High internal phase emulsion templating with self-emulsifying and thermoresponsive chitosan-graft -PNIPAM-graft -oligoproline

Biomacromolecules

Volumn 15, Issue 5, 2014, Pages 1777-1787

  Oh, Bernice H L ^a,b   Bismarck, Alexander ^b,c   Chan Park, Mary B ^a  

^a Nanyang Technological University   (Singapore)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

CHITOSAN; DRUG DELIVERY; GRAFTING (CHEMICAL); LIQUIDS; POLYMERS; POROSITY; SCAFFOLDS; SCAFFOLDS (BIOLOGY); SURFACE ACTIVE AGENTS;

HIGH INTERNAL PHASE EMULSIONS; IMMISCIBLE LIQUIDS; INTERNAL PHASE; POLYMER CONCENTRATIONS; PORE INTERCONNECTIVITY; SELF-EMULSIFYING; THERMO-RESPONSIVE; TISSUE ENGINEERING SCAFFOLD;

EMULSIFICATION;

CHITOSAN DERIVATIVE; COPOLYMER; EMULSIFYING AGENT; GLUTAMIC ACID; PROLINE DERIVATIVE; SURFACTANT; XYLENE; ACRYLIC ACID RESIN; CHITOSAN; EMULSION; POLY-N-ISOPROPYLACRYLAMIDE; PROLINE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL PROCEDURES; CONJUGATION; CONTROLLED STUDY; DISSOLUTION; EMULSION; FREEZE DRYING; GELATION; HIGH INTERNAL PHASE EMULSION; HYDROGEN BOND; ISOELECTRIC POINT; MOLECULAR WEIGHT; PH; POLYMERIZATION; POROSITY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILITY; SURFACE PROPERTY; ZETA POTENTIAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG DELIVERY SYSTEM; PARTICLE SIZE; SYNTHESIS; TEMPERATURE; TISSUE SCAFFOLD;

ACRYLIC RESINS; CHITOSAN; DRUG DELIVERY SYSTEMS; EMULSIONS; MOLECULAR STRUCTURE; PARTICLE SIZE; POROSITY; PROLINE; SURFACE PROPERTIES; TEMPERATURE; TISSUE SCAFFOLDS;

EID: 84900410531     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm500172u     Document Type: Article

References (65)

