Self-Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial |
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Authors: | Dr. Ana M. Garcia Dr. Roy Lavendomme Dr. Slavko Kralj Marina Kurbasic Ottavia Bellotto Maria C. Cringoli Dr. Sabrina Semeraro Dr. Antonella Bandiera Prof. Rita De Zorzi Prof. Silvia Marchesan |
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Affiliation: | 1. Dipartimento di Scienze Chimiche e Farmaceutiche, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy;2. Department of Chemistry, University of Cambridge, Lensfield Road, CB2 1EW Cambridge, UK;3. Materials Synthesis Department, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia;4. Dipartimento di Scienze della Vita, University of Trieste, Via L. Giorgieri 1, 34127 Trieste, Italy |
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Abstract: | N-(4-Nitrobenzoyl)-Phe self-assembled into a transparent supramolecular hydrogel, which displayed high fibroblast and keratinocyte cell viability. The compound showed a mild antimicrobial activity against E. coli both as a hydrogel and in solution. Single-crystal XRD data revealed packing details, including protonation of the C-terminus due to an apparent pKa shift, as confirmed by pH titrations. MicroRaman analysis revealed almost identical features between the gel and crystal states, although more disorder in the former. The hydrogel is thermoreversible and disassembles within a range of temperatures that can be fine-tuned by experimental conditions, such as gelator concentration. At the minimum gelling concentration of 0.63 wt %, the hydrogel disassembles in a physiological temperature range of 39–42 °C, thus opening the way to its potential use as a biomaterial. |
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Keywords: | hydrogels phenylalanine self-assembly supramolecular chemistry |
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