Pickering emulsions based on cyclodextrins: A smart solution for antifungal azole derivatives topical delivery

European Journal of Pharmaceutical Sciences

Volumn 82, Issue , 2016, Pages 126-137

  Leclercq, Loïc ^a   Nardello Rataj, Véronique ^a  

^a UNIV LILLE   (France)

Author keywords

Antifungal drug; Cyclodextrin; Pathogen; Pickering emulsion; Topical delivery

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; ECONAZOLE; GAMMA CYCLODEXTRIN; LIQUID PARAFFIN; MYRISTIC ACID ISOPROPYL ESTER; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CYCLODEXTRIN; EMULSIFYING AGENT; EMULSION;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG DELIVERY SYSTEM; DRUG FORMULATION; EMULSION; FLOW KINETICS; LIGHT SCATTERING; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; TRANSMISSION ELECTRON MICROSCOPY; CHEMISTRY; DRUG EFFECTS; DRUG STABILITY; GROWTH, DEVELOPMENT AND AGING; MEDICINAL CHEMISTRY; MOLECULAR MODEL; TOPICAL DRUG ADMINISTRATION;

ADMINISTRATION, TOPICAL; ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; CANDIDA ALBICANS; CHEMISTRY, PHARMACEUTICAL; CYCLODEXTRINS; DRUG STABILITY; ECONAZOLE; EMULSIFYING AGENTS; EMULSIONS; MODELS, MOLECULAR; RHEOLOGY; STAPHYLOCOCCUS AUREUS;

EID: 84949669190     PISSN: 09280987     EISSN: 18790720     Source Type: Journal    
DOI: 10.1016/j.ejps.2015.11.017     Document Type: Article

References (40)