1. Babak, V. G.; Stébé, M.-J. Highly Concentrated Emulsions: Physicochemical Principles of Formulation J. Dispersion Sci. Technol. 2002, 23, 1-22
2. Jager-Lézer, N.; Tranchant, J.-F.; Alard, V.; Vu, C.; Tchoreloff, P. C.; Grossiord, J. L. Rheological Analysis of Highly Concentrated w/o Emulsions Rheol. Acta 1998, 37, 129-138
3. Cejkova, J.; Stepanek, F. Compartmentalized and Internally Structured Particles for Drug Delivery-A Review Curr. Pharm. Design 2013, 19, 6298-6314
4. Zhang, H. F.; Cooper, A. I. Synthesis and Applications of Emulsion-Templated Porous Materials Soft Matter 2005, 1, 107-113
5. Cameron, N. R. High Internal Phase Emulsion Templating as a Route to Well-Defined Porous Polymers Polymer 2005, 46, 1439-1449
6. Pulko, I.; Krajnc, P. High Internal Phase Emulsion Templating-A Path To Hierarchically Porous Functional Polymers Macromol. Rapid Commun. 2012, 33, 1731-1746
7. Silverstein, M. S.; Cameron, N. R. PolyHIPEs -Porous Polymers from High Internal Phase Emulsions. In Encyclopedia of Polymer Science and Technology; John Wiley & Sons, Inc.: Hoboken, NJ, 2002.
8. Silverstein, M. S. PolyHIPEs: Recent Advances in Emulsion-Templated Porous Polymers Prog. Polym. Sci. 2014, 39, 199-234
9. Kimmins, S. D.; Cameron, N. R. Functional Porous Polymers by Emulsion Templating: Recent Advances Adv. Funct. Mater. 2011, 21, 211-225
10. Ottens, M.; Leene, G.; Beenackers, A. A. C. M.; Cameron, N.; Sherrington, D. C. PolyHipe: A New Polymeric Support for Heterogeneous Catalytic Reactions: Kinetics of Hydration of Cyclohexene in Two-and Three-Phase Systems over a Strongly Acidic Sulfonated PolyHipe Ind. Eng. Chem. Res. 1999, 39, 259-266
11. Bhumgara, Z. Polyhipe Foam Materials as Filtration Media Filtr. Sep. 1995, 32, 245-251
12. Ikem, V. O.; Menner, A.; Horozov, T. S.; Bismarck, A. Highly Permeable Macroporous Polymers Synthesized from Pickering Medium and High Internal Phase Emulsion Templates Adv. Mater. 2010, 22, 3588-3592
13. Zhang, H.; Cooper, A. I. Thermoresponsive "Particle Pumps": Activated Release of Organic Nanoparticles from Open-Cell Macroporous Polymers Adv. Mater. 2007, 19, 2439-2444
14. Ikem, V. O.; Menner, A.; Bismarck, A.; Norman, L. R. Liquid Screen: A Novel Method To Produce an In-Situ Gravel Pack Soc. Pet. Eng. J. 2013, 10.2118/141256-PA
15. Liwarska-Bizukojc, E.; Miksch, K.; Malachowska-Jutsz, A.; Kalka, J. Acute Toxicity and Genotoxicity of Five Selected Anionic and Nonionic Surfactants Chemosphere 2005, 58, 1249-1253
16. Menner, A.; Ikem, V.; Salgueiro, M.; Shaffer, M. S. P.; Bismarck, A. High Internal Phase Emulsion Templates Solely Stabilised by Functionalised Titania Nanoparticles Chem. Commun. 2007, 4274-4276
17. Ikem, V. O.; Menner, A.; Bismarck, A. High Internal Phase Emulsions Stabilized Solely by Functionalized Silica Particles Angew. Chem., Int. Ed. 2008, 47, 8277-8279
18. Yang, Y.; Wei, Z.; Wang, C.; Tong, Z. Lignin-Based Pickering HIPEs for Macroporous Foams and Their Enhanced Adsorption of Copper(II) Ions Chem. Commun. 2013, 49, 7144-7146
19. Zhou, S.; Bismarck, A.; Steinke, J. H. G. Interconnected Macroporous Glycidyl Methacrylate-Grafted Dextran Hydrogels Synthesised from Hydroxyapatite Nanoparticle Stabilised High Internal Phase Emulsion Templates J. Mater. Chem. 2012, 22, 18824-18829
20. VandeVord, P. J.; Matthew, H. W. T.; DeSilva, S. P.; Mayton, L.; Wu, B.; Wooley, P. H. Evaluation of the Biocompatibility of a Chitosan Scaffold in Mice J. Biomed. Mater. Res. 2002, 59, 585-590
21. Bhattarai, N.; Gunn, J.; Zhang, M. Chitosan-Based Hydrogels for Controlled, Localized Drug Delivery Adv. Drug Delivery Rev. 2010, 62, 83-99
22. Pillai, C. K. S.; Paul, W.; Sharma, C. P. Chitin and Chitosan Polymers: Chemistry, Solubility and Fiber Formation Prog. Polym. Sci. 2009, 34, 641-678
23. Madihally, S. V.; Matthew, H. W. T. Porous Chitosan Scaffolds for Tissue Engineering Biomaterials 1999, 20, 1133-1142
