Photo-crosslinked networks prepared from fumaric acid monoethyl ester-functionalized poly(d,l-lactic acid) oligomers and N-vinyl-2-pyrrolidone for the controlled and sustained release of proteins

Acta Biomaterialia

Volumn 8, Issue 10, 2012, Pages 3652-3659

  Jansen, Janine ^a   Tibbe, Martijn P ^a   Mihov, George ^b   Feijen, Jan ^a   Grijpma, Dirk W ^a,c  

^a UNIVERSITY OF TWENTE   (Netherlands)

^b DSM RESOLVE   (Netherlands)

^c UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

Author keywords

Drug delivery systems; Fumarate; Networks; Photo polymerization; Proteins

Indexed keywords

CONTROLLED DRUG DELIVERY; ESTERS; HYDROPHOBICITY; LACTIC ACID; OLIGOMERS; PHOTOPOLYMERIZATION; TARGETED DRUG DELIVERY;

CONTROLLED RELEASE; CROSSLINKED NETWORKS; DRUG-DELIVERY SYSTEMS; FUMARATES; FUMARIC ACIDS; FUNCTIONALIZED; L-LACTIC ACID OLIGOMERS; N-VINYL-2-PYRROLIDONE; NETWORK; PHOTO POLYMERIZATION;

ENZYMES;

1 VINYL 2 PYRROLIDINONE; ALBUMIN; FUMARIC ACID MONOETHYLESTER; LYSOZYME; OLIGOMER; POLYLACTIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CROSS LINKING; ENZYME RELEASE; HYDROLYSIS; HYDROPHILICITY; MOLECULAR WEIGHT; PRIORITY JOURNAL; PROTEIN SECRETION; SYNTHESIS;

EID: 84865459125     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2012.06.011     Document Type: Article

References (34)

