Ionic liquids as ingredients in topical drug delivery systems

International Journal of Pharmaceutics

Volumn 441, Issue 1-2, 2013, Pages 620-627

  Dobler, Dorota ^a   Schmidts, Thomas ^a   Klingenhöfer, Ines ^a   Runkel, Frank ^a  

^a TECHNISCHE HOCHSCHULE MITTELHESSEN   (Germany)

Author keywords

Antimicrobial activity; Emulsion stability; Ionic liquids; Penetration enhancement; Solubility

Indexed keywords

1 BUTYL 3 METHYLIMIDAZOLIUM HEXAFLUOROPHOSPHATE; 1 HEXYL 3 METHYLIMIDAZOLIUM CHLORIDE; FLUORESCENT DYE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PRESERVATIVE; UNCLASSIFIED DRUG; WATER OIL CREAM;

ANIMAL CELL; ANTIMICROBIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG FORMULATION; DRUG PENETRATION; EMULSION; FUNGAL STRAIN; HUMAN; HUMAN CELL; HYDROPHILICITY; HYDROPHOBICITY; IN VITRO STUDY; KERATINOCYTE; NONHUMAN; PRIORITY JOURNAL;

ADMINISTRATION, CUTANEOUS; ANIMALS; ANTI-INFECTIVE AGENTS; DRUG DELIVERY SYSTEMS; DRUG STABILITY; EMULSIONS; FLUORESCENT DYES; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IONIC LIQUIDS; PRESERVATIVES, PHARMACEUTICAL; SKIN ABSORPTION; SOLUBILITY; SWINE; TOXICITY TESTS;

EID: 84872800329     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2012.10.035     Document Type: Article

References (51)

