Abstract
In this study, the electrical conductivity of the antidepressant drug—nortriptyline hydrochloride and conventional surfactant—cetyldimethylethylammoniumbromide are investigated. The experimental critical micelle concentration and related thermodynamic parameters, such as Gibbs free energy, enthalpy, entropy change, as well as and excess change in Gibbs free energy are calculated using standard equations. The values of change in Gibbs free energy for the mixed nortriptyline hydrochloride with cetyldimethylethylammoniumbromide are found to be more negative further suggesting the mixed micellization to be favourable. However, the high values of change in entropy are observed owing to the charge on the head groups which are being partially neutralized by the counter ions upon micelle formation.
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REFERENCES
Tanford, C., The Hydrophobic Effect: Formation of Micelles and Biological Membranes, New York: John Wiley, 1980, 2nd ed.
Müller, R.H., Colloidal Carriers for Controlled Drug Delivery and Targeting: Modification, Characterization and In Vivo Distribution, Taylor & Francis, 1991.
Microparticulate Systems for the Delivery of Proteins and Vaccines, Cohen, S. and Bernstein, H., Eds., CRC Press, 2020.
Khan, F., Siddiqui, U.S., Rub, M.A., Khan, I.A., and Kabir-ud-Din., Micellization behavior of butanediyl-1, 4-bis(dimethyldodecylammonium bromide) gemini surfactant in presence of organic additives, J. Dispersion Sci. Technol., 2015, vol. 36, no. 1, pp. 83–93. https://doi.org/10.1080/01932691.2013.852105
Azum, N., Rub, M.A., and Asiri, A.M., Micellization and interfacial behavior of the sodium salt of ibuprofen–BRIJ-58 in aqueous/brine solutions, J. Solution Chem., 2016, vol. 45, pp. 791–803. https://doi.org/10.1007/s10953-016-0463-0
Marzia, R., Khan, M.A., Rub, M.A., and Hoque, M.D., Effect of temperature and salts on the interaction of cetyltrimethylammonium bromide with ceftriaxone sodium trihydrate drug, J. Mol. Liq., 2016, vol. 223, pp. 716–724. https://doi.org/10.1016/j.molliq.2016.08.049
Schreier, S., Malheiros, S.V.P., and de Paula, E., Surface active drugs: Self-association and interaction with membranes and surfactants. Physicochemical and biological aspects, Biochim. Biophys. Acta, Biomembr., 2000, vol. 1508, nos. 1–2, pp. 210–234. https://doi.org/10.1016/S0304-4157(00)00012-5
Attwood, D. and Florence, A.T., Pharmaceutical Aspects of Solubilization. Surfactant Systems: Their Chemistry, Pharmacy and Biology, Springer, 1983.
Attwood, D., Gibson., Aggregation of antidepressant drugs in aqueous solution, J. Pharm. Pharmacol., 1978, vol. 30, no. 1, pp. 176–180. https://doi.org/10.1111/j.2042-7158.1978.tb13192.x
Taboada, P., Attwood, D., Ruso, J.M., García, M., and Mosquera, V., Static and dynamic light scattering study on the association of some antidepressants in aqueous electrolyte solutions, Phys. Chem. Chem. Phys., 2000, vol. 22, no. 22, pp. 5175–5179. https://doi.org/10.1039/B006400I
Dileep, K. and Rub, M.A., Effect of sodium taurocholate on aggregation behavior of amphiphilic drug solution, Tenside Surfactants Detergents, 2015, vol. 52, no. 6, pp. 464–472.
