Cited by 35Supramolecular Self-Assembly in MaterialsLipid Membrane Structure and BehaviorSilk-based biomaterials and applications

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

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Sato, Kohei, Ji, Wei, Álvarez, Zaida, Palmer, Liam C., Stupp, Samuel I.·2019·ACS Biomaterials Science & Engineering

Abstract

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.

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Crossref · 10.1021/acsbiomaterials.9b00553

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  • There is evidence for diastereoselective permeation and enantioselective membrane binding of amino acids and peptides.

    “Very few studies have probed the interactions between chiral molecules and chiral membranes, but there is evidence for diastereoselective permeation6 and enantioselective membrane binding of amino acids9 and peptides.10,11”

    From Chiral lipid bilayers are enantioselectively permeable (2021) · cites this paper as [9]

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  1. Noyori, R. Asymmetric Catalysis: Science and Opportunities (Novel Lecture). Angew. Chem., Int. Ed. 2002, 41, 2008-2022.

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Authors
Sato, K., Ji, W., Álvarez, Z., Palmer, L. C., & Stupp, S. I.
Affiliations
Northwestern University (US)
Corresponding author
Stupp, Samuel I.
Venue
ACS Biomaterials Science & Engineering
Published
2019-05-29
Volume
5
Issue
6
Pages
2786-2792
ISSN
2373-9878 (ISSN-L)
OpenAlex
W2947557583
Cited by
35
References
51
Citations by year
2026: 1 · 2025: 7 · 2024: 3 · 2023: 5 · 2022: 3 · 2021: 9 · 2020: 5 · 2019: 2
FWCI
1.35
Type
journal article
Language
en
Open access
Locations
  • ACS Biomaterials Science & Engineering (publishedVersion)
  • PubMed (publishedVersion)
  • OSTI OAI (U.S. Department of Energy Office of Scientific and Technical Information) (submittedVersion)
Funders
  • Fonds Wetenschappelijk Onderzoek (V468915N, 12G2718N)
  • Paralyzed Veterans of America Research Foundation (PVA17_RF_0008)
  • Japan Society for the Promotion of Science (18H05971)
  • U.S. Department of Energy (DE-SC0000989)
  • Beatriu de Pin??s - Ag??ncia de Gesti?? d'Ajust Universitaris i de Recerca (2014 BP-A 00007)
  • KU Leuven Junior Mobility Programme (JUMO-15-0514)
Topics
  • Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
  • Physical Sciences › Materials Science › Biomaterials › Silk-based biomaterials and applications
Keywords
chiral recognition, peptide amphiphiles, supramolecular self-assembly, lipid bilayers, L-amino acids, D-amino acids, stereospecific interactions, liposomes, nanofibers, cytotoxicity, mesenchymal stem cells, astroglial cells, homochirality

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