New cyclodextrin hydrogels cross-linked with diglycidylethers with a high drug loading and controlled release ability

Pharmaceutical Research

Volumn 23, Issue 1, 2006, Pages 121-130

  Rodriguez Tenreiro, Carmen ^a   Alvarez Lorenzo, Carmen ^a   Rodriguez Perez, Ana ^a   Concheiro, Angel ^a   Torres Labandeira, Juan J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Amphiphilic drugs; Cross linking; Ethyleneglycol diglycidylether (EGDE); Hydrogels; Hydroxypropyl cyclodextrin (HP CD); Hydroxypropylmethylcellulose (HPMC); Rheology

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; AMPHOPHILE; CYCLODEXTRIN; DICLOFENAC; ETHER; ETHYLENEGLYCOL DIGLYCIDYLETHER; HYDROXYPROPYLMETHYLCELLULOSE; METHYLCELLULOSE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED RELEASE FORMULATION; CROSS LINKING; FLOW MEASUREMENT; HYDROGEL; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SUSTAINED DRUG RELEASE;

ALGORITHMS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BETA-CYCLODEXTRINS; CROSS-LINKING REAGENTS; CYCLODEXTRINS; DELAYED-ACTION PREPARATIONS; DICLOFENAC; HYDROGELS; OXAZINES; PHARMACEUTICAL PREPARATIONS; RHEOLOGY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SPECTRUM ANALYSIS, RAMAN;

EID: 32244442453     PISSN: 07248741     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11095-005-8924-y     Document Type: Article

References (53)