Rub, M.A., Azum, N., Khan, S.B., Marwani, H.M., and Asiri, A.M., Micellization behavior of amphiphilic drug promazine hydrochloride and sodium dodecyl sulfate mixtures at various temperatures: Effect of electrolyte and urea, J. Mol. Liq., 2015, vol. 212, pp. 532–543. https://doi.org/10.1016/j.molliq.2015.09.049
Erdinç, N., Göktürk, S., and Tunçay, M., A study on the adsorption characteristics of an amphiphilic phenothiazine drug on activated charcoal in the presence of surfactants, Colloids Surf. B, 2010, vol. 75, no. 1, pp. 194–203. https://doi.org/10.1016/j.colsurfb.2009.08.031
Barbosa, L.R., Caetano, W., and Itri, R., Homem-de-Mello, P., Santiago, P.S., and Tabak, M., Interaction of phenothiazine compounds with zwitterionic lysophosphatidylcholine micelles: Small angle X-ray scattering, electronic absorption spectroscopy, and theoretical calculations, J. Phys. Chem., 2006, vol. 110, no. 26, pp. 13086–13093. https://doi.org/10.1021/jp056486t
Khan, A.B. and Naqvi, A.Z., Mixed micellization of antidepressant drug amitriptyline hydrochloride with cationic surfactants, Colloids Surf. B, 2010, vol. 80, no. 2, pp. 206–212. https://doi.org/10.1016/j.colsurfb.2010.06.007
Caetano, W. and Tabak, M., Interaction of chlorpromazine and trifluoperazine with anionic sodium dodecyl sulfate (SDS) micelles: Electronic absorption and fluorescence studies, J. Colloid Interface Sci., 2000, vol. 225, no. 1, pp. 69–81. https://doi.org/10.1006/jcis.2000.6720
Al-Ahmadi, Mohammed, D.A., Naqvi, A.Z., and Akram, M., Conductometric study of antidepressant drug-cationic surfactant mixed micelles in aqueous solution, Colloids Surf. B, 2008, vol. 64, no. 1, pp. 65–69. https://doi.org/10.1016/j.colsurfb.2008.01.005
Pethybridge, A.D., Talbot, J.D.R., and House, W.A., Precise conductance measurements on dilute aqueous solutions of sodium and potassium hydrogenphosphate and dihydrogenphosphate, J. Solution Chem., 2006, vol. 35, pp. 381–393. https://doi.org/10.1007/s10953-005-9003-z
Lind, J.E., Jr, Zwolenik, J.J., and Fuoss, R.M., Calibration of conductance cells at 25° with aqueous solutions of potassium chloride, J. Am. Chem. Soc., 1959, vol. 81, no. 7, pp. 1557–1559. https://doi.org/10.1021/ja01516a010
Padday, J.F., Pitt, A.R., and Pashley, R.M., Menisci at a free liquid surface: Surface tension from the maximum pull on a rod, J. Chem. Soc., Faraday Trans., 1975, vol. 71, pp. 1919–1931. https://doi.org/10.1039/F19757101919
Riddick, J.A., Bunger, W.B., and Sakano, T.K., Organic Solvents: Physical Properties and Methods of Purification, 1986.
Mahajan, S., Sharma, R., and Mahajan, R.K., Interactions of new 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) based surface active ionic liquids with amitriptyline hydrochloride: Micellization and interfacial studies, Colloids Surf. A, 2013, vol. 424, no. 5, pp. 96–104. https://doi.org/10.1016/j.colsurfa.2013.02.032
Collins, K.D., Neilson, G.W., and Enderby, J.E., Ions in water: Characterizing the forces that control chemical processes and biological structure, Biophys. Chem., 2007, vol. 128, nos. 2–3, pp. 95–104. https://doi.org/10.1016/j.bpc.2007.03.009
Abezgauz, L., Kuperkar, K., Hassan, P.A., Ramon, O., Bahadur, P., and Danino, D., Effect of Hofmeister anions on micellization and micellar growth of the surfactant cetylpyridinium chloride, J. Colloid Interface Sci., 2010, vol. 342, no. 1, pp. 83–92. https://doi.org/10.1016/j.jcis.2009.08.045
Mehta, S.K., Bhasin, K.K., Chauhan, R., and Dham, S., Effect of temperature on critical micelle concentration and thermodynamic behavior of dodecyldimethylethylammonium bromide and dodecyltrimethylammonium chloride in aqueous media, Colloids Surf. A, 2005, vol. 255, nos. 1–3, pp. 153–157. https://doi.org/10.1016/j.colsurfa.2004.12.038
