New amphiphilic PEG-b-P(ester–ether) micelles as potential drug nanocarriers
Source abstract
Abstract
A range of diblock and triblock copolymers of dioxanone and methyl dioxanone (MeDX) were synthesized by ring-opening polymerization of dioxanone and MeDX initiated by hydroxyl-terminated PEG (MPEG) or di-amino-terminated PEG (Jeffamine®) as macroinitiator in the presence of Sn(Oct)2. The copolymers exhibit amphiphilic behavior in water forming core–shell micelles in the size range 120–300 nm as measured by DLS. DSC measurements exhibit only one melting transition for all copolymers and confirm that increasing MeDX content of the copolymers lead to decreasing crystalline character and hydrophobic–hydrophilic chain entanglement. Anti-inflammatory drug ketoprofen was successfully loaded into the hydrophobic core of the micelles. Various key parameters such as micelle size, drug entrapment efficiency and drug release, which are dependent on crystalline structure and biodegradability characteristics of the hydrophobic core, could effectively be controlled by varying the dioxanone/MeDX ratio of the (ester–ether) copolymer.
Source: openaire · Quality: candidate unverified · Source record ↗
Research context
OpenAlex topics: Nanoparticle-Based Drug Delivery · Advanced Polymer Synthesis and Characterization · Polymer Surface Interaction Studies
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (44)
Show source-provided references
1. Bahadur RKC, Bhattarai SR, Aryal S, Khil MS, Dharmaraj N, Kim HY (2007) Novel amphiphilic triblock copolymer based on PPDO, PCL, and PEG: Synthesis, characterization, and aqueous dispersion. Colloids Surf A Physicochem Eng Asp 292:69–78. doi: 10.1016/j.colsurfa.2006.06.00910.1016/j.colsurfa.2006.06.009 ↗
2. Bhattarai N, Bhattarai SR, Khil MS, Lee DR, Kim HY (2003) Aqueous solution properties of amphiphilic triblock copolymer poly(p-dioxanone-co-l-lactide)-block-poly(ethylene glycol). Eur Polym J 29:1603–1608. doi: 10.1016/S0014-3057(03)00057-010.1016/S0014-3057(03)00057-0 ↗
3. Bhattarai SR, Kim SY, Jang KY, Yi HK, Lee YH, Bhattarai N, Nam SY, Lee DY, Kim HY, Hwang PH (2007) Amphiphilic triblock copolymer poly(p-dioxanone-co-L-lactide)-block-poly(ethylene glycol), enhancement of gene expression and inhibition of lung metastasis by aerosol delivery. Gene Ther 14:476–483. doi: 10.1038/sj.gt.330287610.1038/sj.gt.3302876 ↗
4. Cuong NG, Hsieh MF, Chen YT, Liau I (2010) Synthesis and characterization of PEG–PCL–PEG triblock copolymers as carriers of doxorubicin for the treatment of breast cancer. J App Polym Sci 117:3694–3703. doi: 10.1002/app.3226610.1002/app.32266 ↗
5. Danhier F, Lecouturier N, Vroman B, Jérôme C, Marchand-Brynaert J, Feron O, Préat V (2009) Paclitaxel-loaded PEGylated PLGA-based nanoparticles: in vitro and in vivo evaluation. J Control Release 133:11–17. doi: 10.1016/j.jconrel.2008.09.08610.1016/j.jconrel.2008.09.086 ↗
