Synthesis of amphiphilic [PEO(PCL) 2] triarm star-shaped block copolymers: A promising system for in cell delivery

Journal of Materials Science: Materials in Medicine

Volumn 23, Issue 5, 2012, Pages 1225-1234

  Petrova, Svetlana ^a   Kolev, Iliyan ^b   Miloshev, Stojan ^c   Apostolova, Margarita D ^b   Mateva, Rosa ^c  

^a INSTITUTE OF POLYMERS   (Bulgaria)

^b INSTITUTE OF MOLECULAR BIOLOGY   (Bulgaria)

^c UNIVERSITY OF CHEMICAL TECHNOLOGY AND METALLURGY   (Bulgaria)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIPHILICS; AQUEOUS MEDIA; CAVEOLAE; CELL DELIVERY; CELLULAR UPTAKE; CYTOTOXIC EFFECTS; DRUG DELIVERY SYSTEM; FTIR; H NMR SPECTROSCOPY; HEPATOCELLULAR CARCINOMA CELL; HYDROXYL GROUPS; IN-VITRO; MACROINITIATORS; NEUTRAL RED; POTENTIAL APPLICATIONS; SELF-ASSEMBLY BEHAVIORS; SIMPLE METHOD; STAR-SHAPED BLOCK COPOLYMERS; STAR-SHAPED COPOLYMER; UV-VIS SPECTROSCOPY;

ADDITION REACTIONS; BLOCK COPOLYMERS; CYTOTOXICITY; DRUG DELIVERY; MICELLES; MOLECULAR BIOLOGY; ULTRAVIOLET VISIBLE SPECTROSCOPY;

STARS;

ALPHA METHOXY OMEGA',OMEGA' DIHYDROXY POLY(ETHYLENE OXIDE); AMPHOPHILE; COPOLYMER; UNCLASSIFIED DRUG;

ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; ENDOCYTOSIS; FOURIER TRANSFORM INFRARED PHOTOACOUSTIC SPECTROSCOPY; HUMAN; HUMAN CELL; LIVER CELL CARCINOMA; MICHAEL ADDITION; MORPHOLOGY; PINOCYTOSIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TRANSMISSION ELECTRON MICROSCOPY; ULTRAVIOLET SPECTROSCOPY;

CARCINOMA, HEPATOCELLULAR; DELAYED-ACTION PREPARATIONS; DRUG DELIVERY SYSTEMS; HEP G2 CELLS; HUMANS; LIVER NEOPLASMS; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; MODELS, BIOLOGICAL; MOLECULAR CONFORMATION; POLYESTERS; POLYMERIZATION; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SURFACE-ACTIVE AGENTS;

EID: 84863323000     PISSN: 09574530     EISSN: 15734838     Source Type: Journal    
DOI: 10.1007/s10856-012-4592-8     Document Type: Article

References (51)

