Jump to main content
Jump to site search

Issue 12, 2018
Previous Article Next Article

Fmoc-phenylalanine displays antibacterial activity against Gram-positive bacteria in gel and solution phases

Author affiliations

Abstract

In the quest for new antimicrobial materials, hydrogels of Fmoc-protected peptides and amino acids have gained momentum due to their ease of synthesis and cost effectiveness; however, their repertoire is currently limited, and the mechanistic details of their function are not well understood. Herein, we report the antibacterial activity of the hydrogel and solution phases of Fmoc-phenylalanine (Fmoc-F) against a variety of Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Fmoc-F, a small molecule hydrogelator, reduces the bacterial load both in vitro and in the skin wound infections of mice. The antibacterial activity of Fmoc-F is predominantly due to its release from the hydrogel. Fmoc-F shows surfactant-like properties with critical micelle concentration nearly equivalent to its minimum bactericidal concentration. Similar to Fmoc-F, some Fmoc-conjugated amino acids (Fmoc-AA) have also shown antibacterial effects that are linearly correlated with their surfactant properties. At low concentrations, where Fmoc-F does not form micelles, it inhibits bacterial growth by entering the cell and reducing the glutathione levels. However, at higher concentrations, Fmoc-F triggers oxidative and osmotic stress and, alters the membrane permeabilization and integrity, which kills Gram-positive bacteria. Herein, we proposed the use of the Fmoc-F hydrogel and its solution for several biomedical applications. This study will open up new avenues to enhance the repertoire of Fmoc-AA to act as antimicrobial agents and improve their structure–activity relationship.

Graphical abstract: Fmoc-phenylalanine displays antibacterial activity against Gram-positive bacteria in gel and solution phases

Back to tab navigation

Supplementary files

Publication details

The article was received on 24 Nov 2017, accepted on 22 Feb 2018 and first published on 24 Feb 2018


Article type: Paper
DOI: 10.1039/C7SM02317K
Citation: Soft Matter, 2018,14, 2234-2244
  •   Request permissions

    Fmoc-phenylalanine displays antibacterial activity against Gram-positive bacteria in gel and solution phases

    A. Y. Gahane, P. Ranjan, V. Singh, R. K. Sharma, N. Sinha, M. Sharma, R. Chaudhry and A. K. Thakur, Soft Matter, 2018, 14, 2234
    DOI: 10.1039/C7SM02317K

Search articles by author

Spotlight

Advertisements