Release behavior and intra-articular biocompatibility of celecoxib-loaded acetyl-capped PCLA-PEG-PCLA thermogels

Biomaterials

Volumn 35, Issue 27, 2014, Pages 7919-7928

  Petit, Audrey ^a,b   Sandker, Marjan ^c   Müller, Benno ^a   Meyboom, Ronald ^a   van Midwoud, Paul ^a   Bruin, Peter ^a   Redout, Everaldo M ^d   Versluijs Helder, Marjan ^e   van der Lest, Chris H A ^d   Buwalda, Sytze J ^b   de Leede, Leo G J ^a   Vermonden, Tina ^b   Kok, Robbert Jan ^b   Weinans, Harrie ^f,g   Hennink, Wim E ^b  

^a InGell Labs BV   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

^c ERASMUS MEDICAL CENTER   (Netherlands)

^d UTRECHT UNIVERSITY   (Netherlands)

^e UTRECHT UNIVERSITY   (Netherlands)

^f UNIVERSITY MEDICAL CENTER UTRECHT   (Netherlands)

^g DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Biocompatibility; Celecoxib; Invitro release; PCLA PEG PCLA; Pharmacokinetics; Temperature responsive gelling hydrogel

Indexed keywords

BIOCOMPATIBILITY; BLOCK COPOLYMERS; DRUG DELIVERY; GELATION; GELS; HYDROGELS; JOINTS (ANATOMY); PHARMACOKINETICS; POLYETHYLENE OXIDES; RATS; SOLS;

BIOLOGICAL FLUIDS; CELECOXIB; IN-VITRO; PCLA-PEG-PCLA; POLYMER DISSOLUTION; RELEASE BEHAVIORS; SUSTAINED RELEASE; TEMPERATURE-RESPONSIVE;

POLYETHYLENE GLYCOLS;

ACETIC ACID DERIVATIVE; CAMPTOTHECIN; CELECOXIB; COPOLYMER; EPSILON CAPROLACTONE LACTIDE COPOLYMER; MACROGOL; PACLITAXEL; SULFADIMIDINE; UNCLASSIFIED DRUG; BIOMATERIAL; GEL; MACROGOL DERIVATIVE; POLY(EPSILON-CAPROLACTONE-CO-LACTIDE)-POLY(ETHYLENE GLYCOL); POLYESTER; PYRAZOLE DERIVATIVE; SULFONAMIDE;

ACYLATION; ANALGESIA; ANIMAL EXPERIMENT; AREA UNDER THE CURVE; ARTICLE; BIOCOMPATIBILITY; BODY FLUID; CONTROLLED STUDY; DRUG ABSORPTION; DRUG BLOOD LEVEL; DRUG DEGRADATION; DRUG DELIVERY SYSTEM; DRUG RELEASE; DRUG SAFETY; DRUG SOLUBILITY; HISTOLOGY; HYDROGEL; IN VITRO STUDY; IN VIVO STUDY; KNEE; MACROPHAGE; MALE; MAXIMUM PLASMA CONCENTRATION; MICRO-COMPUTED TOMOGRAPHY; MISCIBILITY; NONHUMAN; OSTEOARTHRITIS; PHARMACOKINETICS; PRIORITY JOURNAL; RAT; ROOM TEMPERATURE; SUSTAINED DRUG RELEASE; TEMPERATURE; TRANSITION TEMPERATURE; ACETYLATION; ANIMAL; CHEMISTRY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG EFFECTS; FLOW KINETICS; GEL; GEL CHROMATOGRAPHY; PHASE TRANSITION; PHYSIOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; WISTAR RAT;

ACETYLATION; ANIMALS; BIOCOMPATIBLE MATERIALS; CALORIMETRY, DIFFERENTIAL SCANNING; CHROMATOGRAPHY, GEL; DRUG LIBERATION; GELS; KNEE JOINT; MALE; PHASE TRANSITION; POLYESTERS; POLYETHYLENE GLYCOLS; PROTON MAGNETIC RESONANCE SPECTROSCOPY; PYRAZOLES; RATS, WISTAR; RHEOLOGY; SULFONAMIDES; TEMPERATURE;

EID: 84903436691     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2014.05.064     Document Type: Article

References (58)