1. Pitsikalis M, Pispas S, Mays JW, Hadjichristidis N. Nonlinear block copolymer architectures. Adv Polym Sci. 1998;135:1-137.
2. Vora A, Singh K, Webster DC. A new approach to 3-miktoarm star polymers using a combination of reversible addition-fragmentation chain transfer (RAFT) and ring opening polymerization (ROP) via "Click" chemistry. Polymer. 2009;50:2768-74.
3. Lele BS, Leroux J-C. Synthesis of novel amphiphilic star-shaped poly(e-caprolactone)-block-poly(N-(2-hydroxypropyl)methacrylamide) by combination of ring-opening and chain transfer polymerization. Polymer. 2002;43:5595-606. (Pubitemid 34919426)
4. Kim KH, Cui GH, Lim HJ, Huh J, Ahn CH, Jo WH. Synthesis and micellization of star-shaped poly(ethylene glycol)-blockpoly( e-caprolactone). Macromol Chem Phys. 2004;205:1684-92.
5. Riva R, Schmeits S, Jérôme C, Jérôme R, Lecomte Ph. Combination of ring-opening polymerization and "click chemistry": toward functionalization and grafting of poly(e-caprolactone). Macromolecules. 2007;40:796-803. (Pubitemid 46383725)
6. Rieger J, Coulembier O, Dubois Ph, Bernaerts KV, Du Prez FE, Jérôme R, Jérôme C. Controlled synthesis of an ABC miktoarm star-shaped copolymer by sequential ring-opening polymerization of ethylene oxide, benzyl beta malolactone, and epsilon-caprolactone. Macromolecules. 2005;38:10650-7. (Pubitemid 43099313)
7. Van Butsele K, Stoffelbach F, Jérôme R, Jérôme C. Synthesis of a novel amphiphilic and pH sensitive ABC miktoarm star terpolymers. Macromolecules. 2006;39:5652-6. (Pubitemid 44366463)
8. Petrova S, Riva R, Jérôme C, Lecomte Ph, Mateva R. Controlled synthesis ofAB2 amphiphilic triarm star-shaped block copolymers by ring-opening polymerization. Euro Polym J. 2009;45(12):3442-50.
9. Rempp PF, Lutz PJ. Star-shaped polymers. In: Salamone JC, editor. Polymeric materials encyclopedia, vol. 10. Boca Raton: CRC Press; 1996. p. 7880-5.
10. Bywater S. Preparation and properties of star-branched polymers. Adv Polym Sci. 1979;30:89-116.
11. Guo A, Liu G, Tao J. Star polymers and nanospheres from crosslinkable diblock copolymers. Macromolecules. 1996;29: 2487-93. (Pubitemid 126597657)
12. Lapienis G. Star-shaped polymers having PEO arms. Prog Polym Sci. 2009;34:852-92.
13. Sanda F, Sanada H, Shibasaki Y, Endo T. Star polymer synthesis from e-caprolactone utilizing polyol/protonic acid initiator. Macromolecules. 2002;35:680-3. (Pubitemid 34138573)
14. Inoue K. Functional dendrimers, hyperbranched and star polymers. Prog Polym Sci. 2000;25:453-571.
15. Joziasse CAP, Grablowitz H, Pennings AJ. Starshaped poly[(trimethylene carbonate)-co-(e-caprolactone)] and its block copolymers with lactide/glycolide: synthesis, characterization and properties. Macromol Chem Phys. 2000;201:107-12.
16. Choi YK, Bae YH, Kim SW. Protein release from microspheres of star-shaped PEO-PLA block copolymers. Proc Int Symp Control Relat Bioact Mater. 1996;23:349-50. (Pubitemid 26294092)
17. Kennedy JP, Jacob S. Cationic polymerization astronomy. Synthesis of polymer stars by cationicmeans.AccChemRes. 1998;31:835-41. (Pubitemid 128473634)
18. Hadjichristidis N, Pitsikalis M, Pispas S, Iatrou H. Polymers with complex architecture by living anionic polymerization. Chem Rev. 2001;101:3747-92. (Pubitemid 35375218)
19. Matthews OA, Shipway AN, Stoddart JF. Dendrimers: branching out from curiosities into new technologies. Prog Polym Sci. 1998;23:1-56. (Pubitemid 128405134)
20. Deng M, Chen X, Piaol L, Zhang X, Dai Z, Zing XJ. Synthesis of four-armed poly(e-caprolactone)-block-poly(ethylene oxide) by diethylzinc catalyst. J Polym Sci Part A Polym Chem. 2004; 42:950-9. (Pubitemid 38245760)
21. Park SY, Han DK, Kim SC. Synthesis and characterization of starshaped PLLA-PEO block copolymers with temperature-sensitive sol-gel transition behavior. Macromolecules. 2001;34:8821-4. (Pubitemid 34050716)
22. Kim SH, Han Y-K, Kim YH, Hong SI. Multifunctional initiation of stannous octoate/pentaerythritol for the polymerization of lactide. Makromol Chem. 1992;193:1623-31.
23. Kim SH, Han Y-K, Ahn K-D, Kim YH, Chang T. Preparation of star-shaped polylactide with pentaerythritol and stannous octoate. Makromol Chem. 1993;194:3229-36.
24. Gonçalves da Silva AM, Filipe EJM, d'Oliveira JMR, Martinho JMG. Interfacial behavior of poly(styrene)-poly(ethylene oxide) diblock copolymer monolayers at the air-water interface. Hydrophilic Block Chain Length and Temperature Influence. Langmuir. 1996;12:6547-53. (Pubitemid 126637982)
25. Gan Z, Jim TF, Li M, Yuer Z, Wang S, Wu C. Enzymatic biodegradation of poly(ethylene oxide-b-e-caprolactone) diblock copolymer and its potential biomedical applications. Macromolecules. 1999;32:590-4.
26. Kumar N, Ravikumar MNV, Domb AJ. Biodegradable block copolymers. Adv Drug Deliv Rev. 2001;53:23-44. (Pubitemid 33152832)
27. Ryu J-G, Jeong Y-I, Kim I-S, Lee J-H, Nay J-W, Kim S-H. Clonazepam release from core-shell type nanoparticles of poly(ecaprolactone)/poly(ethylene glycol)/poly(e-caprolactone) triblock copolymers. Int J Pharm. 2000;200:231-42. (Pubitemid 30364910)
