Functionalized poly(lactic-co-glycolic acid) enhances drug delivery and provides chemical moieties for surface engineering while preserving biocompatibility

Acta Biomaterialia

Volumn 5, Issue 8, 2009, Pages 2860-2871

  Bertram, James P ^a   Jay, Steven M ^a   Hynes, Sara R ^a   Robinson, Rebecca ^a   Criscione, Jason M ^a   Lavik, Erin B ^a  

^a Yale University   (United States)

Author keywords

Block copolymers; CNTF; PLGA; Poly(amino acid); VEGF

Indexed keywords

AMINO ACIDS; BLOCK COPOLYMERS; CELL ENGINEERING; CONTROLLED DRUG DELIVERY; DRUG INTERACTIONS; FUNCTIONAL POLYMERS; MEDICAL APPLICATIONS; MOLECULES; PHASE LOCKED LOOPS; SURFACE CHEMISTRY; TARGETED DRUG DELIVERY; TISSUE; TISSUE ENGINEERING;

AMINE FUNCTIONALITY; BLOCK CO POLYMERS; CHEMICAL MOIETIES; CNTF; POLY LACTIC-CO-GLYCOLIC ACID; POLY(AMINO ACID); POLY(AMINO ACIDS); POLY(LACTIC-CO-GLYCOLIC ACID); VEGF;

BIOCOMPATIBILITY;

CILIARY NEUROTROPHIC FACTOR; DICYCLOHEXYLCARBODIIMIDE; FLUORESCEIN ISOTHIOCYANATE; POLYGLACTIN; VASCULOTROPIN;

ANIMAL CELL; ARTICLE; BIOCOMPATIBILITY; BIOMEDICAL ENGINEERING; CONJUGATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; HUMAN; HUMAN CELL; HYDROPHILICITY; MALE; MICROENCAPSULATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; PROCESS OPTIMIZATION; SYNTHESIS; TISSUE ENGINEERING;

ABSORPTION; ANIMALS; BIOCOMPATIBLE MATERIALS; CELL SURVIVAL; CELLS, CULTURED; DRUG CARRIERS; ENDOTHELIAL CELLS; HUMANS; LACTIC ACID; MATERIALS TESTING; NANOSTRUCTURES; PARTICLE SIZE; POLYGLYCOLIC ACID; RATS; SURFACE PROPERTIES;

EID: 70349106412     PISSN: 17427061     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.actbio.2009.04.012     Document Type: Article

References (60)

