Mixed micelles of the antihistaminic cationic drug diphenhydramine hydrochloride with anionic and non-ionic surfactants show improved solubility, drug release and cytotoxicity of ethenzamide

Srivastava, Anirudh; Uchiyama, Hiromasa; Wada, Yuhei; Hatanaka, Yuta; Shirakawa, Yoshiyuki; Kadota, Kazunori; Tozuka, Yuichi

doi:10.1016/j.molliq.2018.12.070

Cited by 57 publications

(14 citation statements)

References 80 publications

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“…Thermodynamic parameters such as the Gibbs free energy of micellization ( ) income the moment as the amphiphilic monomers are converted from a bulk solution to the micellar form can be assessed by considering a charged pseudo-phase separation model using the following equation [ 44 – 46 ]: …”

Section: Resultsmentioning

confidence: 99%

Investigation of micellar and interfacial phenomenon of amitriptyline hydrochloride with cationic ester-bonded gemini surfactant mixture in different solvent media

Rub

2020

PLoS ONE

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Herein, the interaction among the antidepressant drug amitriptyline hydrochloride (AMT) and a green gemini surfactant, ethane-1, 2-diyl bis(N,N-dimethyl-N-tetradecylammoniumacetoxy) dichloride (14-E2-14), via numerous techniques such as tensiometry, fluorimetry, FT-IR and UV-visible spectroscopy in three different media (aqueous 0.050 mol·kg-1 NaCl, 0.50 and 1.0 mol·kg-1 urea) were investigated. AMT is used to treat mental illness or mood problems, such as depression. The aggregation of biologically active ingredients can enhance the bioavailability of hydrophobic drugs. A significant interaction between AMT and 14-E2-14 was detected by tensiometric study as the critical micelle concentration (cmc) of AMT+14-E2-14 is reduced upon an increase of mole fraction (α1) of 14-E2-14. The decrease in cmc indicates the nonideality of studied mixtures of different compositions. Although, employed drug AMT is freely soluble in the aqueous and non-aqueous system but is not hydrophobic enough to act as its carrier. Instead, gemini surfactant formed spherical micelles in an aqueous system and their high solubilization capability, as well as their relatively lower cmc value, makes them highly stable in vivo. The cmc values of AMT+14-E-14 mixtures in all cases were further decreased and increased in NaCl and urea solutions respectively as compared with the aqueous system. Numerous micellar, interfacial, and thermodynamic parameters have been measured by applying various theoretical models. The obtained changes in the physicochemical assets of AMT upon adding of 14-E2-14 are likely to enhance the industrial and pharmaceutical applications of gemini surfactants. The negative interaction parameters (βm and βσ), indicate synergistic attraction is occurring in the mixed systems. The aggregation number (Nagg), Stern–Volmer constant (Ksv), etc. are attained through the fluorescence method, also supporting the attractive interaction behavior of AMT+14-E2-14 mixtures in all solvents. The Nagg was found to increase in the salt solution and decrease in the urea system compared with the aqueous solution. FT-IR and UV-visible analysis also depict the interaction between the constituent alike tensiometry and fluorimetry methods. The results suggested that gemini surfactants may serve as a capable drug delivery agent for antidepressants, improving their bioavailability.

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Section: Resultsmentioning

confidence: 99%

Investigation of micellar and interfacial phenomenon of amitriptyline hydrochloride with cationic ester-bonded gemini surfactant mixture in different solvent media

Rub

2020

PLoS ONE

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“…Mahajan et al [32] studied the association and solution surface interactions of nortriptyline hydrochloride along with the amitriptyline hydrochloride drug with non-ionic polyoxyethylene alkyl ether surfactants by means of different techniques and they proposed a synergy between the drug and surfactant mixture having enhanced surface properties that can be proficiently used for pharmaceutical applications. Srivastava et al [33] evaluated different parameters of the drug and anionic and non-ionic surfactant mixture micelles and employed a mixed system to improve the solubility along with a decrease in the cytotoxicity of poorly water-soluble pharmaceutical ingredients. However, up until now, according to our information, the aggregation of the IMP drug in the presence of TX-100 of various mole fraction in non-aqueous system (salt, urea) has not been stated elsewhere.…”

