A series of partially self-complementary peptide nucleic acid (PNA) ol
igomers 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 quench
ed when an anthraquinone derivative is covalently attached to the PNA
so that it is bound near the acridine in the hairpin structure. Acridi
ne fluorescence is restored in hairpins containing both the anthraquin
one and the acridine by increasing the temperature and melting the str
ucture 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.