1. Y. W. Chien S. S. Lin 2002 Optimisation of treatment by applying programmable rate-controlled drug delivery technology Clin. Pharmacokinet. 41 1267 1299
2. N. A. Peppas K. M. Wood J. O. Blanchette 2004 Hydrogels for oral delivery of therapeutic proteins Expert Opin. Biol. Ther. 4 881 887
3. D. C. Coughlan F. P. Quilty O. I. Corrigan 2004 Effect of drug physicochemical properties on swelling/deswelling kinetics and pulsatile drug release from thermoresponsive poly(N-isopropylacrylamide) hydrogels J. Control. Release 98 97 114
4. R. Barreiro-Iglesias C. Alvarez-Lorenzo A. Concheiro 2001 Incorporation of small quantities of surfactants as a way to improve rheological and diffusional behavior of carbopol gels J. Control. Release 77 59 75
5. R. Rodriguez C. Alvarez-Lorenzo A. Concheiro 2003 Interactions of ibuprofen with cationic polysaccharides in aqueous dispersions and hydrogels. Rheological and diffusional implications Eur. J. Pharm. Sci. 20 429 438
6. M. Glavas-Dodov K. Goracinova K. Mladenovska E. Fredro-Kumbaradzi 2002 Release profile of lidocaine HCl from topical liposomal gel formulation Int. J. Pharm. 242 381 384
7. C. Alvarez-Lorenzo A. Concheiro 2004 Molecularly imprinted polymers for drug delivery J. Chromatogr., B 804 231 245
8. H. Asanuma T. Hishiya M. Komiyama 2004 Efficient separation of hydrophobic molecules by molecularly imprinted cyclodextrin polymers J. Incl. Phenom. 50 51 55
9. H. Hiratani Y. Mizutani C. Alvarez-Lorenzo 2005 Controlling drug release from imprinted hydrogels by modifying the characteristics of the imprinted cavities Macromol. Biosci. 5 728 733
10. D. C. Bibby N. M. Davies I. G. Tucker 2000 Mechanisms by which cyclodextrins modify drug release from polymeric drug delivery systems Int. J. Pharm. 197 1 11
11. B. Pose-Vilarnovo C. Rodriguez-Tenreiro Sánchez N. Dieguez Moure J. L. Vila-Jato J. J. Torres-Labandeira 2003 Effect of hydroxypropylmethyl cellulose on the complexation of diclofenac with cyclodextrin J. Therm. Anal. Calorim. 73 661 670
12. T. Loftsson H. Friöriksdóttir A. M. Sigurdardóttir T. Guömundsdóttir H. Ueda 1994 The effect of water-soluble polymers on drug-cyclodextrin complexation Int. J. Pharm. 110 169 177
13. V. Stella R. A. Rajewski 1997 Cyclodextrins: their future in drug formulation and delivery Pharm. Res. 14 556 567
14. J. Li X. Ni K. W. Leong 2003 Injectable drug-delivery systems based on supramolecular hydrogels formed by poly(ethylene oxide)s and α-cyclodextrin J. Biomed. Mater. Res. 65 196 202
15. K. M. Huh T. Ooya W. K. Lee S. Sasaki I. C. Kwon S. Y. Jeong N. Yui 2001 Supramolecular-structured hydrogels showing a reversible phase transition by inclusion complexation between poly(ethylene glycol) grafted dextran and alpha-cyclodextrin Macromolecules 34 8657 8662
16. G. Crini M. Morcellet 2002 Synthesis and applications of adsorbents containing cyclodextrins J. Sep. Sci. 25 789 813
17. Y. Y. Liu X. D. Fan H. Hu Z. H. Tang 2004 Release of chlorambucil from (Poly(N-isopropylacrylamide) hydrogels withβ-cyclodextrin moieties Macromol. Biosci. 4 729 736
18. Y. Y. Liu X. D. Fan T. Kang L. Sun 2004 A cyclodextrin microgel for controlled release driven by inclusion effects Macromol. Rapid Commun. 25 1912 1916
19. K. Uekama 2004 Design and evaluation of cyclodextrin-based drug formulation Chem. Pharm. Bull. 52 900 915
20. D. Kanjickal S. Lopina M. M. Evancho-Chapman S. Schmidt D. Donovan 2005 Improving delivery of hydrophobic drugs from hydrogels through cyclodextrins J. Biomed. Mater. Res. 74A 454 460
21. M. E. Davis M. E. Brewster 2004 Cyclodextrin-based pharmaceutics: past, present and future Nat. Rev., Drug Discov. 3 1023 1035
22. F. Quaglia G. Varricchio A. Miro M. I. La Rotonda D. Larobina G. Mensitieri 2001 Modulation of drug release from hydrogels by using cyclodextrins: the case of nicardipine/β-cyclodextrin system in crosslinked polyethyleneglycol J. Control. Release 71 329 337
23. N. Pariot F. Edwards-Lévy M. C. Andry M. C. Lévy 2002 Cross-linked β-cyclodextrin microcapsules: preparation and properties Int. J. Pharm. 232 175 181
24. J. T. Zhang S. W. Huang F. Z. Gao R. X. Zhuo 2005 Novel temperature-sensitive, β-cyclodextrin-incorporated poly(N- isopropylacrylamide) hydrogels for slow release of drug Colloid Polym. Sci. 283 461 464
25. K. Sreenivasan 1997 On the restriction of the release of water-soluble component from polyvinyl alcohol film by blending β-cyclodextrin J. Appl. Polym. Sci. 65 1829 1832
26. A. M. Layre N. M. Gosselet E. Renard B. Sebille C. Amiel 2002 Comparison of the complexation of cosmetical and pharmaceutical compounds with γ-cyclodextrin, 2-hydroxypropyl-β-cyclodextrin and water-soluble β-cyclodextrin-co-epichlorohydrin polymers J. Incl. Phenom. 43 311 317
