title: Hairpin-forming peptide nucleic acid oligomers.
abstract: A series of partially self-complementary peptide nucleic acid (PNA) oligomers was prepared. Examination of their melting behavior, circular dichroism spectra, and fluorescence properties reveals that these PNA oligomers exist as stem-loop ("hairpin") structures. Fluorescence is readily observed in hairpins containing a covalently linked, emissive acridine derivative which is, at least partially, intercalated in the duplex region of the PNA hairpin. The acridine fluorescence is quenched when an anthraquinone derivative is covalently attached to the PNA so that it is bound near the acridine in the hairpin structure. Acridine fluorescence is restored in hairpins containing both the anthraquinone and the acridine by increasing the temperature and melting the structure to its linear form or by opening the hairpin through formation of a hybrid duplex with complementary DNA. The latter process may form the basis for development of selective and sensitive DNA assays.
authors.affiliation: School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta 30332-0400, USA.
authors.forename: B
authors.initials: B
authors.lastname: Armitage
authors.forename: D
authors.initials: D
authors.lastname: Ly
authors.forename: T
authors.initials: T
authors.lastname: Koch
authors.forename: H
authors.initials: H
authors.lastname: Frydenlund
authors.forename: H
authors.initials: H
authors.lastname: Orum
authors.forename: G B
authors.initials: GB
authors.lastname: Schuster
mesh_terms: D000585:Aminacrine / Q000138:chemical synthesis; D000880:Anthraquinones / Q000138:chemical synthesis; D002942:Circular Dichroism; D004247:DNA / Q000737:chemistry*; D004579:Electron Transport; D046911:Macromolecular Substances; D009690:Nucleic Acid Conformation; D009692:Nucleic Acid Heteroduplexes / Q000737:chemistry; D015341:Nucleic Acid Probes; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D000880:Anthraquinones; D046911:Macromolecular Substances; D009692:Nucleic Acid Heteroduplexes; D015341:Nucleic Acid Probes; D010455:Peptides; D000585:Aminacrine; D004247:DNA