Structural Development of Cell-Penetrating Peptides Containing Cationic Proline Derivatives

Hiroyuki Kobayashi; Takashi Misawa; Makoto Oba; Naoya Hirata; Yasunari Kanda; Masakazu Tanaka; Kenji Matsuno; Yosuke Demizu

doi:10.1248/cpb.c18-00079

Regular Articles

Structural Development of Cell-Penetrating Peptides Containing Cationic Proline Derivatives

Hiroyuki Kobayashi, Takashi Misawa , Makoto Oba, Naoya Hirata, Yasunari Kanda, Masakazu Tanaka, Kenji Matsuno, Yosuke Demizu

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Keywords: cell-penetrating peptide, cationic proline derivative, cellular environment, drug delivery system (DDS) carrier

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Supplementary material

2018 Volume 66 Issue 5 Pages 575-580

DOI https://doi.org/10.1248/cpb.c18-00079

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Abstract

We designed and synthesized a series of cell-penetrating peptides containing cationic proline derivatives (Pro^Gu) that exhibited responsive changes in their secondary structures to the cellular environment. Effects of the peptide length and steric arrangement of the side chain in cationic proline derivatives [Pro^4SGu and Pro^4RGu] on their secondary structures and cell membrane permeability were investigated. Moreover, peptides 3 and 8 exhibited efficient intracellular delivery of plasmid DNA.

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