Acid···Amide Supramolecular Synthon for Tuning Amino Acid-Based Hydrogels’ Properties

Eleonora Veronese, Dr. Claudia Pigliacelli, Dr. Greta Bergamaschi, Prof. Giancarlo Terraneo, Prof. Valentina Dichiarante and Prof. Pierangelo Metrangolo have recently published an article on Chemistry—A European Journal about "Pivotal role of the protein corona in the cell uptake of fluorinated nanoparticles with increased sensitivity for 19F-MR imaging".

The full paper can be found at the following link: Acid···Amide Supramolecular Synthon for Tuning Amino Acid-Based Hydrogels’ Properties.

Abstract. Supramolecular hydrogels formed by the self-assembly of N-Fmoc-L-phenylalanine derivatives are gaining relevance for several applications in the materials and biomedical fields. In the challenging attempt to predict or tune their properties, we selected Fmoc-pentafluorophenylalanine (1) as a model efficient gelator, and studied its self-assembly in the presence of benzamide (2), a non-gelator able to form strong hydrogen bonding with the amino acid carboxylic group. Equimolar mixtures of 1 and 2 in organic solvents afforded a 1:1 co-crystal thanks to the formation of an acid···amide heterodimeric supramolecular synthon. The same synthon occurred in the transparent gels formed by mixing the two components in 1:1 ratio in aqueous media, as revealed by structural, spectroscopic, and thermal characterizations performed on both the co-crystal powder and the lyophilized hydrogel. These findings revealed the possibility to modulate the properties of amino acid-based hydrogels, by involving the gelator in the formation of a co-crystal. Such crystal engineering-based approach is demonstrated to be also useful for the time-delayed release of suitable bioactive molecules, when involved as hydrogel coformers.


How to cite:
Eleonora Veronese, Claudia Pigliacelli, Greta Bergamaschi, Giancarlo Terraneo, Valentina Dichiarante and Pierangelo Metrangolo Acid···Amide Supramolecular Synthon for Tuning Amino Acid-Based Hydrogels’ Properties, Chem. Eur. J., 2023, e202301743.



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