Facile fabrication of core cross-linked micelles by RAFT polymerization and enzyme-mediated reaction

Colloids and Surfaces B: Biointerfaces

Volumn 118, Issue , 2014, Pages 298-305

  Wu, Yukun ^a   Lai, Quanyong ^a   Lai, Shuqi ^a   Wu, Jing ^a   Wang, Wei ^a   Yuan, Zhi ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

Core cross linked micelles; Enzymatic reaction; Horseradish peroxidase; Self assembly

Indexed keywords

ACRYLIC MONOMERS; AMIDES; BLOCK COPOLYMERS; CONTROLLED DRUG DELIVERY; CRITICAL MICELLE CONCENTRATION; CROSSLINKING; ENZYMES; FABRICATION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; FOOD PRODUCTS; LIVING POLYMERIZATION; POLYETHYLENE GLYCOLS; POLYETHYLENE OXIDES; SELF ASSEMBLY; TARGETED DRUG DELIVERY;

AMPHIPHILIC BLOCK COPOLYMERS; CORE CROSS-LINKED MICELLES; ENZYMATIC POLYMERIZATION; ENZYMATIC REACTION; ENZYME-MEDIATED REACTION; HORSE-RADISH PEROXIDASE; LOWER CRITICAL SOLUTION TEMPERATURE; REVERSIBLE ADDITION-FRAGMENTATION CHAIN TRANSFER POLYMERIZATION;

MICELLES;

COPOLYMER; DOXORUBICIN; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; POLY(ETHYLENE GLYCOL) BLOCK POLY(N ISOPROPYLACRYLAMIDE CO N (4 HYDROXYPHENETHYL) ACRYLAMIDE) DIBLOCK COPOLYMER; UNCLASSIFIED DRUG; ACRYLAMIDE DERIVATIVE; CROSS LINKING REAGENT; MACROGOL DERIVATIVE; MICELLE; N-ISOPROPYLACRYLAMIDE;

ANALYTIC METHOD; ARTICLE; CHEMICAL MODIFICATION; CRITICAL MICELLE CONCENTRATION; CROSS LINKING; DRUG DELIVERY SYSTEM; DRUG RELEASE; ENZYME MECHANISM; FLUORESCENCE SPECTROSCOPY; LIGHT SCATTERING; MICELLE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN POLYMERIZATION; REVERSIBLE ADDITION FRAGMENTATION CHAIN TRANSFER; CHEMISTRY; HYDRODYNAMICS; LIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; RADIATION SCATTERING; SYNTHESIS; TEMPERATURE;

ARMORACIA RUSTICANA;

ACRYLAMIDES; CROSS-LINKING REAGENTS; HYDRODYNAMICS; LIGHT; MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; POLYETHYLENE GLYCOLS; POLYMERIZATION; SCATTERING, RADIATION; TEMPERATURE;

EID: 84900829864     PISSN: 09277765     EISSN: 18734367     Source Type: Journal    
DOI: 10.1016/j.colsurfb.2014.03.031     Document Type: Article

References (56)

