Loading antifungal drugs onto silica particles grafted with cyclodextrins by means of inclusion complex formation at the solid surface

International Journal of Pharmaceutics

Volumn 439, Issue 1-2, 2012, Pages 234-245

  Hbaieb, Souhaira ^a   Kalfat, Rafik ^a   Chevalier, Yves ^b  

^a Institut National de Recherche et d'Analyse Physico Chimique Tunis   (Tunisia)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

cyclodextrin; Griseofulvin; Inclusion complexes; Silica

Indexed keywords

ANTIFUNGAL AGENT; CYCLODEXTRIN; GRISEOFULVIN; SILICON DIOXIDE;

ADSORPTION; ARTICLE; CONTROLLED STUDY; CRYSTAL; HYDROPHOBICITY; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; SCANNING ELECTRON MICROSCOPY; STOICHIOMETRY; SURFACE PROPERTY; X RAY DIFFRACTION;

ADSORPTION; ANTIFUNGAL AGENTS; BETA-CYCLODEXTRINS; DRUG COMPOUNDING; GRISEOFULVIN; SILICON DIOXIDE;

EID: 84869491444     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.09.035     Document Type: Article

References (50)

1. R. Alvarez-Román, A. Naik, Y.N. Kalia, R.H. Guy, and H. Fessi Skin penetration and distribution of polymeric nanoparticles J. Control. Release 99 2004 53 62
2. D.D. Asouhidou, K.S. Triantafyllidis, N.K. Lazaridis, and K.A. Matis Adsorption of Remazol Red 3BS from aqueous solutions using APTES- and cyclodextrin-modified HMS-type mesoporous silicas Colloids Surf. A: Physicochem. Eng. Aspects 346 2009 83 90
3. L.A. Belyakova, K.A. Kazdobin, V.N. Belyakov, S.V. Rvabov, and A.F. Danil de Namor Synthesis and properties of supramolecular systems based on silica J. Colloid Interface Sci. 283 2005 488 494
4. A. Bibby, and L. Mercier Adsorption and separation of water-soluble aromatic molecules by cyclodextrin-functionalized mesoporous silica Green Chem. 5 2003 15 19
5. U. Blume-Peytavi, and A. Vogt Human hair follicle: reservoir function and selective targeting Br. J. Dermatol. 165 2011 13 17
6. M.A. Bolzinger, S. Briançon, J. Pelletier, and Y. Chevalier Penetration of drugs through skin, a complex rate-controlling membrane Curr. Opin. Colloid Interface Sci. 17 2012 156 165
7. M.L. Calabrò, S. Tommasini, P. Donato, D. Raneri, R. Stancanelli, P. Ficarra, R. Ficarra, C. Costa, S. Catania, C. Rustichelli, and G. Gamberini Effects of alpha- and beta-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones J. Pharm. Biomed. Anal. 35 2004 365 377
8. N.R. Calafato, and G. Picó Griseofulvin and ketoconazole solubilization by bile salts studied using fluorescence spectroscopy Colloids Surf. B: Biointerfaces 47 2006 198 204
9. J.C. Chaumeil Micronization: a method of improving the bioavailability of poorly soluble drugs Exp. Clin. Pharmacol. 20 1998 211 215
10. Y. Chevalier, A.C. Grillet, M.I. Rahmi, C. Lière, M. Masure, P. Hémery, and F. Babonneau The structure of porous silica-polysiloxane hybrid materials Mater. Sci. Eng. C 21 2002 143 150
11. R. Denoyel, and P. Trens Influence of water on adsorption of triethylsilanol onto silica J. Phys. Chem. 99 1995 3711 3714
12. M.D. Dhanaraju, K. Senthil Kumaran, T. Baskaran, and M. Sree Rama Moorthy Enhancement of bioavailability of griseofulvin by its complexation with β-cyclodextrin Drug Develop. Ind. Pharm. 24 1998 583 587
13. D. Duchêne Cyclodextrins and their Industrial Uses 1987 Éditions de la Santé Paris
