Two-component supramolecular hydrogels based on a cholic acid dimer and carboxylic acids
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1
Université de Montréal, Département de Chimie, Canada
Supramolecular gels are a class of soft materials with self-assembled fibrillar networks and may be potentially used in biomedical areas such as drug delivery, tissue engineering, and biosensing[1],[2]. Bile acids are natural compounds existing in humans and most animals, and their derivatives may form two-component supramolecular hydrogels in water by self-assembly[3]. Cholic acid is a primary bile acid and a dimer based on cholic acid may form two-component supramolecular hydrogels with certain carboxylic acids and the properties of the hydrogels depend on the structure of the acids. Two cholic acid molecules are covalently linked via diethylenetriamine to form the dimer. This dimer is insoluble in water, while it may be solubilized with a certain amount of selected carboxylic acids to form hydrogels. Only weak and hydrophilic carboxylic acids interact with the dimer to form hydrogels and their chemical structure may affect the gelation ability of dimer. The best gelation ability is obtained when the dimer interacts with tartaric acid, and only 0.05 wt% of the dimer is needed to form a stable hydrogel. Fourier transform infrared spectroscopy indicates that amide-hydroxyl hydrogen bonds of the dimer are rearranged to amide-carboxylic acid or amide-amide hydrogen bonds after the formation of hydrogel with carboxylic acids. Transmission electron microscopy confirms the existence of 3-dimensional network of self-assembled fibers. Monoacids with longer aliphatic chain may form stronger hydrogels by improved hydrophobic interaction between the alkyl chains of acids. Diacids with more hydroxyl groups significantly improve the mechanical properties of such hydrogels since the hydroxyl groups on the diacids may increase the hydrogen bond density in the hydrogels. This two-component supramolecular hydrogelation system from the cholic acid dimer shows controllable mechanical properties of hydrogels by changing chemical structure of carboxylic acids, as well as the simplicity and the minimal amount of organic matter. These advantages may make such hydrogels potentially useful for a variety of applications.
NSERC of Canada; FQRNT of Quebec; Canada Research Chair program; Chinese Scholarship Council
References:
[1] R. G. Weiss, J. Am. Chem. Soc., 2014, 136, 7519-7530
[2] J. Raeburn and D. J. Adams, Chem. Commun., 2015, 51, 5170-5180
[3] S. Mukhopadhyay, U. Maitra, I. Ira, G. Krishnamoorthy, J. Schmidt and Y. Talmon, J. Am. Chem. Soc., 2004, 126, 15905-15914
Keywords:
Hydrogel,
Tissue Engineering,
self-assembly,
Drug delivery
Conference:
10th World Biomaterials Congress, Montréal, Canada, 17 May - 22 May, 2016.
Presentation Type:
Poster
Topic:
Adhesive biomaterials
Citation:
Zhang
M and
Zhu
X
(2016). Two-component supramolecular hydrogels based on a cholic acid dimer and carboxylic acids.
Front. Bioeng. Biotechnol.
Conference Abstract:
10th World Biomaterials Congress.
doi: 10.3389/conf.FBIOE.2016.01.00860
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Received:
27 Mar 2016;
Published Online:
30 Mar 2016.