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Self-assembly of an amino acid derivative into an antimicrobial hydrogel biomaterial

Ana M. Garcia, Roy Lavendomme (UGent) , Slavko Kralj, Marina Kurbasic, Ottavia Bellotto, Maria C. Cringoli, Sabrina Semeraro, Antonella Bandiera, Rita De Zorzi and Silvia Marchesan
(2020) CHEMISTRY-A EUROPEAN JOURNAL. 26(8). p.1880-1886
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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 pK(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 degrees C, thus opening the way to its potential use as a biomaterial.
Keywords
General Chemistry, hydrogels, phenylalanine, self-assembly, supramolecular chemistry, THIOFLAVIN-T, RAMAN-SPECTRA, PEPTIDE, PHENYLALANINE, DIPEPTIDE, FIBRILS, CRYSTALLIZATION, SENSITIVITY, HISTIDINE, BINDING

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MLA
Garcia, Ana M., et al. “Self-Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial.” CHEMISTRY-A EUROPEAN JOURNAL, vol. 26, no. 8, 2020, pp. 1880–86, doi:10.1002/chem.201905681.
APA
Garcia, A. M., Lavendomme, R., Kralj, S., Kurbasic, M., Bellotto, O., Cringoli, M. C., … Marchesan, S. (2020). Self-assembly of an amino acid derivative into an antimicrobial hydrogel biomaterial. CHEMISTRY-A EUROPEAN JOURNAL, 26(8), 1880–1886. https://doi.org/10.1002/chem.201905681
Chicago author-date
Garcia, Ana M., Roy Lavendomme, Slavko Kralj, Marina Kurbasic, Ottavia Bellotto, Maria C. Cringoli, Sabrina Semeraro, Antonella Bandiera, Rita De Zorzi, and Silvia Marchesan. 2020. “Self-Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial.” CHEMISTRY-A EUROPEAN JOURNAL 26 (8): 1880–86. https://doi.org/10.1002/chem.201905681.
Chicago author-date (all authors)
Garcia, Ana M., Roy Lavendomme, Slavko Kralj, Marina Kurbasic, Ottavia Bellotto, Maria C. Cringoli, Sabrina Semeraro, Antonella Bandiera, Rita De Zorzi, and Silvia Marchesan. 2020. “Self-Assembly of an Amino Acid Derivative into an Antimicrobial Hydrogel Biomaterial.” CHEMISTRY-A EUROPEAN JOURNAL 26 (8): 1880–1886. doi:10.1002/chem.201905681.
Vancouver
1.
Garcia AM, Lavendomme R, Kralj S, Kurbasic M, Bellotto O, Cringoli MC, et al. Self-assembly of an amino acid derivative into an antimicrobial hydrogel biomaterial. CHEMISTRY-A EUROPEAN JOURNAL. 2020;26(8):1880–6.
IEEE
[1]
A. M. Garcia et al., “Self-assembly of an amino acid derivative into an antimicrobial hydrogel biomaterial,” CHEMISTRY-A EUROPEAN JOURNAL, vol. 26, no. 8, pp. 1880–1886, 2020.
@article{8647481,
  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 pK(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 degrees C, thus opening the way to its potential use as a biomaterial.}},
  author       = {{Garcia, Ana M. and Lavendomme, Roy and Kralj, Slavko and Kurbasic, Marina and Bellotto, Ottavia and Cringoli, Maria C. and Semeraro, Sabrina and Bandiera, Antonella and De Zorzi, Rita and Marchesan, Silvia}},
  issn         = {{0947-6539}},
  journal      = {{CHEMISTRY-A EUROPEAN JOURNAL}},
  keywords     = {{General Chemistry,hydrogels,phenylalanine,self-assembly,supramolecular chemistry,THIOFLAVIN-T,RAMAN-SPECTRA,PEPTIDE,PHENYLALANINE,DIPEPTIDE,FIBRILS,CRYSTALLIZATION,SENSITIVITY,HISTIDINE,BINDING}},
  language     = {{eng}},
  number       = {{8}},
  pages        = {{1880--1886}},
  title        = {{Self-assembly of an amino acid derivative into an antimicrobial hydrogel biomaterial}},
  url          = {{http://doi.org/10.1002/chem.201905681}},
  volume       = {{26}},
  year         = {{2020}},
}
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