Aza-macrocyclic triphenylamine ligands for G-quadruplex recognition

6533b85bfe1ef96bd12bad2f

RESEARCH PRODUCT

Aza-macrocyclic triphenylamine ligands for G-quadruplex recognition

Matthew Reynolds Estefanía Delgado‐pinar Jorge González-garcía Jorge González-garcía Isabel Pont Isabel Pont Ramon Vilar Enrique García-españa M. Teresa Albelda Mario Inclán

subject

0301 basic medicine Circular dichroism aggregation-induced emission Chemistry Multidisciplinary amines 010402 general chemistry G-quadruplex Triphenylamine 01 natural sciences Catalysis CIRCULAR-DICHROISM 03 medical and health sciences chemistry.chemical_compound General chemistry fluorescent probes triphenylamine polyamines Molecule Spectroscopy FLUORESCENT-PROBES Science & Technology G-quadruplex Chemistry INTRAMOLECULAR CHARGE-TRANSFER ANTICANCER DRUG DESIGN Organic Chemistry aggregation FORMING REGION DNA General Chemistry Fluorescence G-quadruplexes 0104 chemical sciences Crystallography Chemistry 030104 developmental biology Förster resonance energy transfer 2-PHOTON ABSORPTION PROMOTER REGION Physical Sciences EQUILIBRIUM-CONSTANTS GRAPHENE OXIDE 03 Chemical Sciences macrocyclic ligands

description

A new series of triphenylamine-based ligands with one (TPA1PY), two (TPA2PY) or three pendant aza-macrocycle(s) (TPA3PY) has been synthesised and studied by means of pH-metric titrations, UV/Vis spectroscopy and fluorescence experiments. The affinity of these ligands for G-quadruplex (G4) DNA and the selectivity they show for G4s over duplex DNA were investigated by Forster resonance energy transfer (FRET) melting assays, fluorimetric titrations and circular dichroism spectroscopy. Interestingly, the interactions of the bi- and especially the tri-branched ligands with G4s lead to a very intense redshifted fluorescence emission band that may be associated with intermolecular aggregation between the molecule and DNA. This light-up effect allows the application of the ligands as fluorescence probes to selectively detect G4s.

year	journal	country	edition	language
2018-04-25

10.1002/chem.201802077 http://hdl.handle.net/10044/1/60205

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