1. Thote A.J., Chappell J.T., Gupta R.B., and Kumar R. Reduction in the initial-burst release by surface crosslinking of PLGA microparticles containing hydrophilic or hydrophobic drugs. Drug Dev Ind Pharm 31 1 (2005) 43-57
2. Barichello J.M., Morishita M., Takayama K., and Nagai T. Encapsulation of hydrophilic and lipophilic drugs in PLGA nanoparticles by the nanoprecipitation method. Drug Dev Ind Pharm 25 4 (1999) 471-476
3. Uchida T., Yoshida K., Nakada Y., Nagareya N., Konishi Y., Nakai A., et al. Preparation and characterization of polylactic acid microspheres containing water-soluble anesthetics with small molecular weight. Chem Pharm Bull (Tokyo) 45 3 (1997) 513-517
4. Gu F., Amsden B., and Neufeld R. Sustained delivery of vascular endothelial growth factor with alginate beads. J Control Release 96 3 (2004) 463-472
5. Dusseault J., Tam S.K., Ménard M., Polizu S., Jourdan G., Yahia L., et al. Evaluation of alginate purification methods: effect on polyphenol, endotoxin, and protein contamination. J Biomed Mater Res A 76 2 (2006) 243-251
6. Murphy W.L., Peters M.C., Kohn D.H., and Mooney D.J. Sustained release of vascular endothelial growth factor from mineralized poly(lactide-co-glycolide) scaffolds for tissue engineering. Biomaterials 21 24 (2000) 2521-2527
7. Fahmy T.M., Samstein R.M., Harness C.C., and Saltzman W.M. Surface modification of biodegradable polyesters with fatty acid conjugates for improved drug targeting. Biomaterials 26 28 (2005) 5727-5736
8. Keegan M.E., Royce S.M., Fahmy T., and Saltzman W.M. In vitro evaluation of biodegradable microspheres with surface-bound ligands. J Control Release 110 3 (2006) 574-580
9. Gref R., Couvreur P., Barratt G., and Mysiakine E. Surface-engineered nanoparticles for multiple ligand coupling. Biomaterials 24 24 (2003) 4529-4537
10. Barrera D.A., Zylstra E., Lansbury P.T., and Langer R. Copolymerization and degradation of poly(lactic acid co-lysine). Macromolecules 28 2 (1995) 425-432
11. Jo S., Engel P.S., and Mikos A.G. Synthesis of poly(ethylene glycol)-tethered poly(propylene fumarate) and its modification with GRGD peptide. Polymer 41 21 (2000) 7595-7604
12. Keegan M.E., Falcone J.L., Leung T.C., and Saltzman W.M. Biodegradable microspheres with enhanced capacity for covalently bound surface ligands. Macromolecules 37 26 (2004) 9779-9784
13. Caponetti G., Hrkach J.S., Kriwet B., Poh M., Lotan N., Colombo P., et al. Microparticles of novel branched copolymers of lactic acid and amino acids: preparation and characterization. J Pharm Sci 88 1 (1999) 136-141
14. Cook A.D., Hrkach J.S., Gao N.N., Johnson I.M., Pajvani U.B., Cannizzaro S.M., et al. Characterization and development of RGD-peptide-modified poly(lactic acid-co-lysine) as an interactive, resorbable biomaterial. J Biomed Mater Res 35 4 (1997) 513-523
15. Yavin E., and Yavin Z. Attachment and culture of dissociated cells from rat embryo cerebral hemispheres on polylysine-coated surface. J Cell Biol 62 2 (1974) 540-546
16. Edwards D.A., Hanes J., Caponetti G., Hrkach J., Ben-Jebria A., Eskew M.L., et al. Large porous particles for pulmonary drug delivery. Science 276 5320 (1997) 1868-1871
17. Cook A.D., Pajvani U.B., Hrkach J.S., Cannizzaro S.M., and Langer R. Colorimetric analysis of surface reactive amino groups on poly(lactic acid-co-lysine):poly(lactic acid) blends. Biomaterials 18 21 (1997) 1417-1424
18. Jain R.A. The manufacturing techniques of various drug loaded biodegradable poly(lactide-co-glycolide) (PLGA) devices. Biomaterials 21 23 (2000) 2475-2490
19. Jalil R., and Nixon J.R. Biodegradable poly(lactic acid) and poly(lactide-co-glycolide) microcapsules: problems associated with preparative techniques and release properties. J Microencapsul 7 3 (1990) 297-325
20. Elcin A.E., and Elcin Y.M. Localized angiogenesis induced by human vascular endothelial growth factor-activated PLGA sponge. Tissue Eng 12 4 (2006) 959-968