Section: Introductionmentioning

confidence: 99%

“…Numerous hypothetical models are utilized to describe the formation of the mixed micelles of IMP + TX-100 mixtures [34,35]. Regardless of the tensiometry technique, UV-Visible analysis was also operated to check the consistency in the interaction of the IMP drug with TX-100 in the aqueous system as a means to gain several basic pieces of evidence regarding the nature of interactions amongst the employed components [5,33,35].…”

Section: Introductionmentioning

confidence: 99%

Investigation of Solution Behavior of Antidepressant Imipramine Hydrochloride Drug and Non-Ionic Surfactant Mixture: Experimental and Theoretical Study

et al. 2021

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In this paper, the interaction of imipramine hydrochloride (IMP, antidepressant drug) and a non-ionic surfactant Triton X-100 (TX-100) mixture in five different ratios through the tensiometric method in different solvents (aqueous/0.050 mol·kg−1 aqueous NaCl/0.250 mol·kg−1 aqueous urea (U)) were examined thoroughly at a temperature of 298 K. UV–Visible studies in an aqueous system of IMP + TX-100 mixtures were also investigated and discussed in detail. The pure (IMP and TX-100) along with the mixtures’ critical micelle concentration (cmc) were assessed by a tensiometric technique. The obtained deviation of the mixtures’ cmc values from their ideal values revealed the nonideal behavior of IMP + TX-100 mixtures amongst IMP and TX-100. Compared to aqueous systems, in the presence of aqueous NaCl, several changes in micelles/mixed micelles occurred, and hence a synergism/attractive interaction amongst components was found increased while in the existence of U, the synergism/attractive interaction between them decreased. The evaluated interaction parameter (βRb) value of mixed micelles showed the attractive or synergism between the IMP and TX-100. Various evaluated thermodynamic parameters in an aqueous system showed that the mixed micellization of the IMP + TX-100 mixture was an entropically spontaneous phenomenon, although the existence of salt in all studied systems can somewhat increase the spontaneity of the micellization process and in the aqueous U system, the spontaneity of the micellization process decreased. In an aqueous system, the interaction between IMP and TX-100 was also confirmed by UV–Visible study.

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“…Diphenhydramine (DPH) is an ethanolamine, an antihistamine of H 1 receptor, a first-generation drug, and has anticholinergic properties [ 27 , 28 , 29 ]. The reported value of pKa for DPH is 8.87, so the DPH ionized in an aqueous solution and acquired a positive charge.…”

Section: Introductionmentioning

confidence: 99%

Interaction of Diphenhydramine Hydrochloride with Cationic and Anionic Surfactants: Mixed Micellization and Binding Studies

et al. 2021

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The focus of the present work is to evaluate the interactions of an anti-allergic drug (diphenhydramine hydrochloride, DPH) with anionic (sodium dodecyl sulfate, SDS) and cationic (cetylpyridinium chloride, CPC) surfactants in the aqueous medium. The mixed micellization behavior and surface properties of drug-surfactant mixtures have been examined by surface tension measurements. Various theoretical approaches were applied to explore the synergistic or non-ideal behavior of the current mixed systems. Furthermore, the binding studies of drug with surfactants have been elaborated by UV–visible spectroscopy. Benesi–Hildebrand (B-H) theory was used to compute stoichiometric ratio, binding constant, and free energy change for the drug-surfactant mixtures. The outputs are deliberated taking into consideration the use of surfactants as capable drug delivery agents for DPH and hence advance bioavailability.

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Mixed micelles of the antihistaminic cationic drug diphenhydramine hydrochloride with anionic and non-ionic surfactants show improved solubility, drug release and cytotoxicity of ethenzamide

Cited by 57 publications

References 80 publications

Investigation of micellar and interfacial phenomenon of amitriptyline hydrochloride with cationic ester-bonded gemini surfactant mixture in different solvent media

Investigation of micellar and interfacial phenomenon of amitriptyline hydrochloride with cationic ester-bonded gemini surfactant mixture in different solvent media

Investigation of Solution Behavior of Antidepressant Imipramine Hydrochloride Drug and Non-Ionic Surfactant Mixture: Experimental and Theoretical Study

Interaction of Diphenhydramine Hydrochloride with Cationic and Anionic Surfactants: Mixed Micellization and Binding Studies

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