Amino acid containing amphiphilic hydrogelators with antibacterial and antiparasitic activities. Issue 37 (13th September 2022)

• Record Type: Journal Article
• Authors: Mondal, Biplab; Gupta, Vivek Kumar; Hansda, Biswanath; Bhoumik, Arpita; Mondal, Tanushree; Majumder, Hemanta K.; Edwards-Gayle, Charlotte J. C.; Hamley, Ian W.; Jaisankar, Parasuraman; Banerjee, Arindam
• Is Part Of: Soft matter. Volume 18:Issue 37(2022)
• Page Start: 7201
• Page End: 7216
• Publication Date: 2022-09-13
• Subjects: Soft condensed matter -- Periodicals; 530.413
• DOI: 10.1039/d2sm00562j
• Languages: English
• ISSNs: 1744-683X

Abstract

Abstract : Nanoscale self-assembly of peptide constructs represents a promising means to present bioactive motifs to develop new functional materials. Abstract : 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, MIL R and CPT R 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.