Base-triggerable lauryl sarcosinate–dodecyl sulfate catanionic liposomes: structure, biophysical characterization, and drug entrapment/release studies

Abstract

Equimolar mixtures of oppositely charged single-chain amphiphiles form a variety of phases, including vesicles. Such catanionic mixed lipid systems show high stability and exhibit versatile physicochemical properties. In the present study we have investigated the aggregation behaviour of lauryl sarcosinate hydrochloride (LS·HCl) in aqueous dispersion as well as its interaction with the anionic surfactant sodium dodecyl sulfate (SDS). The CMC of LS·HCl was estimated to be ∼5 mM by isothermal titration calorimetry (ITC) and fluorescence spectroscopy using pyrene as the fluorescent probe. Turbidimetric and ITC studies on the interaction of LS·HCl with SDS demonstrated that the two surfactants form an equimolar catanionic complex. The crystal structure of the lauryl sarcosinate–dodecyl sulfate (LS–DS) complex revealed that the complex is stabilized by classical N–H⋯O as well as C–H⋯O hydrogen bonds, besides the electrostatic attraction between LS (cation) and DS (anion) and dispersion interactions between the hydrocarbon chains. Differential scanning calorimetry studies revealed that the phase transition of the equimolar LS–DS complex is significantly reduced compared to the analogous LG–DS and LA–DS complexes in the fully hydrated state. Dynamic light scattering, atomic force microscopy and transmission electron microscopy studies demonstrated that the LS–DS catanionic complex forms stable medium-sized vesicles (diameter of ∼300–500 nm). In vitro studies with 5-fluorouracil and rhodamine 6G showed efficient entrapment and release of these two anti-cancer drugs in the physiologically relevant pH range of 6.0–8.0, but with contrasting pH dependences. These observations indicate that LS–DS catanionic vesicles may find application in designing drug delivery systems.