21. Park T.G. Degradation of poly(d,l-lactic acid) microspheres - effect of molecular-weight. J Control Release 30 2 (1994) 161-173
22. Park T.G. Degradation of poly(lactic-co-glycolic acid) microspheres - effect of copolymer composition. Biomaterials 16 15 (1995) 1123-1130
23. Hans M.L., and Lowman A.M. Biodegradable nanoparticles for drug delivery and targeting. Curr Opin Solid State Mater Sci 6 4 (2002) 319-327
24. Lavik E.B., Hrkach J.S., Lotan N., Nazarov R., and Langer R. A simple synthetic route to the formation of a block copolymer of poly(lactic-co-glycolic acid) and polylysine for the fabrication of functionalized, degradable structures for biomedical applications. J Biomed Mater Res 58 3 (2001) 291-294
25. Fischer D., Li Y.X., Ahlemeyer B., Krieglstein J., and Kissel T. In vitro cytotoxicity testing of polycations: influence of polymer structure on cell viability and hemolysis. Biomaterials 24 7 (2003) 1121-1131
26. Strand B.L., Ryan L., Veld P.I., Kulseng B., Rokstad A.M., Skjak-Braek G., et al. Poly-l-lysine induces fibrosis on alginate microcapsules via the induction of cytokines. Cell Transpl 10 3 (2001) 263-275
27. Ferruti P., Knobloch S., Ranucci E., Duncan R., and Gianasi E. A novel modification of poly(l-lysine) leading to a soluble cationic polymer with reduced toxicity and with potential as a transfection agent. Macromol Chem Phys 199 11 (1998) 2565-2575
28. Wang Y.X., Robertson J.L., Spillman W.B., and Claus R.O. Effects of the chemical structure and the surface properties of polymeric biomaterials on their biocompatibility. Pharm Res 21 8 (2004) 1362-1373
29. Mikos A.G., Thorsen A.J., Czerwonka L.A., Bao Y., Langer R., Winslow D.N., et al. Preparation and characterization of poly(l-lactic acid) foams. Polymer 35 5 (1994) 1068-1077
30. Jones B.N., Paabo S., and Stein S. Amino-acid-analysis and enzymatic sequence determination of peptides by an improved ortho-phthaldialdehyde pre-column labelling procedure. J Liq Chromatogr 4 4 (1981) 565-586
31. Madri J.A., and Williams S.K. Capillary endothelial cell-cultures - phenotypic modulation by matrix components. J Cell Biol 97 1 (1983) 153-165
32. Denizot F., and Lang R. Rapid colorimetric assay for cell-growth and survival-modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Method 89 2 (1986) 271-277
33. Faranesh A.Z., Nastley M.T., de la Cruz C.P., Haller M.F., Laquerriere P., Leong K.W., et al. In vitro release of vascular endothelial growth factor from gadolinium-doped biodegradable microspheres. Magn Reson Med 51 6 (2004) 1265-1271
34. Perez C., Castellanos I.J., Costantino H.R., Al-Azzam W., and Griebenow K. Recent trends in stabilizing protein structure upon encapsulation and release from bioerodible polymers. J Pharm Pharmacol 54 3 (2002) 301-313
35. Bilati U., Allemann E., and Doelker E. Strategic approaches for overcoming peptide and protein instability within biodegradable nano- and microparticles. Eur J Pharm Biopharm 59 3 (2005) 375-388
36. van de Weert M., Hennink W.E., and Jiskoot W. Protein instability in poly(lactic-co-glycolic acid) microparticles. Pharm Res 17 10 (2000) 1159-1167
37. Smith P.K., Krohn R.I., Hermanson G.T., Mallia A.K., Gartner F.H., Provenzano M.D., et al. Measurement of protein using bicinchoninic acid. Anal Biochem 150 1 (1985) 76-85
38. Cohen S., Yoshioka T., Lucarelli M., Hwang L.H., and Langer R. Controlled delivery systems for proteins based on poly(lactic glycolic acid) microspheres. Pharm Res 8 6 (1991) 713-720
39. Hermanson G.T. Bioconjugate techniques (1996), Academic Press, San Diego, CA
40. Deng C., Chen X., Yu H., Sun J., Lu T., and Jing X. A biodegradable triblock copolymer poly(ethylene glycol)-b-poly(l-lactide)-b-poly(l-lysine): synthesis, self-assembly, and RGD peptide modification. Polymer 48 1 (2007) 139-149
41. Wang N., Qiu J.S., and Wu X.S. Tailored polymeric materials for controlled delivery systems. In: Mc Culloch I., and Shalaby S.W. (Eds). ACS symposium series vol. 709 (1998), ACS, Washington DC 242-254
