 3 (TRIMETHOXYSILYL)PROPYL METHACRYLATE] B POLYMETHYL METHACRYLATE; POLYMER; SP 1049C; UNCLASSIFIED DRUG; VITAMIN K GROUP;

ADENOCARCINOMA; ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; CONTROLLED DRUG RELEASE; CROSS LINKING; CYTOTOXICITY; DRUG CLEARANCE; DRUG DELIVERY SYSTEM; DRUG DESIGN; DRUG DISTRIBUTION; DRUG DOSAGE FORM COMPARISON; DRUG FORMULATION; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HEAT SENSITIVITY; HIGH TEMPERATURE; HUMAN; LOW TEMPERATURE; LOWER CRITICAL SOLUTION TEMPERATURE; MICELLE; MOLECULAR SIZE; MOLECULAR WEIGHT; NONHUMAN; PHASE 1 CLINICAL TRIAL (TOPIC); PHASE 2 CLINICAL TRIAL (TOPIC); POLYMERIZATION; PRIORITY JOURNAL; REVIEW; SOLID TUMOR; UNSPECIFIED SIDE EFFECT;

ANIMALS; DRUG DELIVERY SYSTEMS; HUMANS; MICELLES; PHARMACEUTICAL PREPARATIONS; POLYMERS; TEMPERATURE;

EID: 80053101166     PISSN: 17435889     EISSN: 17486963     Source Type: Journal    
DOI: 10.2217/nnm.11.91     Document Type: Review

References (78)

1. Riess G. Micellization of block copolymers. Prog. Polym. Sci. 28(7), 1107-1170 (2003).
2. Oerlemans C, Bult W, Bos M, Storm G, Nijsen JFW, Hennink WE. Polymeric micelles in anticancer therapy: targeting, imaging and triggered release. Pharm. Res. 27(12), 2569-2589 (2010).
3. Aliabadi HM, Lavasanifar A. Polymeric micelles for drug delivery. Expert Opin. Drug Del. 3(1), 139-162 (2006). (Pubitemid 43056397)
4. Kwon GS, Naito M, Kataoka K, Yokoyama M, Sakurai Y, Okano T. Block copolymer micelles as vehicles for hydrophobic drugs. Colloid Surface B 2(4), 429-434 (1994).
5. Nishiyama N, Kataoka K. Nanostructured devices based on block copolymer assemblies for drug delivery: designing structures for enhanced drug function. Adv. Polym. Sci. 193, 67-101 (2006).
6. Torchilin VP. Micellar nanocarriers: pharmaceutical perspectives. Pharm. Res. 24(1), 1-16 (2007). (Pubitemid 44902565)
7. Forster S, Plantenberg T. From self-organizing polymers to nanohybrid and biomaterials. Angew. Chem. Int. Ed. 41(5), 689-714 (2002). (Pubitemid 34218507)
8. Talelli M, Rijcken CJF, van Nostrum CF, Storm G, Hennink WE. Micelles based on HPMA copolymers. Adv. Drug Delivery Rev. 62(2), 231-239 (2010).
9. Mathot F, Van Beijsterveldt L, Preat V, Brewster M, Arien A. Intestinal uptake and biodistribution of novel polymeric micelles after oral administration. J. Control. Release 111(1-2), 47-55 (2006). (Pubitemid 43289994)
10. Sant VP, Smith D, Leroux JC. Enhancement of oral bioavailability of poorly water-soluble drugs by poly(ethylene glycol)-block-poly(alkyl acrylate-co-methacrylic acid) self-assemblies. J. Control. Release 104(2), 289-300 (2005). (Pubitemid 40724930)
11. Van Hasselt PM, Janssens GEPJ, Slot TK et al. The influence of bile acids on the oral bioavailability of vitamin K encapsulated in polymeric micelles. J. Control. Release 133(2), 161-168 (2009).
