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 distinc...

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Bibliographic Details
Published in:Tetrahedron letters 2018-01, Vol.59 (3), p.295-298
Main Authors: Amirbekyan, Karen, Mansot, Justine, Ohara, Keiichiro, Markarian, Shiraz A., Vasseur, Jean-Jacques, Smietana, Michael
Format: Article
Language:English
Subjects:
Analytical chemistry
Chemical Sciences
Excimer fluorescence
G-quadruplex
Medicinal Chemistry
Nucleic acids
Organic chemistry
Pyrene
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Summary:[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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.12.046