42. Wang Y.D., Ameer G.A., Sheppard B.J., Langer R., and Nm. A tough biodegradable elastomer. Nat Biotechnol 20 6 (2002) 602-606
43. Mooney D.J., Organ G., Vacanti J.P., and Langer R. Design and fabrication of biodegradable polymer devices to engineer tubular tissues. Cell Transpl 3 2 (1994) 203-210
44. Neufeld G., Cohen T., Gengrinovitch S., and Poltorak Z. Vascular endothelial growth factor (VEGF) and its receptors. FASEB J 13 1 (1999) 9-22
45. Jay SM, Shepherd BR, Bertram JP, Pober JS, Saltzman WM. Engineering of multifunctional gels integrating highly efficient growth factor delivery with endothelial cell transplantation. FASEB J 2008;22:2949-56.
46. Niwa T., Takeuchi H., Hino T., Kunou N., and Kawashima Y. Preparations of biodegradable nanospheres of water-soluble and insoluble drugs wtih d,l-lactide glycolide copolymer by a novel spontaneous emulsification solvent diffusion method, and the drug release behavior. J Control Release 25 1-2 (1993) 89-98
47. Clatterbuck R.E., Price D.L., and Koliatsos V.E. Ciliary neurotrophic factor prevents retrograde neuronal death in the adult central-nervous-system. Proc Natl Acad Sci USA 90 6 (1993) 2222-2226
48. Clatterbuck R.E., Price D.L., and Koliatsos V.E. Ciliary neurotrophic factor prevents retrograde neuronal death in the adult central nervous system. Proc Natl Acad Sci USA 90 6 (1993) 2222-2226
49. Emerich D.F., Winn S.R., Hantraye P.M., Peschanski M., Chen E.Y., Chu Y., et al. Protective effect of encapsulated cells producing neurotrophic factor CNTF in a monkey model of Huntington's disease. Nature 386 6623 (1997) 395-399
50. Dittrich F., Thoenen H., and Sendtner M. Ciliary neurotrophic factor: pharmacokinetics and acute-phase response in rat. Ann Neurol 35 2 (1994) 151-163
51. Nkansah M.K., Tzeng S.Y., Holdt A.M., and Lavik E.B. Poly(lactic-co-glycolic acid) nanospheres and microspheres for short- and long-term delivery of bioactive ciliary neurotrophic factor. Biotechnol Bioeng 100 5 (2008) 1010-1019
52. Alexis F. Factors affecting the degradation and drug-release mechanism of poly(lactic acid) and poly[(lactic acid)-co-(glycolic acid)]. Polym Int 54 1 (2005) 36-46
53. Peters M.C., Isenberg B.C., Rowley J.A., and Mooney D.J. Release from alginate enhances the biological activity of vascular endothelial growth factor. J Biomater Sci Polym Ed 9 12 (1998) 1267-1278
54. Siegel S.J., Kahn J.B., Metzger K., Winey K.I., Werner K., and Dan N. Effect of drug type on the degradation rate of PLGA matrices. Eur J Pharm Biopharm 64 3 (2006) 287-293
55. Diwan M., and Park T.G. Pegylation enhances protein stability during encapsulation in PLGA microspheres. J Control Release 73 2-3 (2001) 233-244
56. Viswanathan N.B., Patil S.S., Pandit J.K., Lele A.K., Kulkarni M.G., and Mashelkar R.A. Morphological changes in degrading PLGA and P(DL)LA microspheres: implications for the design of controlled release systems. J Microencapsul 18 6 (2001) 783-800
57. Bouillot P., Ubrich N., Sommer F., Duc T.M., Loeffler J.P., Dellacherie E., et al. Protein encapsulation in biodegradable amphiphilic microspheres. Int J Pharm 181 2 (1999) 159-172
58. Avgoustakis K., Beletsi A., Panagi Z., Klepetsanis P., Karydas A.G., and Ithakissios D.S. PLGA-mPEG nanoparticles of cisplatin: in vitro nanoparticle degradation, in vitro drug release and in vivo drug residence in blood properties. J Control Release 79 1-3 (2002) 123-135
59. Reich G. Ultrasound-induced degradation of PLA and PLGA during microsphere processing: influence of formulation variables. Eur J Pharm Biopharm 45 2 (1998) 165-171
60. Eldridge J.H., Hammond C.J., Meulbroek J.A., Staas J.K., Gilley R.M., and Tice T.R. Controlled vaccine release in the gut-associated lymphoid-tissues. 1. Orally-administered biodegradable microspheres target the peyers patches. J Control Release 11 1-3 (1990) 205-214