Poly(hydroxyethyl methacrylate-co-methacrylated-β-cyclodextrin) hydrogels: Synthesis, cytocompatibility, mechanical properties and drug loading/release properties

Acta Biomaterialia

Volumn 4, Issue 3, 2008, Pages 745-755

  dos Santos, Jose Fernando Rosa ^a   Couceiro, Ramiro ^a   Concheiro, Angel ^a   Torres Labandeira, Juan Jose ^a   Alvarez Lorenzo, Carmen ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Acetazolamide; Cyclodextrin complexation; Cytotoxicity; Hydrocortisone; Soft contact lenses

Indexed keywords

CONTACT LENSES; CYCLODEXTRINS; DRUG PRODUCTS; GLASS TRANSITION; HYDROGELS; MEDICAL APPLICATIONS; TARGETED DRUG DELIVERY;

ACETAZOLAMIDE; COPOLYMERISATION; CYCLODEXTRIN COMPLEXATION; CYTOCOMPATIBILITY; DRUG LOADING; HYDROXYETHYL METHACRYLATE; POLY HYDROXYETHYL METHACRYLATES; RELEASE PROPERTY; SOFT CONTACT LENS; TUNABLES;

CONTROLLED DRUG DELIVERY;

ACETAZOLAMIDE; COPOLYMER; GLASS; HYDROCORTISONE; MONOMER; POLYMACON CO METHACRYLATED BETA CYCLODEXTRIN; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; BIOCOMPATIBILITY; BIOMECHANICS; COMPLEX FORMATION; CONTROLLED STUDY; CROSS LINKING; CYTOTOXICITY; DRUG DELIVERY SYSTEM; HYDROGEL; LACRIMAL FLUID; MACROPHAGE; MOUSE; NONHUMAN; POLYMERIZATION; PRIORITY JOURNAL; SOFT CONTACT LENS; STORAGE; SUSTAINED DRUG RELEASE; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 41549085941     PISSN: 17427061     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.actbio.2007.12.008     Document Type: Article

References (46)