24. Nettles, D. L.; Elder, S. H.; Gilbert, J. A. Potential Use of Chitosan as a Cell Scaffold Material for Cartilage Tissue Engineering Tissue Eng. 2002, 8, 1009-1016
25. Li, Z.; Ramay, H. R.; Hauch, K. D.; Xiao, D.; Zhang, M. Chitosan-Alginate Hybrid Scaffolds for Bone Tissue Engineering Biomaterials 2005, 26, 3919-3928
26. Wang, L.; Stegemann, J. P. Thermogelling Chitosan and Collagen Composite Hydrogels Initiated with β-Glycerophosphate for Bone Tissue Engineering Biomaterials 2010, 31, 3976-3985
27. Li, P.; Zhou, C.; Rayatpisheh, S.; Ye, K.; Poon, Y. F.; Hammond, P. T.; Duan, H.; Chan-Park, M. B. Cationic Peptidopolysaccharides Show Excellent Broad-Spectrum Antimicrobial Activities and High Selectivity Adv. Mater. 2012, 24, 4130-4137
28. Kurita, K.; Kamiya, M.; Nishimura, S.-I. Solubilization of a Rigid Polysaccharide: Controlled Partial N-Acetylation of Chitosan to Develop Solubility Carbohydr. Polym. 1991, 16, 83-92
29. Heskins, M.; Guillet, J. E. Solution Properties of Poly(N -isopropylacrylamide) J. Macromol. Sci., Chem. 1968, 2, 1441-1455
30. Cooperstein, M. A.; Canavan, H. E. Assessment of Cytotoxicity of (N -Isopropyl Acrylamide) and Poly(N -isopropyl acrylamide)-Coated Surfaces Biointerphases 2013, 8, 1-12
31. Yamato, M.; Utsumi, M.; Kushida, A.; Konno, C.; Kikuchi, A.; Okano, T. Thermo-responsive culture dishes allow the intact harvest of multilayered keratinocyte sheets without Dispase by reducing temperature Tissue Eng. 2001, 7, 473-480
32. Chen, J. P.; Cheng, T. H. Thermo-Responsive Chitosan-graft -Poly(N -isopropylacrylamide) Injectable Hydrogel for Cultivation of Chondrocytes and Meniscus Cells Macromol. Biosci. 2006, 6, 1026-1039
33. Ohya, S.; Matsuda, T. Poly(N -isopropylacrylamide) (PNIPAM)-Grafted Gelatin as Thermoresponsive Three-Dimensional Artificial Extracellular Matrix: Molecular and Formulation Parameters vs. Cell Proliferation Potential J. Biomater. Sci., Polym. Ed. 2005, 16, 809-827
34. Saleh, N.; Sarbu, T.; Sirk, K.; Lowry, G. V.; Matyjaszewski, K.; Tilton, R. D. Oil-in-Water Emulsions Stabilized by Highly Charged Polyelectrolyte- Grafted Silica Nanoparticles Langmuir 2005, 21, 9873-9878
35. Kumat, T. K. S.; Samuel, D.; Jayaraman, G.; Srimathi, T.; Yu, C. The Role of Proline in the Prevention of Aggregation during Protein Folding in Vitro IUBMB Life 1998, 46, 509-517
36. Pourjavadi, A.; Mahdavinia, G.; Zohuriaan-Mehr, M.; Omidian, H. Modified Chitosan. I. Optimized Cerium Ammonium Nitrate-Induced Synthesis of Chitosan-graft -Polyacrylonitrile J. Appl. Polym. Sci. 2003, 88, 2048-2054
37. Joshi, J. M.; Sinha, V. K. Ceric Ammonium Nitrate Induced Grafting of Polyacrylamide onto Carboxymethyl Chitosan Carbohydr. Polym. 2007, 67, 427-435
38. Joshi, J. M.; Sinha, V. K. Graft Copolymerization of 2- Hydroxyethylmethacrylate onto Carboxymethyl Chitosan Using CAN as an Initiator Polymer 2006, 47, 2198-2204
39. Jayakumar, R.; Prabaharan, M.; Reis, R. L.; Mano, J. F. Graft Copolymerized Chitosan-Present Status and Applications Carbohydr. Polym. 2005, 62, 142-158
40. Feng, Z.-Q.; Chu, X.; Huang, N.-P.; Wang, T.; Wang, Y.; Shi, X.; Ding, Y.; Gu, Z.-Z. The Effect of Nanofibrous Galactosylated Chitosan Scaffolds on the Formation of Rat Primary Hepatocyte Aggregates and the Maintenance of Liver Function Biomaterials 2009, 30, 2753-2763
41. Poon, Y. F.; Cao, Y.; Liu, Y.; Chan, V.; Chan-Park, M. B. Hydrogels Based on Dual Curable Chitosan-graft -Polyethylene Glycol-graft -Methacrylate: Application to Layer-by-Layer Cell Encapsulation ACS Appl. Mater. Interfaces 2010, 2, 2012-2025
42. Hirai, A.; Odani, H.; Nakajima, A. Determination of Degree of Deacetylation of Chitosan by 1H NMR Spectroscopy Polym. Bull. 1991, 26, 87-94
43. Bao, H. Q.; Li, L.; Leong, W. C.; Gan, L. H. Thermo-Responsive Association of Chitosan-graft -Poly(N -isopropylacrylamide) in Aqueous Solutions J. Phys. Chem. B 2010, 114, 10666-10673
