Cholesterol-Based Compounds: Recent Advances in Synthesis and Applications

Abstract

This review reports on the latest developments (since 2014) in the chemistry of cholesterol and its applications in different research fields. These applications range from drug delivery or bioimaging applications to cholesterol-based liquid crystals and gelators. A brief overview of the most recent synthetic procedures to obtain new cholesterol derivatives is also provided, as well as the latest anticancer, antimicrobial, and antioxidant new cholesterol-based derivatives. This review discusses not only the synthetic details of the preparation of new cholesterol derivatives or conjugates, but also gives a short summary concerning the specific application of such compounds.

<p>Evaluation of Cytotoxic Effect of Cholesterol End-Capped Poly(<em>N</em>-Isopropylacrylamide)s on Selected Normal and Neoplastic Cells</p>

“…Due to its hydroxyl group which can easily be derivatized, largescale availability and relatively low cost, cholesterol has been used as a starting material for the synthesis of diverse steroid-based molecules. 10,11 A variety of polymers comprising cholesterol moieties in the main chain or as side chains have been reported. 12 Cholesterol end-capped polymers can be synthesized by polymerizations performed in the presence of cholesterolbased molecules that initiate polymerization of monomers.…”

The Efficacy of Cholesterol-Based Carriers in Drug Delivery

“…Cholesterol ( Figure 1 ) ( 1 ) is a fatty substance or a lipid-type molecule that is essential in the human body and also a very important component in the structure of cell membranes [ 11 ]. It is a precursor of hormone production [ 12 ] (e.g., estrogen and testosterone) and it is used to produce bile, which is essential in aiding digestion.…”

“…The presence of a hydrophilic 3-hydroxy group on cholesterol, together with a hydrophobic hydrocarbon domain, gives it an amphiphilic nature, making it the most recognized sterol [ 11 ]. Over the years, several organic syntheses have involved the use of cholesterol as a starting material because it is readily available, affordable and its functional groups are easily derivatized.…”

“…Cholesterol has been successfully used as carriers for different kinds of drugs including antivirals, antimalarials, anticancer, etc. [ 11 ]. Similar to any other lipid-based carriers, cholesterol-based carriers can be produced fairly easily in large quantities at low cost, they are biodegradable and biocompatible [ 19 ] and they are easily manipulated.…”

“…The nature of the target organ and the distance from the site of administration determines the type of system that will be used for drug delivery. Furthermore, cholesterol, an important component in cell membranes [ 11 , 12 , 13 , 14 ], has been utilized in the development of drug delivery systems. Its efficacy as a major component in drug delivery systems has been reported by several researchers.…”