27. T. Amiya T. Tanaka 1987 Phase transitions in cross-linked gels of natural polymers Macromolecules 20 1162 1164
28. N. Yui T. Okano Y. Sakurai 1992 Inflammation responsive degradation of crosslinked hyaluronic acid gels J. Control. Release 22 105 116
29. R. Rodriguez C. Alvarez-Lorenzo A. Concheiro 2003 Cationic cellulose hydrogels: kinetics of the cross-linking process and characterization as pH-/ion-sensitive drug delivery systems J. Control. Release 86 253 265
30. National Library of Medicine. Bis(1,2-epoxypropylether)ethanediol. http://chem.sis.nlm.nih.gov/chemidplus/jsp/common/ChemFull.jsp (accessed June 2005).
31. A. Poole P. van Herwijnen H. Weideli M. C. Thomas G. Ransbotyn C. Vance 2004 Review of the toxicology, human exposure and safety assessment for bisphenol A diglycidylether (BADGE) Food Addit. Contam. 21 905 919
32. L. A. Hussain S. H. Dickens R. L. Bowen 2005 Properties of eight methacrylated beta-cyclodextrin composite formulations Dent. Mater. 21 210 216
33. J. Cassidy B. Berner K. Chan V. John S. Toon B. Holt M. Rowland 1993 Human transbuccal absorption of diclofenac sodium from a prototype hydrogel delivery device Pharm. Res. 10 126 129
34. M. D. Kurkuri T. M. Aminabhavi 2004 Poly(vinyl alcohol) and poly(acrylic acid) sequential interpenetrating network pH-sensitive microspheres for the delivery of diclofenac sodium to the intestine J. Control. Release 96 9 20
35. C. M. Adeyeye P. K. Li 1990 Diclofenac sodium K. Florey Analytical Profiles of Drug Substances, Vol. 19 Academic Press New York 123 144
36. S. H. Gehrke D. Biren J. J. Hopkins 1994 Evidence for Fickian water transport in initially glassy poly(2-hydroxyethyl methacrylate) J. Biomater. Sci., Polym. Ed. 6 375 390
37. T. Iliescu M. Baia V. Miclau 2004 A Raman spectroscopic study of the diclofenac sodium-β-cyclodextrin interaction Eur. J. Pharm. Sci. 22 487 495
38. K. P. C. Vollhardt N. E. Schore 2003 Further reactions of alcohols and the chemistry of ethers K. P. C. Vollhardt Organic Chemistry, Structure and Function W.H. Freeman and Company New York 346 350
39. H. M. Cabral Marques 1994 Applications of cyclodextrins. Thermodynamic aspects of cyclodextrin complexes Rev. Port. Farm. 44 77 84
40. T. Loftsson M. E. Brewster 1996 Pharmaceutical applications of cyclodextrins J. Pharm. Sci. 85 1017 1025
41. T. F. Chin P. H. Chung J. L. Lach 1968 Influence of cyclodextrins on ester hydrolysis J. Pharm. Sci. 57 44
42. C. Alvarez-Lorenzo R. A. Lorenzo-Ferreira J. L. Gomez-Amoza R. Martinez-Pacheco C. Souto A. Concheiro 1999 Acomparison of gas-liquid chromatography, NMR spectroscopy and Raman spectroscopy of the substituent content of general non-ionic cellulose ethers J. Pharm. Biomed. Anal. 20 373 383
43. 13C solid state NMR determination of cross-linking degree in superabsorbing cellulose-based networks Macromolecules 33 430 437
44. C. Alvarez-Lorenzo R. Duro J. L. Gomez-Amoza R. Martinez-Pacheco C. Souto A. Concheiro 2001 Influence of polymer structure on the rheological behavior of hydroxypropyl- methylcellulose-sodium carboxymethylcellulose Colloid Polym. Sci. 279 1045 1057
45. F. W. Langkilde A. Svantesson 1995 Identification of celluloses with Fourier-transform (FT) mid-infrared, FT-Raman and near-infrared spectrometry J. Pharm. Biomed. Anal. 13 409 414
46. S. W. Kim Y. H. Bae T. Okano 1992 Hydrogels: swelling, drug loading and release Pharm. Res. 9 283 290
47. A. Magnusdottir M. Másson T. Loftsson 2002 Self association and cyclodextrin solubilization of NSAIDs J. Incl. Phenom. Macrocycl. Chem. 44 213 218
48. V. J. Stella V. M. Rao E. A. Zannou V. Zia 1999 Mechanisms of drug release from cyclodextrin complexes Adv. Drug Deliv. Rev. 36 3 16
49. A. Ridell H. Evertsson S. Nilsson L. O. Sundelof 1999 Amphiphilic association of ibuprofen and two non-ionic cellulose derivatives in aqueous solution J. Pharm. Sci. 88 1175 1181
50. P. Bustamante M. A. Peña J. Barra 2000 The modified extended Hansen method to determine partial solubility parameters of drugs containing a single hydrogen bonding group and their sodium derivatives: benzoic acid/Na and ibuprofen/Na Int. J. Pharm. 194 117 124
51. K. Uekama F. Hirayama T. Irie 1994 Application of cyclodextrins in pharmaceutical preparations Drug Target. Deliv. 3 411 456
52. C. B. [tmp] McCrystal J. L. Ford A. R. Rajabi-Siahboomi 1999 Water distribution studies within cellulose ethers using differential scanning calorimetry. 1. Effect of polymer molecular weight and drug addition J. Pharm. Sci. 88 792 801
53. Martindale. The Complete Drug Reference. K. Parfitt (ed.). Pharmaceutical Press, Tauton, MA 1999, p 32.