1. J.L. Anderson, V. Pino, E.C. Hagberg, V.V. Sheares, and D.W. Armstrong Surfactant solvation effects and micelle formation in ionic liquids Chem. Commun. 2003 2444 2445
2. R.P. Austin, P. Barton, A.M. Davis, C.N. Manners, and M.C. Stansfield The effect of ionic strength on liposome-buffer and 1-octanol-buffer distribution coefficients J. Pharm. Sci. 87 1998 599 607
3. A. Avranas, and G. Stalidis Interfacial properties and stability of oil-in-water emulsions stabilized with binary mixtures of surfactants: II. Effect of a cationic surfactant on a nonionic surfactant stabilized emulsion J. Colloid Interface Sci. 143 1991 180 187
4. H. Bataller, S. Lamaallam, J. Lachaise, A. Graciaa, and C. Dicharry Cutting fluid emulsions produced by dilution of a cutting fluid concentrate containing a cationic/nonionic surfactant mixture J. Mater. Process. Technol. 152 2004 215 220
5. K. Bica, C. Rijksen, M. Nieuwenhuyzen, and R.D. Rogers In search of pure liquid salt forms of aspirin: ionic liquid approaches with acetylsalicylic acid and salicylic acid Phys. Chem. Chem. Phys. 12 2010 2011 2017
6. M. Blesic, M.H. Marques, N.V. Plechkova, K.R. Seddon, L.P.N. Rebelo, and A. Lopes Self-aggregation of ionic liquids: micelle formation in aqueous solution Green Chem. 9 2007 481 490
7. S. Carda-Broch, A. Berthod, and D.W. Armstrong Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid Anal. Bioanal. Chem. 375 2003 191 199
8. L. Carson, P.K.W. Chau, M.J. Earle, M.A. Gilea, B.F. Gilmore, S.P. Gorman, M.T. McCann, and K.R. Seddon Antibiofilm activities of 1-alkyl-3-methylimidazolium chloride ionic liquids Green Chem. 11 2009 492 497
9. D. Chakrabarty, P. Hazra, A. Chakraborty, D. Seth, and N. Sarkar Dynamics of solvent relaxation in room temperature ionic liquids Chem. Phys. Lett. 381 2003 697 704
10. R. Chanamai, G. Horn, and D.J. McClements Influence of oil polarity on droplet growth in oil-in-water emulsions stabilized by a weakly adsorbing biopolymer or a nonionic surfactant J. Colloid Interface Sci. 247 2002 167 176
11. B.H. Cipriano, S.R. Raghavan, and P.M. McGuiggan Surface tension and contact angle measurements of a hexadecyl imidazolium surfactant adsorbed on a clay surface Colloid Surf. A: Physicochem. Eng. Aspects 262 2005 8 13
12. E.G. Cockbain, and T.S. McRoberts The stability of elementary emulsion drops and emulsions J. Colloid Sci. 8 1953 440 451
13. J. Cross Cationic Surfactants: Analytical and Biological Evaluation 1994 Marcel Dekker, Inc. New York
14. W. Diembeck, H. Beck, F. Benech-Kieffer, P. Courtellemont, J. Dupuis, W. Lovell, M. Paye, J. Spengler, and W. Steiling Test guidelines for in vitro assessment of dermal absorption and percutaneous penetration of cosmetic ingredients. European Cosmetic, Toiletry and Perfumery Association Food Chem. Toxicol. 37 1999 191 205
15. K.M. Docherty, and J.C.F. Kulpa Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids Green Chem. 7 2005 185 189
16. European Pharmacopoeia Commission 5.0, 2005. Efficacy of Antimicrobial Preservation Group of Experts No. 1CM (Microbial Contamination).
17. Y. Gao, S. Han, B. Han, G. Li, D. Shen, Z. Li, J. Du, W. Hou, and G. Zhang TX-100/water/1-butyl-3-methylimidazolium hexafluorophosphate microemulsions Langmuir 21 2005 5681 5684
18. R.H. Guy Current status and future prospects of transdermal drug delivery Pharm. Res. 13 1996 1765 1769
19. J. Hao, and T. Zemb Self-assembled structures and chemical reactions in room-temperature ionic liquids Curr. Opin. Colloid Interface Sci. 12 2007 129 137
20. W.L. Hough, and R.D. Rogers Ionic liquids then and now: from solvents to materials to active pharmaceutical ingredients Bull. Chem. Soc. Jpn. 80 2007 2262 2269
21. W.L. Hough, M. Smiglak, H. Rodriguez, R.P. Swatloski, S.K. Spear, D.T. Daly, J. Pernak, J.E. Grisel, R.D. Carliss, M.D. Soutullo, J.J.H. Davis, and R.D. Rogers The third evolution of ionic liquids: active pharmaceutical ingredients New J. Chem. 31 2007 1429 1436
22. J.G. Huddleston, A.E. Visser, W.M. Reichert, H.D. Willauer, G.A. Broker, and R.D. Rogers Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation Green Chem. 3 2001 156 164
23. V. Jaitely, A. Karatas, and A.T. Florence Water-immiscible room temperature ionic liquids (RTILs) as drug reservoirs for controlled release Int. J. Pharm. 354 2008 168 173
24. 2O systems: a thermodynamic study J. Phys. Chem. B 108 2004 19451 19457
25. T.R. Kurup, L.S. Wan, and L.W. Chan Availability and activity of preservatives in emulsified systems Pharmaceut. Acta Helv. 66 1991 76 82
26. J. Li, J. Zhang, H. Gao, B. Han, and L. Gao Nonaqueous microemulsion-containing ionic liquid [bmim][PF4] as polar microenvironment Colloid Polym. Sci. 283 2005 1371 1375