12. Rijcken CJF, Soga O, Hennink WE, van Nostrum CF. Triggered destabilisation of polymeric micelles and vesicles by changing polymers polarity: an attractive tool for drug delivery. J. Control. Release 120(3), 131-148 (2007). (Pubitemid 47058635)
13. Owens III DE, Peppas NA. Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int. J. Pharm. 307(1), 93-102 (2006). (Pubitemid 41773257)
14. Illum L, Jacobsen LO, Muller RH. Surface characteristics and the interaction of colloidal particles with mouse peritoneal macrophages. Biomaterials 8(2), 113-117 (1987). (Pubitemid 17032519)
15. Storm G, Belliot SO, Daemen T, Lasic DD. Surface modification of nanoparticles to oppose uptake by the mononuclear phagocyte system. Adv. Drug Delivery Rev. 17(1), 31-48 (1995).
16. Maeda H, Wu J, Sawa T, Matsumura Y, Hori K. Tumor vascular permeability and the EPR effect in macromolecular therapeutics: a review. J. Control. Release 65(1-2), 271-284 (2000). (Pubitemid 30122932)
17. Maeda H. Tumor-selective delivery of macromolecular drugs via the EPR effect: background and future prospects. Bioconj. Chem. 21(5), 797-802 (2010).
18. van Nostrum CF, Neradovic D, Soga O, Hennink WE. Polymeric micelles with transient stability: a novel delivery concept. ACS Sym. Ser. 923, 40-54 (2006).
19. Lee AS, Gast AP, Butun V, Armes SP. Characterizing the structure of pH dependent polyelectrolyte block copolymer micelles. Macromolecules 32(13), 4302-4310 (1999).
20. Chilkoti A, Dreher MR, Meyer DE, Raucher D. Targeted drug delivery by thermally responsive polymers. Adv. Drug Delivery Rev. 54(5), 613-630 (2002). (Pubitemid 35247519)
21. Katayama Y, Sonoda T, Maeda M. A polymer micelle responding to the protein kinase a signal. Macromolecules 34(24), 8569-8573 (2001). (Pubitemid 33093162)
22. Batrakova EV, Kabanov AV. Pluronic block copolymers: evolution of drug delivery concept from inert nanocarriers to biological response modifiers. J. Control. Release 130(2), 98-106 (2008).
23. Almgren M, Brown W, Hvidt S. Self-aggregation and phase behavior of poly(ethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymers in aqueous solution. Colloid Polym. Sci. 273(1), 2-15 (1995).
24. Topp MDC, Dijkstra PJ, Talsma H, Feijen J. Thermosensitive micelle-forming block copolymers of poly(ethylene glycol) and poly(N-isopropylacrylamide).Macromolecules 30(26), 8518-8520 (1997). (Pubitemid 127569672)
25. Zhang W, Shi L, Wu K, An Y. Thermoresponsive micellization of poly(ethylene glycol)-b-poly(N-isopropylacrylamide) in water. Macromolecules 38(13), 5743-5747 (2005). (Pubitemid 41028151)
26. Qin S, Geng Y, Discher DE, Yang S. Temperature-controlled assembly and release from polymer vesicles of poly(ethylene oxide)-block-poly(N- isopropylacrylamide).Adv. Mater. 18(21), 2905-2909 (2006). (Pubitemid 44759500)
27. Kohori F, Sakai K, Aoyagi T, Yokoyama M, Sakurai Y, Okano T. Preparation and characterization of thermally responsive block copolymer micelles comprising poly(N-isopropylacrylamide-b-dl-lactide).J. Control. Release 55(1), 87-98 (1998). (Pubitemid 28477567)
28. Wei H, Zhang XZ, Zhou Y, Cheng SX, Zhuo RX. Self-assembled thermoresponsive micelles of poly(N-isopropylacrylamide-b-methyl methacrylate).Biomaterials 27(9), 2028-2034 (2006). (Pubitemid 41759496)
29. Chung JE, Yokoyama M, Yamato M, Aoyagi T, Sakurai Y, Okano T. Thermo-responsive drug delivery from polymeric micelles constructed using block copolymers of poly(N-isopropylacrylamide) and poly(butylmethacrylate).J. Control. Release 62(1-2), 115-127 (1999). (Pubitemid 29486490)
30. Kohori F, Sakai K, Aoyagi T et al. Control of adriamycin cytotoxic activity using thermally responsive polymeric micelles composed of poly(N-isopropylacrylamide-co-N,N-dimethylacrylamide)-b-poly(d,l-lactide). Colloid Surface B 16(1-4), 195-205 (1999). (Pubitemid 29486806)
31. Nakayama M, Okano T, Miyazaki T, Kohori F, Sakai K, Yokoyama M. Molecular design of biodegradable polymeric micelles for temperature-responsive drug release. J. Control. Release 115(1), 46-56 (2006). (Pubitemid 44419528)
32. Yang M, Ding Y, Zhang L, Qian X, Jiang X, Liu B. Novel thermosensitive polymeric micelles for docetaxel delivery. J. Biomed. Mater. Res. A 81(4), 847-858 (2007). (Pubitemid 46835080)
33. Liu B, Yang M, Li R et al. The antitumor effect of novel docetaxel-loaded thermosensitive micelles. Eur. J. Pharm. Biopharm. 69(2), 527-534 (2008).
