Araştırma Makalesi
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Interactions of procaine hydrochloride with different micellar environments: A study on mimetic single and mixed micelle models

Yıl 2025, Cilt: 6 Sayı: 2, 122 - 130, 30.08.2025
https://doi.org/10.51753/flsrt.1675794

Öz

The micellar environment formed by surfactants behaves like a simple biological membrane system. Based on this property of micelles, which can be considered a pseudo-model of the biological systems, the presented study aimed to study the interactions of procaine hydrochloride (PrHy) with ionic, nonionic, and mixed micelles of nonionic and ionic surfactants. As a model for mimetic systems, nonionic Brij 35, lithium lauryl sulfate (LDS; anionic), sodium lauryl sulfate (SLS; anionic), sodium hexadecane-1-sulfonic acid (SHSA; anionic), dodecyltrimethyl ammonium bromide (DTAB; cationic), and didodecyldimethylammonium bromide (DDAB; cationic) were selected. Absorption spectrophotometry was employed to characterize the degree of association between the drug and surfactant micelles and to determine the micellar binding constants. The binding ability of PrHy is also further compared to the ionization degree and counterion binding parameter, which have been obtained from conductivity measurements. When the behavior of PrHy in micelle systems with different hydrophobicity was evaluated and the magnitude of binding constants was compared, it was determined that the most potent interaction was in the presence of Brij 35 micelles. The binding constant values of PrHy to micelles had been calculated via the Benesi-Hildebrand Equation, and the binding of PrHy accompanied the order as: Brij 35 > SHSA > SLS > LDS > DDAB > DTAB To understand the influence of mixed micelles on the binding degree of PrHy, constant concentrations of ionic micelles concerning their interaction with Brij 35 were also monitored. It was concluded that the micellar binding of PrHy on mixed micelle systems was due to hydrophobic interaction, with the contribution of electrostatic interactions. In an attempt to better understand the nature of the drug-surfactant interaction, this study employed both conductometric and spectrophotometric methods. The binding ability of PrHy for all anionic micelles examined enhanced considerably as the hydrophobic nature increased; however, the presence of PrHy lowered the CMC of anionic surfactants. The experimental results were compatible with both the conductivity and spectrophotometric techniques.