1. Horak D., Jayakrishnan A., and Arshady R. Poly(2-hydroxyethyl methacrylate) hydrogels: preparation and properties. In: Arshady R. (Ed). Introduction to Polymeric Biomaterials (2003), Kentus Books, London 65-107
2. Lou X., Munro S., and Wang S. Drug release characteristics of phase separation pHEMA sponge materials. Biomaterials 25 (2004) 5071-5080
3. Tomic S.L., Suljovrujic E.H., and Filipovic J.M. Biocompatible and bioadhesive hydrogels based on 2-hydroxyethyl methacrylate, monofunctional poly(alkylene glycol)s and itaconic acid. Polym Bull 57 (2006) 691-702
4. Mabilleau G., Stancu I.C., Honore T., Legeay G., Cincu C., Basle M.F., and Chappard D. Effects of the length of crosslink chain on poly(2-hydroxyethyl methacrylate) (pHEMA) swelling and biomechanical properties. J Biomed Mater Res A 77A (2006) 35-42
5. Andrade-Vivero P., Fernandez-Gabriel E., Alvarez-Lorenzo C., and Concheiro A. Improving the loading and release of NSAIDs from pHEMA hydrogels by copolymerization with functionalized monomers. J Pharm Sci 96 (2007) 802-813
6. Satish C.S., and Shivakumar H.G. Formulation and evaluation of self-regulated insulin delivery system based on poly(HEMA-co-DMAEMA) hydrogels. J Macromol Sci A 44 (2007) 379-387
7. Alvarez-Lorenzo C., Hiratani H., and Concheiro A. Contact lenses for drug delivery: achieving sustained release with novel systems. Am J Drug Del 4 (2006) 131-151
8. Karlgard C.C.S., Wong N.S., Jones L.W., and Moresoli C. In vitro uptake and release studies of ocular pharmaceutical agents by silicon-containing and p-HEMA hydrogel contact lens materials. Int J Pharm 257 (2003) 141-151
9. Gallardo A., Parejo C., and San Román J. NSAIDs bound to methacrylic carriers: microstructural characterization and in vitro release analysis. J Control Release 71 (2001) 127-140
10. Ende M.T.A., and Peppas N.A. Transport of ionizable drugs and proteins in crosslinked poly(acrylic acid) and poly(acrylic acid-co-2-hydroxyethyl methacrylate) hydrogels. 2. Diffusion and release studies. J Control Release 48 (1997) 47-56
11. Sato T., Uchida R., Tanigawa H., Uno K., and Murakami A. Application of polymer gels containing side-chain phosphate groups to drug-delivery contact lenses. J Appl Polym Sci 98 (2005) 731-735
12. Alvarez-Lorenzo C., and Concheiro A. Molecularly imprinted polymers for drug delivery. J Chromatogr B 804 (2004) 231-245
13. Alvarez-Lorenzo C., Hiratani H., Gomez-Amoza J.L., Martinez-Pacheco R., Souto C., and Concheiro A. Soft contact lenses capable of sustained delivery of timolol. J Pharm Sci 91 (2002) 2182-2192
14. Crini G., and Morcellet M. Synthesis and applications of adsorbents containing cyclodextrins. J Sep Sci 25 (2002) 789-813
15. Uekama K. Design and evaluation of cyclodextrin-based drug formulation. Chem Pharm Bull 52 (2004) 900-915
16. Liu Y.Y., Fan X.D., Hu H., and Tang Z.H. Release of chlorambucil from poly(N-isopropylacrylamide) hydrogels with β-cyclodextrin moieties. Macromol Biosci 4 (2004) 729-736
17. Liu Y.Y., and Fan X.D. Synthesis, properties and controlled release behaviors of hydrogel networks using cyclodextrin as pendant groups. Biomaterials 26 (2005) 6367-6374
18. Kanjickal D., Lopina S., Evancho-Chapman M.M., Schmidt S., and Donovan D. Improving delivery of hydrophobic drugs from hydrogels through cyclodextrins. J Biomed Mater Res A 74 (2005) 454-460
19. Rodriguez-Tenreiro C., Alvarez-Lorenzo C., Rodriguez-Perez A., Concheiro A., and Torres-Labandeira J.J. New cyclodextrin hydrogels cross-linked with diglycidylethers with a high drug loading and controlled release ability. Pharm Res 23 (2006) 121-130
20. Lepretre S., Boschin F., Tabary N., Bria M., Martel B., Blanchemain N., et al. Guided tissue regeneration membranes with controlled delivery properties of chlorhexidine by their functionalization with cyclodextrins. J Incl Phenom Macro 57 (2007) 297-302
21. Ohashi H., Hiraoka Y., and Yamaguchi T. An autonomous phase transition - complexation/decomplexation polymer system with a molecular recognition property. Macromolecules 39 (2006) 2614-2620
22. Pariot N., Edwards-Levy F., Andry M.C., and Levy M.C. Cross-linked β-cyclodextrin microcapsules. II. Retarding effect on drug release through semi-permeable membranes. Int J Pharm 232 (2002) 175-181