1. Davies N.M., McLachlan A.J., Day R.O., Williams K.M. Clinical pharmacokinetics and pharmacodynamics of celecoxib: a selective cyclo-oxygenase-2 inhibitor. Clin Pharmacokinet 2000, 38:225-242.
2. Zweers M.C., de Boer T.N., van Roon J., Bijlsma J.W., Lafeber F.P., Mastbergen S.C. Celecoxib: considerations regarding its potential disease-modifying properties in osteoarthritis. Arthritis Res Ther 2011, 13:239.
3. Tsutsumi R., Ito H., Hiramitsu T., Nishitani K., Akiyoshi M., Kitaori T., et al. Celecoxib inhibits production of MMP and NO via down-regulation of NF-kappaB and JNK in a PGE2 independent manner in human articular chondrocytes. Rheumatol Int 2008, 28:727-736.
4. Mastbergen S.C., Bijlsma J.W., Lafeber F.P. Selective COX-2 inhibition is favorable to human early and late-stage osteoarthritic cartilage: a human invitro study. Osteoarthr Cartil 2005, 13:519-526.
5. Paulson S.K., Kaprak T.A., Gresk C.J., Fast D.M., Baratta M.T., Burton E.G., et al. Plasma protein binding of celecoxib in mice, rat, rabbit, dog and human. Biopharm Drug Dispos 1999, 20:293-299.
6. Gong L., Thorn C.F., Bertagnolli M.M., Grosser T., Altman R.B., Klein T.E. Celecoxib pathways: pharmacokinetics and pharmacodynamics. Pharmacogenet Genomics 2012, 22:310-318.
7. Zvonar A., Kristl J., Kerč J., Grabnar P.A. High celecoxib-loaded nanoparticles prepared by a vibrating nozzle device. JMicroencapsul 2009, 26:748-759.
8. 2, VEGF, and vascular leakage. Invest Ophthalmol Vis Sci 2006, 47:1149-1160.
9. McCarron P.A., Donnelly R.F., Marouf W. Celecoxib-loaded poly(D,L-lactide-co-glycolide) nanoparticles prepared using a novel and controllable combination of diffusion and emulsification steps as part of the salting-out procedure. JMicroencapsul 2006, 23:480-498.
10. Bohr A., Kristensen J., Stride E., Dyas M., Edirisinghe M. Preparation of microspheres containing low solubility drug compound by electrohydrodynamic spraying. Int J Pharm 2011, 412:59-67.
11. Ayalasomayajula S.P., Kompella U.B. Subconjunctivally administered celecoxib-PLGA microparticles sustain retinal drug levels and alleviate diabetes-induced oxidative stress in a rat model. Eur J Pharmacol 2005, 511:191-198.
12. Homar M., Ubrich N., Ghazouani F.E., Kristl J., Kerč J., Maincent P. Influence of polymers on the bioavailability of microencapsulated celecoxib. JMicroencapsul 2007, 24:621-633.
13. Larsen S.W., Frost A.B., Østergaard J., Thomsen M.H., Jacobsen S., Skonberg C., et al. Invitro and invivo characteristics of celecoxib in situ formed suspensions for intra-articular administration. JPharm Sci 2011, 100:4330-4337.
14. Van Tomme S.R., Storm G., Hennink W.E. In situ gelling hydrogels for pharmaceutical and biomedical applications. Int J Pharm 2008, 355:1-18.
15. Petit A., Müller B., Meijboom R., Bruin P., van de Manakker F., Versluijs-Helder M., et al. Effect of polymer composition on rheological and degradation properties of temperature-responsive gelling systems composed of acyl-capped PCLA-PEG-PCLA. Biomacromolecules 2013, 14:3172-3182.
16. Petit A., Müller B., Bruin P., Meijboom R., Piest M., Kroon-Batenburg L.M.J., et al. Modulating the rheological and degradation properties of hydrogels composed of blends of PCLA-PEG-PCLA triblock copolymers and their fully hexanoyl-capped derivatives. Acta Biomater 2012, 8:4260-4267.
17. Sandker M.J., Petit A., Redout E.M., Siebelt M., Müller B., Bruin P., et al. In situ forming acyl-capped PCLA-PEG-PCLA triblock copolymer based hydrogels. Biomaterials 2013, 34:8002-8011.
18. Lee D.S., Shim M.S., Kim S.W., Lee H., Park I., Chang T. Novel thermoreversible gelation of biodegradable PLGA-block-PEO-block-PLGA triblock copolymers in aqueous solution. Macromol Rapid Commun 2001, 22:587-592.