Kaynakça

  • Agatić, Z. F., Tepavčević, V., Puača, G., & Poša, M. (2024). Interaction of drug molecules with surfactants below (Benesi–Hildebrand equation) and above the critical micelle concentration (Kawamura equation). International Journal of Pharmaceutics, 665, 124675.
  • Amani, S., Soltani, T., & Gholamian, M. (2023). A recent overview of surfactant–drug interactions and their importance. Journal of Molecular Liquids, 380, 121768.
  • Attwood, D., & Florence, A. T. (1983). Surfactant systems: Their chemistry, pharmacy and biology (pp. 1-794). Chapman and Hall.
  • Banipal, T. S., Kaur, R., & Banipal, P. K. (2017). Interactions of diazepam with sodium dodecyl sulfate and hexadecyl trimethyl ammonium bromide: Conductometric, UV–visible spectroscopy, fluorescence and NMR studies. Journal of Molecular Liquids, 236, 331-337.
  • Bawazir, W. A., Al-Mahmood, M. A., Almalki, R. S., Alofi, G. F., Alharbi, R. S., & Zaheer, Z. (2024). Surfactants interaction with sulfathiazole: Spectroscopic, conductometric, and thermodynamic approach. Arabian Journal of Chemistry, 17(1), 105436.
  • Benesi, H. A., & Hildebrand, J. H. (1949). A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8), 2703-2707.
  • Caetano, W., & Tabak, M. (2000). Interaction of chlorpromazine and trifluoperazine with anionic sodium dodecyl sulfate (SDS) micelles: Electronic absorption and fluorescence studies. Journal of Colloid and Interface Science, 225(1), 69-81.
  • Čudina, O., Brborić, J., Janković, I., Karljiković-Rajić, K., & Vladimirov, S. (2008). Study of valsartan interaction with micelles as a model system for biomembranes. Colloids and Surfaces B: Biointerfaces, 65(1), 80-84.
  • Enache, M., & Volanschi, E. (2011). Spectral studies on the molecular interaction of anticancer drug mitoxantrone with CTAB micelles. Journal of Pharmaceutical Sciences, 100(2), 558-565.
  • Erdinc, N., Gokturk, S., & Tuncay, M. (2004). Interaction of epirubicin HCl with surfactants: Effect of NaCl and glucose. Journal of Pharmaceutical Sciences, 93(6), 1566-1576.
  • Evans, H. C. (1956). Alkyl sulphates. Part I. Critical micelle concentrations of the sodium salts. Journal of the Chemical Society (Resumed), 579-586.
  • Florence, A. T., & Atwood, D. (1998). Physicochemical principles of pharmacy. 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., & Cirit, O. (2025). Düşük çözünürlüklü ilaç etken maddeleri ve setrimid temelli yüzey aktif madde miselleri arasındaki etkileşimlere polaritenin etkisi. Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, 25(2), 305-311.
  • 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., & Toprak, C. (2024). Solubilization of insoluble and poorly water-soluble drugs in micellar systems. Pharmedicine Jo, 1(2), 74-84.
  • Gokturk, S., & Tuncay, M. (2003). Dye‐surfactant interaction in the premicellar region. Journal of Surfactants and Detergents, 6(4), 325-330.
  • 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.
  • Gokturk, S., Caliskan, E., Talman, R. Y., & Var, U. (2012). A study on solubilization of poorly soluble drugs by cyclodextrins and micelles: Complexation and binding characteristics of sulfamethoxazole and trimethoprim. The Scientific World Journal, 2012, 718791.
  • Gokturk, S., Keskin, G., Talman, R. Y. C., & Çakır, N. (2017). Spectroscopic and conductometric studies on the interactions of thionine with anionic and nonionic surfactants. Coloration Technology, 133(5), 362-368.
  • Gokturk, S., Talman, R. Y., Erdinç, N., & Tunçay, M. (2006). Solution behaviour of rivanol in micellar environments. Spectroscopy Letters, 39(4), 357-372.
  • Guzeloglu, A., Bhattarai, A., & Wilczura-Wachnik, H. (2024). Interactions between quercetin and surfactants/solvents. Results in Chemistry, 8, 101573.
  • Hiemenz, P. C., & Rajogopalan, R. (1986). Principles of colloid and surface chemistry. Marcel Dekker. Hou, L., Wu, B., Han, Y., & Qi, H. (2024). Synergistic effects of an amphiphilic drug (propranolol hydrochloride) with cationic surfactants in an aqueous medium: A physicochemical study. Journal of Molecular Liquids, 408, 125327.
  • Jia, Y., & Wei, X. (2024). Advances in utilizing reverse micelles to investigate membrane proteins. Current Opinion in Colloid & Interface Science, 69, 101826.
  • Joshi, D., Joshi, D., Gupta, S., & Bhardwaj, V. (2016). Mitoxantrone–surfactant interactions: A physicochemical overview. Molecules, 21(9), 1152.
  • Li, C., Chen, F., & Zhang, Y. (2024). From the surfactant–drug interactions to the rational design of micelle-based nanocarriers for drug delivery applications. ACS Applied Materials & Interfaces, 16(10), 12797–12808.
  • Ozcam, H. T., Tamer, Z. B., & Gokturk, S. (2022). Self-assembling of surface active drug amitriptyline hydrochloride in association with additives: Role of surface activity in the pharmaceutical applications. Frontiers in Life Sciences and Related Technologies, 3(3), 113-120.
  • Rosen, M. J. (1978). Surfactants and interfacial phenomena (431 pp.). John Wiley & Sons.
  • Shoukat, J., Abd-Ur-Rahman, H. M., Muhammad, A. J., Obaid, S., Imtiaz, F., Kanwal, N., & Iqbal, M. (2024). The interaction between formylphenoxyacetic acid derivatives (chalcone and flavones) and ionic surfactants: Insights into binding constants, solubilisation and physiochemical properties. Colloids and Surfaces B: Biointerfaces, 240, 113976.
  • Srivastava, A., Tiwari, S., Khan, J. M., Deb, D. K., & Ullah, M. W. (2025). Investigating the binding interactions of cetirizine and diphenhydramine in SDS-SDBS mixed micelles. Colloid and Polymer Science, 303, 985-1001.
  • Tiwari, S., Kumar, A., & Srivastava, A. (2025). Improving sorghum growth under organic salt stress using SDS–AOT mixed micelle encapsulated indole-3-butyric acid. Journal of Molecular Liquids, 430, 127754.
  • Virk, D., & Munjal, S. (2019). Biophysical interactions with model lipid membranes: Applications in drug discovery and drug delivery. Journal of Lipid Research, 60(1), 180-192.
  • Wang, R., Li, B., Chen, S., & Wang, X. (2023). Interface adsorption versus bulk micellization of surfactants: Insights from molecular simulations. Journal of Physical Chemistry B, 127(12), 2634-2643.