28. Van Butsele K, Jérôme R, Jérôme C. Functional amphiphilic and biodegradable copolymers for intravenous vectorisation. Polymer. 2007;48:7431-43. (Pubitemid 350192500)
29. Mikhail AS, Allen C. Block copolymer micelles for delivery of cancer therapy: transport at the whole body, tissue and cellular levels. J Control Release. 2009;138:214-23.
30. Allen C,Han J,Yu Y,MaysingerD, Eisenberg A. Polycaprolactoneb- poly(ethylene oxide) copolymer micelles as a delivery vehicle for dihydrotestosterone. J Control Release. 2000;63:275-86.
31. Forresta ML, Wonb Ch-Y, Malickb AW, Kwon GS. In vitro release of the mTOR inhibitor rapamycin from poly(ethylene glycol)-b-poly(e-caprolactone) micelles. J Control Release. 2006;110(2):370-7. (Pubitemid 41827491)
32. Wang Y, Wang C, Fu S, Liu Q, Dou DY, Lv H, Fan M, Guo G, Luo F, Qian Z. Preparation of tacrolimus loaded micelles based on poly(e-caprolactone)- poly(ethylene glycol)-poly(e-caprolactone). Int J Pharm. 2011;407(1-2):184-9.
33. Meier MAR, Aerts SNH, Staal BBP, Rasa M, Schubert US. PEOb- PCL block copolymers: synthesis, detailed characterization, and selected micellar drug encapsulation behavior. Macromol Rapid Commun. 2005;26:1918-24. (Pubitemid 43051767)
34. Coleman R, Roma MG. Hepatocyte couplets. Biochem Soc Trans. 2000;28:136-40. (Pubitemid 30103229)
35. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65:55-63. (Pubitemid 14203433)
36. Kavros A, Robinson LY, Rimmer S. Effect of dimethylformamide on the ring opening insertion polymerization of e-caprolactone. J Chem Res (S) 1999;452-3.
37. Dong PW, Wang XH, Gu YC, Wang YJ, Wang YJ, Gong CY, Luo F, Guo G, Zhao X, Wei YQ, Qian ZY. Self-assembled biodegradable micelles based on star-shaped PCL-b-PEG copolymers for chemotherapeutic drug delivery. Colloids Surf A Physicochem Eng Aspec. 2010;358:128-34.
38. Van Butsele K, Sibret P, Fustin CA, Gohy JF, Passirani C, Benoit J-P, Jérôme R, Jérôme CJ. Synthesis and pH-dependent micellization of diblock copolymer mixtures. Colloid Interf Sci. 2009;329:235-43.
39. Allen C, Yu Y, Maysinger D, Eisenberg A. Polycaprolactone-bpoly( ethylene oxide) block copolymer micelles as a novel drug delivery vehicle for neurotrophic agents FK506 and L-685,818. Bioconjug Chem. 1998;9:564-72.
40. Lu C, Liu L, Guo S-R, Zhang Y, Li Z, Gu J. Micellization and gelation of aqueous solutions of star-shaped PEG-PCL block copolymers consisting of branched 4-arm poly(ethylene glycol) and polycaprolactone blocks. Euro Polym J. 2007;43:1857-65. (Pubitemid 46660868)
41. Zhang Y, Zhuo R-X. Synthesis and in vitro drug release behavior of amphiphilic triblock copolymer nanoparticles based on poly (ethylene glycol) and polycaprolactone. Biomaterials. 2005;26: 6736-42. (Pubitemid 41021767)
42. Richter A, Olbrich C, Krause M, Hoffmann J, Kissel T. Polymeric micelles for parenteral delivery of Sagopilone: physicochemical characterization, novel formulation approaches and their toxicity assessment in vitro as well as in vivo. Eur J Pharm Biopharm. 2010;75(2):80-9.
43. GongCY, Shi S,WuL,GouML, YinQQ,GuoQF,DongPW,Zhang F, Luo F, Zhao X, Wei YQ, Qian ZY. Biodegradable in situ gelforming controlled drug delivery system based on thermosensitive PCL-PEG-PCL hydrogel. Part 2: Sol-gel-sol transition and drug delivery behavior. Acta Biomater. 2009;5:3358-70.
44. Lin C-M, Chen Y-Z, Sheng Y-J, Tsao H-K. Effects of macromolecular architecture on the micellization behavior of complex block copolymers. React Funct Polym. 2009;69:539-45.
45. Hatefi Y. The mitochondrial electron transport and oxidative phosphorylation system. Annu Rev Biochem. 1985;54:1015-69. (Pubitemid 15073670)
46. Serrano MC, Pagani R, Vallet-Regí M, Peña J, Rámila A, Izquierdo I, Portolés MT. In vitro biocompatibility assessment of poly(e-caprolactone) films using L929 mouse fibroblasts. Biomaterials. 2004;25(25):5603-11. (Pubitemid 38680488)
47. Ignatius AA, Claes LE. In vitro biocompatibility of bioresorbable polymers: poly(l, dl-lactide) and poly(l-lactide-coglycolide). Biomaterials. 1996;17:831-9. (Pubitemid 26108352)
48. Foster KA, Yazdanian M, Audus KL. Microparticulate uptake mechanisms of in vitro cell culture models of the respiratory epithelium. J Pharm Pharmacol. 2001;53:57-66. (Pubitemid 32123700)
49. Jule E, Nagasaki Y, Kataoka K. Lactose-installed poly(ethylene glycol)-poly(D,L-lactide) block copolymer micelles exhibit fastrate binding and high affinity toward a protein bed simulating a cell surface. A surface plasmon resonance study. Bioconjug Chem. 2003;14:177-86. (Pubitemid 36169031)
50. Allen C, Yu Y, Eisenberg A, Maysinger D. Cellular internalization of PCL20-b-PEO44 block copolymer micelles. Biochim Biophys Acta. 1999;1421:32-8. (Pubitemid 29421855)
51. Repetto G, del Peso A, Zurita JL. Neutral red uptake assay for the estimation of cell viability/cytotoxicity. Nat Protoc. 2008;3(7): 1125-31.