Evans, F.D. and Ninham, B.W., Ion binding and the hydrophobic effect, J. Phys. Chem., 1983, vol. 87, no. 24, pp. 5025–5032. https://doi.org/10.1021/j150642a050
Chen, L.J., Lin, S.Y., Huang, C.C., and Chen, E.M., Temperature dependence of critical micelle concentration of polyoxyethylenated non-ionic surfactants, Colloids Surf. A, 1998, vol. 135, nos. 1–3, pp. 175–181. https://doi.org/10.1016/S0927-7757(97)00238-0
Soumen, G., Burman, A.D., Gobinda, C.D., and Das, A.R., Interfacial and self-aggregation of binary mixtures of anionic and nonionic amphiphiles in aqueous medium, J. Phys.Chem. B, 2011, vol. 115, no. 38, pp. 11098–11112. https://doi.org/10.1021/jp204223t
Malik, N.A. and Farooq, U., Effect of caffeine on the micellization and related thermodynamic parameters of sodium dodecyl sulphate, hexadecyltrimethylammonium bromide and triton X-100: A physicochemical study, Phys. Chem. Liq., 2022, vol. 60, no. 2, pp. 265–274. https://doi.org/10.1080/00319104.2021.1949594
Moroi, Y., Micelles: Theoretical and Applied Aspects, Springer Science & Business Media, 1992.
Kale, K.M. and Cussler, E.L., and. Evans, D.F., Characterization of micellar solutions using surfactant ion electrodes, J. Phys. Chem, 1980, vol. 84, no. 6, pp. 593–598. https://doi.org/10.1021/j100443a007
Bandhopadhyay, A. and Moulik, S.P., Counterion binding behaviour of micelles of sodium dodecyl sulphate and bile salts in the pure state, in mutually mixed states and mixed with a nonionic surfactant, Colloid Polym. Sci., 1988, vol. 266, pp. 455–461. https://doi.org/10.1007/BF01457263
Khan, A.B., Ali, M., Malik, N.A., Ali, A., and Patel, R., Role of 1-methyl-3-octylimidazolium chloride in the micellization behavior of amphiphilic drug amitriptyline hydrochloride, Colloids Surf. B, 2013, vol. 112, no. 1, pp. 460–465. https://doi.org/10.1016/j.colsurfb.2013.08.018
Javadian, S. and Ruhi, V., Asadzadeh Shahir, A., Heydari, A., and Akbari. J., Imidazolium-based ionic liquids as modulators of physicochemical properties and nanostructures of CTAB in aqueous solution: The effect of alkyl chain length, hydrogen bonding capacity, and anion type, Ind. Eng. Chem. Res., 2013, vol. 52, no. 45, pp. 15838–15846. https://doi.org/10.1021/ie402188n
Malik, N.A., Drug solubilization by surfactants: Experimental methods and theoretical perspectives, Mini-Rev. Med. Chem., 2022, vol. 22, no. 4, pp. 579–585. https://doi.org/10.2174/1389557521666210805111425
Chen, L.J., Lin, S.Y., Huang, C.C., and Chen, E.M., Temperature dependence of critical micelle concentration of polyoxyethylenated non-ionic surfactants, Colloids Surf. A, 1998, vol. 135, nos. 1–3, pp. 175–181. https://doi.org/10.1016/S0927-7757(97)00238-0
El Seoud, O.A., Pires, P.A., Abdel-Moghny, T., and Bastos, E.L., Synthesis and micellar properties of surface-active ionic liquids: 1-Alkyl-3-methylimidazolium chlorides, J. Colloid Interface Sci., 2007, vol. 313, no. 1, pp. 296–304. https://doi.org/10.1016/j.jcis.2007.04.028
Malik, N.A., Farooq, U., Rather, M.A., and Shalla, A.H., Interactions of tricyclic antidepressant drug chlomipramine hydrochloride with imidazolium based surface active ionic liquid in aqueous solution, J. Mol. Liq., 2021, vol. 342, no. 15, p. 117427. https://doi.org/10.1016/j.molliq.2021.117427
Zana, R., Ionization of cationic micelles: Effect of the detergent structure, J. Colloid Interface Sci., 1980, vol. 78, no. 2, pp. 330–337. https://doi.org/10.1016/0021-9797(80)90571-8
Markina, Z.N., Panicheva, L.P., and Zadymova, N.M., Anomalous concentration dependence of equivalent electric conductivity in aqueous solutions of ionic micellar surfactants at various temperatures, Colloid J., 1997, vol. 59, no. 3, pp. 315–323.
