Supercritical fluid-assisted preparation of imprinted contact lenses for drug delivery

Acta Biomaterialia

Volumn 7, Issue 3, 2011, Pages 1019-1030

  Yañez, Fernando ^a   Martikainen, Lahja ^b   Braga, Mara E M ^b   Alvarez Lorenzo, Carmen ^a   Concheiro, Angel ^a   Duarte, Catarina M M ^c,d   Gil, Maria H ^b   De Sousa, Hermínio C ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c INSTITUTO DE BIOLOGIA EXPERIMENTAL E TECNOLÓGICA   (Portugal)

^d INSTITUTO DE TECNOLOGIA QUÍMICA E BIOLÓGICA   (Portugal)

Author keywords

Controlled drug release; Flurbiprofen; Molecular imprinting; Supercritical fluid technology; Therapeutic contact lenses

Indexed keywords

BIOSYNTHESIS; CARBON DIOXIDE; DRUG PRODUCTS; EFFLUENT TREATMENT; GLASS TRANSITION; IMPREGNATION; MOLECULAR MODELING; POLYMERIZATION; SOLUTIONS; SUPERCRITICAL FLUID EXTRACTION; SUPERCRITICAL FLUIDS; TARGETED DRUG DELIVERY;

CONTROLLED DRUG RELEASE; DRUG SOLUTIONS; FLURBIPROFEN; IMPRINTED CONTACT LENS; MOLECULAR IMPRINTING; SOFT CONTACT LENS; SUPERCRITICAL CARBONDIOXIDES; SUPERCRITICAL FLUID TECHNOLOGY; THERAPEUTIC CONTACT LENS; WATER SOLUBLE DRUGS;

CONTROLLED DRUG DELIVERY;

1 VINYL 2 PYRROLIDINONE; 2 HYDROXYETHYL METHACRYLATE; DEXAMETHASONE; ETHYLENE GLYCOL DIMETHACRYLATE; FLURBIPROFEN; IBUPROFEN;

ARTICLE; ASSAY; DRUG DELIVERY SYSTEM; DRUG SOLUTION; MOLECULAR IMPRINTING; POLYMERIZATION; PRIORITY JOURNAL; SOFT CONTACT LENS; SUPERCRITICAL CARBON DIOXIDE IMPREGNATION ASSAY;

EID: 79251612858     PISSN: 17427061     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.actbio.2010.10.003     Document Type: Article

References (72)

