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Cell-penetrating peptides (CPP) are received a lot of attention as an intracellular delivery tool for hydrophilic molecules such as drugs, proteins, and DNAs. We designed and synthesized nona-arginine analogues  1 – 5  [FAM-β-Ala-( l -Arg- l -Arg- l -Pro) 3 -(Gly) 3 -NH 2  ( 1 ), FAM-β-Ala-( l -Arg- l -Arg- l -Pro NH2 ) 3 -(Gly) 3 -NH 2  ( 2 ), FAM-β-Ala-( l -Arg- l -Arg- l -Pro Gu ) 3 -(Gly) 3 -NH 2  ( 3 ), FAM-β-Ala-( l -Arg) 2 -( l -Pro Gu ) 2 -( l -Arg) 4 - l -Pro Gu -(Gly) 3 -NH 2  ( 4 ), and FAM-β-Ala-( l -Arg) 6 -( l -Pro Gu ) 3 -(Gly) 3 -NH 2  ( 5 )] containing  l -proline ( l -Pro) or cationic proline derivatives ( l -Pro NH2  and  l -Pro Gu ), and investigated their cell-penetrating abilities. Interestingly, only peptide  3  having the side-chain guanidinyl  l -Pro Gu  exhibited a secondary structural change in cellular environment. Specifically, peptide  3  formed a random structure in hydrophilic conditions, whereas it formed a helical structure under amphipathic conditions. Furthermore, during cellular permeability tests, peptide  3  demonstrated greater cell-penetrating activity than other peptides and effectively transported plasmid DNA into HeLa cells. Thus,  l -Pro Gu -containing peptide  3  may be a useful candidate as a gene delivery carrier.

Development of a Cell-penetrating Peptide that Exhibits Responsive Changes in its Secondary Structure in the Cellular Environment