Lipophilic peptide nucleic acids containing a 1,3-diyne function: synthesis, characterization and production of derived polydiacetylene liposomes

Abstract

Adenine-, cytosine- and thymine-containing peptide nucleic acid (PNA) monomers have been synthesized in which either diacetylenic or stearoyl moieties are attached to the N-or C-terminus; the diacetylenic group is embedded within a long hydrocarbon chain. A range of analogous lipophilic functionalized PNA oligomers have been prepared using either solid phase synthesis or a post-synthetic solution phase procedure following cleavage of the PNA oligomer from the solid support. Selected functionalized PNA monomers and oligomers have been incorporated into liposomal polydiacetylenes and characterized by UV–vis absorption spectroscopy. Preliminary investigations show that blue PDA-liposomes containing thymine-based PNAs can be formed and that production of liposomes with other PNA systems are viable.