1. V.R. Kearns, and R.L. Williams Drug delivery systems for the eye Exp Rev Med Dev 6 2009 277 290
2. P. Calvo, J.L. Vila-Jato, and M.J. Alonso Comparative in vitro evaluation of several colloidal systems, nanoparticles, nanocapsules, and nanoemulsions, as ocular drug carriers J Pharmacol Sci 85 1996 530 536
3. C. Le Bourlais, L. Acar, H. Zia, P.A. Sado, T. Needham, and R. Leverge Ophthalmic drug delivery systems; recent advances Prog Retin Eye Res 17 1998 33 58
4. J. Sedlacek Possibility of application of eye drugs with the aid of gel-contact lenses Cesk Oftalmol 21 1965 509 512
5. S.R. Waltman, and H.E. Kaufman Use of hydrophilic contact lenses to increase ocular penetration of topical drugs Invest Ophthalmol Vis Sci 9 1970 250 259
6. M.R. Jain Drug delivery through contact lenses Br J Ophthalmol 72 1988 150 154
7. G.A. Lesher, and G.G. Gunderson Continuous drug delivery through the use of disposable contact lenses Optom Vis Sci 70 1993 1012 1018
8. H. Hiratani, A. Fujiwara, Y. Tamiya, Y. Mizutani, and C. Alvarez-Lorenzo Ocular release of timolol from molecularly imprinted soft contact lenses Biomaterials 26 2005 1293 1298
9. D. Gulsen, and A. Chauhan Ophthalmic drug delivery through contact lenses Invest Ophthalmol Vis Sci 45 2004 2342 2347
10. D. Gulsen, C.C. Li, and A. Chauhan Dispersion of DMPC liposomes in contact lenses for ophthalmic drug delivery Curr Eye Res 30 2005 1071 1080
11. G.D. Novack Ophthalmic drug delivery: development and regulatory considerations Clin Pharmacol Ther 85 2009 539 543
12. G. Wajs, and J.C. Meslard Release of therapeutic agents from contact lenses Crit Rev Ther Drug 2 1986 275 289
13. T.T. McMahon, and K. Zadnik Twenty-five years of contact lenses - the impact on the cornea and ophthalmic practice Cornea 19 2000 730 740
14. C.C.S. Karlgard, N.S. Wong, L.W. Jones, and C. Moresoli 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
15. C. Alvarez-Lorenzo, H. Hiratani, and A. Concheiro Contact lenses for drug delivery. Achieving sustained release with novel systems Am J Drug Deliv 4 2006 131 151
16. L. Xinming, C. Yingde, A.W. Lloyd, S.V. Mikhalovsky, S.R. Sandeman, and C.A. Howel Polymeric hydrogels for novel contact lens-based ophthalmic drug delivery systems: a review Cont Lens Anterior Eye 31 2008 57 64
17. C.C. Peng, J. Kim, and A. Chauhan Extended delivery of hydrophilic drugs from silicone-hydrogel contact lenses containing vitamin E diffusion barriers Biomaterials 31 2010 4032 4047
18. C. Alvarez-Lorenzo, F. Yañez, R. Barreiro-Iglesias, and A. Concheiro Imprinted soft contact lenses as norfloxacin delivery systems J Control Release 113 2006 236 244
19. C. Alvarez-Lorenzo, F. Yañez, and A. Concheiro Ocular drug delivery from molecularly-imprinted contact lenses J Drug Deliv Sci Technol 20 2010 237 248
20. C.J. White, and M.E. Byrne Molecularly imprinted therapeutic contact lenses Expert Opin Drug Deliv 7 2010 765 780
21. M. Komiyama, T. Takeuchi, T. Mukawa, and H. Asanuma Molecular imprinting, from fundamentals to applications 2003 Wiley-VCH Weinheim
22. C. Alvarez-Lorenzo, and A. Concheiro Molecularly imprinted polymers for drug delivery J Chromatogr B 804 2004 231 245
23. B. Sellergren, and C.J. Allender Molecularly imprinted polymers: a bridge to advanced drug delivery Adv Drug Deliv Rev 57 2005 1733 1741
24. D. Cunliffe, A. Kirby, and C. Alexander Molecularly imprinted drug delivery systems Adv Drug Deliv Rev 57 2005 1836 1853
25. S. Pilestky, and A. Turner Molecular imprinting of polymers 2006 Landes Bioscience Georgetown, TX
26. M.E. Byrne, K. Park, and N.A. Peppas Molecular imprinting within hydrogels Adv Drug Deliv Rev 54 2002 149 161
27. N.A. Peppas, and Y. Huang Polymers and gels as molecular recognition agents Pharm Res 19 2002 577 578
