Abstract
Pyrene derivatives can be incorporated into nucleic acid analogs in order to obtain switchable probes or supramolecular architectures. In this paper, peptide nucleic acids (PNAs) containing 1 to 3 1-pyreneacetic acid units (PNA1–6) 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 triplex 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 PNA2, bearing two distant pyrene units.
Highlights
Peptide nucleic acid (PNA) probes are very selective in the recognition of DNA and have been used in a large variety of diagnostic methods, allowing the detection of point mutations at very low concentrations [1,2,3]
We have recently reported the modification of uracil at C5 by hydroxymethylation, followed by substitution with chloride and with azide, which can be used for click chemistry or as a masked amino group both in a PNA monomer and in PNA oligomers, allowing to produce a variety of modified PNAs from a single precursor [35]
Two different approaches were followed for the introduction of the pyrene units in the PNA strands
Summary
Peptide nucleic acid (PNA) probes are very selective in the recognition of DNA and have been used in a large variety of diagnostic methods, allowing the detection of point mutations at very low concentrations [1,2,3].
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
