Ordered Nanostructured Amphiphile Self-Assembly Materials from Endogenous Nonionic Unsaturated Monoethanolamide Lipids in Water

Abstract

The self-assembly, solid state and lyotropic liquid crystalline phase behavior of a series of endogenous n-acylethanolamides (NAEs) with differing degrees of unsaturation, viz., oleoyl monoethanolamide, linoleoyl monoethanolamide, and linolenoyl monoethanolamide, have been examined. The studied molecules are known to possess inherent biological function. Both the monoethanolamide headgroup and the unsaturated hydrophobe are found to be important in dictating the self-assembly behavior of these molecules. In addition, all three molecules form lyotropic liquid crystalline phases in water, including the inverse bicontinuous cubic diamond (Q(II)(D)) and gyroid (Q(II)(G)) phases. The ability of the NAE's to form inverse cubic phases and to be dispersed into ordered nanostructured colloidal particles, cubosomes, in excess water, combined with their endogenous nature and natural medicinal properties, makes this new class of soft mesoporous amphiphile self-assembly materials suitable candidates for investigation in a variety of advanced multifunctional applications, including encapsulation and controlled release of therapeutic agents and incorporation of medical imaging agents.

Nonionic diethanolamide amphiphiles with saturated hydrocarbon chains: Neat crystalline and lyotropic liquid crystalline phase behavior

“…1 shows the chemical and energy minimized structures of the saturated diethanolamide amphiphiles examined in the current study. This sixth paper in the series [25][26][27]32,33] completes our study of the physicochemical and self-assembly behavior of nonionic mono-and diethanolamide amphiphiles. A thorough physicochemical characterization of ethanolamide-based amphiphiles provides a framework to design future fit for purpose amphiphile systems for a range of applications including drug delivery, cosmetic formulations, or household detergents.…”

“…Our group has previously examined in detail the structureproperty correlation via hydrophobe and headgroup modification for a variety of surfactant families including ureas, monoethanolamides, and ethoxylates and examined them as possible drug delivery matrices [22][23][24][25][26][27][28][29][30][31]. We have also recently reported on the physicochemical properties of diethanolamide amphiphiles with unsaturated hydrocarbon chains and isoprenoid-type chains [32,33].…”

Lamellar crystalline self-assembly behaviour and solid lipid nanoparticles of a palmityl prodrug analogue of Capecitabine—A chemotherapy agent

“…A number of systems have been examined for their ability to effectively deliver active drugs including liposomes, hexosomes, cubosomes, solid lipid nanoparticles, polymer nanoparticles, dendrimers and nanoshells [1,[8][9][10][11][12][13][14][15][16][17]. These systems however lack any specific targeting mechanism necessary for selective delivery and are thus limited in effectively delivering drugs to the target site.…”

Nonionic diethanolamide amphiphiles with unsaturated C18 hydrocarbon chains: thermotropic and lyotropic liquid crystalline phase behavior

“…16,17,[25][26][27][28] In addition, we and others have recently reported on the effect of hydrocarbon chain modification on the physicochemical properties of monoethanolamide amphiphiles demonstrating that hydrophobe unsaturation promotes inverse cubic phase formation within the monoethanolamide family. 22,[29][30][31] Here, similar to the urea based amphiphiles, we have aimed to further extend our understanding of structureproperty correlation of ethanolamide based amphiphiles by a systematic examination of the self-assembly, including neat and lyotropic liquid crystalline phase behavior of a series of C18 diethanolamides with one, two, and three carbon double bonds. Fig.…”

“…Fig. 1 provides the chemical structures and compares the energy minimized structures of the previously examined unsaturated monoethanolamides, 30 as well as the unsaturated diethanolamide amphiphiles examined in the current study.…”