Interactions of procaine hydrochloride with different micellar environments: A study on mimetic single and mixed micelle models

Yıl 2025, Cilt: 6 Sayı: 2, 122 - 130, 30.08.2025
https://doi.org/10.51753/flsrt.1675794

Öz

The micellar environment formed by surfactants behaves like a simple biological membrane system. Based on this property of micelles, which can be considered a pseudo-model of the biological systems, the presented study aimed to study the interactions of procaine hydrochloride (PrHy) with ionic, nonionic, and mixed micelles of nonionic and ionic surfactants. As a model for mimetic systems, nonionic Brij 35, lithium lauryl sulfate (LDS; anionic), sodium lauryl sulfate (SLS; anionic), sodium hexadecane-1-sulfonic acid (SHSA; anionic), dodecyltrimethyl ammonium bromide (DTAB; cationic), and didodecyldimethylammonium bromide (DDAB; cationic) were selected. Absorption spectrophotometry was employed to characterize the degree of association between the drug and surfactant micelles and to determine the micellar binding constants. The binding ability of PrHy is also further compared to the ionization degree and counterion binding parameter, which have been obtained from conductivity measurements. When the behavior of PrHy in micelle systems with different hydrophobicity was evaluated and the magnitude of binding constants was compared, it was determined that the most potent interaction was in the presence of Brij 35 micelles. The binding constant values of PrHy to micelles had been calculated via the Benesi-Hildebrand Equation, and the binding of PrHy accompanied the order as: Brij 35 > SHSA > SLS > LDS > DDAB > DTAB To understand the influence of mixed micelles on the binding degree of PrHy, constant concentrations of ionic micelles concerning their interaction with Brij 35 were also monitored. It was concluded that the micellar binding of PrHy on mixed micelle systems was due to hydrophobic interaction, with the contribution of electrostatic interactions. In an attempt to better understand the nature of the drug-surfactant interaction, this study employed both conductometric and spectrophotometric methods. The binding ability of PrHy for all anionic micelles examined enhanced considerably as the hydrophobic nature increased; however, the presence of PrHy lowered the CMC of anionic surfactants. The experimental results were compatible with both the conductivity and spectrophotometric techniques.

