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

Nicola M. Howarth, W. Edward Lindsell, Euan Murray, Peter N. Preston

Research output: Contribution to journalArticle

14 Citations (Scopus)

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. © 2005 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)8875-8887
Number of pages13
JournalTetrahedron
Volume61
Issue number37
DOIs
Publication statusPublished - 12 Sep 2005

Keywords

  • Liposomes
  • Nucleic acid biosensors
  • PNA
  • Polydiacetylenes

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