Abstract
In the present study mixed micelles of the amphiphilic phenothiazine drug promazine hydrochloride (PMZ) and the anionic surfactant sodium bis(2-ethylhexyl)sulfosuccinate (AOT) have been studied using conductometry at different compositions and temperatures in aqueous as well as aqueous electrolyte (25 mmol·kg−1 NaCl) solutions to determine various physicochemical properties of the solutions. The experimental and ideal critical micelle concentration (CMC and CMC id) values suggest attractive interactions in PMZ–AOT mixed systems. The negative values of interaction parameter (β) obtained from regular solution theory indicate synergistic interactions; the negative values of β decrease further with the addition of salt. From the CMC values obtained as a function of temperature, various other thermodynamic properties have been evaluated.
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References
Tanford, C.: The Hydrophobic Effect. Formation of Micelles and Biological Membranes, 2nd edn. Wiley, New York (1980)
Attwood, D., Tolley, J.A.: Self-association of analgesics in aqueous solution: association models for codeine, oxycodone, ethylmorphine and pethidine. J. Pharm. Pharmacol. 32, 761–765 (1980)
Rub, M.A., Asiri, A.M., Khan, J.M., Khan, R.H., Kabir-ud, D.: A study of interaction between antidepressant drug nortriptyline hydrochloride with gelatin. J. Taiwan Inst. Chem. Eng. 45, 2068–2074 (2014)
Hwang, P.M., Vogel, J.H.: Structure-function relationships of antimicrobial peptides. Biochem. Cell Biol. 76, 235–246 (1998)
Taboada, P., Attwood, D., Ruso, J.M., Garcia, M., Sarmiento, F., Mosquera, V.: Influence of molecular structure on the ideality of mixing in micelles formed in binary mixtures of surface-active drugs. J. Colloid Interface Sci. 216, 270–275 (1999)
Schreier, S., Malheiros, S.V.P., de Paula, E.: Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochim. Biophys. Acta 1508, 210–234 (2000)
Attwood, D., Florence, A.T., Gillan, J.M.N.: Micellar properties of drugs: properties of micellar aggregates of phenothiazines and their aqueous solutions. J. Pharm. Sci. 63, 988–993 (1974)
Atherton, A.D., Barry, B.W.: Micellar properties of phenothiazine drugs: a laser light scattering study. J. Colloid Interface Sci. 106, 479–489 (1985)
Rub, M.A., Asiri, A.M., Khan, J.M., Khan, R.H., Kabir-ud, D.: Interaction of gelatin with promethazine hydrochloride: conductimetry, tensiometry and circular dichroism studies. J. Mol. Struc. 1050, 35–42 (2013)
Canto, G.S., Dalmora, S.L., Oliveira, A.G.: Piroxicam encapsulated in liposomes: characterization and in vivo evaluation of topical anti-inflammatory effect. Drug Dev. Ind. Pharm. 25, 1235–1239 (1999)
Lipinski, C.A., Lombardo, F., Dominy, B.W., Feeney, P.J.: Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev. 46, 3–26 (2001)
Fernandez, A.M., Van Derpoorten, K., Dasnois, L., Lebtahi, K., Dubois, V., Lobl, T.J., Gangwar, S., Oliyai, C., Lewis, E.R., Shochat, D., Trouet, A.: N-Succinyl-(beta-alanyl-L-leucyl-L-alanyl-L-leucyl)doxorubicin: an extracellularly tumor-activated prodrug devoid of intravenous acute toxicity. J. Med. Chem. 44, 3750–3753 (2001)
Rangel-Yagui, C.O., Pessoa Jr, A., Tavares, L.C.: Micellar solubilization of drugs. J. Pharm. Pharm. Sci. 8, 147–165 (2005)
Torchilin, V.P.: Structure and design of polymeric surfactant–based drug delivery systems. J. Control Release 73, 137–172 (2001)
Yang, C., Chen, F., Luo, S., Xie, G., Zeng, G., Fan, C.: Effects of surfactants and salt on Henry’s constant of n-hexane. J. Hazard. Mater. 175, 187–192 (2010)
Dar, A.A., Rather, G.M., Ghosh, S., Das, A.R.: Micellization and interfacial behavior of binary and ternary mixtures of model cationic and nonionic surfactants in aqueous NaCl medium. J. Colloid Interface Sci. 322, 572–581 (2008)
Clint, J.H.: Micellization of mixed nonionic surface active agents. J. Chem. Soc., Faraday Trans. 1(71), 1327–1334 (1975)
Holland, P.M., Rubingh, D.N.: Nonideal multicomponent mixed micelle model. J. Phys. Chem. 87, 1984–1990 (1983)
