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A Helix‐Stabilized Cell‐Penetrating Peptide as an Intracellular Delivery Tool
Author(s) -
Yamashita Hiroko,
Oba Makoto,
Misawa Takashi,
Tanaka Masakazu,
Hattori Takayuki,
Naito Mikihiko,
Kurihara Masaaki,
Demizu Yosuke
Publication year - 2016
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201500468
Subject(s) - intracellular , cell penetrating peptide , peptide , helix (gastropod) , cell , chemistry , biophysics , nanotechnology , biochemistry , microbiology and biotechnology , materials science , biology , ecology , snail
Two types of cationic cyclic α,α‐disubstituted α‐amino acids: ApiC 2 NH2(which possesses a lysine mimic side chain) and Api C2Gu (which possesses an arginine mimic side chain), were developed. These amino acids were incorporated into an arginine‐based peptide sequence [( l ‐Arg‐ l ‐Arg‐dAA) 3 : dAA=ApiC 2 NH2or Api C2Gu ], and the relationship between the secondary structures of the resulting peptides and their ability to pass through cell membranes was investigated. The peptide containing Api C2Gu formed a stable α‐helical structure and was more effective at penetrating cells than the nonhelical Arg nonapeptide (R 9 ). Furthermore, the peptide was able to deliver plasmid DNA into various types of cells in a highly efficient manner.