6. Derakhshandeh K, Soheili M, Dadashzadeh S, Saghiri R (2010) Preparation and in vitro characterization of 9-nitrocamptothecin-loaded long circulating nanoparticles for delivery in cancer patients. Int J Nanomed 5:463–471. doi: 10.2147/IJN.S1158610.2147/IJN.S11586 ↗
7. Deshayes G, Delcourt C, Verbruggen I, Trouillet-Fonti L, Touraud F, Fleury E, Degee P, Destarac M, Willem R, Dubois P (2011) Eur Polym J 47:98–110. doi: 10.1016/j.eurpolymj.2010.07.00510.1016/j.eurpolymj.2010.07.005 ↗
8. Di Tommaso C, Como C, Gurny R, Möller M (2010) Investigations on the lyophilisation of MPEG-hexPLA micelle based pharmaceutical formulations. Eur J Pharm Sci 40:38–47. doi: 10.1016/j.ejps.2010.02.00610.1016/j.ejps.2010.02.006 ↗
9. Genta I, Conti B, Perugini P, Pavanetto F, Sparado A, Puglisi G (1997) Bioadhesive microspheres for ophthalmic administration of acyclovir. J Pharm Pharmacol 49:737–742. doi: 10.1111/j.2042-7158.1997.tb06103.x10.1111/j.2042-7158.1997.tb06103.x ↗
10. Han X, Liu J, Xie C, Zhan C, Gu B, Liu Y, Feng L, Lu W (2009) 9-NC-loaded folate-conjugated polymer micelles as tumor targeted drug delivery system: preparation and evaluation in vitro. Int J Pharm 372:125–131. doi: 10.1016/j.ijpharm.2008.12.03510.1016/j.ijpharm.2008.12.035 ↗
11. Hu Y, Jiang X, Ding Y, Zhang L, Yang C, Zhang J, Chen J, Yang Y (2003) Preparation and drug release behaviors of nimodipine-loaded poly(caprolactone)–poly(ethylene oxide)–polylactide amphiphilic copolymer nanoparticles. Biomaterials 24:2395–2404. doi: 10.1016/S0142-9612(03)00021-810.1016/S0142-9612(03)00021-8 ↗
12. Hu K, Li J, Shen Y, Lu W, Gao X, Zhang Q, Jiang X (2009) Lactoferrin-conjugated PEG-PLA nanoparticles with improved brain delivery: In vitro and in vivo evaluations. J Control Release 134:55–61. doi: 10.1016/j.jconrel.2008.10.01610.1016/j.jconrel.2008.10.016 ↗
13. Hussain H, Tan BH, Mya K, Liu Y, He CB, Davis TP (2010) Synthesis, micelle formation, and bulk properties of poly(ethylene glycol)-b-poly(pentafluorostyrene)-g-polyhedral oligomeric silsesquioxane amphiphilic hybrid copolymers. J Polym Sci Part A 48:152–163. doi: 10.1002/pola.2377310.1002/pola.23773 ↗
14. Kalangos A (2005) Polydioxanone polymers for annuloplasty in valve repair. Macromol Symp 231:81–83. doi: 10.1002/masy.20059002710.1002/masy.200590027 ↗
15. Kumar N, Ravikumar MN, Domb AJ (2001) Biodegradable block copolymers. Adv Drug Del Rev 53:23–44. doi: 10.1016/S0169-409X(01)00219-810.1016/S0169-409X(01)00219-8 ↗
16. Latere Dwan’Isa JP, Rouxhet L, Brewster ME, Préat V, Ariën A (2008) Spontaneously self-assembled micelles from poly(ethylene glycol)-b-poly(ε-caprolactone-co-trimethylene carbonate) for drug solubilization. Pharmazie 63:235–240. doi: 10.1691/ph.2008.7324
17. Li MX, Zhuo RX, Qu FQ (2003) Study on the preparation of novel functional poly(dioxanone) and for the controlled release of protein. React Funct Polym 55:185–195. doi: 10.1016/S1381-5148(02)00246-810.1016/S1381-5148(02)00246-8 ↗
18. Li Y, Qi XR, Maitani Y, Nagai T (2009) PEG–PLA diblock copolymer micelle-like nanoparticles as all-trans-retinoic acid carrier: in vitro and in vivo characterizations. Nanotechnology 20:1–10. doi: 10.1088/0957-4484/20/5/055106
