Spectroscopic study of benzothiophene partitioning in sodium dodecyl sulfate and cetyl trimethyl ammonium bromide micellar media

Abstract

This manuscript reports the partitioning of benzothiophene (BNP), a bioactive organic compound, between the aqueous phase and micellar media of an anionic surfactant, sodium dodecyl sulphate (SDS) and a cationic surfactant, cetyl trimethyl ammonium bromide (CTAB). Simple and differential UV/visible spectroscopic studies of said systems have been conducted in premicellar and post‐micellar concentration ranges. The experimental results reveal that in the premicellar region, the molecules of BNP get attached with monomeric surfactant molecules, while in the post‐micellar region; they are accommodated within the micelle. The bathochromic shift is observed in the UV/visible spectra of BNP in the presence of both surfactants. The water/micelle partition coefficient (Kx) and binding constant (Kb) were calculated using differential absorption data and subsequently the values of free energy of partition (∆Gp) and free energy of binding (∆Gb) were calculated. The values of Kx show that the solubilization of BNP is more spontaneous and takes place to a greater extent in micellar media of SDS than in CTAB.

Interactions and Solubilization of Poorly Soluble Drugs in Aerosol‐OT Micelles

“…In this context, the binding constants of drugs to micelles can be quantitatively determined using the simple mathematical model known as the Benesi–Hildebrand equation based on the Beer–Lambert law valid in the high micelle concentration region (Benesi and Hildebrand, ). In spite of many reports on the interactions between drugs and conventional surfactants in the literature (Azum et al, , ; Cai et al, ; Chauhan et al, ; Enache and Volanschi, ; Hanif et al, ; Hossain and Hoque, ; Kabir‐ud‐Din et al, ; Kaushal et al, ; Khan et al, ; Khan and Shah, ; Lazaro et al, ; Mukhija and Kishore, ; Naqvi et al, ; Noori et al, ; Rub et al, , , ; Sharma and Jani, ; Ullah et al, ), there is limited number of studies that combine spectroscopy with surface tension measurements or conductometry for the understanding of the mechanism of these types of interactions (Ali et al, ; Ansari et al, ; Gokturk et al, ; Kabir‐ud‐Din et al, , ; Maswal et al, ; Rub et al, ). Previously, we reported a study on the binding characteristics of poorly soluble drugs sulfamethoxazole (SMX) and trimethoprim (TMP) in the presence of sodium dodecyl sulfate (SDS) and Triton X‐100 (TX‐100) micelles employing spectroscopy and surface tension measurements.…”

Physicochemical parameters and modes of interaction associated with the micelle formation of a mixture of tetradecyltrimethylammonium bromide and cefixime trihydrate: effects of hydrotropes and temperature

“…Polymer-based surfactant system (CTAB/PEO system) also experienced an upsurge of micellar concentration with an augmentation of the composition of the polymer. 35 Hanif and co-workers 39 described the upsurge of CMC for the micellization of SDS with the introduction of benzothiophene (BZT). They illustrated the water structure breaking impact of BZT by disrupting H-bond of water and thereby the micellization of SDS becomes delayed.…”

“…They illustrated the water structure breaking impact of BZT by disrupting H-bond of water and thereby the micellization of SDS becomes delayed. 39 There is a possibility of generation of positively charged nitrogen atom in the resonance structure of PABA, which repels the head group of TTAB and inhibits micellization. Therefore, there is an increase in the values of CMC in the manifestation of PABA.…”

“…and surfactants occurred which signicantly modied the aggregation character of the surfactants. [34][35][36][37][38][39] Measurement of conductivity, [34][35][36] surface tension, [36][37][38] light scattering techniques, 35,37,38 steady-state uorescence spectroscopy, 36,37 simple and differential UV/visible spectroscopic studies, 39 and small-angle neutron scattering (SANS) 40 methods were used to evaluate the physicochemical features of the aggregation process of the solutes-surfactant system. In the literature, several studies have revealed the mode of interaction of surfactants and HTs, emphasizing the widespread applications in antibacterial medicines.…”

“…Islam et al 42 also revealed their report that the ceftriaxone sodium drug had the hydrophilic interaction with surfactant TX-100 in the presence of NaS, but for NaBz, this interaction was found insignificant. However, at various temperatures, Rehman et al 34 discovered the presence of electrostatic interactions in the association process of polylactic acid (PLA) with ionic surfactants-hexadecyltrimethylammonium bromide (CTAB) and sodium dodecyl sulphate (SDS), whereas Hanif et al 39 reported benzothiophene (BZT) partitioning in micellar medium was aided by both electrostatic and hydrophobic factors. Rub et al 44 reported that H-bonding and electrostatic contacts are the predominant forces amid TX-100 and MNH in the occurrence of PABA, although hydrophobic interactions are thought to be the dominant force among the component species used in aq.…”