Self-assembling of surface active drug amitriptyline hydrochloride in association with additives: Role of surface activity in the pharmaceutical applications

Year 2022, Volume: 3 Issue: 3, 113 - 120, 30.12.2022

Hasan Tolga Özçam Zeynep Berna Tamer Sinem Gokturk

https://doi.org/10.51753/flsrt.1131218

Abstract

The self-assembling of surface active antidepressant drug amitriptyline hydrochloride (AMT) has been studied to determine the micellar solution behavior in the presence of polar (methanol and ethanol), dipolar aprotic solvents (acetone and 1,4 dioxane), salt (NaCl) and water structure-breakers (urea) at 298 K using surface tension and electrical conductivity measurements. The counterion binding parameter and the ionization degree of AMT micelles have been determined by electrical conductivity measurements. To better analyze the influences of additives on micellar behavior of AMT, surface features of AMT were defined using Gibbs Adsorption Isotherm in water and in association with various amounts of additives conducted by surface tension measurements. Both conductometric and surface tension experiments were also used to detect the critical micelle concentration (CMC) of AMT. The experimental results indicated that CMCs of AMT were influenced in the presence of additives. Self-aggregation of AMT was totally inhibited when methanol, ethanol, acetone, 1,4 dioxane, and urea concentration is attained to a certain value while the CMC of AMT reduced with the increase in concentration of NaCl.

Keywords

Amitriptyline hydrochloride, amphiphilic drugs, conductivity, critical micelle concentration, surface active drugs, surface tension

Supporting Institution

Marmara Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi

Project Number

SAG-C-YLP-280214-0041.

Thanks

This work was financially supported by the Research Fund of Marmara University with the project number SAG-C-YLP-280214-0041.

