Four novel bile acid ethyl amides were synthetized using a well-known method. All the four compounds were characterized by IR, SEM, and X-ray crystal analyses. In addition, the cytotoxicity of the compounds was tested. Two of the prepared compounds formed organogels. Lithocholic acid derivative 1 formed hydrogels as 1% and 2% (w/v) in four different aqueous solutions. This is very intriguing regarding possible uses in biomedicine.
The self‐assembly properties of nine low‐molecular‐weight gelators (LMWGs) based on bile acid alkyl amides were studied in detail. Based on the results, the number of hydroxyl groups attached to the steroidal backbone plays a major role in the gelation, although the nature of the aliphatic side chain also modulates the gelation abilities. Of the 50 gel systems studied, 35 are based on lithocholic acid and 15 on cholic acid derivatives. The deoxycholic acid derivatives did not form any gels. The gelation occurred primarily in aromatic solvents and the gels manifested typical fibrous or spherical morphologies. The 13C cross‐polarized magic angle spinning (CPMAS) NMR spectra measured on the crystalline materials and the corresponding wet organogels were analogous, suggesting that the chemical environments, that is, the intermolecular interactions found in the two materials were similar. The single‐crystal X‐ray structures of all nine bile‐acid amide derivatives studied revealed very similar molecular conformations in the solid state and gave insights into the possible intermolecular interactions in the gel state.
The review deals with an expanding number of steroidal compounds that are capable of forming a metallogel providing a multitude of novel materials rich in their properties. The future of steroidal metallogels holds a myriad of potential applications as new intelligent materials. Detection of potentially harmful compounds without expensive instrumentation, entrapment of environmentally hazardous substances, and sensitive and selective nanomaterials represent only a few of these potential applications.This article reviews the design, synthesis, characterization, and applications of steroidal metallogels.
Six bile acid alkyl amide derivatives were studied with respect to their gelation properties. The derivatives were composed of three different bile acids with hexyl or cyclohexyl side chains. The gelation behaviour of all six compounds were studied for 36 solvents with varying polarities. Gelation was observed mainly in aromatic solvents, which is characteristic for bile‐acid‐based low molecular weight gelators. Out of 108 bile acid‐solvent combinations, a total of 44 gel systems were formed, 28 of which from lithocholic acid derivatives, only two from deoxycholic acid derivatives, and 14 from cholic acid derivatives. The majority of the gel systems were formed from bile acids with hexyl side chains, contrary to the cyclohexyl group, which seems to be a poor gelation moiety. These results indicate that the spatial demand of the side chain is the key feature for the gelation properties of the bile acid amides.
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