34. Cheng C, Wei H, Zhang XZ, Cheng SX, Zhuo RX. Thermo-triggered and biotinylated biotin-P(NIPAAm-co-HMAAm)-b-PMMA micelles for controlled drug release. J. Biomed. Mater. Res. A 88(3), 814-822 (2009).
35. Wadajkar AS, Koppolu B, Rahimi M, Nguyen KT. Cytotoxic evaluation of N-isopropylacrylamide monomers and temperature-sensitive poly(N- isopropylacrylamide) nanoparticles. J. Nanopart. Res. 11(6), 1375-1382 (2009).
36. Shah SS, Wertheim J, Wang CT, Pitt CG. Polymer-drug conjugates: manipulating drug delivery kinetics using model LCST systems. J. Control. Release 45(1), 95-101 (1997). (Pubitemid 27055797)
37. Neradovic D, Hinrichs WLJ, Kettenes-Van Den Bosch JJ, Hennink WE. Poly(N-isopropylacrylamide) with hydrolyzable lactic acid ester side groups: a new type of thermosensitive polymer. Macromol. Rapid Comm. 20(11), 577-581 (1999). (Pubitemid 129717491)
38. Lee BH, Vernon B. Copolymers of N-isopropylacrylamide HEMA-lactate and acrylic acid with time-dependent lower critical solution temperature as a bioresorbable carrier. Polym. Int. 54(2), 418-422 (2005). (Pubitemid 40252206)
39. Neradovic D, van Nostrum CF, Hennink WE. Thermoresponsive polymeric micelles with controlled instability based on hydrolytically sensitive N-isopropylacrylamide copolymers. Macromolecules 34(22), 7589-7591 (2001). (Pubitemid 33074518)
40. Neradovic D, van Steenbergen MJ, Vansteelant L, Meijer YJ, van Nostrum CF, Hennink WE. Degradation mechanism and kinetics of thermosensitive polyacrylamides containing lactic acid side chains. Macromolecules 36(20), 7491-7498 (2003).
41. Soga O, van Nostrum CF, Hennink WE. Poly(N-(2-hydroxypropyl) methacrylamide mono/di lactate): a new class of biodegradable polymers with tuneable thermosensitivity. Biomacromolecules 5(3), 818-821 (2004). (Pubitemid 38702250)
42. Soga O, van Nostrum CF, Ramzi A et al. Physicochemical characterization of degradable thermosensitive polymeric micelles. Langmuir 20(21), 9388-9395 (2004).
43. Moghimi SM, Hunter AC, Murray JC. Long-circulating and target-specific nanoparticles: theory to practice. Pharmacol. Rev. 53(2), 283-318 (2001). (Pubitemid 32476118)
44. Soga O, van Nostrum CF, Fens M et al. Thermosensitive and biodegradable polymeric micelles for paclitaxel delivery. J. Control. Release 103(2), 341-353 (2005). (Pubitemid 40342534)
45. Rijcken CJF, Hofman JW, van Zeeland F, Hennink WE, van Nostrum CF. Photosensitiser-loaded biodegradable polymeric micelles: preparation, characterisation and in vitro PDT efficacy. J. Control. Release 124(3), 144-153 (2007). (Pubitemid 350101885)
46. Talelli M, Rijcken CJF, Lammers T et al. Superparamagnetic iron oxide nanoparticles encapsulated in biodegradable thermosensitive polymeric micelles: toward a targeted nanomedicine suitable for image-guided drug delivery. Langmuir 25(4), 2060-2067 (2009).
