Synthetic ultra-long chain fatty acyl based amphiphilic lipids as a dual function excipient for the production of surfactant-free solid lipid nanoparticles (SF-SLNs): a physico-chemical study

Abstract

Two arrays of behenoyl (22:0) based amphiphilic lipids with sugar alcohols as a flexible linker were synthesized through acylation of sugar alcohol mono-behenates with diacetyl tartaric anhydride or acetoxy succinic anhydride; and some of the resulting products are capable to yield stable and uniform solid lipid nanoparticles (SLNs) (mean diameter ~100nm, PDI<0.2) without any additive surfactant, displaying excellent dual functions (as both solid lipid excipient and emulsifier). Graphic abstractTwo groups of behenoyl (22:0) based amphiphilic lipids with sugar alcohols as a flexible linker were synthesized; among which some resulting products are capable to produce stable and uniform solid lipid nanoparticles (SLNs) (mean diameter ~100nm, PDI<0.2) without any additive surfactant, demonstrating excellent dual functions (as both solid lipid excipient and emulsifier).

A new group of synthetic phenolic-containing amphiphilic molecules for multipurpose applications: Physico-chemical characterization and cell-toxicity study

“…The amphiphilic lipids were characterized by means of DSC to determine their melting transition temperatures. This is relevant for applications as emulsifiers 12 , skin lipids 5 , 6 , or nanocarriers 9 . No clear melting transition temperatures were observed for compounds C10 ‒ C16 when temperature scanning from was done −60 °C to 60 °C.…”

“…Even though DSC provides valuable information about the thermal transitions of compounds, little is gained about their molecular organizations 9 . FT-IR is a powerful tool to acquire detailed information about the conformations and molecular orientations of alky side chains of lipids 13 .…”

“…~70% fish oil) for lipophilic ingredients due to their multifunctional properties (surface activity and antioxidant property), and ability to interact with macromolecules. In addition, due to structural similarities to other compounds in the literature 1 – 9 , the synthesized amphiphiles could potentially find applications not only in food but also in cosmetics, or as nanocarriers. For instance, longer alkyl chain derivatives of this series of compounds could be applied in cosmetic formulations as protective skin barriers 5 , 6 .…”

“…Fats and oils, carbohydrates, carboxylic acids and phenolic acids have been demonstrated to be valuable raw materials for the development of functional materials for various applications 1 – 9 . However, the aforementioned raw materials are either hydrophilic (e.g.…”

“…However, the aforementioned raw materials are either hydrophilic (e.g. carboxylic acids, carbohydrates and phenolic acids) or hydrophobic (fats, oils and fatty acids) which limit their application in foods, drugs and cosmetics, where amphiphilic molecules are needed 1 – 9 .…”