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Biological and Physico-Chemical Characteristics of Arginine-Rich Peptide Gemini Surfactants with Lysine and Cystine Spacers
- Source :
- International Journal of Molecular Sciences, Volume 22, Issue 7, International Journal of Molecular Sciences, Vol 22, Iss 3299, p 3299 (2021)
- Publication Year :
- 2021
- Publisher :
- MDPI, 2021.
-
Abstract
- Ultrashort cationic lipopeptides (USCLs) and gemini cationic surfactants are classes of potent antimicrobials. Our recent study has shown that the branching and shortening of the fatty acids chains with the simultaneous addition of a hydrophobic N-terminal amino acid in USCLs result in compounds with enhanced selectivity. Here, this approach was introduced into arginine-rich gemini cationic surfactants. L-cystine diamide and L-lysine amide linkers were used as spacers. Antimicrobial activity against planktonic and biofilm cultures of ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter spp.) strains and Candida sp. as well as hemolytic and cytotoxic activities were examined. Moreover, antimicrobial activity in the presence of human serum and the ability to form micelles were evaluated. Membrane permeabilization study, serum stability assay, and molecular dynamics were performed. Generally, critical aggregation concentration was linearly correlated with hydrophobicity. Gemini surfactants were more active than the parent USCLs, and they turned out to be selective antimicrobial agents with relatively low hemolytic and cytotoxic activities. Geminis with the L-cystine diamide spacer seem to be less cytotoxic than their L-lysine amide counterparts, but they exhibited lower antibiofilm and antimicrobial activities in serum. In some cases, geminis with branched fatty acid chains and N-terminal hydrophobic amino acid resides exhibited enhanced selectivity to pathogens over human cells.
- Subjects :
- 0301 basic medicine
Lysine
antimicrobial lipopeptides
Amino Acid Motifs
Peptide
Micelle
lcsh:Chemistry
chemistry.chemical_compound
Amide
arginine-rich lipopeptides
lcsh:QH301-705.5
Spectroscopy
Micelles
Candida
chemistry.chemical_classification
Fatty Acids
General Medicine
Antimicrobial
Computer Science Applications
Amino acid
Biochemistry
Cystine
Hydrophobic and Hydrophilic Interactions
gemini surfactants
Lipoproteins
030106 microbiology
ESKAPE
Arginine
Hemolysis
Catalysis
Article
Inorganic Chemistry
03 medical and health sciences
Surface-Active Agents
cationic lipopeptides
Enterobacteriaceae
Cationic Lipopeptides
Physical and Theoretical Chemistry
Molecular Biology
antibiofilm
Organic Chemistry
Cell Membrane
Fatty acid
antibacterial
030104 developmental biology
lcsh:Biology (General)
lcsh:QD1-999
chemistry
Biofilms
gemini lipopeptides
antifungal
Antimicrobial Cationic Peptides
Subjects
Details
- Language :
- English
- ISSN :
- 14220067
- Volume :
- 22
- Issue :
- 7
- Database :
- OpenAIRE
- Journal :
- International Journal of Molecular Sciences
- Accession number :
- edsair.doi.dedup.....8dadeafb0944347464c4e8ee4ffc9cd9