Azum, N., Rub, M.A., Asiri, A.M.: Experimental and theoretical approach to mixed surfactant system of cationic gemini surfactant with nonionic surfactant in aqueous medium. J. Mol. Liq. 196, 14–20 (2014)
Rub, M.A., Kumar, D., Azum, N., Khan, F., Asiri, A.M.: Study of the interaction between promazine hydrochloride and surfactant (conventional/gemini) mixtures at different temperatures. J. Solution Chem. 43, 930–949 (2014)
Rub, M.A., Azum, N., Kumar, D., Asiri, A.M., Marwani, H.M.: Micellization and microstructural studies between amphiphilic drug ibuprofen with non-ionic surfactant in aqueous urea solution. J. Chem. Thermodyn. 74, 91–102 (2014)
Vethamuthu, M.S., Almgren, M., Karlsson, G., Bahadur, P.: Effect of sodium chloride and varied alkyl chain length on aqueous cationic surfactant–bile salt systems. Cryo-TEM and fluorescence quenching studies. Langmuir 12, 2173–2185 (1996)
Mandal, A.B., Moulik, S.P.: In: Mittal, K.L., Fendler, E.J. (eds.) Solution Behavior of Surfactants. Plenum Press, New York (1982)
Elworthy, P.H., Florence, A.T., Macfarlane, G.B.: Solubilization by Surface-Active Agents and Its Application in Chemistry and Biological Sciences. Chapman and Hall, Suffolk (1968)
Chakraborty, A., Chakraborty, S., Saha, S.K.: Temperature dependant micellization of AOT in aqueous medium: effect of the nature of counterions. J. Dispers. Sci. Technol. 28, 984–989 (2007)
Chatterjee, A., Moulik, S.P., Sanyal, S.K., Mishra, B.K., Puri, P.M.: Thermodynamics of micelle formation of ionic surfactants: a critical assessment for sodium dodecyl sulfate, cetyl pyridinium chloride and dioctyl sulfosuccinate (Na salt) by microcalorimetric, conductometric, and tensiometric measurements. J. Phys. Chem. B 105, 12823–12831 (2001)
Rub, M.A., Azum, N., Khan, S.B., Khan, F., Asiri, A.M.: Physicochemical properties of amphiphilic drug and anionic surfactant mixtures: experimental and theoretical approach. J. Dispers. Sci Technol. 36, 521–531 (2015)
Para, G., Jarek, E., Warszynski, P.: The Hofmeister series effect in adsorption of cationic surfactants–theoretical description and experimental results. Adv. Colloid Interface Sci. 122, 39–55 (2006)
Shamsipur, M., Alizadeh, N., Gharibi, H.: Physicochemical studies of the hexadecylpyridinium bromide micellar system in the presence of various concentrations of sodium bromide using a surfactant-selective electrode. Indian J. Chem. 36A, 1031–1037 (1997)
Rosen, M.J.: Surfactants and Interfacial Phenomena, 3rd edn. Wiley, New York (2004)
Akhtar, F., Hoque, M.A., Khan, M.A.: Interaction of cefadroxyl monohydrate with hexadecyltrimethyl ammonium bromide and sodium dodecyl sulfate. J. Chem. Thermodyn. 40, 1082–1086 (2008)
Hoque, M.A., Khan, M.A., Hossain, M.D.: Interaction of cefalexin monohydrate with cetyldimethylethylammonium bromide. J. Chem. Thermodyn. 60, 71–75 (2013)
Hoque, M.A., Hossain, M.D., Khan, M.A.: Interaction of cephalosporin drugs with dodecyltrimethylammonium bromide. J. Chem. Thermodyn. 63, 135–141 (2013)
Prasad, M., Chakraborty, I., Rakshit, A.K., Moulik, S.P.: Critical evaluation of micellization behavior of nonionic surfactant MEGA 10 in comparison with ionic surfactant tetradecyltriphenylphosphonium bromide studied by microcalorimetric method in aqueous medium. J. Phys. Chem. B 110, 9815–9821 (2006)
La Mesa, C.: Dependence of critical micelle concentrations on intensive variables: a reduced variables analysis. J. Phys. Chem. 94, 323–326 (1990)
Das, C., Das, B.: Thermodynamic and interfacial adsorption studies on the micellar solutions of alkyltrimethylammonium bromides in ethylene glycol (1) + water (2) mixed solvent media. J. Chem. Eng. Data 54, 559–565 (2009)
Islam, M.N., Kato, T.: Temperature dependence of the surface phase behavior and micelle formation of some nonionic surfactants. J. Phys. Chem. B 107, 965–971 (2003)
Lopez-Fontan, J.L., Costa, V., Ruso, J.M., Prieto, G., Sarmiento, F.: Electrical conductivities and critical micelle concentrations (determined by the local polynomial regression method) of imipramine and clomipramine hydrochlorides from (283 to 313) K. J. Chem. Eng. Data 49, 1008–1012 (2004)