1. Nicolas J., Mura S., Brambilla D., Mackiewicz N., Couvreur P. Design, functionalization strategies and biomedical applications of targeted biodegradable/biocompatible polymer-based nanocarriers for drug delivery. Chem. Soc. Rev. 2013, 42:1147-1235.
2. Tian H., Tang Z., Zhuang X., Chen X., Jing X. Biodegradable synthetic polymers: preparation, functionalization and biomedical application. Prog. Polym. Sci. 2012, 37:237-280.
3. Ganta S., Devalapally H., Shahiwala A., Amiji M. A review of stimuli-responsive nanocarriers for drug and gene delivery. J. Control. Release 2008, 126:187-204.
4. Kataoka K., Harada A., Nagasaki Y. Block copolymer micelles for drug delivery: design, characterization and biological significance. Adv. Drug Deliv. Rev. 2001, 47:113-131.
5. Chauhan V.P., Jain R.K. Strategies for advancing cancer nanomedicine. Nat. Mater. 2013, 12:958-962.
6. Gotrik K.W., Hannon A.F., Son J.G., Keller B., Alexander-Katz A., Ross C.A. Morphology control in block copolymer films using mixed solvent vapors. ACS Nano 2012, 6:8052-8059.
7. Bastakoti B.P., Ishihara S., Leo S.-Y., Ariga K., Wu K.C.-W., Yamauchi Y. Polymeric micelle assembly for preparation of large-sized mesoporous metal oxides with various compositions. Langmuir 2014, 30:651-659.
8. Bastakoti B.P., Liao S.-H., Inoue M., Yusa S.-I., Imura M., Nakashima K., et al. pH-responsive polymeric micelles with core-shell-corona architectures as intracellular anti-cancer drug carriers. Sci. Technol. Adv. Mater. 2013, 14:44402-44407.
9. Discher D.E., Eisenberg A. Polymer vesicles. Science 2002, 297:967-973.
10. Tyrrell Z.L., Shen Y., Radosz M. Fabrication of micellar nanoparticles for drug delivery through the self-assembly of block copolymers. Prog. Polym. Sci. 2010, 35:1128-1143.
11. Kwon I.K., Lee S.C., Han B., Park K. Analysis on the current status of targeted drug delivery to tumors. J. Control. Release 2012, 164:108-114.
12. Kanasty R., Dorkin J.R., Vegas A., Anderson D. Delivery materials for siRNA therapeutics. Nat. Mater. 2013, 12:967-977.
13. Kohori F., Sakai K., Aoyagi T., Yokoyama M., Yamato M., Sakurai Y., et al. Control of adriamycin cytotoxic activity using thermally responsive polymeric micelles composed of poly(N-isopropylacrylamide-co-N,N-dimethylacrylamide)-b-poly(-lactide). Colloids Surf. B: Biointerfaces 1999, 16:195-205.
14. Bastakoti B.P., Hsu Y.-C., Liao S.-H., Wu K.C.-W., Inoue M., Yusa S., et al. Inorganic-organic hybrid nanoparticles with biocompatible calcium phosphate thin shells for fluorescence enhancement. Chem. Asian J. 2013, 8:1301-1305.
15. Li Y., Xiao K., Luo J., Xiao W., Lee J.S., Gonik A.M., et al. Well-defined, reversible disulfide cross-linked micelles for on-demand paclitaxel delivery. Biomaterials 2011, 32:6633-6645.
16. Rodríguez-Hernández J., Chécot F., Gnanou Y., Lecommandoux S. Toward smart nano-objects by self-assembly of block copolymers in solution. Prog. Polym. Sci. 2005, 30:691-724.
17. Thurmond K.B., Huang H., Clark C.G., Kowalewski T., Wooley K.L. Shell cross-linked polymer micelles: stabilized assemblies with great versatility and potential. Colloids Surf. B: Biointerfaces 1999, 16:45-54.
18. Gao H., Xiong J., Cheng T., Liu J.J., Chu L., Ma R., et al. In vivo biodistribution of mixed shell micelles with tunable hydrophilic/hydrophobic surface. Biomacromolecules 2013, 14:460-467.
19. Thurmond K.B., Kowalewski T., Wooley K.L. Water-soluble knedel-like structures: the preparation of shell-cross-linked small particles. J. Am. Chem. Soc. 1996, 118:7239-7240.
20. Wu Y., Chen W., Meng F., Wang Z., Cheng R., Deng C., et al. Core-crosslinked pH-sensitive degradable micelles: a promising approach to resolve the extracellular stability versus intracellular drug release dilemma. J. Control. Release 2012, 164:338-345.