19. Jo S., Kim J., Kim S.W. Reverse thermal gelation of aliphatically modified biodegradable triblock copolymers. Macromol Biosci 2006, 6:923-928.
20. Vermonden T., Censi R., Hennink W.E. Hydrogels for protein delivery. Chem Rev 2012, 112:2853-2888.
21. Ko D.Y., Shinde U.P., Yeon B., Jeong B. Recent progress of in situ formed gels for biomedical applications. Prog Polym Sci 2013, 0(38):672-701.
22. Bonacucina G., Cespi M., Mencarelli G., Giorgioni G., Palmieri G.F. Thermosensitive self-assembling block copolymers as drug delivery systems. Polymers 2011, 3:779-811.
23. Bae K.H., Wang L., Kurisaw M. Injectable biodegradable hydrogels: progress and challenges. JMater Chem B 2013, 1:5371-5388.
24. Zentner G.M., Rathi R., Shih C., McRea J.C., Seo M., Oh H., et al. Biodegradable block copolymers for delivery of proteins and water-insoluble drugs. JControl Release 2001, 72:203-215.
25. Qiao M., Chen D., Ma X., Liu Y. Injectable biodegradable temperature-responsive PLGA-PEG-PLGA copolymers: synthesis and effect of copolymer composition on the drug release from the copolymer-based hydrogels. Int J Pharm 2005, 294:103-112.
26. Gao Y., Ren F., Ding B., Sun N., Liu X., Ding X., et al. Athermo-sensitive PLGA-PEG-PLGA hydrogel for sustained release of docetaxel. JDrug Target 2011, 19:516-527.
27. ®/paclitaxel) - clinical applications for a novel paclitaxel delivery system. Adv Drug Deliv Rev 2009, 61:785-794.
28. Bramfeldt H., Sarazin P., Vermette P. Characterization, degradation, and mechanical strength of poly(D,L-lactide-co-ε-caprolactone)-poly(ethylene glycol)-poly(D,L-lactide-co-ε-caprolactone). JBiomed Mater Res A 2007, 83A:503-511.
29. Zhang Z., Ni J., Chen L., Yu L., Xu J., Ding J. Biodegradable and thermoreversible PCLA-PEG-PCLA hydrogel as a barrier for prevention of post-operative adhesion. Biomaterials 2011, 7(32):4725-4736.
30. Yu L., Zhang H., Ding J. Asubtle end-group effect on macroscopic physical gelation of triblock copolymer aqueous solutions. Angew Chem Int Ed Engl 2006, 45:2232-2235.
31. Patist A., Bhagwat S., Penfield K., Aikens P., Shah D. On the measurement of critical micelle concentrations of pure and technical-grade nonionic surfactants. JSurfactants Deterg 2000, 3:53-58.
32. Bozdaǧ-Pehlivan S., Subaşi B., Vural I., Unlü N., Capan Y. Evaluation of drug-excipient interaction in the formulation of celecoxib tablets. Acta Pol Pharm 2011, 68:423-433.
33. Gika H.G., Theodoridou A., Michopoulos F., Theodoridis G., Diza E., Settas L., et al. Determination of two COX-2 inhibitors in serum and synovial fluid of patients with inflammatory arthritis by ultra performance liquid chromatography-inductively coupled plasma mass spectroscopy and quadrupole time-of-flight mass spectrometry. JPharm Biomed Anal 2009, 49:579-586.
34. Zhang Y., Huo M., Zhou J., Xie S. PKSolver: an add-in program for pharmacokinetic and pharmacodynamic data analysis in Microsoft Excel. Comput Methods Programs Biomed 2010, 99:306-314.
35. Palmer A.W., Guldberg R.E., Levenston M.E. Analysis of cartilage matrix fixed charge density and three-dimensional morphology via contrast-enhanced microcomputed tomography. Proc Natl Acad Sci U S A 2006, 103:19255-19260.
36. Siebelt M. Increased physical activity severely induces osteoarthritic changes in knee joints with sulphate-glycosaminoglycan depleted cartilage. Arthritis Res Ther 2014, 16(1):R32.
37. Silvast T.S., Jurvelin J.S., Lammi M.J., Töyräs J. pQCT study on diffusion and equilibrium distribution of iodinated anionic contrast agent in human articular cartilage - associations to matrix composition and integrity. Osteoarthr Cartil 2009, 1(17):26-32.
38. Schneider H.A., Di Marzio E.A. The glass temperature of polymer blends: comparison of both the free volume and the entropy predictions with data. Polymer 1992, 33:3453-3461.