19. Lim Soo P, Luo L, Maysinger D, Eisenberg A (2002) Incorporation and release of hydrophobic probes in biocompatible polycaprolactone-block-poly (ethylene oxide) micelles: implications for drug delivery. Langmuir 18:9996–10004. doi: 10.1021/la026339b10.1021/la026339b ↗
20. Lin WJ, Juang LW, Wang CL, Juang LW (2006) Characterization and comparison of diblock and triblock amphiphilic copolymers of poly(delta-valerolactone). J Appl Polym Sci 100:1831–1836. doi: 10.1002/app.2258010.1002/app.22058 ↗
21. Lin WJ, Juang LW, Wang CL, Chen YC, Lin CC, Chang KL (2010) Pegylated polyester polymeric micelles as a nano-carrier: synthesis, characterization, degradation, and biodistribution. J Exp Clin Med 2:4–10. doi: 10.1016/S1878-3317(10)60002-210.1016/S1878-3317(10)60002-2 ↗
22. Liu J, Xiao Y, Allen C (2004) Polymer-drug compatibility: a guide to the development of delivery systems for the anticancer agent, ellipticine. J Pharm Sci 93:132–143. doi: 10.1002/jps.1053310.1002/jps.10533 ↗
23. Liu J, Lee H, Allen C (2006) Formulation of drugs in block copolymer micelles: drug loading and release. Curr Pharm Des 12:4685–4701. doi: 10.2174/13816120677902626310.2174/138161206779026263 ↗
24. Lochee Y, Bhaw-Luximon A, Jhurry D, Kalangos A (2009) Novel biodegradable poly(ester–ether)s: copolymers from 1,4-dioxan-2-one and d,l-3-methyl-1,4-dioxan-2-one. Macromolecules 42:7285–7291. doi: 10.1021/ma900747q10.1021/ma900747q ↗
25. Lochee Y, Jhurry D, Bhaw-Luximon A, Kalangos A (2010) Biodegradable poly(ester–ether)s: ring-opening polymerization of d,l-3-methyl-1,4-dioxan-2-one using various initiator systems. Polym Int 59:1310–1318. doi: 10.1002/pi.287110.1002/pi.2871 ↗
26. Lukyanov AN, Gao Z, Mazzola L, Torchilin VP (2002) Polyethylene glycol-diacyllipid micelles demonstrate increased acculumation in subcutaneous tumors in mice. Pharm Res 19:1424–1429. doi: 10.1023/A:102048801226410.1023/A:1020488012264 ↗
27. Moretton MA, Chiappetta DA, Sosnik A (2011) Cryoprotection-lyophilization and physical stabilization of rifampicin-loaded flower-like polymeric micelles. J R Soc Interface 9:487–502. doi: 10.1098/rsif.2011.041410.1098/rsif.2011.0414 ↗
28. Nagy M, Szöllösi L, Kéki S, Faust R, Zsuga M (2009) Poly(vinyl alcohol)-based amphiphilic copolymer aggregates as drug carrying nanoparticles. J Macromol Sci Part A 46:331–338. doi: 10.1080/1060132090271937010.1080/10601320902719370 ↗
29. Nishiyama N, Kataoka K (2006) Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery. Pharmacol Ther 112:630–648. doi: 10.1016/j.pharmthera.2006.05.00610.1016/j.pharmthera.2006.05.006 ↗
30. Owens DE, III Peppas NA (2006) Opsonization, biodistribution, and pharmacokinetics of polymeric nanoparticles. Int J Pharm 307:93–102. doi: 10.1016/j.ijpharm.2005.10.01010.1016/j.ijpharm.2005.10.010 ↗
