Solubilisation of (+)-Usnic Acid in Aqueous Micellar Solutions of Gemini and Heterogemini Surfactants and their Equimolar Mixture

M. Lukáč 1 , I. Prokipčák 2 , I. Lacko 2 ,  and F. Devínsky 2
  • 1 Comenius University in Bratislava, Faculty of Pharmacy, Department of Chemical Theory of Drugs, Kalinčiakova 8, 832 32, Bratislava, Slovak Republic
  • 2 Comenius University in Bratislava, Faculty of Pharmacy, Department of Chemical Theory of Drugs

Abstract

The solubilisation of natural compound, (+)-usnic acid, in micellar solutions of gemini (N,N’-didecyl-N,N,N’,N’-tetramethylethane-1,2-diyldiammonium dibromide) and heterogemini (decyl 2-[decyl(dimethyl)ammonio]ethylphosphate) surfactants and their equimolar mixture has been studied. The highest solubility was found for gemini surfactant. The relationship between synergism in surface properties of mixture of surfactants and their solubilisation properties is also discussed.

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  • Bačkorova M, Bačkor M, Mikeš J, Jendželovsky R, Fedoročko P. Variable responses of different human cancer cells to the lichen compounds parietin, atranorin, usnic acid and gyrophoric acid. Toxicol Vitro. 2011;25:37-44.

  • Bazin MA, Le Lamer AC, Decros JG, et al. Synthesis and cytotoxic activities of usnic acid derivatives. Bioorg Med Chem. 2008;16:6860-6866.

  • Cansaran D, Kahya D, Yurdakulol E, Atakol O. Identification and quantitation of usnic acid from the lichen Usnea species of Anatolia and antimicrobial activity. Z Naturforsch C. 2006;61:773-776.

  • Cetin H, Tufan-Cetin O, Turk AO, et al. Insecticidal activity of major lichen compounds (-)- and (+)- usnic acid, against the larvae of house mosquito, Culex pipiens L. Parasitol Res. 2008;102:1277-1279.

  • da Silva Santos NP, Nascimento SC, Wanderley MSO, et al. Nanoencapsulation of usnic acid: An attempt to improve antitumor activity and reduce hepatotoxicity. Eur J Pharm Biopharm. 2006;64:154-160.

  • Einarsdottir E, Groneweg J, Bjornsdottir GG, et al. Cellular mechanisms of the anticancer effects of the lichen compound usnic acid. Planta Med. 2010;76:969-974.

  • Halonen P, Clerc P, Goward T, Brodo IM, Wulff K. Synopsis of the genus Usnea (Lichenized Ascomycetes) in British Columbia, Canada. Bryologist. 1998;101:36-60.

  • Ingolfsdottir K. Usnic acid. Phytochemistry. 2002;61:729-736.

  • Ingolfsdotir K, Chung GAC, Skulason VG, Gissurason SR, Vilhelmsdottir M. Antimycobacterial activity of lichen metabolites in vitro. Eur J Pharm Sci. 1998;6:141-144.

  • Kristmundsdottir T, Aradottir HA, Ingolfsdottir K, Ogmundsdottir HM. Solubilization of the lichen metabolite (+)-usnic acid for testing in tissue culture. J Pharm Pharmacol. 2002;54:1447-1452.

  • Kristmundsdottir T, Jonsdottir E, Ogmundsdottir HM, Ingolfsdottir K. Solubilisation of poorly soluble lichen metabolites for biological testing on cell lines. Eur J Pharm Sci. 2005;24:539-543.

  • Lira MCB, Ferraz MS, Da Silva DGVC, et al. Inclusion complex of usnic acid with β- cyclodextrin: characterization and nanoencapsulation into liposomes. J Incl Phenom Macro. 2009;64:215-224.

  • Lukač M. Contribution to the genus Usnea (Parmeliaceae) in Slovakia III: apotheciate specimens of U. filipendula, U. florida, U. intermedia and U. subfloridana. Acta Facult Pharm Univ Comenianae. 2010;57:57-67.

  • Lukač M, Mrva M, Fischer-Fodor E, et al. Synthesis and biological activity of dialkylphosphocholines. Bioorg Med Chem Lett. 2009;19:6346-6349.

  • Lukač M, Prokipčak I, Lacko I, Devinsky F. Solubilisation of griseofulvin and rutin in aqueous micellar solutions of gemini and heterogemini surfactants and their mixtures. Eur J Pharm Sci. 2011;44:194-199.

  • Matteucci E, Munzi S, Potenza G. Unea workshop. Not Soc Lich Ital. 2006;19:129-137.

  • Melgarejo M, Sterner O, Castro JV, Mollinedo P. More investigations in potent activity and relationship structure of the lichen antibiotic (+)-usnic acid and its derivate dibenzoylusnic acid. Revista Boliviana de Quimica. 2008;25:24-29.

  • Menger FM, Peresypkin AV. A combinatorially-derived structure phase diagram for 42 zwitterionic geminis. J Am Chem Soc. 2001;123:5614-5615.

  • Randlane T, Tōrra T, Saag A, Saag L. Key to European Usnea species. Bibl Lichenol. 2009;100:419-462.

  • Rangel-Yagui CO, Pessoa Jr A, Tavares LC. Micellar solubilisation of drugs. J Pharm Pharm Sci. 2005;8:147-163.

  • Ranković B, Mišić M, Sukdolak S. The antimicrobial activity of substances derived from lichens Physcia aipolia, Umbilicaria polyphylla, Parmelia caperata, and Hypogymnia physodes. World J Microbiol Biotechnol. 2008;24:1239-1242.

  • Segure-Sanchez F, Bouchemal K, Lebas G, Vauthier C, Santos-Magalhaes NSS, Ponchel G. Elucidation of the complexation mechanism between (+)-usnic acid and cyclodextrins studied by isothermal titration calorimetry and phase-solubility diagram experiments. J Mol Rocognit. 2009;22:232-241.

  • Tay T, Turk AO, Yilmaz M, Turk M, Kivanc M. Evaluation of the antimicrobial activity of the acetone extract of the lichen Ramalina farinacea and its (+)-usnic acid, norstictic acid, protocetraric acid constituent. Z Naturforsch C. 2004;59:384-388.

  • Tōrra T, Randlane T. The lichen genus Usnea (lichenized Ascomycetes, Parmeliaceae) in Estonia with a key to the species in the Baltic countries. Lichenologist. 2007;39:415-438.

  • Ullah I, Baloch MK, Durrani GF. Solubility of lidocaine in ionic, nonionic, and zwitterionic surfactants. J Solution Chem. 2012;41:215-222.

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