Supramolecular Gels from Conjugates of Bile Acids and Amino Acids and Their Applications

Hydrogels composed of low molecular weight molecules are gaining increasing importance in biomedical applications. In this work, we report the formation of injectable hydrogels from bile acid–amino acid conjugates. The hydrogelation ability was dependent on multiple factors such as the bile acid bac...

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Bibliographic Details
Published in:European journal of organic chemistry 2017-04, Vol.2017 (13), p.1713-1720
Main Authors: Maity, Mitasree, Maitra, Uday
Format: Article
Language:English
Subjects:
Amino acids
Bile
Bile acids
Composite materials
Gels
Hydrogels
Supramolecular chemistry
X‐ray crystallography
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Summary:Hydrogels composed of low molecular weight molecules are gaining increasing importance in biomedical applications. In this work, we report the formation of injectable hydrogels from bile acid–amino acid conjugates. The hydrogelation ability was dependent on multiple factors such as the bile acid backbone, linkage between the bile acid and the amino acid, and pH. We have shown that the gelation properties depend on multiple noncovalent interactions and on the balance between hydrophobic and hydrophilic characteristics of the molecules. Crystal structures of lithocholyl‐l‐phenylalanine, lithocholyl‐glycine, lithocholyl‐l‐valine, and lithocholyl‐l‐alanine were also determined and compared. Finally, the rigid hydrogel frameworks were utilized to produce inorganic–organic composite materials with gold and ZnO nanoparticles. A number of new bile acid–amino acid conjugates exhibited pH dependent hydrogelation. These gels were used as templates for in situ synthesis of ZnO and Au nanoparticle–gel composites.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201601616