1. R. Aveyard, B.P. Binks, and J.H. Clint Emulsions stabilized solely by colloidal particles Adv. Colloid Interf. Sci. 100-102 2003 503 546
2. B.P. Binks Particles as surfactants,similarities and differences Curr. Opin. Colloid Interface Sci. 7 2002 21 41
3. R.A. Calderone, and C.J. Clancy Candida and Candidiasis 2011 ASM Press Washington, D.C., U.S.A.
4. H.B. Co-Minh, P. Demoly, B. Guillot, and N. Raison-Peyron Anaphylactic shock after oral intake and contact urticaria due to polyethylene glycols Allergy 62 2007 92 93
5. Core Safety Profile: http://www.bfarm.de/SharedDocs/Downloads/EN/Drugs/vigilance/PSURs/csp/e-f/econazole-dermatol.pdf?--blob=publicationFile&v=2
6. A.A. Fisher Immediate and delayed allergic contact reactions to polyethylene glycol Contact Dermatitis 4 1978 135 138
7. P. Gaillard, P.A. Carrupt, B. Testa, and A. Boudon Molecular lipophilicity potential, a tool in 3D QSAR: method and applications J. Comput. Aided Mol. Des. 8 1994 83 96
8. K. Hashizaki, T. Kageyama, M. Inoue, H. Taguchi, and Y. Saito Preparation and characterization of cycloalkanol/water emulsion using α-cyclodextrin as an emulsifier J. Dispers. Sci. Technol. 30 2009 852 856
9. K. Hashizaki, T. Kageyama, M. Inoue, H. Taguchi, H. Ueda, and Y. Saito Study on preparation and formation mechanism of n-alkanol/water emulsion using α-cyclodextrin Chem. Pharm. Bull. 55 2007 1620 1625
10. R.C. Heel, R.N. Brogden, T.M. Speight, and G.S. Avery Econazole: a review of its antifungal activity and therapeutic efficacy Drugs 16 1978 177 201
11. M. Inoue, K. Hashizaki, H. Taguchi, and Y. Saito Emulsion preparation using β-cyclodextrin and its derivatives acting as an emulsifier Chem. Pharm. Bull. 56 2008 1335 1337
12. M. Inoue, K. Hashizaki, H. Taguchi, and Y. Saito Formation and characterization of emulsions using β-cyclodextrin as emulsifier Chem. Pharm. Bull. 56 2008 668 671
13. M. Inoue, K. Hashizaki, H. Taguchi, and Y. Saito Preparation and characterization of n-alkane/water emulsion stabilized by cyclodextrin J. Oleo Sci. 58 2009 85 90
14. M. Inoue, K. Hashizaki, H. Taguchi, and Y. Saito Emulsifying ability of β-cyclodextrins for common oils J. Dispers. Sci. Technol. 31 2010 1648 1651
15. C.T. Jackson, M. Paye, and H.I. Mailbach Mechanism of skin irritation by surfactants and anti-irritants for surfactants-based products A.O. Barel, M. Paye, H.I. Maibach, Handbook of Cosmetic Science and Technology 2014 CRC Press Boca Raton, FL, U.S.A. 353 366
16. J. Jacobsen, S. Bjerregaard, and M. Pedersen Cyclodextrin inclusion complexes of antimycotics intended to act in the oral cavity-drug supersaturation, toxicity on TR146 cells and release from a delivery system Eur. J. Pharm. Biopharm. 48 1999 217 224
17. D.R. Karsa, and M.R. Porter Biodegradability of Surfactants 1995 Blackies Academic & Professional Glasgow, U.K.
18. L. Leclercq, R. Company, A. Mühlbauer, A. Mouret, J.-M. Aubry, and V. Nardello-Rataj Versatile eco-friendly Pickering emulsions based on substrate/native cyclodextrin complexes: a winning approach for solvent-free oxidations ChemSusChem 6 2013 1533 1540
19. L. Leclercq, Q. Lubart, A. Dewilde, J.-M. Aubry, and V. Nardello-Rataj Supramolecular effects on the antifungal activity of cyclodextrin/di-n-decyldimethylammonium chloride mixtures Eur. J. Pharm. Sci. 46 2012 336 345
20. L. Leclercq, A. Mouret, A. Proust, V. Schmitt, P. Bauduin, J.-M. Aubry, and V. Nardello-Rataj Pickering emulsion sabilized by catalytic polyoxometalate nanoparticles: a new effective medium for oxidation reactions Chem. Eur. J. 18 2012 14352 14358
21. L. Leclercq, V. Nardello-Rataj, G. Rauwel, and J.-M. Aubry Structure-activity relationship of cyclodextrin/biocidal double-tailed ammonium surfactant host-guest complexes: towards a delivery molecular mechanism? Eur. J. Pharm. Sci. 41 2010 265 275
22. F. Macaev, V. Boldescu, A. Geronikaki, and N. Sucman Recent advances in the use of cyclodextrins in antifungal formulations Curr. Top. Med. Chem. 13 2013 2677 2683
23. D. Marku, M. Wahlgren, M. Rayner, M. Sjöö, and A. Timgren Characterization of starch Pickering emulsions for potential applications in topical formulations Int. J. Pharm. 428 2012 1 7
24. B.G. Mathapa, and V.N. Paunov Cyclodextrin stabilised emulsions and cyclodextrinosomes Phys. Chem. Chem. Phys. 15 2013 17903 17914
25. R. Miller, V.B. Fainerman, V.I. Kovalchuk, D.O. Grigoriev, M.E. Leser, and M. Michel Composite, interfacial layers containing micro-size and nano-size particles Adv. Colloid Interf. Sci. 128-130 2006 17 26
26. A.K. Mitra, D. Kwatra, and A.D. Vadlapudi Drug Delivery 2015 Jones & Bartelett Burlington, MA, U.S.A. 237
27. A. Mouret, L. Leclercq, A. Mühlbauer, and V. Nardello-Rataj Eco-friendly solvents and amphiphilic catalytic polyoxometalate nanoparticles: a winning combination for olefin epoxidation Green Chem. 16 2014 269 278
28. V. Nardello-Rataj, and L. Leclercq Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens Beilstein J. Org. Chem. 10 2014 2603 2622
29. M. Pedersen, M. Edelsten, V.F. Nielsen, A. Scarpellini, S. Skytte, and C. Slot Formation and antimycotic effect of cyclodextrin inclusion complexes of econazole and miconazole Int. J. Pharm. 90 1993 247 254
30. A. Pedretti, L. Villa, and G. Vistoli VEGA - an open platform to develop chemo-bio-informatics applications, using plug-in architecture and script programming J. Comput. Aided Mol. Des. 2004 18 2004 167 173
31. J. Potier, S. Menuel, M.-H. Chambrier, L. Burylo, J.-F. Blach, P. Woisel, E. Monflier, and F. Hapiot Pickering emulsions based on supramolecular hydrogels: application to higher olefins' hydroformylation ACS Catal. 3 2013 1618 1621
32. W. Raab Clinical pharmacology of modern topical broad-spectrum antimicrobials Curr. Ther. Res. 1977 22 1977 65 82
33. S.S. Rahman, I. Simovic, S. Gibbons, and M. Zloh In silico screening for antibiotic escort molecules to overcome efflux J. Mol. Model. 17 2011 2863 2872
34. K. Shimada, Y. Ohe, T. Ohguni, K. Kawano, J. Ishii, and T. Nakamura Emulsifying properties of α-, β-and γ-cyclodextrins Nippon Shokuhin Kogyo Gakkaishi 38 1991 16 20
35. J.J.P. Stewart Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters J. Mol. Model. 19 2013 1 32
36. J. Szejtli Cyclodextrin technology 1988 Kluwer Academic Publishers Dordrecht, The Netherlands
37. S. Tenjarla, P. Puranajoti, R. Kasina, and T. Mandal Preparation, characterization, and evaluation of miconazole-cyclodextrin complexes for improved oral and topical delivery J. Pharm. Sci. 87 1998 425 429
38. D. Thienpont, J. Van Cutsem, J.M. Van Nueten, C.J. Niemegeers, and R. Marsboom Biological and toxicological properties of econazole, a broad spectrum antimycotic Arzneimittelforschung 25 1975 224 230
39. Y. Xia, X. Zhi, X. Wang, M. Chen, and J. Cheng Ultrasound-enhanced surfactant-assisted dispersive liquid-liquid microextraction and high-performance liquid chromatography for determination of ketoconazole and econazole nitrate in human blood Anal. Bioanal. Chem. 402 2012 1241 1247
40. M. Zloh, and S. Gibbons The role of small molecule-small molecule interactions in overcoming biological barriers for antibacterial drug action Theor. Chem. Accounts 117 2007 231 238