21. Kadam V.S., Nicol E., Gaillard C. Synthesis of flower-like poly(ethylene oxide) based macromolecular architectures by photo-cross-linking of block copolymers self-assemblies. Macromolecules 2012, 45:410-419.
22. Weaver J.V.M., Tang Y., Liu S., Iddon P.D., Grigg R., Billingham N.C., et al. Preparation of shell cross-linked micelles by polyelectrolyte complexation. Angew. Chem. Int. Ed. 2004, 43:1389-1392.
23. Kurisawa M., Chung J.E., Yang Y.Y., Gao S.J., Uyama H. Injectable biodegradable hydrogels composed of hyaluronic acid-tyramine conjugates for drug delivery and tissue engineering. Chem. Commun. (Camb.) 2005, 4312-4314.
24. Fukuoka T., Uyama H., Kobayashi S. Polymerization of polyfunctional macromolecules: synthesis of a new class of high molecular weight poly(amino acid)s by oxidative coupling of phenol-containing precursor polymers. Biomacromolecules 2004, 5:977-983.
25. Kobayashi S., Makino A. Enzymatic polymer synthesis: an opportunity for green polymer chemistry. Chem. Rev. 2009, 109:5288-5353.
26. Kobayashi S., Uyama H., Kimura S. Enzymatic polymerization. Chem. Rev. 2001, 101:3793-3818.
27. Hu J., Zhang G., Liu S. Enzyme-responsive polymeric assemblies, nanoparticles and hydrogels. Chem. Soc. Rev. 2012, 41:5933-5949.
28. Singh S., Topuz F., Hahn K., Albrecht K., Groll J. Embedding of active proteins and living cells in redox-sensitive hydrogels and nanogels through enzymatic cross-linking. Angew. Chem. Int. Ed. 2013, 52:3000-3003.
29. Teixeira L.S.M., Feijen J., van Blitterswijk C.A., Dijkstra P.J., Karperien M. Enzyme-catalyzed crosslinkable hydrogels: emerging strategies for tissue engineering. Biomaterials 2012, 33:1281-1290.
30. Kim B.Y., Park K.M., Joung Y.K., Park K.D. Preparation and characterizations of in situ shell cross-linked 4-arm-poly(propylene oxide)-poly(ethylene oxide) micelles via enzyme-mediated reaction for controlled drug delivery. J. Bioact. Compat. Polym. 2012, 27:185-197.
31. Huang X., Lan T., Zhang B., Ren J. Gold nanoparticle-enzyme conjugates based FRET for highly sensitive determination of hydrogen peroxide, glucose and uric acid using tyramide reaction. Analyst 2012, 137:30-32.
32. Minamihata K., Goto M., Kamiya N. Protein heteroconjugation by the peroxidase-catalyzed tyrosine coupling reaction. Bioconjugate Chem. 2011, 22:2332-2338.
33. Sakai S., Ito S., Ogushi Y., Hashimoto I., Hosoda N., Sawae Y., et al. Enzymatically fabricated and degradable microcapsules for production of multicellular spheroids with well-defined diameters of less than 150 microm. Biomaterials 2009, 30:5937-5942.
34. Boyer C., Granville A., Davis T.P., Bulmus V. Modification of RAFT-polymers via thiol-ene reactions: a general route to functional polymers and new architectures. J. Polym. Sci. A: Polym. Chem. 2009, 47:3773-3794.
35. Achanta S., Liautard V., Paugh R., Organ M.G. The development of a general strategy for the synthesis of tyramine-based natural products by using continuous flow techniques. Chem. Eur. J. 2010, 16:12797-12800.
36. Huang W., Wang W., Wang P., Tian Q., Zhang C., Wang C., et al. Glycyrrhetinic acid-modified poly(ethylene glycol)-b-poly(gamma-benzyl l-glutamate) micelles for liver targeting therapy. Acta Biomater. 2010, 6:3927-3935.
37. Zhang C., Wang W., Liu T., Wu Y., Guo H., Wang P., et al. Doxorubicin-loaded glycyrrhetinic acid-modified alginate nanoparticles for liver tumor chemotherapy. Biomaterials 2012, 33:2187-2196.
38. Willcock H., O'Reilly R.K. End group removal and modification of RAFT polymers. Polym. Chem. 2010, 1:149-157.