28. O. Bruggemann, K. Haupt, L. Ye, E. Yilmaz, and K. Mosbach New configurations and applications of molecularly imprinted polymers J Chromatogr A 889 2000 15 24
29. L. Ye, and K. Mosbach The technique of molecular imprinting - principle, state of the art, and future aspects J Inclusion Phenom Macrocyclic Chem 41 2001 107 113
30. T. Enoki, K. Tanaka, T. Watanabe, T. Oya, T. Sakiyama, and Y. Takeoka Frustrations in polymer conformation in gels and their minimization through molecular imprinting Phys Rev Lett 85 2000 5000 5003
31. H. Hiratani, C. Alvarez-Lorenzo, J. Chuang, O. Guney, A.Y. Grosberg, and T. Tanaka Effect of reversible cross-linker, N,N′-bis(acryloyl)cystamine, on calcium ion adsorption by imprinted gels Langmuir 17 2001 4431 4436
32. C. Alvarez-Lorenzo, O. Guney, T. Oya, Y. Sakai, M. Kobayashi, and T. Enoki Polymer gels that memorize elements of molecular conformation Macromolecules 33 2000 8693 8697
33. N. Elvassore, and I. Kikic Pharmaceutical processing with supercritical fluids A. Bertucco, G. Vetter, High pressure process technology: fundamentals and applications 2001 Elsevier Science Amsterdam 612 625
34. M.A. McHugh, and V.J. Krukonis Supercritical fluid extraction 2nd ed. 1994 Butterworth-Heinemann Boston, MA
35. 2 in green chemical synthesis and processing J Supercrit Fluids 28 2004 121 191
36. S.G. Kazarian Supercritical fluid impregnation of polymers for drug delivery P. York, U.B. Kompella, B.Y. Shekunov, Supercritical fluid technology for drug product development 2004 Marcel Dekker New York
37. 2 in the fabrication of polymer systems for drug delivery and tissue engineering Adv Drug Deliv Rev 60 2008 373 387
38. I. Kikic, and F. Vecchione Supercritical impregnation of polymers Curr Opin Solid State Mater Sci 7 2003 399 405
39. I. Kikic Polymer-supercritical fluid interactions J Supercrit Fluids 47 2009 458 465
40. M.F. Kemmere, and T. Meyer Supercritical carbon dioxide in polymer reaction engineering 2005 Wiley-VCH Weinheim
41. S.G. Kazarian Polymer processing with supercritical fluids Polymer Sci Ser C 42 2000 78 101
42. de Sousa HC, Gil MHM, Leite EOB, Duarte CMM, Duarte ARC. Method for preparing sustained-release therapeutic ophthalmic articles using compressed fluids for impregnation of drugs. EP Patent No. 1611877A1; 2006.
43. de Sousa HC, Gil MHM, Leite EOB, Duarte CMM, Duarte ARC. Method for preparing therapeutic ophthalmic articles using compressed fluids. US Patent No. US20060008506A1; 2006.
44. A.R.C. Duarte, A.L. Simplício, A. Vega-Gonzalez, P. Subra-Paternault, P. Coimbra, and M.H. Gil Impregnation of an intraocular lens for ophthalmic drug delivery Curr Drug Deliv 5 2008 102 107
45. M.E.M. Braga, M.T. Vaz, H.S.R. Costa, E.I. Ferreira, M.H. Gil, and C.M.M. Duarte Supercritical solvent impregnation of ophthalmic drugs on chitosan derivatives J Supercrit Fluids 44 2008 245 257
46. M.V. Natu, M.H. Gil, and H.C. de Sousa Supercritical solvent impregnation of poly(-caprolactone)/poly(oxyethylene-b-oxypropylene-b-oxyethylene) and poly(-caprolactone)/poly(ethylene-vinyl acetate) blends for controlled release applications J Supercrit Fluids 47 2008 93 1027
47. V.P. Costa, M.E.M. Braga, J.P. Guerra, A.R.C. Duarte, C.M.M. Duarte, and E.O.B. Leite Development of therapeutic contact lenses using a supercritical solvent impregnation method J Supercrit Fluids 52 2010 306 316
48. V.P. Costa, M.E.M. Braga, C.M.M. Duarte, C. Alvarez-Lorenzo, A. Concheiro, and M.H. Gil Anti-glaucoma drug-loaded contact lenses prepared using supercritical solvent impregnation J Supercrit Fluids 53 2010 165 173
49. B. Sellergren Polymer- and template-related factors influencing the efficiency in molecularly imprinted solid-phase extractions Trends Anal Chem 18 1999 164 174