Rub, M.A., Sheikh, M.S., Khan, F., Khan, S.B., Asiri, A.M.: Bile salts aggregation behavior at various temperatures under the influence of amphiphilic drug imipramine hydrochloride in aqueous medium. Z. Phys. Chem. 228, 747–767 (2014)
Zana, R.: Ionization of cationic micelles: effect of the detergent structure. J. Colloid Interface Sci. 78, 330–337 (1980)
Asakawa, T., Kitano, H., Ohta, A., Miyagishi, S.: Priority communication convenient estimation for counterion dissociation of cationic micelles using chloride-sensitive fluorescence probe. J. Colloid Interface Sci. 242, 284–287 (2001)
Iijima, H., Kato, T., Soderman, A.: Variation in degree of counterion binding to cesium perfluorooctanoate micelles with surfactant concentration studied by 133Cs and 19F NMR. Langmuir 16, 318–323 (2000)
Gorski, N., Kalus, J.: Temperature dependence of the sizes of tetradecyltrimethylammonium bromide micelles in aqueous solutions. Langmuir 17, 4211–4215 (2001)
Chauhan, M.S., Sharma, K., Kumar, G., Chauhan, S.: A conductometric study of dimethylsulfoxide effect on micellization of sodium dodecyl sulfate in dilute aqueous electrolyte solutions. Colloid Surf. A 221, 135–140 (2003)
Rubingh, D.N.: In: Mittal, K.L. (ed.) Solution Chemistry of Surfactants. Plenum, New York (1979)
Motomura, K., Yamanaka, M., Aratono, M.: Thermodynamic consideration of the mixed micelle of surfactants. Colloid Polym. Sci. 262, 948–955 (1984)
Rodenas, V., Valiente, M., Villafruela, M.S.: Different theoretical approaches for the study of the mixed tetraethylene glycol mono-n-dodecyl ether/hexadecyltrimethylammonium bromide micelles. J. Phys. Chem. B 103, 4549–4554 (1999)
Lange, H., Beck, K.H.: Zur Mizellbildung in Mischlösungen homologer und nichthomologer. Kolloid Z. Z. Polym. 251, 424–431 (1973)
Singh, O.G., Ismail, K.: Effect of sodium chloride on the aggregation, adsorption and counterion binding behavior of mixtures of sodium dioctylsulfosuccinate and sodium dodecylsulfate in water. Colloids Surf. A 414, 209–215 (2012)
Clint, J.H.: Surfactant Aggregation. Blackie/Chapman and Hall, New York (1992)
Nusselder, J.J.H., Engberts, J.B.F.N.: Toward a better understanding of the driving force for micelle formation and micellar growth. J. Colloid Interface Sci. 148, 353–361 (1992)
Kresheck, G.C.: In: Franks, F. (ed.) Water. A Comprehensive Treatise. Plenum, New York (1995)
Hall, D.G.: Electrostatic effects in dilute solutions containing charged colloidal entities. J. Chem. Soc., Faraday Trans. 87, 3529–3535 (1991)
Rub, M.A., Asiri, A.M., Azum, N., Kumar, D., Khan, F.: Temperature dependant mixed micellization behavior of a drug–AOT mixture in an aqueous medium. Acta Phys.-Chim. Sin. 30, 699–707 (2014)
Rub, M.A., Khan, F., Kumar, D., Asiri, A.M.: Study of mixed micelles of promethazine hydrochloride (PMT) and nonionic surfactant (TX-100) mixtures at different temperature and composition. Tenside Surfactants Deterg. 52, 236–244 (2015)
Azum, N., Rub, M.A., Asiri, A.M.: Analysis of surface and bulk properties of amphiphilic drug ibuprofen and surfactant mixture in the absence and presence of electrolyte. Colloids Surf. B 121, 158–164 (2014)
Javadian, S., Gharibi, H., Bromand, Z., Sohrabi, B.: Electrolyte effect on mixed micelle and interfacial properties of binary mixtures of cationic and nonionic surfactants. J. Colloid Interface Sci. 318, 449–456 (2008)
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Center of Excellence for Advanced Materials Research and Chemistry Department, King Abdulaziz University, Jeddah are highly acknowledged.
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Khan, F., Rub, M.A., Azum, N. et al. Interaction of an Amphiphilic Drug and Sodium Bis(2-ethylhexyl)sulfosuccinate at Low Concentrations in the Absence and Presence of Sodium Chloride. J Solution Chem 44, 1937–1961 (2015). https://doi.org/10.1007/s10953-015-0386-1
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DOI: https://doi.org/10.1007/s10953-015-0386-1