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Self‐Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial
Author(s) -
Garcia Ana M.,
Lavendomme Roy,
Kralj Slavko,
Kurbasic Marina,
Bellotto Ottavia,
Cringoli Maria C.,
Semeraro Sabrina,
Bandiera Antonella,
De Zorzi Rita,
Marchesan Silvia
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905681
Subject(s) - biomaterial , protonation , titration , self healing hydrogels , supramolecular chemistry , antimicrobial , chemistry , fibroblast , derivative (finance) , polymer chemistry , materials science , nuclear chemistry , stereochemistry , crystal structure , crystallography , biochemistry , organic chemistry , in vitro , ion , economics , financial economics
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 p K a 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.