PubReading [146] - Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA2DNA triplexes - A. Manicardi, L. Guidi, A. Ghidini and R. Corradini

<p><strong>Pyrene</strong> derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, <strong>peptide nucleic acids</strong> (PNAs) containing 1 to 3 1-pyreneacetic acid units (<strong>PNA1</strong>–<strong>6</strong>) with a sequence with prevalence of pyrimidine bases, complementary to cystic fibrosis W1282X point mutation were synthesized. These compounds showed sequence-selective switch-on of pyrene excimer emission in the presence of target DNA, due to PNA2DNA <strong>triplex</strong> formation, with stability depending on the number and positioning of the pyrene units along the chain. An increase in triplex stability and a very high mismatch-selectivity, derived from combined stacking and base-pairing interactions, were found for <strong>PNA2</strong>, bearing two distant pyrene units.</p><p><em>doi:10.3762/bjoc.10.154 - 2014</em></p>