Kaynakça

  • Agatić, Z. F., Tepavčević, V., Puača, G., & Poša, M. (2024). Interaction of drug molecules with surfactants below (Benesi–Hildebrand equation) and above the critical micelle concentration (Kawamura equation). International Journal of Pharmaceutics, 665, 124675.
  • Amani, S., Soltani, T., & Gholamian, M. (2023). A recent overview of surfactant–drug interactions and their importance. Journal of Molecular Liquids, 380, 121768.
  • Attwood, D., & Florence, A. T. (1983). Surfactant systems: Their chemistry, pharmacy and biology (pp. 1-794). Chapman and Hall.
  • Banipal, T. S., Kaur, R., & Banipal, P. K. (2017). Interactions of diazepam with sodium dodecyl sulfate and hexadecyl trimethyl ammonium bromide: Conductometric, UV–visible spectroscopy, fluorescence and NMR studies. Journal of Molecular Liquids, 236, 331-337.
  • Bawazir, W. A., Al-Mahmood, M. A., Almalki, R. S., Alofi, G. F., Alharbi, R. S., & Zaheer, Z. (2024). Surfactants interaction with sulfathiazole: Spectroscopic, conductometric, and thermodynamic approach. Arabian Journal of Chemistry, 17(1), 105436.
  • Benesi, H. A., & Hildebrand, J. H. (1949). A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society, 71(8), 2703-2707.
  • Caetano, W., & Tabak, M. (2000). Interaction of chlorpromazine and trifluoperazine with anionic sodium dodecyl sulfate (SDS) micelles: Electronic absorption and fluorescence studies. Journal of Colloid and Interface Science, 225(1), 69-81.
  • Čudina, O., Brborić, J., Janković, I., Karljiković-Rajić, K., & Vladimirov, S. (2008). Study of valsartan interaction with micelles as a model system for biomembranes. Colloids and Surfaces B: Biointerfaces, 65(1), 80-84.
  • Enache, M., & Volanschi, E. (2011). Spectral studies on the molecular interaction of anticancer drug mitoxantrone with CTAB micelles. Journal of Pharmaceutical Sciences, 100(2), 558-565.
  • Erdinc, N., Gokturk, S., & Tuncay, M. (2004). Interaction of epirubicin HCl with surfactants: Effect of NaCl and glucose. Journal of Pharmaceutical Sciences, 93(6), 1566-1576.
  • Evans, H. C. (1956). Alkyl sulphates. Part I. Critical micelle concentrations of the sodium salts. Journal of the Chemical Society (Resumed), 579-586.
  • Florence, A. T., & Atwood, D. (1998). Physicochemical principles of pharmacy. 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., & Cirit, O. (2025). Düşük çözünürlüklü ilaç etken maddeleri ve setrimid temelli yüzey aktif madde miselleri arasındaki etkileşimlere polaritenin etkisi. Afyon Kocatepe Üniversitesi Fen ve Mühendislik Bilimleri Dergisi, 25(2), 305-311.
  • 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., & Toprak, C. (2024). Solubilization of insoluble and poorly water-soluble drugs in micellar systems. Pharmedicine Jo, 1(2), 74-84.
  • Gokturk, S., & Tuncay, M. (2003). Dye‐surfactant interaction in the premicellar region. Journal of Surfactants and Detergents, 6(4), 325-330.
  • 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.
  • Gokturk, S., Caliskan, E., Talman, R. Y., & Var, U. (2012). A study on solubilization of poorly soluble drugs by cyclodextrins and micelles: Complexation and binding characteristics of sulfamethoxazole and trimethoprim. The Scientific World Journal, 2012, 718791.
  • Gokturk, S., Keskin, G., Talman, R. Y. C., & Çakır, N. (2017). Spectroscopic and conductometric studies on the interactions of thionine with anionic and nonionic surfactants. Coloration Technology, 133(5), 362-368.
  • Gokturk, S., Talman, R. Y., Erdinç, N., & Tunçay, M. (2006). Solution behaviour of rivanol in micellar environments. Spectroscopy Letters, 39(4), 357-372.
  • Guzeloglu, A., Bhattarai, A., & Wilczura-Wachnik, H. (2024). Interactions between quercetin and surfactants/solvents. Results in Chemistry, 8, 101573.
  • Hiemenz, P. C., & Rajogopalan, R. (1986). Principles of colloid and surface chemistry. Marcel Dekker. Hou, L., Wu, B., Han, Y., & Qi, H. (2024). Synergistic effects of an amphiphilic drug (propranolol hydrochloride) with cationic surfactants in an aqueous medium: A physicochemical study. Journal of Molecular Liquids, 408, 125327.
  • Jia, Y., & Wei, X. (2024). Advances in utilizing reverse micelles to investigate membrane proteins. Current Opinion in Colloid & Interface Science, 69, 101826.
  • Joshi, D., Joshi, D., Gupta, S., & Bhardwaj, V. (2016). Mitoxantrone–surfactant interactions: A physicochemical overview. Molecules, 21(9), 1152.
  • Li, C., Chen, F., & Zhang, Y. (2024). From the surfactant–drug interactions to the rational design of micelle-based nanocarriers for drug delivery applications. ACS Applied Materials & Interfaces, 16(10), 12797–12808.
  • Ozcam, H. T., Tamer, Z. B., & Gokturk, S. (2022). Self-assembling of surface active drug amitriptyline hydrochloride in association with additives: Role of surface activity in the pharmaceutical applications. Frontiers in Life Sciences and Related Technologies, 3(3), 113-120.
  • Rosen, M. J. (1978). Surfactants and interfacial phenomena (431 pp.). John Wiley & Sons.
  • Shoukat, J., Abd-Ur-Rahman, H. M., Muhammad, A. J., Obaid, S., Imtiaz, F., Kanwal, N., & Iqbal, M. (2024). The interaction between formylphenoxyacetic acid derivatives (chalcone and flavones) and ionic surfactants: Insights into binding constants, solubilisation and physiochemical properties. Colloids and Surfaces B: Biointerfaces, 240, 113976.
  • Srivastava, A., Tiwari, S., Khan, J. M., Deb, D. K., & Ullah, M. W. (2025). Investigating the binding interactions of cetirizine and diphenhydramine in SDS-SDBS mixed micelles. Colloid and Polymer Science, 303, 985-1001.
  • Tiwari, S., Kumar, A., & Srivastava, A. (2025). Improving sorghum growth under organic salt stress using SDS–AOT mixed micelle encapsulated indole-3-butyric acid. Journal of Molecular Liquids, 430, 127754.
  • Virk, D., & Munjal, S. (2019). Biophysical interactions with model lipid membranes: Applications in drug discovery and drug delivery. Journal of Lipid Research, 60(1), 180-192.
  • Wang, R., Li, B., Chen, S., & Wang, X. (2023). Interface adsorption versus bulk micellization of surfactants: Insights from molecular simulations. Journal of Physical Chemistry B, 127(12), 2634-2643.
Toplam 32 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kolloit ve Yüzey Kimyası, Fiziksel Kimya (Diğer)
Bölüm Araştırma Makaleleri
Yazarlar

Sogol Beygi 0009-0008-4594-831X

Sinem Gokturk 0000-0001-7979-3020

Yayımlanma Tarihi 30 Ağustos 2025
Gönderilme Tarihi 15 Nisan 2025
Kabul Tarihi 22 Temmuz 2025
Yayımlandığı Sayı Yıl 2025 Cilt: 6 Sayı: 2

Kaynak Göster

APA Beygi, S., & Gokturk, S. (2025). Interactions of procaine hydrochloride with different micellar environments: A study on mimetic single and mixed micelle models. Frontiers in Life Sciences and Related Technologies, 6(2), 122-130. https://doi.org/10.51753/flsrt.1675794


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