ABSTRACT
Continuing our research on the development of nucleopeptides as ODN analogs for biomedical and bioengineering applications, here we report the synthesis and the chemical-physical characterization of a homoadenine hexamer based on a l-diaminobutyric acid (l-DABA) backbone (dabPNA), and its binding studies with a complementary aegPNA. We demonstrated by CD and UV experiments that the l-dabPNA binds the aegPNA forming a complex with good thermal stability, that we identified as a left-handed triplex.
Subject(s)
Aminobutyrates/chemistry , Aminobutyrates/metabolism , Glycine/analogs & derivatives , Peptide Nucleic Acids/chemistry , Peptide Nucleic Acids/metabolism , Adenine Nucleotides/chemical synthesis , Adenine Nucleotides/chemistry , Adenine Nucleotides/metabolism , Circular Dichroism , DNA/chemistry , DNA/metabolism , Drug Design , Glycine/chemistry , Glycine/metabolism , Magnetic Resonance Spectroscopy , Peptide Nucleic Acids/chemical synthesis , Peptide Nucleic Acids/isolation & purification , Spectrometry, Mass, Electrospray IonizationABSTRACT
In continuing our research efforts for developing new oligodeoxynucleotide (ODN)-like drugs and diagnostics, we designed diaminobutyric peptide nucleic acids (dabPNAs), nucleopeptides characterized by a diaminobutyric-based building block that is an isomer of the aminoethylglycyl PNA (aegPNA) unit and the acyclic modification of the aminoprolyl PNA (ampPNA) monomer. In this work we present the solid phase synthesis of a dabPNA oligomer and of two aegPNAs containing a single dabPNA unit. A study relative to their binding ability towards DNA is also reported even in comparison with the well known aegPNAs.