44. Lee, J.; Jung, M.; Park, H.; Park, K.; Ryu, G. Synthesis and Characterization of Thermosensitive Chitosan Copolymer as a Novel Biomaterial J. Biomater. Sci. Polym. Ed. 2004, 15, 1065-1079
45. Overberger, C. G.; Morishima, Y. Synthesis and Optical Properties of Polyethylenimine Containing l -Proline and Optically Active Thymine Derivatives J. Polym. Sci., Polym. Chem. Ed. 1980, 18, 1433-1446
46. Stenflo, J.; Fernlund, P.; Egan, W.; Roepstorff, P. Vitamin K Dependent Modifications of Glutamic Acid Residues in Prothrombin Proc. Natl. Acad. Sci. 1974, 71, 2730-2733
47. 15N Random Coil NMR Chemical Shifts of the Common Amino Acids. I. Investigations of Nearest-Neighbor Effects J. Biomol. NMR 1995, 5, 67-81
48. Zhang, K.; Ma, J.; Zhang, B.; Zhao, S.; Li, Y.; Xu, Y.; Yu, W.; Wang, J. Synthesis of Thermoresponsive Silica Nanoparticle/PNIPAM Hybrids by Aqueous Surface-Initiated Atom Transfer Radical Polymerization Mater. Lett. 2007, 61, 949-952
49. Barth, A. The Infrared Absorption of Amino Acid Side Chains Prog. Biophys. Mol. Biol. 2000, 74, 141-173
50. Kumar, M. N. V. R.; Muzzarelli, R. A. A.; Muzzarelli, C.; Sashiwa, H.; Domb, A. J. Chitosan Chemistry and Pharmaceutical Perspectives Chem. Rev. 2004, 104, 6017-6084
51. Schobert, B.; Tschesche, H. Unusual Solution Properties of Proline and Its Interaction with Proteins Biochim. Biophys. Acta, Gen. Subj. 1978, 541, 270-277
52. McLain, S. E.; Soper, A. K.; Watts, A. Structural Studies on the Hydration of l -Glutamic Acid in Solution J. Phys. Chem. B 2006, 110, 21251-21258
53. Schimmel, P. R.; Flory, P. J. Conformational Energy and Configurational Statistics of Poly-l -Proline Proc. Natl. Acad. Sci. U.S.A. 1967, 58, 52
54. Schild, H. G. Poly(N -isopropylacrylamide): Experiment, Theory and Application Prog. Polym. Sci. 1992, 17, 163-249
55. Feil, H.; Bae, Y. H.; Feijen, J.; Kim, S. W. Effect of Comonomer Hydrophilicity and Ionization on the Lower Critical Solution Temperature of N -Isopropylacrylamide Copolymers Macromolecules 1993, 26, 2496-2500
56. Liu, H.; Zhu, X. Lower Critical Solution Temperatures of N-Substituted Acrylamide Copolymers in Aqueous Solutions Polymer 1999, 40, 6985-6990
57. Risbud, M. V.; Hardikar, A. A.; Bhat, S. V.; Bhonde, R. R. pH-Sensitive Freeze-Dried Chitosan-Polyvinyl Pyrrolidone Hydrogels as Controlled Release System for Antibiotic Delivery J. Controlled Release 2000, 68, 23-30
58. Maresov, E. A.; Semenov, A. N. Mesoglobule Morphologies of Amphiphilic Polymers Macromolecules 2008, 41, 9439-9457
59. Zhou, S.; Bismarck, A.; Steinke, J. H. Thermoresponsive Macroporous Scaffolds Prepared by Emulsion Templating Macromol. Rapid Commun. 2012, 33, 1833-1839
60. Wong, L. L. C.; Ikem, V. O.; Menner, A.; Bismarck, A. Macroporous Polymers with Hierarchical Pore Structure from Emulsion Templates Stabilised by Both Particles and Surfactants Macromol. Rapid Commun. 2011, 32, 1563-1568
61. Hainey, P.; Huxham, I. M.; Rowatt, B.; Sherrington, D. C.; Tetley, L. Synthesis and Ultrastructural Studies of Styrene-Divinylbenzene Polyhipe Polymers Macromolecules 1991, 24, 117-121
62. Cameron, N. R.; Sherrington, D. C. High internal phase emulsions (HIPEs) -Structure, properties and use in polymer preparation. In Biopolymers Liquid Crystalline Polymers Phase Emulsion; Springer: Berlin Heidelberg, 1996; Vol. 126, pp 163-214.
63. Moglia, R. S.; Holm, J. L.; Sears, N. A.; Wilson, C. J.; Harrison, D. M.; Cosgriff-Hernandez, E. Injectable PolyHIPEs as High-Porosity Bone Grafts Biomacromolecules 2011, 12, 3621-3628
64. Zhou, S.; Bismarck, A.; Steinke, J. H. Ion-Responsive Alginate Based Macroporous Injectable Hydrogel Scaffolds Prepared by Emulsion Templating J. Mater. Chem. B 2013, 1, 4736-4745
65. Williams, J. M.; Wrobleski, D. A. Spatial Distribution of the Phases in Water-in-Oil Emulsions. Open and Closed Microcellular Foams from Cross-Linked Polystyrene Langmuir 1988, 4, 656-662