Biocompatible photocrosslinked poly(ester anhydride) based on functionalized poly(ε-caprolactone) prepolymer shows surface erosion controlled drug release in vitro and in vivo

Journal of Controlled Release

Volumn 146, Issue 3, 2010, Pages 349-355

  Monkare J ^a   Hakala, R A ^b   Vlasova, M A ^a   Huotari, A ^a   Kilpelainen M ^a,c   Kiviniemi, A ^a   Meretoja, V ^d   Herzig, K H ^c,e   Korhonen, H ^b   Seppala J V ^b   Jarvinen K ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b AALTO UNIVERSITY   (Finland)

^c UNIVERSITY OF OULU   (Finland)

^d UNIVERSITY OF TURKU   (Finland)

^e KUOPIO UNIVERSITY HOSPITAL   (Finland)

Author keywords

Controlled release; Photocrosslinking; Poly(ester anhydride); Surface erosion; Toxicity

Indexed keywords

CAPROLACTONE; CELL VIABILITY; CONTROLLED DRUG RELEASE; CONTROLLED RELEASE; CYTOKINE ACTIVITY; DRUG LOADING; DRUG RELEASE; FUNCTIONALIZED; IN-VITRO; IN-VIVO; MODEL DRUGS; PHOTOCROSS-LINKING; POLY(ESTER ANHYDRIDE); PREPOLYMERS; STRONG CORRELATION; SUCCINIC ANHYDRIDE; SURFACE EROSION; WATER SOLUBLE DRUGS;

BIOCOMPATIBILITY; DRUG DELIVERY; ESTERIFICATION; ESTERS; OLIGOMERS; RATS; TOXICITY;

EROSION;

CYTOKINE; POLYCAPROLACTONE; POLYESTER; PROPRANOLOL;

ANIMAL EXPERIMENT; ARTICLE; BIOCOMPATIBILITY; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG SAFETY; IN VITRO STUDY; IN VIVO STUDY; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; SURFACE PROPERTY;

ANIMALS; BIOCOMPATIBLE MATERIALS; CELL LINE; CELL SURVIVAL; DELAYED-ACTION PREPARATIONS; HUMANS; MALE; PHOTOCHEMISTRY; POLYESTERS; PROPRANOLOL; RATS; RATS, WISTAR; SURFACE PROPERTIES;

EID: 77956275002     PISSN: 01683659     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jconrel.2010.06.005     Document Type: Article

References (47)

