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Amino acid containing amphiphilic hydrogelators with antibacterial and antiparasitic activity

Banerjee, A., Mondal, B., Gupta, V. K., Hansda, B., Bhoumik, A., Mondal, T., Majumder, H., Edwards-Gayle, C. J. C., Hamley, I. ORCID: and Jaisankar, P. (2022) Amino acid containing amphiphilic hydrogelators with antibacterial and antiparasitic activity. Soft Matter. ISSN 1744-683X (In Press)

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To link to this item DOI: 10.1039/D2SM00562J


Here we present a series of peptide amphiphiles which form hydrogels based on beta-sheet nanofibril networks, several of which have very promising anti-microbial and anti-parasitic activities, in particular against multiple strains of Leishmania including drug-resistant ones. Aromatic amino acid based amphiphilic supramolecular gelators C14-Phe-CONH-(CH2)n-NH2 (n=6 for P1 and n=2 for P3) and C14-Trp-CONH-(CH2)n-NH2 (n=6 for P2 and n=2 for P4) have been synthesized, characterized, and their self-assembly and gelation behaviour has been investigated in the presence of ultrapure water (P1, P2, P4) or 2% DMSO(v/v) in ultrapure water (P3). The rheological, morphological and structural properties of the gels have been comprehensively examined. The amphiphilic gelators (P1 and P3) were found to be active against both Gram-positive bacteria B. subtilis and Gram-negative bacteria E. coli and P. aeruginosa. Interestingly, amphiphiles P1 and P3 containing L-phenyl alanine residue show both antibacterial and antiparasitic activity. Herein, we report that synthetic amphiphiles with an amino acid residue exhibit a potent anti-protozoan activity and are cytotoxic towards a wide array of protozoal parasites, which includes Indian varieties of Leishmania donovani and also kill resistant parasitic strains including BHU575, MILR and CAMR cells. These gelators are highly cytotoxic to promastigotes of Leishmania and trigger apoptotic-like events inside the parasite. The mechanism of killing the parasite is shown and these gelators are non-cytotoxic to host macrophage cells indicating a potential use of these gels as therapeutic agents against multiple forms of leishmaniasis in the near future.

Item Type:Article
Divisions:Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:106975
Publisher:Royal Society of Chemistry

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