47. Kabanov AV, Batrakova EV, Alakhov VY. Pluronic® block copolymers as novel polymer therapeutics for drug and gene delivery. J. Control. Release 82(2-3), 189-212 (2002). (Pubitemid 34880178)
48. Oh KT, Bronich TK, Kabanov AV. Micellar formulations for drug delivery based on mixtures of hydrophobic and hydrophilic Pluronica® block copolymers. J. Control. Release 94(2-3), 411-422 (2004). (Pubitemid 38117151)
49. Bae KH, Choi SH, Park SY, Lee Y, Park TG. Thermosensitive pluronic micelles stabilized by shell cross-linking with gold nanoparticles. Langmuir 22(14), 6380-6384 (2006). (Pubitemid 44140340)
50. Song MJ, Lee DS, Ahn JH, Kim DJ, Kim SC. Thermosensitive sol-gel transition behaviors of poly(ethylene oxide)/aliphatic polyester/ poly(ethylene oxide) aqueous solutions. J. Polym. Sci. A1 42(3), 772-784 (2004). (Pubitemid 38158974)
51. Nolan SL, Phillips RJ, Cotts PM, Dungan SR. Light scattering study on the effect of polymer composition on the structural properties of PEO-PPO-PEO micelles. J. Colloid Interf. Sci. 191(2), 291-302 (1997). (Pubitemid 27470681)
52. Garripelli VK, Kim JK, Namgung R, Kim WJ, Repka MA, Jo S. A novel thermosensitive polymer with pH-dependent degradation for drug delivery. Acta Biomater. 6(2), 477-485 (2010)
53. Petrov P, Bozukov M, Burkhardt M, Muthukrishnan S, Muller AHE, Tsvetanov CB. Stabilization of polymeric micelles with a mixed poly(ethylene oxide)/ poly(2-hydroxyethyl methacrylate) shell by formation of poly(pentaerythritol tetraacrylate) nanonetworks within the micelles. J. Mater. Chem. 16(22), 2192-2199 (2006). (Pubitemid 43839359)
54. Fusco S, Borzacchiello A, Netti PA. Perspectives on: PEO-PPO-PEO triblock copolymers and their biomedical applications. J. Bioact. Compat. Pol. 21(2), 149-164 (2006). (Pubitemid 43260606)
55. Danson S, Ferry D, Alakhov V et al. Phase I dose escalation and pharmacokinetic study of Pluronic polymer-bound doxorubicin (SP1049C) in patients with advanced cancer. Br. J. Cancer 90(11), 2085-2091 (2004). (Pubitemid 38869710)
56. Okabe S, Sugihara S, Aoshima S, Shibayama M. Heat-induced self-assembling of thermosensitive block copolymer. 1: Small-angle neutron scattering study. Macromolecules 35(21), 8139-8146 (2002). (Pubitemid 35173626)
57. Boddu SHS, Jwala J, Chowdhury MR, Mitra AK. In vitro evaluation of a targeted and sustained release system for retinoblastoma cells using doxorubicin as a model drug. J. Ocul. Pharmacol. Ther. 26(5), 459-468 (2010).
58. Park KM, Choi JH, Bae JW, Joung YK, Park KD. Nano-aggregates using thermosensitive chitosan copolymers as a nanocarrier for protein delivery. J. Exp. Nanosci. 4(3), 269-275 (2009).
59. Bian F, Xiang M, Yu W, Liu M. Preparation and self-assembly behavior of thermosensitive polymeric micelles comprising poly(styrene-b-N,N- diethylacrylamide).J. Appl. Polym. Sci. 110(2), 900-907 (2008).
60. Yang J, Zhang D, Jiang S, Nie J. Synthesis of Y-shaped poly(solketal acrylate)-containing block copolymers and study on the thermoresponsive behavior for micellar aggregates. J. Colloid Interf. Sci. 352(2), 405-414 (2010).
61. Zhao A, Zhou S, Zhou Q, Chen T. Thermosensitive micelles from PEG-based ether-anhydride triblock copolymers. Pharm. Res. 27(8), 1627-1643 (2010).