31. Park J, Fong PM, Lu J, Russell KS, Booth CJ, Saltzmann WM, Fahmy TM (2009) PEGylated PLGA nanoparticles for the improved delivery of doxorubicin. Nanomedicine 5:410–418. doi: 10.1016/j.nano.2009.02.00210.1016/j.nano.2009.02.002 ↗
32. Qiu LY, Bae YH (2006) Polymer architecture and drug delivery. Pharm Res 23:1–30. doi: 10.1007/s11095-005-9046-210.1007/s11095-005-9046-2 ↗
33. Ryu J, Jeong YI, Kim IS, Lee JH, Nah JW, Kim SH (2000) Clonazepam release from core-shell type nanoparticles of poly(epsilon-caprolactone)/poly(ethylene glycol)/poly(epsilon-caprolactone) triblock copolymers. Int J Pharm 200:231–242. doi: 10.1016/S0378-5173(00)00392-610.1016/S0378-5173(00)00392-6 ↗
34. Schindler A, Pitt CG (1982) Biodegradable elastomeric polyesters. Polym Prep Am Chem Soc 23:111–112
35. Sutton D, Wang S, Nasongkla N, Gao J, Dormidontova EE (2007) Doxorubicin and β-lapachone release and interaction with micellar core materials: experiment and modeling. Exp Biol Med 232:1090–1099. doi: 10.3181/0702-RM-3110.3181/0702-RM-31 ↗
36. Takeishi M, Hirase Y, Kojima T (1992) Microsurgical use of polydioxanone (PDS) suture: an experimental report. Microsurgery 13:268–272. doi: 10.1002/micr.192013051510.1002/micr.1920130515 ↗
37. Tian W, Chen Q, Yu C, Shen J (2003) Amino-terminated poly(ethylene glycol) as the initiator for the ring-opening polymerization of 3-methylmorpholine-2,5-dione. Europ Polym J 39:1935–1938. doi: 10.1016/S0014-3057(03)00091-010.1016/S0014-3057(03)00091-0 ↗
38. Trimaille T, Mondon K, Gurny R, Moller M (2006) Novel polymeric micelles for hydrophobic drug delivery based on biodegradable poly(hexyl-substituted lactides). Int J Pharm 319:147–154. doi: 10.1016/j.ijpharm.2006.03.03610.1016/j.ijpharm.2006.03.036 ↗
39. Venkatraman SS, Jie P, Min F, Freddy BYC, Leong-Huat G (2005) Micelle-like nanoparticles of PLA–PEG–PLA triblock copolymer as chemotherapeutic carrier. Int J Pharm 298:219–223. doi: 10.1016/j.ijpharm.2005.03.02310.1016/j.ijpharm.2005.03.023 ↗
40. Xu RL, Winnik MA, Hallett FR, Gerrard R, Croucher MD (1991) Light-scattering study of the association behavior of styrene-ethylene oxide block copolymers in aqueous solution. Macromolecules 24:87–93. doi: 10.1021/ma00001a01410.1021/ma00001a014 ↗
41. Yan Q, Yuan J, Kang Y, Yin Y (2010) Dynamic supramacromolecular self-assembly: deformable polymer fabricated nanostructures through a host-controlled approach. Polym Chem 1:423–425. doi: 10.1039/C0PY00024H10.1039/c0py00024h ↗
42. Yang KK, Wang XL, Wang YZ (2002) Poly(p-dioxanone) and its copolymers. J Macromol Sci Part C 42:373–398. doi: 10.1081/MC-12000645310.1081/MC-120006453 ↗
43. Yokoyama M, Kwon GS, Okano T, Sakurai Y, Seto Y, Kataoka K (1992) Preparation of micelle-forming polymer–drug conjugates. Bioconjug Chem 2:295–301. doi: 10.1021/bc00016a00710.1021/bc00016a007 ↗
44. Zweers ML, Engbers GH, Grijpma DW, Feijen J (2006) Release of anti-restenosis drugs from poly (ethylene oxide)-poly(dl-lactic-co-glycolic acid) nanoparticles. J Control Release 114:317–324. doi: 10.1016/j.jconrel.2006.05.02110.1016/j.jconrel.2006.05.021 ↗