title: Cyclization Improves Membrane Permeation by Antimicrobial Peptoids.
abstract: The peptidomimetic approach has emerged as a powerful tool for overcoming the inherent limitations of natural antimicrobial peptides, where the therapeutic potential can be improved by increasing the selectivity and bioavailability. Restraining the conformational flexibility of a molecule may reduce the entropy loss upon its binding to the membrane. Experimental findings demonstrate that the cyclization of linear antimicrobial peptoids increases their bactericidal activity against Staphylococcus aureus while maintaining high hemolytic concentrations. Surface X-ray scattering shows that macrocyclic peptoids intercalate into Langmuir monolayers of anionic lipids with greater efficacy than for their linear analogues. It is suggested that cyclization may increase peptoid activity by allowing the macrocycle to better penetrate the bacterial cell membrane.
authors: Department of Physics, Center for Molecular Study of Condensed Soft Matter (μCoSM), Pritzker Institute of Biomedical Science and Engineering, Illinois Institute of Technology , 3440 South Dearborn Street, Chicago, Illinois 60616, United States.
authors: Konstantin
authors: K
authors: Andreev
authors: Department of Physics, Center for Molecular Study of Condensed Soft Matter (μCoSM), Pritzker Institute of Biomedical Science and Engineering, Illinois Institute of Technology , 3440 South Dearborn Street, Chicago, Illinois 60616, United States.|Advanced Photon Source, Argonne National Laboratory, 9700 South Cass Avenue, Lemont, Illinois 60439, United States.
authors: Michael W
authors: MW
authors: Martynowycz
authors: Department of Physics, Center for Molecular Study of Condensed Soft Matter (μCoSM), Pritzker Institute of Biomedical Science and Engineering, Illinois Institute of Technology , 3440 South Dearborn Street, Chicago, Illinois 60616, United States.
authors: Andrey
authors: A
authors: Ivankin
authors: Department of Chemistry, New York University , 100 Washington Square East, New York, New York 10003, United States.
authors: Mia L
authors: ML
authors: Huang
authors: Advanced Photon Source, Argonne National Laboratory, 9700 South Cass Avenue, Lemont, Illinois 60439, United States.
authors: Ivan
authors: I
authors: Kuzmenko
authors: The Center for Advanced Radiation Sources (CARS), University of Chicago , Chicago, Illinois 60637, United States.
authors: Mati
authors: M
authors: Meron
authors: The Center for Advanced Radiation Sources (CARS), University of Chicago , Chicago, Illinois 60637, United States.
authors: Binhua
authors: B
authors: Lin
authors: Department of Chemistry, New York University , 100 Washington Square East, New York, New York 10003, United States.
authors: Kent
authors: K
authors: Kirshenbaum
authors: Department of Physics, Center for Molecular Study of Condensed Soft Matter (μCoSM), Pritzker Institute of Biomedical Science and Engineering, Illinois Institute of Technology , 3440 South Dearborn Street, Chicago, Illinois 60616, United States.
authors: David
authors: D
authors: Gidalevitz
mesh_terms: D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002462:Cell Membrane / Q000187:drug effects; D003500:Cyclization; D034444:Peptoids / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000900:Anti-Bacterial Agents; D034444:Peptoids