1. B. Baroli Photopolymerization of biomaterials: issues and potentialities in drug delivery, tissue engineering, and cell encapsulation applications J Chem Technol Biol 81 2006 491 499
2. K. Davis Controlled release from crosslinked degradable networks Crit Rev Ther Drug Carrier Syst 19 2002 385 423
3. B.D. Ratner, A.S. Hofmann, F.J. Schoen, and J.E. Lemons Biomaterials science 2004 Elsevier San Diego, CA
4. H. Shin, J.S. Temenoff, and A.G. Mikos In vitro cytotoxicity of unsaturated oligo[poly(ethylene glycol) fumarate] macromers and their cross-linked hydrogels Biomacromolecules 4 2003 552 560
5. J. Jansen, M.J. Boerakker, J. Heuts, J. Feijen, and D.W. Grijpma Rapid photo-crosslinking of fumaric acid monoethyl ester-functionalized poly(trimethylene carbonate) oligomers for drug delivery applications J Control Release 147 2010 54 61
6. R. Censi, T. Vermonden, M.J. van Steenbergen, H. Deschout, K. Braeckmans, and S.C. De Smedt Photopolymerized thermosensitive hydrogels for tailorable diffusion-controlled protein delivery J Control Release 140 2009 230 236
7. S. Lu, and K.S. Anseth Release behavior of high molecular weight solutes from poly(ethylene glycol)-based degradable networks Macromolecules 33 2000 2509 2515
8. J.L. West, and J.A. Hubbell Photopolymerized hydrogel materials for drug delivery applications React Polym 25 1995 139 147
9. R. Chapanian, and B.G. Amsden Combined and sequential delivery of bioactive VEGF165 and HGF from poly(trimethylene carbonate) based photo-cross-linked elastomers J Control Release 143 2010 53 63
10. F. Gu, H.M. Younes, A.O.S. El-Kadi, R.J. Neufeld, and B.G. Amsden Sustained interferon-γ delivery from a photocrosslinked biodegradable elastomer J Control Release 102 2005 607 617
11. J. Mönkäre, R.A. Hakala, M.A. Vlasova, A. Huotari, M. Kilpeläinen, and A. Kiviniemi Biocompatible photocrosslinked poly(ester anhydride) based on functionalized poly(-caprolactone) prepolymer shows surface erosion controlled drug release in vitro and in vivo J Control Release 146 2010 349 355
12. S. Sharifi, H. Mirzadeh, M. Imani, Z. Rong, A. Jamshidi, and M. Shokrgozar Injectable in situ forming drug delivery system based on poly(-caprolactone fumarate) for tamoxifen citrate delivery: gelation characteristics, in vitro drug release and anti-cancer evaluation Acta Biomater 5 2009 1966 1978
13. B. Amsden, G. Misra, M. Marshall, and N. Turner Synthesis and characterization of biodegradable networks providing saturated-solution prolonged delivery J Pharm Sci 97 2008 860 874
14. A.A. Weiner, E.A. Bock, M.E. Gipson, and V.P. Shastri Photocrosslinked anhydride systems for long-term protein release Biomaterials 29 2008 2400 2407
15. D. Wu, X. Zhang, and C.C. Chu Synthesis, characterization and drug release from three-arm poly(-caprolactone) maleic acid/poly(ethylene glycol) diacrylate hydrogels J Biomater Sci Polym Ed 14 2003 777 802
16. A. Haesslein, M.C. Hacker, H. Ueda, D.M. Ammon, R.N. Borazjani, and J.F. Kunzler Matrix modifications modulate ophthalmic drug delivery from photo-cross-linked poly(propylene fumarate)-based networks J Biomater Sci Polym Ed 20 2009 49 69
17. A. Haesslein, H. Ueda, M.C. Hacker, S. Jo, D.M. Ammon, and R.N. Borazjani Long-term release of fluocinolone acetonide using biodegradable fumarate-based polymers J Control Release 114 2006 251 260
18. J. Jansen, F.P.W. Melchels, D.W. Grijpma, and J. Feijen Fumaric acid monoethyl ester-functionalized poly(d,l-lactide)/N-vinyl-2-pyrrolidone resins for the preparation of tissue engineering scaffolds by stereolithography Biomacromolecules 10 2009 214 220
19. S.P. Schwendeman, H.R. Constantino, R.K. Gupta, and R. Langer Peptide, protein, and vaccine delivery from implantable polymeric systems K. Park, Controlled drug delivery, challenges and strategies 1997 American Chemical Society Washington, DC
20. M. van de Weert, W.E. Hennink, and W. Jiskoot Protein instability in poly(lactic-co-glycolic acid) microparticles Pharm Res 17 2000 1159 1167
21. C.C. Lin, S.M. Sawicki, and A.T. Metters Free-radical-mediated protein inactivation and recovery during protein photoencapsulation Biomacromolecules 9 2007 75 83
22. F. Gu, R. Neufeld, and B. Amsden Maintenance of vascular endothelial growth factor and potentially other therapeutic proteins bioactivity during a photo-initiated free radical cross-linking reaction forming biodegradable elastomers Eur J Pharm Biopharm 66 2007 21 27
23. J. Jansen, M.B. Bosman, M.J. Boerakker, J. Feijen, and D.W. Grijpma Photo-crosslinked poly(trimethylene carbonate)-fumarate/N-vinyl pyrrolidone networks for the controlled release of proteins J Control Release 148 2010 e79 e80
24. D.W. Grijpma, Q. Hou, and J. Feijen Preparation of biodegradable networks by photo-crosslinking lactide, -caprolactone and trimethylene carbonate-based oligomers functionalized with fumaric acid monoethyl ester Biomaterials 26 2005 2795 2802
25. A. Hassner, and V. Alexanian Direct room temperature esterification of carboxylic acids Tetrahedron Lett 19 1978 4475 4478
26. P.K. Smith, R.I. Krohn, G.T. Hermanson, A.K. Mallia, F.H. Gartner, and M.D. Provenzano Measurement of protein using bicinchoninic acid Anal Biochem 150 1985 76 85
27. P. Shih, B. Malcolm, S. Rosenberg, J. Kirch, and A. Wilson Reconstruction and testing of ancestral proteins Methods Enzymol 224 1993 576 590
28. T.G. Fox, and S. Loshaek Influence of molecular weight and degree of crosslinking on the specific volume and glass temperature of polymers J Polym Sci 15 1955 371 390
29. J. Brandrup, E.H. Immergut, A. Abe, and D.R. Bloch Polymer handbook 1999 Wiley-Interscience New York
30. D. Blanco, and M.J. Alonso Protein encapsulation and release from poly(lactide-co-glycolide) microspheres: effect of the protein and polymer properties and of the co-encapsulation of surfactants Eur J Pharm Biopharm 45 1998 285 294
31. G. Jiang, B.H. Woo, F. Kang, J. Singh, and P.P. DeLuca Assessment of protein release kinetics, stability and protein polymer interaction of lysozyme encapsulated poly(lactide-co-glycolide) microspheres J Control Release 79 2002 137 145
32. A. Paillard-Giteau, V.T. Tran, O. Thomas, X. Garric, J. Coudane, and S. Marchal Effect of various additives and polymers on lysozyme release from PLGA microspheres prepared by an s/o/w emulsion technique Eur J Pharm Biopharm 75 2010 128 136
33. T.G. Park Yong Lee H, Sung Nam Y. A new preparation method for protein loaded poly(d,l-lactic-co-glycolic acid) microspheres and protein release mechanism study J Control Release 55 1998 181 191
34. J. Chesko, J. Kazzaz, M. Ugozzoli, D.T. O'Hagan, and M. Singh An investigation of the factors controlling the adsorption of protein antigens to anionic PLG microparticles J Pharm Sci 94 2005 2510 2519