39. Fouad E.A., El-Badry M., Mahrous G.M., Alanazi F.K., Neau S.H., Alsarra I.A. The use of spray-drying to enhance celecoxib solubility. Drug Dev Ind Pharm 2011, 37:1463-1472.
40. Chawla G., Gupta P., Thilagavathi R., Chakraborti A.K., Bansal A.K. Characterization of solid-state forms of celecoxib. Eur J Pharm Sci 2003, 20:305-317.
41. Fox T.G. Influence of diluent and of copolymer composition. Polymer 1956, 1:123.
42. Seedher N.B.S. Solubility enhancement of cox-2 inhibitors using various solvent systems. AAPS PharmSciTech 2003, 4:E33.
43. Vijaya Kumar S.G., Mishra D.N. Preparation, characterization and invitro dissolution studies of solid dispersion of meloxicam with PEG 6000. Yakugaku Zasshi 2006, 126:657-664.
44. Biswal S., Sahoo J., Murthy P.N., Giradkar R.P., Avari J.G. Enhancement of dissolution rate of gliclazide using solid dispersions with polyethylene glycol 6000. AAPS PharmSciTech 2008, 9:563-570.
45. Liu C., Liu C., Desai K.G. Enhancement of dissolution rate of valdecoxib using solid dispersions with polyethylene glycol 4000. Drug Dev Ind Pharm 2005, 31:1-10.
46. Gupta P., Thilagavathi R., Chakraborti A.K., Bansal A.K. Role of molecular interaction in stability of Celecoxib-PVP amorphous systems. Mol Pharm 2005, 2:384-391.
47. Yu L., Chang G.T., Zhang H., Ding J.D. Injectable block copolymer hydrogels for sustained release of a PEGylated drug. Int J Pharm 2008, 348:95-106.
48. Shim W.S., Kim J., Kim K., Kim Y., Park R., Kim I., et al. pH- and temperature-sensitive, injectable, biodegradable block copolymer hydrogels as carriers for paclitaxel. Int J Pharm 2007, 331(1):11-18.
49. de Graaf A.J., Azevedo Próspero dos Santos, Pieters E.H., Rijkers D.T., van Nostrum C.F., Vermonden T., et al. Amicelle-shedding thermosensitive hydrogel as sustained release formulation. JControl Release 2012, 162:582-590.
50. Wang W., Deng L., Liu S., Li X., Zhao X., Hu R., et al. Adjustable degradation and drug release of a thermosensitive hydrogel based on a pendant cyclic ether modified poly(ε-caprolactone) and poly(ethylene glycol)co-polymer. Acta Biomater 2012, 8:3963-3973.
51. Qiao M., Chen D., Hao T., Zhao X., Hu H., Ma X. Effect of bee venom peptide-copolymer interactions on thermosensitive hydrogel delivery systems. Int J Pharm 2007, 345:116-124.
52. Yu T., Singh J. Thermosensitive drug delivery system of salmon calcitonin: invitro release, invivo absorption, bioactivity and therapeutic efficacies. Pharm Res 2010, 27:272-284.
53. Dunne A., O'Hara T., Devane J. Level A invivo-invitro correlation: nonlinear models and statistical methodology. JPharm Sci 1997, 86:1245-1249.
54. Guirguis M.S., Sattari S., Jamali F. Pharmacokinetics of celecoxib in the presence and absence of interferon-induced acute inflammation in the rat: application of a novel HPLC assay. JPharm Sci 2001, 4:1-6.
55. Paulson S.K., Vaughn M.B., Jessen S.M., Lawal Y., Gresk C.J., Yan B., et al. Pharmacokinetics of celecoxib after oral administration in dogs and humans: effect of food and site of absorption. JPharmacol Exp Ther 2001, 297:638-645.
56. Martinez M., Rathbone M., Burgess D., Huynh M. Invitro and invivo considerations associated with parenteral sustained release products: a review based upon information presented and points expressed at the 2007 controlled release society annual meeting. JControl Release 2008, 129:79-87.
57. D'Aurizio E., Sozio P., Cerasa L.S., Vacca M., Brunetti L., Orlando G., et al. Biodegradable microspheres loaded with an anti-Parkinson prodrug: an invivo pharmacokinetic study. Mol Pharm 2011, 8:2408-2415.
58. van der Kraan P.M., van den Berg W.B. Osteophytes: relevance and biology. Osteoarthr Cartil 2007, 15:237-244.