Chiral Recognition of Lipid Bilayer Membranes by Supramolecular Assemblies of Peptide Amphiphiles

Kohei Sato, Wei Ji, Zaida Álvarez, Liam C. Palmer, Samuel I. Stupp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Scopus citations


On the basis of the exclusive existence of homochirality in biomolecules and the well-known phenomenon of chiral recognition, it is obvious that chirality is a crucial factor in biological events. We report here that supramolecular assemblies of peptide amphiphiles interact with lipid bilayer membranes in a stereospecific manner. When negatively charged chiral phospholipid bilayer vesicles were subjected to the assemblies, we found that peptide amphiphiles with l-amino acids show stronger affinity for the liposomes compared to the ones with d-amino acids. To examine their biological functions, we tested the cytotoxicity of nanofibers against mammalian primary cells using human bone marrow mesenchymal stem cells and murine astroglial cells. We demonstrated that cell viability increased when d-amino acids were incorporated in the structure of peptide amphiphiles, which is consistent with our finding of their weaker interactions with lipid bilayer membranes.

Original languageEnglish (US)
Pages (from-to)2786-2792
Number of pages7
JournalACS Biomaterials Science and Engineering
Issue number6
StatePublished - Jun 10 2019


  • chiral recognition
  • lipid bilayer membrane
  • mammalian primary cells
  • peptide amphiphile
  • supramolecular assembly

ASJC Scopus subject areas

  • Biomedical Engineering
  • Biomaterials


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