1. Storey R.F., Taylor A.E. Synthesis of novel biodegradable poly(ester-anhydride)s. J. Macromol. Sci. Part A Pure Appl. Chem. 1997, 34:265-280.
2. Korhonen H., Seppälä J.V. Synthesis of poly(ester-anhydride)s based on poly(ε-caprolactone) prepolymer. J. Appl. Polym. Sci. 2001, 81:176-185.
3. Jiang H.L., Zhu K.L. Synthesis, characterization and in vitro degradation of a new family of alternate poly(ester-anhydrides) based on aliphatic and aromatic diacids. Biomaterials 2001, 22:211-218.
4. Slivniak R., Domb A.J. Stereocomplexes of enantiomeric lactic acid and sebacic acid ester - anhydride triblock copolymers. Biomacromolecules 2002, 3:754-760.
5. Jaszcz K., Lukaszczyk J., Smigamatuszowicz M. Synthesis of functional poly(ester-andydride)s based on succinic acid. React. Funct. Polym. 2008, 68:351-360.
6. Pfeifer B., Burdick J., Langer R. Formulation and surface modification of poly(ester-anhydride) micro- and nanospheres. Biomaterials 2005, 26:117-124.
7. Albertsson A.C., Varma I.K. Recent developments in ring opening polymerization of lactones for biomedical applications. Biomacromolecules 2003, 4:1466-1486.
8. Tamada J.A., Langer R. Erosion kinetics of hydrolytically degradable polymers. Proc. Natl. Acad. Sci. U.S.A. 1993, 90:552-556.
9. Göpferich A., Tessmar J. Polyanhydride degradation and erosion. Adv. Drug Deliv. Rev. 2002, 54:911-931.
10. A.J. Domb, Polyanhydrides, US Patent No. 7297347, 2007.
11. Shikanov S., Shikanov A., Gofrit O., Nyska A., Corn B., Domb A.J. Intratumoral delivery of paclitaxel for treatment of orthotopic prostate cancer. J. Pharm. Sci. 2009, 98:1005-1014.
12. Shikanov A., Shikanov S., Vaisman B., Golenser J., Domb A. Paclitaxel tumor biodistribution and efficacy after intratumoral injection of a biodegradable extended release implant. Int. J. Pharm. 2008, 358:114-120.
13. Shikanov A., Vaisman B., Krasko M.Y., Nyska A., Domb A.J. Poly(sebacic acid-co-ricinoleic acid) biodegradable carrier for paclitaxel: In vitro release and in vivo toxicity. J. Biomed. Mater. Res. A 2004, 69A:47-54.
14. Pfeifer B., Burdick J., Little S., Langer R. Poly(ester-anhydride):poly(ε-amino ester) micro- and nanospheres: DNA encapsulation and cellular transfection. Int. J. Pharm. 2005, 304:210-219.
15. J. Seppälä, R. Hakala, H. Korhonen, Novel Biodegradable Polymer, US Patent Application No. US 2009/0176943 A1, 2009.
16. Korhonen H., Hakala R.A., Helminen A.O., Seppälä J.V. Synthesis and hydrolysis behaviour of poly(ester anhydrides) from polylactone precursors containing alkenyl moieties. Macromol. Biosci. 2006, 6:496-505.
17. Hakala R., Korhonen H., Holappa S., Seppälä J. Hydrophobicities of poly(ε-caprolactone) oligomers functionalized with different succinic anhydrides. Eur. Polym. J. 2009, 45:557-564.
18. Baroli B. Photopolymerization of biomaterials: issues and potentialities in drug delivery, tissue engineering, and cell encapsulation applications. J. Chem. Technol. Biotechnol. 2006, 81:491-499.
19. Quick D.J., Macdonald K.K., Anseth K.S. Delivering DNA from photocrosslinked, surface eroding polyanhydrides. J. Control. Release 2004, 97:333-343.
20. Elisseeff J., Anseth K., Sims D., Mcintosh W., Randolph M., Langer R. Transdermal photopolymerization for minimally invasive implantation. Proc. Natl. Acad. Sci. U.S.A. 1999, 96:3104-3107.
21. Anseth K.S., Shastri V.R., Langer R. Photopolymerizable degradable polyanhydrides with osteocompatibility. Nat. Biotechnol. 1999, 17:156-159.
22. Takao A., Fusae M., Yu N. Preparation of cross-linked aliphatic polyester and application to thermo-responsive material. J. Control. Release 1994, 32:87-96.
23. West J.F., Hubbell J.A. Photopolymerized hydrogel materials for drug delivery applications. React. Polym. 1995, 25:139-147.
24. Wu D., Zhang X., Chu C.C. Synthesis, characterization and drug release from three-arm poly(epsilon-caprolactone) maleic acid/poly(ethylene glycol) diacrylate hydrogels. J. Biomater. Sci. Polym. Ed. 2003, 14:777-802.
