The retro-inverso form of a homeobox-derived short peptide is rapidly internalised by cultured neurones: a new basis for an efficient intracellular delivery system

Biochem Biophys Res Commun. 1995 Sep 14;214(2):685-93. doi: 10.1006/bbrc.1995.2340.

Abstract

The capacity of a retro-inverso form of a 16-residue peptide from the Antennapedia homeodomain to be taken up by cultured neurones was tested. Like its homologue made of L-amino acids, it was rapidly internalised and distributed throughout the cytoplasm and even the cell nucleus. The amount of retro-inverso peptide in cells after incubation in culture medium was 3.4 times that of the L-peptide form. With a cholesteryl moiety attached to the C-terminus to increase its lipophilicity, the retro-inverso peptide was internalised 8 times better than the L-form. The greater efficiency of the peptidomimetic is probably due to the resistance to proteolytic degradation conferred by the D-amino acids, as the sequence contains two sites sensitive to neuronal endoproteases. The peptide might be the basis for development of system for delivering a variety of molecules into cells.

Publication types

  • Comparative Study

MeSH terms

  • Amino Acid Sequence
  • Animals
  • Antennapedia Homeodomain Protein
  • Biological Transport
  • Biotin
  • Brain / metabolism*
  • Cells, Cultured
  • DNA-Binding Proteins / metabolism*
  • Drug Carriers
  • Embryo, Mammalian
  • Homeodomain Proteins*
  • Isoleucine
  • Molecular Sequence Data
  • Neurons / metabolism*
  • Nuclear Proteins*
  • Peptides / chemical synthesis
  • Peptides / chemistry
  • Peptides / metabolism*
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • Transcription Factors / metabolism

Substances

  • Antennapedia Homeodomain Protein
  • DNA-Binding Proteins
  • Drug Carriers
  • Homeodomain Proteins
  • Nuclear Proteins
  • Peptides
  • Transcription Factors
  • Isoleucine
  • Biotin