Enhanced micellization of Gemini surfactants using diphenhydramine hydrochloride as an organic counterion

Abstract

Micellization of the Gemini surfactant sodium dilauramidoglutamide lysine (SDGL) in the presence of an antihistamine drug, diphenhydramine hydrochloride (DPC) was investigated. The anionic surfactant sodium dodecyl sulfate (SDS) was used for comparison. DPC significantly decreased the critical micelle concentration (cmc) of both SDGL and SDS in aqueous media and increasing the DPC concentration decreased the pyrene excimer/monomer polarity ratio in SDGL micelles but increased it in SDS micelles, suggesting that SDGL and SDS micelles have different shapes. The counterion binding and binding constant values reveal that SDGL micelles interact more strongly with DPC than SDS micelles. Thus, DPC, as an organic counterion, can enhance surfactant micellization. The evaluation of the solubility of a poorly water-soluble drug (clotrimazole) in SDGL and SDS micelles containing DPC revealed that the drug was more soluble in SDS micelles than SDGL micelles, indicating that the cmc and the shape and size of micelles are essential factors for controlling drug solubilization.