Membrane anchoring of a curvature-inducing peptide, EpN18, promotes membrane translocation of octaarginine

Kakeru Kuroki; Takayuki Sakai; Toshihiro Masuda; Kenichi Kawano; Shiroh Futaki

doi:10.1016/j.bmcl.2021.128103

Membrane anchoring of a curvature-inducing peptide, EpN18, promotes membrane translocation of octaarginine

Bioorg Med Chem Lett. 2021 Jul 1:43:128103. doi: 10.1016/j.bmcl.2021.128103. Epub 2021 May 10.

Authors

Kakeru Kuroki¹, Takayuki Sakai¹, Toshihiro Masuda¹, Kenichi Kawano¹, Shiroh Futaki²

Affiliations

¹ Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
² Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan. Electronic address: futaki@scl.kyoto-u.ac.jp.

PMID: 33984474
DOI: 10.1016/j.bmcl.2021.128103

Abstract

EpN18 is a curvature-inducing peptide, which loosens lipid packing upon interaction with the cell membrane, and facilitates cell-membrane penetration by arginine-rich cell-penetrating peptides, including octaarginine (R8). In the present study, we conjugated the N-terminal of EpN18 with a pyrenebutyryl (pBu) moiety, which acts as an anchoring unit that increases membrane interactions. Enhanced lipid-packing loosening and cytosolic translocation of R8 were observed by the pBu anchoring of EpN18.

Keywords: Cell membrane translocation; Curvature-inducing peptide; Lipid packing loosening; Octaarginine; Pyrenebutyric acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cell Membrane / chemistry
Cell Membrane / metabolism*
Humans
Molecular Structure
Oligopeptides / chemistry
Oligopeptides / metabolism*
Peptides / chemistry
Peptides / metabolism*
Protein Transport

Substances

Oligopeptides
Peptides
octaarginine