23. Asanuma H., Akiyama T., Kajiya K., Hishiya T., and Komiyama M. Molecular imprinting of cyclodextrin in water for the recognition of nanometer-scaled guests. Anal Chim Acta 435 (2001) 25-33
24. Nozaki T., Maeda Y., and Kitano H. Cyclodextrin gels which have a temperature responsiveness. J Polym Sci Pol Chem 35 (1997) 1535-1541
25. Siemoneit U., Schmitt C., Alvarez-Lorenzo C., Luzardo A., Otero-Espinar F., Concheiro A., and Blanco-Mendez J. Acrylic/cyclodextrin hydrogels with enhanced drug loading and sustained release capability. Int J Pharm 312 (2006) 66-74
26. Abay I., Denizii A., Kin E.B., and Salih B. Removal and pre-concentration of phenolic species onto beta-cyclodextrin modified poly(hydroxyethylmethacrylate-ethyleneglycoldimethacrylate) microbeads. Chemosphere 61 (2005) 1263-1272
27. Janus L., Crini G., El-Rezzi V., Morcellet M., Cambiaghi A., Torri G., et al. New sorbents containing β-cyclodextrin. Synthesis, characterization, and sorption properties. React Funct Polym 42 (1999) 173-180
28. Hussain L.A., Dickens S.H., and Bowen R.L. Shear bond strength of experimental methacrylated betacyclodextrin-based formulations. Biomaterials 26 (2005) 3973-3979
29. Hussain L.A., Dickens S.H., and Bowen R.L. Properties of eight methacrylated beta-cyclodextrin composite formulations. Dent Mater 21 (2005) 210-216
30. Lin N.J., Bailey L.O., Becker M.L., Washburn N.R., and Henderson L.A. Macrophage response to methacrylate conversion using a gradient approach. Acta Biomater 3 (2007) 163-173
31. Kaur I.P., Smitha R., Aggarwal D., and Kapil M. Acetazolamide: future perspective in topical glaucoma therapeutics. Int J Pharm 248 (2002) 1-14
32. Bary A.R., Tucker I.G., and Davies N.M. Considerations in the use of hydroxypropyl-beta-cyclodextrin in the formulation of aqueous ophthalmic solutions of hydrocortisone. Eur J Pharm Biopharm 50 (2000) 237-244
33. Friedman Z., Allen R.C., and Raph S.M. Topical acetazolamide and methazolamide delivered by contact lenses. Arch Ophthalmol 103 (1985) 963-966
34. Li C.C., and Chauhan A. Ocular transport model for ophthalmic delivery of timolol through p-HEMA contact lenses. J Drug Deliv Sci Tec 17 (2007) 69-79
35. Saito R., and Yamaguchi K. Synthesis of bimodal methacrylic acid oligomers by template polymerization. Macomolecules 36 (2003) 9005-9013
36. Stjernschantz J., and Astin M. Anatomy and physiology of the eye. Physiological aspects of ocular drug therapy. In: Edman P. (Ed). Biopharmaceutics of Ocular Drug Delivery (1993), CRC Press, Boca Raton, FL 1-25
37. Higuchi T., and Connors K.A. Phase-solubility techniques. In: Reilly C.N. (Ed). Advances in Analytical Chemistry and Instrumentation vol. 4 (1965), Wiley-Interscience, NY 117-212
38. Ye Q., Wang Y., Williams K., and Spencer P. Characterization of photopolymerization of dentin adhesives as a function of light source and irradiance. J Biomed Mater Res B 80 (2007) 440-446
39. Fundueanu G., Constantin M., Mihai D., Bortolotti F., Cortesi R., Ascenzi P., et al. Pullulan-cyclodextrin microspheres. A chromatographic approach for the evaluation of the drug-cyclodextrin interactions and the determination of the drug release profiles. J Chromatogr B 791 (2003) 407-419
40. Loftsson T., Hreinsdottir D., and Masson M. Evaluation of cyclodextrin solubilization of drugs. Int J Pharm 302 (2005) 18-28
41. Parasrampuria J. Acetazolamide. In: Brittain H.G. (Ed). Analytical Profiles of Drug Substances and Excipients vol. 22 (1993), Academic Press, San Diego, CA 1-32
42. Refojo M.F., and Leong F.L. Poly(methylacrylate-co-hydroxyethylacrylate) hydrogel implant material of strength and softness. J Biomed Materials Res 15 (1981) 497-509
43. Rassing J., Oesterberg O., and Bak T.A. Rates of dimerisation of substituted benzoic acids. Acta Chem Scand 21 (1967) 1443-1448
44. Kim S.W., Bae Y.H., and Okano T. Hydrogels: swelling, drug loading and release. Pharm Res 9 (1992) 283-290
45. Sreenivasan K. On the application of molecularly imprinted poly(HEMA) as a template responsive release system. J Appl Polym Sci 71 (1999) 1819-1821
46. Gulsen D., and Chauhan A. Ophthalmic drug delivery through contact lenses. Invest Ophth Vis Sci 45 (2004) 2342-2347