25. Haesslein A., Ueda H., Hacker M., Jo S., Ammon D.M., Borazjani R., Kunzler J.F., Salamone J.C., Mikos A.G. Long-term release of fluocinolone acetonide using biodegradable fumarate-based polymers. J. Control. Release 2006, 114:251-260.
26. Gu F., Neufeld R., Amsden B. Sustained release of bioactive therapeutic proteins from a biodegradable elastomeric device. J. Control. Release 2007, 117:80-89.
27. Weiner A.A., Bock E.A., Gipson M.E., Shastri V.P. Photocrosslinked anhydride systems for long-term protein release. Biomaterials 2008, 29:2400-2407.
28. Helminen A.O., Korhonen H., Seppälä J.V. Crosslinked poly(ester anhydride)s based on poly(ε-caprolactone) and polylactide oligomers. J. Polym. Sci., Part A: Polym. Chem. 2003, 41:3788-3797.
29. Rich J., Korhonen H., Hakala R., Korventausta J., Elomaa L., Seppälä J. Porous biodegradable scaffold: predetermined porosity by dissolution of poly(ester-anhydride) fibers from polyester matrix. Macromol. Biosci. 2009, 9:654-660.
30. Burdick J.A., Peterson A.J., Anseth K.S. Conversion and temperature profiles during the photoinitiated polymerization of thick orthopaedic biomaterials. Biomaterials 2001, 22:1779-1786.
31. Siegel S., Castellan N.J. The case of k independent samples. Nonparametric statistics for the behavioral sciences 1988, 190-223. McGraw-Hill Inc, New York. 2nd Ed. J.D. Anker (Ed.).
32. Leuner C., Dressman J. Improving drug solubility for oral delivery using solid dispersions. Eur. J. Pharm. Biopharm. 2000, 50:47-60.
33. Kluin O.S., van der Mei H.C., Busscher H.J., Neut D. A surface-eroding antibiotic delivery system based on poly-(trimethylene carbonate). Biomaterials 2009, 30:4738-4742.
34. Huang X., Brazel C.S. On the importance and mechanisms of burst release in matrix-controlled drug delivery system. J. Control. Release 2001, 73:121-136.
35. O'Brien J., Wilson I., Orton T., Pognan F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. Eur. J. Biochem. 2000, 267:5421-5426.
36. Nair L., Laurencin C. Biodegradable polymers as biomaterials. Prog. Polym. Sci. 2007, 32:762-798.
37. Davis K., Burdick J.A., Anseth K.S. Photoinitiated crosslinked degradable copolymer networks for tissue engineering applications. Biomaterials 2003, 24:2485-2495.
38. Poshusta A.K., Burdick J.A., Mortisen D.J., Padera R.F., Ruehlman D., Yaszemski M.J., Anseth K.S. Histocompatibility of photocrosslinked polyanhydrides: a novel in situ forming orthopaedic biomaterial. J. Biomed. Mater. Res. A 2003, 64A:62-69.
39. Bruining M.J., Blaauwgeers H.G.T., Kuijer R., Pels E., Nuijts R.M.M.A., Koole L.H. Biodegradable three-dimensional networks of poly(dimethylamino ethyl methacrylate). Synthesis, characterization and in vitro studies of structural degradation and cytotoxicity. Biomaterials 2000, 21:595-604.
40. Anderson J.M. Biological responses to materials. Annu. Rev. Mater. Res. 2001, 31:81-110.
41. Anderson J.M., Rodriguez A., Chang D.T. Foreign body reaction to biomaterials. Semin. Immunol. 2008, 20:86-100.
42. Schutte R.J., Xie L., Klitzman B., Reichert W.M. In vivo cytokine-associated responses to biomaterials. Biomaterials 2009, 30:160-168.
43. Rodriguez A., Meyerson H., Anderson J.M. Quantitative in vivo cytokine analysis at synthetic biomaterial implant sites. J. Biomed. Mater. Res. A 2009, 89A:152-159.
44. Bridges A., Singh N., Burns K., Babensee J., Andrewlyon L., Garcia A. Reduced acute inflammatory responses to microgel conformal coatings. Biomaterials 2008, 29:4605-4615.
45. Baldwin L., Hunt J. The in vivo cytokine release profile following implantation. Cytokine 2008, 41:217-222.
46. Jiang H.L., Tang G.P., Weng L.H., Zhu K.J. In vivo degradation and biocompatibility of a new class of alternate poly(ester-anhydrides) based on aliphatic and aromatic diacids. J. Biomater. Sci., Polym. Ed. 2001, 12:1281-1292.
47. Krasko M., Golenser J., Nyska A., Nyska M., Brin Y., Domb A. Gentamicin extended release from an injectable polymeric implant. J. Control. Release 2007, 117:90-96.