39. Gregory A., Stenzel M.H. Complex polymer architectures via RAFT polymerization: from fundamental process to extending the scope using click chemistry and nature's building blocks. Prog. Polym. Sci. 2012, 37:38-105.
40. Chiefari J., Chong Y.K.(Bill), Ercole F., Krstina J., Jeffery J., Le T.P.T., et al. Living free-radical polymerization by reversible addition-fragmentation chain transfer: the RAFT process. Macromolecules 1998, 31:5559-5562.
41. Liu Y., Ibricevic A., Cohen J.A., Cohen J.L., Gunsten S.P., Fréchet J.M.J., et al. Impact of hydrogel nanoparticle size and functionalization on in vivo behavior for lung imaging and therapeutics. Mol. Pharm. 2009, 6:1891-1902.
42. Li Y., Lokitz B.S., Armes S.P., McCormick C.L. RAFT synthesis of a thermally responsive ABC triblock copolymer incorporating N-acryloxysuccinimide for facile in situ formation of shell cross-linked micelles in aqueous media. Macromolecules 2006, 39:81-89.
43. Schild H.G. Poly(N-isopropylacrylamide): experiment, theory and application. Prog. Polym. Sci. 1992, 17:163-249.
44. Wei H., Cheng S.-X., Zhang X.-Z., Zhuo R.-X. Thermo-sensitive polymeric micelles based on poly(N-isopropylacrylamide) as drug carriers. Prog. Polym. Sci. 2009, 34:893-910.
45. Yang R., Meng F., Ma S., Huang F., Liu H., Zhong Z. Galactose-decorated cross-linked biodegradable poly(ethylene glycol)-b-poly(e-caprolactone) block copolymer micelles for enhanced hepatoma-targeting delivery of paclitaxel. Biomacromolecules 2011, 12:3047-3055.
46. Zhang W., Shi L., Wu K., An Y. Thermoresponsive micellization of poly(ethylene glycol)-b-poly(N-isopropylacrylamide) in water. Macromolecules 2005, 38:5743-5747.
47. Qin S., Geng Y., Discher D.E., Yang S. Temperature-controlled assembly and release from polymer vesicles of poly(ethylene oxide)-block-poly(N-isopropylacrylamide). Adv. Mater. 2006, 18:2905-2909.
48. Zhang J., Jiang X., Zhang Y., Li Y., Liu S. Facile fabrication of reversible core cross-linked micelles possessing thermosensitive swellability. Macromolecules 2007, 40:9125-9132.
49. Xu X., Flores J.D., McCormick C.L. Reversible imine shell cross-linked micelles from aqueous RAFT-synthesized thermoresponsive triblock copolymers as potential nanocarriers for pH-triggered drug release. Macromolecules 2011, 44:1327-1334.
50. Li Y., Xiao W., Xiao K., Berti L., Luo J., Tseng H.P., et al. Well-defined, reversible boronate crosslinked nanocarriers for targeted drug delivery in response to acidic pH values and cis-diols. Angew. Chem. Int. Ed. 2012, 51:2864-2869.
51. Quan C.-Y., Wei H., Shi Y., Li Z., Cheng S.-X., Zhang X.-Z., et al. Fabrication of multifunctional shell cross-linked micelles for targeting drug release. Colloid Polym. Sci. 2011, 289:667-675.
52. Nakabayashi K., Oya H., Mori H. Cross-linked core-shell nanoparticles based on amphiphilic block copolymers by RAFT polymerization and palladium-catalyzed suzuki coupling reaction. Macromolecules 2012, 45:3197-3204.
53. Seo M., Beck B.J., Paulusse J.M.J., Hawker C.J., Kim S.Y. Polymeric nanoparticles via noncovalent cross-linking of linear chains. Macromolecules 2008, 41:6413-6418.
54. Yhaya F., Binauld S., Kim Y., Stenzel M.H. Shell cross-linking of cyclodextrin-based micelles via supramolecular chemistry for the delivery of drugs. Macromol. Rapid Commun. 2012, 33:1868-1874.
55. Samarajeewa S., Shrestha R., Li Y., Wooley K.L. Degradability of poly(lactic acid)-containing nanoparticles: enzymatic access through a cross-linked shell barrier. J. Am. Chem. Soc. 2012, 134:1235-1242.
56. Xiong W., Wang W., Wang Y., Zhao Y., Chen H., Xu H., et al. Dual temperature/pH-sensitive drug delivery of poly(N-isopropylacrylamide-co-acrylic acid) nanogels conjugated with doxorubicin for potential application in tumor hyperthermia therapy. Colloids Surf. B 2011, 84:447-453.