Mata, J., Varade, D., and Bahadur, P., Aggregation behavior of quaternary salt based cationic surfactants, Thermochim. Acta, 2005, vol. 428, nos. 1–2, pp. 147–155. https://doi.org/10.1016/j.tca.2004.11.009
Malik, N.A., Solubilization and interaction studies of bile salts with surfactants and drugs: A review, Appl. Biochem. Biotechnol., 2016, vol. 179, pp. 179–201. https://doi.org/10.1007/s12010-016-1987-x
Chatterjee, A.M., Moulik, S.P., Sanyal, S.K., Mishra, B.K., and 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, 2001, vol. 105, no. 51, pp. 12823–12831. https://doi.org/10.1021/jp0123029
Galgano, P.D. and El Seoud, O.A., Micellar properties of surface active ionic liquids: A comparison of 1-hexadecyl-3-methylimidazolium chloride with structurally related cationic surfactants, J. Colloid Interface Sci., 2010, vol. 345, no. 1, pp. 1–11. https://doi.org/10.1016/j.jcis.2010.01.078
Moroi, Y., Micelles: Theoretical and Applied Aspects, Springer Science & Business Media, 1992.
Rosen, M.J., Surfactants and Interfacial Phenomena, New York: John Wiley and Sons, 2004, 3rd ed.
Li, F., Li, G.Z., and Chen, J.B., Synergism in mixed zwitterionic-anionic surfactant solutions and the aggregation numbers of the mixed micelles, Colloids Surf. A, 1998, vol. 145, nos. 1–3, pp. 167–174. https://doi.org/10.1016/S0927-7757(98)00543-3
Farooq, U., Ali, A., Patel, R., and Malik, N.A., Interaction between amphiphilic antidepressant drug nortriptyline hydrochloride and conventional cationic surfactants: A physicochemical study, J. Mol. Liq., 2017, vol. 233, pp. 310–318. https://doi.org/10.1016/j.molliq.2017.03.032
Haque, M.E., Das, A.R., Rakshit, A.K., and Moulik, S.P., Properties of mixed micelles of binary surfactant combinations, Langmuir, 1996, vol. 12, no. 17, pp. 4084–4089. https://doi.org/10.1021/la9403587
Dar, A.A., Rather, G.M., Ghosh, S., and 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., 2008, vol. 322, no. 2, pp. 572–581. https://doi.org/10.1016/j.jcis.2008.03.022
Azum, N., Rub, M.A., Asiri, A.M., Khan, A.A.P., Khan, A., Khan, S.B., Rahman, M.M., and Al-Youbi, A.O., Interaction of the amphiphilic drug amitriptyline hydrochloride with gemini and conventional surfactants: A physicochemical approach, J. Solution Chem., 2013, vol. 42, pp. 1532–1544. https://doi.org/10.1007/s10953-013-0047-1
Buckingham, S.A., Christopher, J.G., and Warr, G.G., Effect of head-group size on micellization and phase behavior in quaternary ammonium surfactant systems, J. Phys. Chem., 1993, vol. 97, pp. 10236–10244.
ACKNOWLEDGMENTS
N.A. Malik would like to thank the Head Department of Chemistry, IUST for providing the necessary facilities.
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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.
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Malik, N.A., Farooq, U., Malik, A. et al. Influence of Antidepressant Drug on the Conductivity of Cationic Surfactant. Colloid J 85, 846–853 (2023). https://doi.org/10.1134/S1061933X22600555
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DOI: https://doi.org/10.1134/S1061933X22600555