References

• Alam, M. S., Ghosh, G., & Din, K. (2008). Light scattering studies of amphiphilic drugs promethazine hydrochloride and imipramine hydrochloride in aqueous electrolyte solutions. The Journal of Physical Chemistry B, 112(41), 12962-12967.
• Alam, S., Mandal, A., & Mandal, A. B. (2011). Thermodynamics of amphiphilic drug imipramine hydrochloride in presence of additives. In: Moreno-Piraján J. C. (ed) Thermodynamics-Systems in Equilibrium and Non-Equilibrium (pp. 229-254). IntechOpen.
• Ali, M. S., Rub, M. A., Khan, F., & Al-Lohedan, H. A. (2013). Thermodynamic, interfacial and hydrodynamic aspects of interaction of cationic drug amitriptyline hydrochloride with anionic and nonionic polymers. Journal of Molecular Liquids, 180, 200-206.
• Attwood, D., & Florence, A. T. (1983). Surfactant systems: Their chemistry, pharmacy and biology. (pp. 1-794). New York, Chapman and Hall.
• Attwood, D. (1995). The mode of association of amphiphilic drugs in aqueous solution. Advances in colloid and interface science, 55, 271-303.
• Attwood, D., Mosquera, V., & Villar, V. P. (1989). Thermodynamic properties of amphiphilic drugs in aqueous solution. Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 85(9), 3011-3017.
• Din, K., Rub, M. A., & Naqvi, A. Z. (2010). Mixed micelle formation between amphiphilic drug amitriptyline hydrochloride and surfactants (conventional and gemini) at 293.15− 308.15 K. The Journal of Physical Chemistry B, 114(19), 6354-6364.
• Erdinc, N., Gokturk, S., & Tuncay, M. (2010). A study on the adsorption characteristics of an amphiphilic phenothiazine drug on activated charcoal in the presence of surfactants. Colloids and Surfaces B: Biointerfaces, 75(1), 194-203.
• Evans, H. C. (1956). 117. Alkyl sulphates. Part I. Critical micelle concentrations of the sodium salts. Journal of the Chemical Society (Resumed), 78, 579-586.
• Florence, A. T., & Atwood, D. (1998). Physicochemical principles of pharmacy. (pp. 1-564). Pharmaceutical Press.
• Gokturk, S., & Aslan, S. (2014). Study on binding properties of poorly soluble drug trimethoprim in anionic micellar solutions. Journal of Dispersion Science and Technology, 35(1), 84-92.
• Gokturk, S., & Tamer, Z. B. (2018). Interactions and solubilization of poorly soluble drugs in aerosol‐ot micelles. Journal of Surfactants and Detergents, 21(6), 889-898.
• Gokturk, S., & Var, U. (2012). Effect of pharmaceutically important cosolvents on the interaction of promethazine and trifluopromazine hydrochloride with sodium dodecyl sulfate micelles. Journal of Dispersion Science and Technology, 33(4), 527-535.
• Hiemenz, P. C., & Rajogopalan, R. (1986). Principles of colloid and surface chemistry. (pp. 1-671). Marcel Dekker.
• Junquera, E., Romero, J. C., & Aicart, E. (2001). Behavior of tricyclic antidepressants in aqueous solution: Self-aggregation and association with β-cyclodextrin. Langmuir, 17(6), 1826-1832.
• Kuharski, R. A., & Rossky, P. J. (1984). Solvation of hydrophobic species in aqueous urea solution: a molecular dynamics study. Journal of the American Chemical Society, 106(20), 5794-5800.
• Liu, Y., & Guo, R. (2007). Microenvironment effect on the location distribution of phenothiazine in cetyltrimethylammonium bromide/n-pentanol/H2O W/O and bi-continuous microemulsions. Journal of Solution Chemistry, 36(9), 1079-1092.
• Mizutani, Y., Kamogawa, K., & Nakanishi, K. (1989). Effect of urea on hydrophobic interaction: Raman difference spectroscopy on the carbon-hydrogen stretching vibration of acetone and the carbon-nitrogen stretching vibration of urea. The Journal of Physical Chemistry, 93(15), 5650-5654.
• Ozan, M., & Gokturk, S. (2021). Effect of ionic liquids as active pharmaceutical ingredients on the micellar binding of an amphiphilic drug trifluopromazine hydrochloride. Journal of Dispersion Science and Technology, 42(2), 214-222.
• Ozcam, H. T. (2015). A study on micelle formation of amphipilic drug amitriptyline hydrochloride, Master Dissertation, (pp. 1-102). Marmara University, İstanbul, Türkiye.
• Rosen, M. J. (1978). Surfactants and interfacial phenomena. (pp. 1-431). John Wiley and Sons.
• Rub, M. A., Asiri, A. M., Sheikh, M. S., Azum, N., Khan, A., Khan, A. A. P., & Rahman, M. M. (2014). Aggregation and phase separation phenomenon of amitriptyline hydrochloride under the influence of pharmaceutical excipients. Journal of Surfactants and Detergents, 17(1), 37-48.
• Rub, M. A., Asiri, A. M., Khan, A., Khan, A. A. P., Azum, N., & Khan, S. B. (2013). Investigation of micellar and phase separation phenomenon of the amphiphilic drug amitriptyline hydrochloride with cationic hydrotropes. Journal of Solution Chemistry, 42(2), 390-411.
• Schreier, S., Malheiros, S. V., & de Paula, E. (2000). Surface active drugs: self-association and interaction with membranes and surfactants. Physicochemical and biological aspects. Biochimica et Biophysica Acta (BBA)-Biomembranes, 1508(1-2), 210-234.
• Sharma, R., Nandni, D., & Mahajan, R. K. (2014). Interfacial and micellar properties of mixed systems of tricyclic antidepressant drugs with polyoxyethylene alkyl ether surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 451, 107-116.
• Srivastava, R. C., & Nagappa, A. N. (2005). Surface activity in drug action. (pp.1-327). Amsterdam, Elsevier.
• Stellner, K. L., & Scamehorn, J. F. (1989). Hardness tolerance of anionic surfactant solutions. 1. Anionic surfactant with added monovalent electrolyte. Langmuir, 5(1), 70-77.
• Taboada, P., Attwood, D., Ruso, J. M., García, M., & Mosquera, V. (2000). Static and dynamic light scattering study on the association of some antidepressants in aqueous electrolyte solutions. Physical Chemistry Chemical Physics, 2(22), 5175-5179.
• Zana, R. (1995). Aqueous surfactant-alcohol systems: a review. Advances in Colloid and Interface Science, 57, 1-64.