50. A.R.C. Duarte, T. Casimiro, A. Aguiar-Ricardo, A.L. Simplício, and C.M.M. Duarte Supercritical fluid polymerisation and impregnation of molecularly imprinted polymers for drug delivery J Supercrit Fluids 39 2006 102 106
51. R. Paulini, K. Muller, and F. Diederich Orthogonal multipolar interactions in structural chemistry and biology Angew Chem Int Ed 44 2005 1788 1805
52. W.K. Hagmann The many roles for fluorine in medicinal chemistry J Med Chem 51 2008 4359 4369
53. A.R.C. Duarte, P. Coimbra, H.C. de Sousa, and C.M.M. Duarte Solubility of flurbiprofen in supercritical carbon dioxide J Chem Eng Data 49 2004 449 452
54. D.K. Owens, and R.C. Wendt Estimation of the surface free energy of polymers J Appl Polym Sci 13 1969 1741 1747
55. A. Rudawska, and E. Jacniacka Analysis for determining surface free energy uncertainly by the Owens-Wendt method Int J Adhes Adhes 29 2009 451 457
56. R.W. Korsmeyer, R. Gurny, E. Doelker, P. Buri, and N.A. Peppas Mechanisms of solute release from porous hydrophilic polymers Int J Pharm 15 1983 25 35
57. P.L. Ritger, and N.A. Peppas A simple equation for description of solute release II. Fickian and anomalous release from swellable devices J Control Release 5 1987 37 42
58. C.C. Lin, and A.T. Metters Hydrogels in controlled release formulations: network design and mathematical modelling Adv Drug Deliv Rev 58 2006 1379 1408
59. B.D. Anderson, and R.A. Conradi Predictive relationships in the water solubility of salts of a nonsteroidal anti-inflammatory drug J Pharmacol Sci 74 1985 815 820
60. G.L. Perlovich, S.V. Kurkov, and A. Bauer-Brandl The difference between partitioning and distribution from a thermodynamic point of view: NSAIDs as an example Eur J Pharm Sci 27 2006 150 157
61. R.B. Gupta, and J.J. Shim Solubility in supercritical carbon dioxide 2006 CRC Press Boca Raton, FL
62. P.D. Condo, S.R. Sumpter, M.L. Lee, and K.P. Johnston Partition coefficients and polymer-solute interaction parameters by inverse supercritical fluid chromatography Ind Eng Chem Res 35 1996 1115 1123
63. 2/polymer ternary systems and factors governing the impregnation efficiency J Appl Polym Sci 93 2004 742 748
64. P. Raveendran, Y. Ikushima, and S.L. Wallen Polar attributes of supercritical carbon dioxide Acc Chem Res 38 2005 478 485
65. S.G. Kazarian, and G.G. Martirosyan Spectroscopy of polymer/drug formulations processed with supercritical fluids: in situ ATR-IR Raman study of impregnation of ibuprofen into PVP Int J Pharm 232 2002 81 90
66. S.H. Yalkowsky, and H. Yan Handbook of aqueous solubility data: an extensive compilation of aqueous solubility data for organic compounds extracted from the AQUASOL database 2003 CRC Press Boca Raton, FL
67. R.F. Fedors A method for estimating both the solubility parameters and molar volumes of liquids Pol Eng Sci 14 1974 147 154
68. W.J. Lyman, W.F. Reehl, and D.H. Rosenblatt Handbook of chemical property estimation methods 1982 McGraw-Hill New York
69. B.E. Poling, J.M. Prausnitz, and J.P. O'Connell The properties of gases and liquids 5th ed. 2001 McGraw-Hill New York
70. J.A. Olsen, D.W. Banner, P. Seiler, U. Obst-Sander, A. D'Arcy, and M. Stihle A fluorine scan of thrombin inhibitors to map the fluorophilicity/ fluorophobicity of an enzyme active site: evidence for C-F/CO interactions Angew Chem Int Ed 42 2003 2507 2511
71. M. Pagliaro, and R. Ciriminna New fluorinated functional materials J Mater Chem 15 2005 4981 4991
72. M.L. Read, P.B. Morgan, and C. Maldonado-Codina Measurement errors related to contact angle analyses of hydrogel and silicone hydrogel contact lenses J Biomed Mater Res Part B 91 2009 662 668