Synthesis, characterization and hybridization studies of an alternate nucleo-epsilon/gamma-peptide: complexes formation with natural nucleic acids

Amino Acids. 2010 Jan;38(1):103-11. doi: 10.1007/s00726-008-0214-7. Epub 2008 Dec 7.

Abstract

In order to develop new oligodeoxyribonucleotide (ODN) analogs to be used in biotechnological applications, we report here the synthesis, characterization and nucleic acid binding studies of novel nucleopeptides, that we called epsilon-lys/gamma-dabPNAs, containing a backbone of alternated L-diaminobutyric acid and L-lysine moieties. Exploring the hybridization properties of the new ODN analog, we found, by circular dichroism and UV spectroscopies, that a homothymine epsilon-lys/gamma-dabPNA hexamer binds both DNA and RNA of complementary sequence. Furthermore, human serum stability assays on the alternate nucleopeptide evidenced a noteworthy degradation resistance. These results encourage us to deepen the knowledge of this analog, in order to evaluate its possible use in antigene/antisense or diagnostic applications.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA / chemistry
  • Humans
  • Molecular Structure
  • Nucleic Acid Hybridization
  • Oligodeoxyribonucleotides / chemical synthesis
  • Oligodeoxyribonucleotides / chemistry*
  • Peptide Nucleic Acids / chemistry*
  • Peptides / chemical synthesis
  • Peptides / chemistry*
  • RNA / chemistry

Substances

  • Oligodeoxyribonucleotides
  • Peptide Nucleic Acids
  • Peptides
  • RNA
  • DNA