14. D. Duchêne, G. Ponchel, and D. Wouessidjewe Cyclodextrins in targeting: applications to nanoparticles Adv. Drug Deliv. Rev. 36 1999 29 40
15. D. Duchêne, D. Wouessidjewe, and G. Ponchel Cyclodextrins and carrier systems J. Control. Release 62 1999 263 268
16. A. El Fagui, and C. Amiel PLA nanoparticles coated with a β-cyclodextrin polymer shell: Preparation, characterization and release kinetics of a hydrophobic compound Int. J. Pharm. 436 2012 644 651
17. P.H. Elworthy, and F.J. Lipscomb Solubilization of griseofulvin by nonionic surfactants J. Pharm. Pharmacol. 20 1968 817 824
18. P.H. Elworthy, and M.S. Patel Demonstration of maximum solubilization in a polyoxyethylene alkyl ether series of non-ionic surfactants J. Pharm. Pharmacol. 34 1982 543 546
19. W.L. Epstein, V.P. Shah, H.E. Jones, and S. Riegelman Topically applied griseofulvin in prevention and treatment of Trichophyton mentagrophytes Arch. Dermatol. 111 1975 1293 1297
20. A. Farcas, N. Jarroux, A.M. Farcas, V. Harabagiu, and P. Guegan Synthesis and characterization of furosemide complex in β-cyclodextrin Digest J. Nanomater. Biostruct. 1 2006 55 60
21. M. Fujii, M. Bouno, S. Fujita, M. Yoshida, Y. Watanabe, and M. Matsumoto Preparation of griseofulvin for topical application using N-methyl-2-pyrrolidone Biol. Pharm. Bull. 23 2000 1341 1345
22. A.A. Kassem, and N.M. Mursi Solubilization of griseofulvin as a function of low temperature and different nonionic surface active agents Bull. Faculty Pharm. Cairo Univ. 9 1970 11 23
23. J. Lademann, H. Richter, U.F. Schaefer, U. Blume-Peytavi, A. Teichmann, N. Otberg, and W. Sterry Hair follicles - a long-term reservoir for drug delivery Skin Pharmacol. Physiol. 19 2006 232 236
24. I. Langmuir The adsorption of gases on plane surfaces of glass, mica and platinum J. Am. Chem. Soc. 40 1918 1361 1403
25. C. Lin, J. Magat, R. Chang, J. McGlotten, and S. Symchowicz Absorption, metabolism and excretion of 14C-griseofulvin in man J. Pharmacol. Exp. Ther. 187 1973 415 422
26. B. Martel, Y. Leckchiri, A. Pollet, and M. Morcellet Cyclodextrin- poly(vinylamine) systems. I. Synthesis, characterization and conformational properties Eur. Polym. J. 31 1995 1083 1088
27. M. Mooguee, Y. Omidi, and S. Davaran Synthesis and in vitro release of Adriamycin from star-shaped poly(lactide-co-glycolide) nano-and microparticles J. Pharm. Sci. 99 2010 3389 3397
28. A. Noomen, S. Hbaieb, H. Parrot-Lopez, R. Kalfat, H. Fessi, N. Amdouni, and Y. Chevalier Emulsions of β-cyclodextrins grafted to silicone for the transport of antifungal drugs Mater. Sci. Eng. C 28 2008 705 715
29. A. Noomen, A. Penciu, S. Hbaieb, H. Parrot-Lopez, N. Amdouni, Y. Chevalier, and R. Kalfat Grafting β-cyclodextrins to silicone, formulation of emulsions and encapsulation of antifungal drug. Advances in synthesis and supramolecular organization F. Ganachaud, S. Boileau, B. Boury, Silicon Based Polymers 2008 Springer-Verlag New York 163 179
30. A. Oki, L. Adams, V. Khabashesku, Y. Edigin, P. Biney, and Z. Luo Dispersion of aminoalkylsilyl ester or amine alkyl-phosphonic acid side wall functionalized carbon nanotubes in silica using sol-gel processing Mater. Lett. 62 2008 918 922
31. R.C. Petter, J.S. Salek, C.T. Sikorski, G. Kumaravel, and F.T. Lin Cooperative binding by aggregated mono-6-(alky1amino)-β-cyclodextrins J. Am. Chem. Soc. 112 1990 3860 3868
