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Synthesis, Self‐Assembly, and Nucleic Acid Recognition of an Acylhydrazone‐Conjugated Cationic Tetraphenylethene Ligand
Author(s) -
Coste Maëva,
Kotras Clément,
Bessin Yannick,
Gervais Virginie,
Dellemme David,
Leclercq Maxime,
Fossépré Mathieu,
Richeter Sébastien,
Clément Sébastien,
Surin Mathieu,
Ulrich Sébastien
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001420
Subject(s) - nucleic acid , isothermal titration calorimetry , chemistry , supramolecular chemistry , dna , conjugated system , combinatorial chemistry , intercalation (chemistry) , self assembly , molecular recognition , cationic polymerization , stereochemistry , covalent bond , polymer , organic chemistry , biochemistry , molecule
Supramolecular polymers are of interest in the pursuit of multivalent nucleic acids recognition. However, their formation often relies on non‐covalent forces that are also at play in the interaction with nucleic acids. In this work, we designed a novel compound ( TPE‐Gir ) combining a tetraphenylethene aromatic core tethered to four quaternary ammoniums through acylhydrazone spacers, and we investigated in detail its self‐assembly and interaction with different types of nucleic acids. The spectroscopic analyses indicate the self‐assembly of regular fluorescent nanoparticles (observed by DLS and TEM) in the absence of nucleic acids, the strong propensity to intercalate into single‐stranded DNA, the ability to bind into the minor groove of double‐stranded DNA, and the selective binding to G‐quadruplex (G4) structures by fitting within a wide G4‐groove. Those recognition events are quantified by isothermal titration calorimetry and the proposed binding models are supported by docking simulations.