title: Self-assembly to function: design, synthesis, and broad spectrum antimicrobial properties of short hybrid E-vinylogous lipopeptides.
abstract: Nonribosomal E-vinylogous γ-amino acids are widely present in many peptide natural products and have been exploited as inhibitors for serine and cysteine proteases. Here, we are reporting the broad spectrum antimicrobial properties and self-assembled nanostructures of various hybrid lipopeptides composed of 1:1 alternating α- and E-vinylogous residues. Analysis of the results revealed that self-assembled nanostructures also play a significant role in the antimicrobial and hemolytic activities. In contrast to the α-peptide counterparts, vinylogous hybrid peptides displayed excellent antimicrobial properties against various bacterial and fungal strains. Peptides that adopted nanofiber structures displayed less hemolytic activity, while peptides that adopted nanoneedle structures displayed the highest hemolytic activity.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research , Dr. Homi Bhabha Road, Pune-41108, India.
authors.forename: S Shiva
authors.initials: SS
authors.lastname: Shankar
authors.forename: Sushil N
authors.initials: SN
authors.lastname: Benke
authors.forename: Narem
authors.initials: N
authors.lastname: Nagendra
authors.forename: Prabhakar Lal
authors.initials: PL
authors.lastname: Srivastava
authors.forename: Hirekodathakallu V
authors.initials: HV
authors.lastname: Thulasiram
authors.forename: Hosahudya N
authors.initials: HN
authors.lastname: Gopi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002176:Candida albicans / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D015195:Drug Design; D004926:Escherichia coli / Q000166:cytology / Q000187:drug effects*; D006461:Hemolysis; D055666:Lipopeptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D018625:Microscopy, Atomic Force; D015394:Molecular Structure; D010316:Particle Size; D013329:Structure-Activity Relationship; D013499:Surface Properties
chemical_list: D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D055666:Lipopeptides