32. T.N.T. Phan, M. Bacquet, and M. Morcellet The removal of organic pollutants from water using new silica-supported β-cyclodextrin derivatives Reactive Functional Polym. 52 2002 117 125
33. M.P.Y. Piemi, D. Korner, S. Benita, and J.P. Martey Positively and negatively charged submicron emulsions for enhanced topical delivery of antifungal drugs J. Control. Release 58 1999 177 187
34. E.P. Plueddemann Silane Coupling Agents 1982 Plenum Press New York
35. A. Ponchel, S. Abramson, J. Quartararo, D. Bormann, Y. Barbaux, and E. Monflier Cyclodextrin silica-based materials: advanced characterizations and study of their complexing behavior by diffuse reflectance UV-vis spectroscopy Microporous Mesoporous Mater. 75 2004 261 272
36. S.T. Reddy, M.A. Swartz, and J.A. Hubbell Targeting dendritic cells with biomaterials: developing the next generation of vaccines Trends Immunol. 27 2006 573 579
37. W.A. Ritschel, and A.S. Hussain In vitro skin penetration of griseofulvin in rat and human skin from an ointment dosage form Arzneim.-Forsch./Drug Res. 38 1988 1630 1632
38. Shishu, and N. Aggarwal Preparation of hydrogels of griseofulvin for dermal application Int. J. Pharm. 326 2006 20 24
39. V.J. Stella, V.M. Rao, E.A. Zannou, and V. Zia Mechanism of drug release from cyclodextrin complexes Adv. Drug Deliv. Rev. 36 1999 3 16
40. Y.V. Subba Rao, D.E. De Vos, T. Bein, and P.A. Jacobs Practical heterogenisation of an active manganese triazacyclononaneepoxidation catalyst via surface glycidylation Chem. Commun. 1997 355 356
41. S. Tolle, T. Zuberi, W. Warisnoicharoen, and M.J. Lawrence Physicochemical and solubilization properties of N,N-dimethyl-N-(3- dodecylcarbonyloxypropyl)amineoxide: a biodegradable nonionic surfactant J. Pharm. Sci. 89 2000 798 806
42. P. Trens, and R. Denoyel Adsorption of (γ-aminopropyl) triethoxysilane and related molecules at the silica/heptane interface Langmuir 12 1996 2781 2784
43. M. Trotta, M. Gallarate, M.E. Carlotti, and S. Morel Preparation of griseofulvin nanoparticles from water-dilutable microemulsions Int. J. Pharm. 254 2003 235 242
44. M. Trotta, R. Cavalli, and D. Chirio Griseofulvin nanosuspensions from triacetin-in-water emulsions STP Pharma Sci. 13 2003 423 426
45. K. Uekama, F. Hirayama, and T. Irie Cyclodextrin drug carrier systems Chem. Rev. 98 1998 2045 2076
46. L. Valentini, D. Puglia, I. Armentano, and J.M. Kenny Sidewall functionalization of single-walled carbon nanotubes through CF4 plasma treatment and subsequent reaction with aliphatic amines Chem. Phys. Lett. 403 2005 385 389
47. E.F. Vansant, P. Van Der Voort, and K.C. Vrancken Modification with silicon compounds: mechanistic studies Studies in Surface Science and Catalysis 1995 Elsevier Amsterdam pp. 193-265 (Chapter 9)
48. M.D. Veiga, P.J. Diaz, and F. Ahsan Interactions of griseofulvin with cyclodextrins in solid binary systems J. Pharm. Sci. 87 1998 891 900
49. M. Wulff, M. Alden, M. Seiersten, and S. Stolen Phase equilibria in drug-polymer-surfactant systems Thermochim. Acta 256 1995 151 165
50. L.T. Zhuravlev, and V.V. Potapov Density of silanol groups on the surface of silica precipitated from a hydrothermal solution Russ. J. Phys. Chem. 80 2006 1272 1282