Highly efficient (R-X-R)-type carbamates as molecular transporters for cellular delivery

J Am Chem Soc. 2012 May 2;134(17):7196-9. doi: 10.1021/ja210026m. Epub 2012 Apr 17.

Abstract

The (R-X-R) motif-containing arginine-rich peptides are among the most effective cell-penetrating peptides. The replacement of amide linkages in the (R-X-R) motif by carbamate linkages as in (r-ahx-r)(4) or (r-ahx-r-r-apr-r)(2) increases the efficacy of such oligomers several-fold. Internalization of these oligomers in mammalian cell lines occurs by an energy-independent process. These oligomers show efficient delivery of biologically active plasmid DNA into CHO-K1 cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arginine / chemistry*
  • Arginine / metabolism
  • CHO Cells
  • Carbamates / chemistry*
  • Carbamates / metabolism
  • Cell Membrane Permeability
  • Cell-Penetrating Peptides / chemistry*
  • Cell-Penetrating Peptides / metabolism
  • Cricetinae
  • DNA / administration & dosage*
  • Plasmids / administration & dosage*
  • Transfection

Substances

  • Carbamates
  • Cell-Penetrating Peptides
  • DNA
  • Arginine