Cholesterol as synthetic building blocks for artificial lipids with characteristic physical, chemical and biological properties

Abstract

Cholesterol is one of the most widely distributed natural materials and has a unique chemical structure such as a steroid skeleton. Many types of chemical transformations of cholesterol functional groups have been developed. There is an interest in the derivatization of cholesterol and to introduce alkyl branched fatty acids into the molecule. These have found applications in the formulation of cosmetics and toiletries over the past few decades. An extraordinary interesting case is related to cholesteryl esters and their use in gene therapy delivery systems. These results can be attributed to their potential for forming cell-mimic membranes, because cholesterol is the most important building block of living cell membranes. In terms of organic synthesis, cholesterol is a strategically useful material. A typical case is remote functionalization by chemical reactions or by biocatalysis. In the future, cholesterol should be considered as a key compound, a building block for the construction of artificial lipid-like membranes by self-assembly. Also, as cholesterol is one of the members of the fat and oil family, fat and oil chemists should study and develop cholesterol chemistry even further.

Sterol-Modified Phospholipids: Cholesterol and Phospholipid Chimeras with Improved Biomembrane Properties

“…After an extensive review of the literature we have been unable to find examples of phospholipids where a sterol is attached to either the glycerol or sphingosine 40–44. Indeed, the recently introduced lipid classification system 27 does not have a category for the SML and to the best of our knowledge such lipids have not as yet been identified or isolated from biological systems.…”

Limitations extractives des ingrédients fonctionnels natifs : lipides bioactifs par modifications chimiques

“…La réactivité de ces sites a donné naissance à la formation d'esters ou éthers cholestériques (figure 3) [31].…”

Controlled synthesis of new amphiphilic glycopolymers with liquid crystal grafts

“…Cholesterol mesogen group is a good candidate to produce such rod‐coil amphiphilic copolymers because its liquid crystalline (LC) nature facilitates copolymer self‐assembly . In addition, biocompatibility, anticoagulant properties, and the good cell adhesion of cholesterol enable its use in drug delivery systems . Often, polymer chains are just modified by cholesteryl mesogen groups .…”

“…[27][28][29] In addition, biocompatibility, anticoagulant properties, and the good cell adhesion of cholesterol enable its use in drug delivery systems. 30,31 Often, polymer chains are just modified by cholesteryl mesogen groups. [32][33][34] Copolymers produced from a cholesterol-based monomer have more rarely been reported.…”