Short alkylated peptoid mimics of antimicrobial lipopeptides.
We report the creation of alkylated poly-N-substituted glycine (peptoid) mimics of antimicrobial lipopeptides with alkyl tails ranging from 5 to 13 carbons. In several cases, alkylation significantly improved the selectivity of the peptoids with no loss in antimicrobial potency. Using this technique, we synthesized an antimicrobial peptoid only 5 monomers in length with selective, broad-spectrum antimicrobial activity as potent as previously reported dodecameric peptoids and the antimicrobial peptide pexiganan.
Department of Chemical and Biological Engineering, Northwestern University, Evanston, Illinois 60208, USA.
Nathaniel P
NP
Chongsiriwatana
Tyler M
TM
Miller
Modi
M
Wetzler
Sergei
S
Vakulenko
Amy J
AJ
Karlsson
Sean P
SP
Palecek
Shahriar
S
Mobashery
Annelise E
AE
Barron
D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D002478:Cells, Cultured; D006461:Hemolysis / Q000187:drug effects; D006801:Humans; D055666:Lipopeptides / Q000737:chemistry* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D034444:Peptoids / Q000737:chemistry* / Q000494:pharmacology*
D000890:Anti-Infective Agents; D055666:Lipopeptides; D034444:Peptoids