Template-directed excimer formation via specific non-covalent interactions between pyrene guanidinium derivatives and nucleic acids

[Display omitted] •Nucleic acids strongly interact with pyrene gunidinium derivatives.•The interaction leads to strong excimer formation.•The highest excimer formation was obtained with G-rich sequences.•A binding preference for antiparallel G quadruplex structures was observed. Structurally distinct guanidinium derivatives were evaluated for their ability to interact non-covalently with various nucleic acid sequences. Among the evaluated derivatives, 4-[(pyrene-1-ylmethyl)amino]butyl] guanidinium (pbg) was found to demonstrate strong excimer emission upon nucleic acid addition and high levels of discrimination between ds- and ss-DNA. The intensity of excimer emission proved to be dependent on the length of the linker probe as well as the oligonucleotide length and sequence. In particular, G-quadruplex prone structures were found to induce the highest excimer emissions among all nucleic acids tested.