NDLI: Structure–activity relationships in ultrashort cationic lipopeptides: the effects of amino acid ring constraint on antibacterial activity

Content Provider	Springer Nature Link
Author	Domalaon, Ronald Yang, Xuan O’Neil, Joe Zhanel, George G. Mookherjee, Neeloffer Schweizer, Frank
Copyright Year	2014
Abstract	Taking a minimalistic approach in efforts to lower the cost for the development of new synthetic antimicrobial peptides, ultrashort cationic lipopeptides were designed to mimic the amphiphilic nature crucial for their activity but with only a very short peptide sequence ligated to a lipidic acid. Nine ultrashort cationic lipopeptides were prepared to study the effects of ring constraint in the amino acid side chain of the peptide component. USCL-PCat1, consisting of only four l-4R-aminoproline residues and acylated with palmitic acid at the N-terminus, was found to populate a polyproline II helical secondary conformation that is stable to different pHs and temperatures using circular dichroism. The synthesized lipopeptides were found to have a micellar structure in water using negative staining transmission electron microscopy. We found that constraining the side chain of the amino acid component is not beneficial to the antimicrobial activity. USCL-Dab1, USCL-Dab3 and USCL-K1 showed promising activity against a panel of laboratory reference and clinically isolated Gram-positive and Gram-negative bacterial strains, some of which are multidrug resistant. No appreciable cytotoxicity against human monocytic THP-1 cells was observed up to concentrations of 20–40 µM for all synthesized compounds. Moreover, all USCLs did not induce the production of either pro-inflammatory cytokines or chemokines up to 40 µM.
Starting Page	2517
Ending Page	2530
Page Count	14
File Format	PDF
ISSN	09394451
Journal	Amino Acids
Volume Number	46
Issue Number	11
e-ISSN	14382199
Language	English
Publisher	Springer Vienna
Publisher Date	2014-07-29
Publisher Place	Vienna
Access Restriction	Subscribed
Subject Keyword	Antimicrobial peptides Ultrashort cationic lipopeptides Polyproline II helix Circular dichroism Cationic amphiphiles Biochemistry Analytical Chemistry Biochemical Engineering Life Sciences Proteomics Neurobiology
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Clinical Biochemistry

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