Self‐Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial

Abstract

N-(4-Nitrobenzoyl)-Phe self-assembled into at ransparent supramolecular hydrogel, whichd isplayed high fibroblast and keratinocyte cell viability.T he compound showed am ild antimicrobial activity against E. coli both as ah ydrogel and in solution.S ingle-crystal XRD data revealed packing details,i ncluding protonation of the C-terminus due to an apparent pK a shift, as confirmed by pH titrations. MicroRaman analysisr evealed almosti denticalf eaturesb etween the gel and crystal states,a lthough more disorder in the former. The hydrogel is thermoreversible and disassemblesw ithin a range of temperaturest hat can be fine-tunedb ye xperimental conditions, such as gelator concentration. At the minimum gellingc oncentration of 0.63 wt %, the hydrogel disassembles in ap hysiological temperature range of 39-42 8C, thus opening the way to its potential use as ab iomaterial.[a] Dr.Supporting information and the ORCID identification number(s) for the author(s) of this articlecan be found under: https://doi.

Biocatalysis of d,l-Peptide Nanofibrillar Hydrogel

“…Another major signal at 1540 cm −1 was due to the His imidazole ring [24], as well as the peak at 1568 cm −1 . Furthermore, a minor peak at 1694 cm −1 suggested presence of the C-terminal carboxylic group in its neutral form [25], as already reported for other amyloids, whereby the supramolecular organization disfavored deprotonation [26][27][28][29][30][31].…”

Stable Formulations of Peptide-Based Nanogels

“…The emulsion is achieved between an aqueous phase containing the gelling DMSO/H 2 O peptide solution and an organic phase consisting of a mineral oil, in which one or more stabilizing surfactants are dispersed. This method was previously proposed by Gazit’s group for fabrication of Fmoc-FF hydrogel nanoparticles coated using d-α-tocopheryl polyethylene glycol 1000 succinate (E-TPGS, Figure 2 ) surfactant as the stabilizing agent [ 24 ]. According to the reported experimental protocol, we prepared six nanogel formulations (see Table 1 ), all of them containing the same amount of Fmoc-FF (10 mg/mL, final gel at 0.25 %wt) and a different percentage of two biocompatible surfactants, TWEEN ® 60 (polyethylene glycol sorbitan monostearate, see Figure 2 ) and SPAN ® 60 (sorbitan stearate, see Figure 2 ).…”

“…The peptide chosen for nanogel preparation is the ultrashort Fmoc-FF peptide. It is well known that many short and ultrashort peptide sequences can spontaneously self-assemble into HGs, as a consequence of physical and noncovalent interactions, thus, avoiding the employment of crosslinking agents [ 22 , 23 , 24 ]. Among these peptides, one of the most studied is Fmoc-FF.…”

Facile construction of a family of supramolecular gels with good levofloxacin hydrochloride loading capacity

“…40,41 Marchesan et al constructed an antimicrobial hydrogel using a phenylalanine derivative. 42 Feng et al developed phenylalanine-based chiral co-assembled hydrogels with enhanced mechanical properties and antimicrobial activity, which were prepared using a phenylalanine derivative and a dihydrazide compound. 43 To the best of our knowledge, simultaneously taking advantage of phenylalanine and hydrazide groups to construct LMWGs for antimicrobial therapy has not been reported.…”