Synthesis and Properties of Sucrose- and Lactose-Based Aromatic Ester Surfactants as Potential Drugs Permeability Enhancers

The delivery of therapeutics across biological membranes (e.g., mucosal barriers) by avoiding invasive routes (e.g., injection) remains a challenge in the pharmaceutical field. As such, there is the need to discover new compounds that act as drug permeability enhancers with a favorable toxicological profile. A valid alternative is represented by the class of sugar-based ester surfactants. In this study, sucrose and lactose alkyl aromatic and aromatic ester derivatives have been synthesized with the aim to characterize them in terms of their physicochemical properties, structure–property relationship, and cytotoxicity, and to test their ability as permeability enhancer agents across Calu-3 cells. All of the tested surfactants showed no remarkable cytotoxic effect on Calu-3 cells when applied both below and above their critical micelle concentration. Among the explored molecules, lactose p-biphenyl benzoate (URB1420) and sucrose p-phenyl benzoate (URB1481) cause a reversible ~30% decrease in transepithelial electrical resistance (TEER) with the respect to the basal value. The obtained result matches with the increased in vitro permeability coefficients (Papp) calculated for FTIC-dextran across Calu-3 cells in the presence of 4 mM solutions of these surfactants. Overall, this study proposes sucrose- and lactose-based alkyl aromatic and aromatic ester surfactants as novel potential and safe permeation enhancers for pharmaceutical applications

Toxicological profiles and surface properties at physiological pH of N-decanoyl amino acids

Meeting title: From Food to Pharma: the polyhedral nature of polymersPURPOSE: N-acyl amino acids based surfactants are an attractive class of anionic amphiphiles alternative to sulphate-based surfactants potentially employed as excipients in all pharmaceutical applications at which an anionic surfactant (eg. sodium dodecyl sulphate SDS) is needed (1, 2). The aim of this work is to correlate surface properties of N-decanoyl amino acids at physiological pH and their toxicological profile in order to explore the potential use of these surfactants for …postprin

Environmentally Friendly Method of Assembly of Cardanol and Cholesterol into Nanostructures Using a Continuous Flow Microfluidic Device

This study shows a viable and straightforward microfluidic method of assembly of cardanol (CA) and cholesterol (CH) into amphiphile nanostructures obtained through a hydrodynamic focusing approach according to which an alcoholic solution of CA and CH is constrained within a two-dimensional lamina shape by two lateral streams of borate buffer solution. The process is performed within glass-made cross-shaped micro-sized fluidic chips specially designed to achieve a laminar regime. CA, distilled from the cashew nut shell liquid, is demonstrated as a surface-active molecule in borate buffer basic medium and when mixed with CH it produces versatile nanovesicles through an in-batch solvent-free process. Compared to this conventional method, the microfluidic route allows operating under continuous flows, with a reduced amount of reagents and at lower experimental temperatures, ensuring no waste formation and the achievement of size-monodisperse amphiphile nanostructures that do not need further steps of purification. Electron microscopy analyses demonstrate that upon increasing CH in the lipid mixture, a switchover from spherical CA micelles to CA/CH mixed closed vesicles occurs. Differential scanning microcalorimetry confirms the formation of vesicular structures and evidences the primary role of CH, which increasingly lowers the temperature of transition depending on its concentration