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Amino acid containing amphiphilic hydrogelators with antibacterial and antiparasitic activities

Mondal, B., Gupta, V. K., Hansda, B., Bhoumik, A., Mondal, T., Majumder, H. K., Edwards-Gayle, C. J. C., Hamley, I. W. ORCID:, Jaisankar, P. and Banerjee, A. (2022) Amino acid containing amphiphilic hydrogelators with antibacterial and antiparasitic activities. Soft Matter, 18 (37). pp. 7201-7216. ISSN 1744-683X

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To link to this item DOI: 10.1039/D2SM00562J


Nanoscale self-assembly of peptide constructs represents a promising means to present bioactive motifs to develop new functional materials. Here, we present a series of peptide amphiphiles which form hydrogels based on β-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 and characterized, and their self-assembly and gelation behaviour have been investigated in the presence of ultrapure water (P1, P2, and 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 an L-phenylalanine residue show both antibacterial and antiparasitic activities. 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 BHU-575, MILR and CPTR 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 the 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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