27. J. Luczak, J. Hupka, J. Thöming, and C. Jungnickel Self-organization of imidazolium ionic liquids in aqueous solution Colloid Surf. A: Physicochem. Eng. Aspects 329 2008 125 133
28. H. Mizuuchi, V. Jaitely, S. Murdan, and A.T. Florence Room temperature ionic liquids and their mixtures: potential pharmaceutical solvents Eur. J. Pharm. Sci. 33 2008 326 331
29. M. Młynarczyk, M. Sznitowska, and D. Watrobska-Swietlikowska Antimicrobial activity of parabens in submicron emulsions stabilized with lecithin Drug Dev. Ind. Pharm. 34 2008 355 362
30. M. Moniruzzaman, Y. Tahara, M. Tamura, N. Kamiya, and M. Goto Ionic liquid-assisted transdermal delivery of sparingly soluble drugs Chem. Commun. (Camb.) 46 2010 1452 1454
31. M. Moniruzzaman, M. Tamura, Y. Tahara, N. Kamiya, and M. Goto Ionic liquid-in-oil microemulsion as a potential carrier of sparingly soluble drug: characterization and cytotoxicity evaluation Int. J. Pharm. 400 2010 243 250
32. M.J. Muldoon, C.M. Gordon, and I.R. Dunkin Investigations of solvent-solute interactions in room temperature ionic liquids using solvatochromic dyes J. Chem. Soc. Perkin Trans. 2 2001 433 435
33. C. Patrascu, F. Gauffre, F. Nallet, R. Bordes, J. Oberdisse, N. de Lauth-Viguerie, and C. Mingotaud Micelles in ionic liquids: aggregation behavior of alkyl poly(ethyleneglycol)-ethers in 1-butyl-3-methyl-imidazolium type ionic liquids Chemphyschem 7 2006 99 101
34. J. Pernak, K. Sobaszkiewicz, and I. Mirska Anti-microbial activities of ionic liquids Green Chem. 5 2003 52 56
35. Z. Qiu, and J. Texter Ionic liquids in microemulsions Curr. Opin. Colloid Interface Sci. 13 2008 252 262
36. J. Ranke, K. Mölter, F. Stock, U. Bottin-Weber, J. Poczobutt, J. Hoffmann, B. Ondruschka, J. Filser, and B. Jastorff Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays Ecotoxicol. Environ. Saf. 58 2004 396 404
37. C. Reichardt Pyridinium N-phenoxide betaine dyes and their application to the determination of solvent polarities. Part 29-Polarity of ionic liquids determined empirically by means of solvatochromic pyridinium N-phenolate betaine dyes Green Chem. 7 2005 339 351
38. A.L. Rollet, P. Porion, M. Vaultier, I. Billard, M. Deschamps, C. Bessada, and L. Jouvensal Anomalous diffusion of water in [BMIM][TFSI] room-temperature ionic liquid J. Phys. Chem. B 111 2007 11888 11891
39. H. Schott, and A.E. Royce Effect of inorganic additives on solutions of nonionic surfactants V: emulsion stability J. Pharm. Sci. 72 1983 1427 1436
40. D. Seth, A. Chakraborty, P. Setua, and N. Sarkar Interaction of ionic liquid with water in ternary microemulsions (Triton X-100/water/1-butyl-3- methylimidazolium hexafluorophosphate) probed by solvent and rotational relaxation of coumarin 153 and coumarin 151 Langmuir 22 2006 7768 7775
41. P. Stepnowski, A.C. Skladanowski, A. Ludwiczak, and E. Laczynska Evaluating the cytotoxicity of ionic liquids using human cell line HeLa Hum. Exp. Toxicol. 23 2004 513 517
42. R.P. Swatloski, J.D. Holbrey, and R.D. Rogers Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate Green Chem. 5 2003 361 363
43. S. Thomaier, and W. Kunz Aggregates in mixtures of ionic liquids J. Mol. Liq. 130 2007 104 107
44. H. Tokuda, K. Hayamizu, K. Ishii, M.A.B.H. Susan, and M. Watanabe Physicochemical properties and structures of room temperature ionic liquids. 2. Variation of alkyl chain length in imidazolium cation J. Phys. Chem. B 109 2005 6103 6110
45. H. Tokuda, K. Ishii, M.A. Susan, S. Tsuzuki, K. Hayamizu, and M. Watanabe Physicochemical properties and structures of room-temperature ionic liquids. 3. Variation of cationic structures J. Phys. Chem. B 110 2006 2833 2839
46. C. Tourne-Peteilh, J.M. Devoisselle, A. Vioux, P. Judeinstein, M. In, and L. Viau Surfactant properties of ionic liquids containing short alkyl chain imidazolium cations and ibuprofenate anions Phys. Chem. Chem. Phys. 13 2011 15523 15529
47. K.P. Wilhelm, A.B. Cua, H.H. Wolff, and H.I. Maibach Surfactant-induced stratum corneum hydration in vivo: prediction of the irritation potential of anionic surfactants J. Invest. Dermatol. 101 1993 310 315
48. A.C. Williams, and B.W. Barry Penetration enhancers Adv. Drug Deliv. Rev. 56 2004 603 618
49. O. Zech, S. Thomaier, P. Bauduin, T. Ruck, D. Touraud, and W. Kunz Microemulsions with an ionic liquid surfactant and room temperature ionic liquids as polar pseudo-phase J. Phys. Chem. B 113 2009 465 473
50. L. Zhang, Z. Xu, Y. Wang, and H. Li Prediction of the solvation and structural properties of ionic liquids in water by two-dimensional correlation spectroscopy J. Phys. Chem. B 112 2008 6411 6419
51. Y. Zheng, W. Eli, and G. Li FTIR study of Tween80/1-butyl-3- methylimidazolium hexafluorophosphate/toluene microemulsions Colloid Polym. Sci. 287 2009 871 876