62. Liu J, Zeng F, Allen C. Influence of serum protein on polycarbonate-based copolymer micelles as a delivery system for a hydrophobic anti-cancer agent. J Control. Release 103(2), 481-497 (2005). (Pubitemid 40342543)
63. Opanasopit P, Yokoyama M, Watanabe M, Kawano K, Maitani Y, Okano T. Influence of serum and albumins from different species on stability of camptothecin-loaded micelles. J. Control. Release 104(2), 313-321 (2005). (Pubitemid 40724932)
64. Rijcken CJ, Snel CJ, Schiffelers RM, van Nostrum CF, Hennink WE. Hydrolysable core-crosslinked thermosensitive polymeric micelles: synthesis, characterisation and in vivo studies. Biomaterials 28(36), 5581-5593 (2007). (Pubitemid 47599643)
65. Harada A, Kataoka K. Supramolecular assemblies of block copolymers in aqueous media as nanocontainers relevant to biological applications. Prog. Polym. Sci. 31(11), 949-982 (2006). (Pubitemid 44738012)
66. Wei H, Quan CY, Chang C, Zhang XZ, Zhuo RX. Preparation of novel ferrocene-based shell cross-linked thermoresponsive hybrid micelles with antitumor efficacy. J. Phys. Chem. B 114(16), 5309-5314 (2010).
67. Wei H, Chen WQ, Chang C et al. Synthesis of star block, thermosensitive poly(l-lactide)-star block-poly(N-isopropylacrylamide-co-N- hydroxymethylacrylamide) copolymers and their self-assembled micelles for controlled release. J. Phys. Chem. C 112(8), 2888-2894 (2008). (Pubitemid 351362316)
68. Zeng Y, Pitt WG. Poly(ethylene oxide)-b-poly(N-isopropylacrylamide) nanoparticles with cross-linked cores as drug carriers. J. Biomat. Sci. Polym. E. 16(3), 371-380 (2005). (Pubitemid 40796478)
69. Wei H, Cheng, Chang C et al. Synthesis and applications of shell cross-linked thermoresponsive hybrid micelles based on poly(N- isopropylacrylamide-co-3-(trimethoxysilyl)propyl methacrylate)-b-poly(methyl methacrylate).Langmuir 24(9), 4564-4570 (2008). (Pubitemid 351725134)
70. Yang TF, Chen CN, Chen MC, Lai CH, Liang HF, Sung HW. Shell-crosslinked Pluronic L121 micelles as a drug delivery vehicle. Biomaterials 28(4), 725-734 (2007).
71. Kim JH, Emoto K, Iijima M et al. Core-stabilized polymeric micelle as potential drug carrier: increased solubilization of taxol. Polym. Advan. Technol. 10(11), 647-654 (1999). (Pubitemid 30509479)
72. Iijima M, Nagasaki Y, Okada T, Kato M, Kataoka K. Core-polymerized reactive micelles from heterotelechelic amphiphilic block copolymers. Macromolecules 32(4), 1140-1146 (1999).
73. Talelli M, Iman M, Varkouhi AK et al. Core-crosslinked polymeric micelles with controlled release of covalently entrapped doxorubicin. Biomaterials 31(30), 7797-7804 (2010).
74. Liu SQ, Wiradharma N, Gao SJ, Tong YW, Yang YY. Bio-functional micelles self-assembled from a folate-conjugated block copolymer for targeted intracellular delivery of anticancer drugs. Biomaterials 28(7), 1423-1433 (2007). (Pubitemid 46001461)
75. Alakhov V, Klinski E, Li S et al. Block copolymer-based formulation of doxorubicin. From cell screen to clinical trials. Colloid Surface B 16(1-4), 113-134 (1999). (Pubitemid 29486800)
76. Batrakova EV, Dorodnych TY, Klinskii EY et al. Anthracycline antibiotics non-covalently incorporated into the block copolymer micelles: in vivo evaluation of anti-cancer activity. Br. J. Cancer 74(10), 1545-1552 (1996). (Pubitemid 26386080)
77. Valle JW, Armstrong A, Newman C et al. A phase 2 study of SP1049C, doxorubicin in P-glycoprotein-targeting Pluronics, in patients with advanced adenocarcinoma of the esophagus and gastroesophageal junction. Invest. New Drug. 1-9 (2010) (In Press).
78. Talelli M, Rijcken CJF, Oliveira S et al. Nanobody-shell functionalized thermosensitive core-crosslinked polymeric micelles for active drug targeting. J. Control. Release (2011) (In Press).