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© K. Melican.
Human microvessel (red) colonized by N. meningitidis (green).
Publication : Bioorganic & medicinal chemistry

Effect of replacing main-chain ureas with thiourea and guanidinium surrogates on the bactericidal activity of membrane active oligourea foldamers

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Bioorganic & medicinal chemistry - 29 Apr 2017

Antunes S, Corre JP, Mikaty G, Douat C, Goossens PL, Guichard G

Link to Pubmed [PMID] – 28687228

Bioorg. Med. Chem. 2017 Aug;25(16):4245-4252

Membrane-active foldamers have recently emerged as potential mimics of antimicrobial peptides (AMPs). Amphiphilic cationic helical N,N’-linked oligoureas are one such class of AMP mimics with activities in vitro against a broad range of bacteria including Bacillus anthracis, a Gram-positive sporulating bacillus and causing agent of anthrax. Here we have used site-selective chemical modifications of the oligourea backbone to gain additional insight into the relationship between structure and function and modulate anthracidal activity. A series of analogues in which urea linkages at selected positions are replaced by thiourea and guanidium surrogates have been prepared on solid support and tested against different bacterial forms of B. anthracis (germinated spores and encapsulated bacilli). Urea→thiourea and urea→guanidinium replacements close to the negative end of the helix dipole led to analogues with increased potency and selectivity for B. anthracis versus mammalian cells.

https://www.ncbi.nlm.nih.gov/pubmed/28687228