Aza-macrocyclic triphenylamine ligands for G-quadruplex recognition

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Title: Aza-macrocyclic triphenylamine ligands for G-quadruplex recognition
Authors: Pont, I
González-García, J
Inclán, M
Reynolds, M
Delgado-Pinar, E
Albelda, MT
Vilar, R
García-España, EV
Item Type: Journal Article
Abstract: A new series of triphenylamine-based ligands with one (TPA1PY), two (TPA2PY) or three pending aza-macrocycle(s) (TPA3PY) have 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 its selectivity over duplex DNA were investigated by FRET melting assays, fluorimetric titrations and circular dichroism (CD) spectroscopy. Interestingly, the interaction of the bi- and specially the tri-branched ligand with G4 leads to a very intense red-shifted fluorescence emission band which may be associated with intermolecular aggregation between the molecule and the DNA. This light-up effect allows the application of the ligands as fluorescence probes to selectivity detect G4.
Issue Date: 25-Jul-2018
Date of Acceptance: 16-May-2018
URI: http://hdl.handle.net/10044/1/60205
DOI: https://doi.org/10.1002/chem.201802077
ISSN: 0947-6539
Publisher: Wiley
Start Page: 10850
End Page: 10858
Journal / Book Title: Chemistry - A European Journal
Volume: 24
Issue: 42
Copyright Statement: © 2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim. This is the pre-peer reviewed version of the following article, which has been published in final form at https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201802077.
Sponsor/Funder: The Royal Society
Funder's Grant Number: NF140726
Keywords: Science & Technology
Physical Sciences
Chemistry, Multidisciplinary
Chemistry
aggregation
amines
DNA
fluorescent probes
G-quadruplexes
macrocyclic ligands
AGGREGATION-INDUCED EMISSION
INTRAMOLECULAR CHARGE-TRANSFER
ANTICANCER DRUG DESIGN
EQUILIBRIUM-CONSTANTS
2-PHOTON ABSORPTION
CIRCULAR-DICHROISM
FLUORESCENT-PROBES
PROMOTER REGION
FORMING REGION
GRAPHENE OXIDE
DNA
G-quadruplexes
aggregation
amines
fluorescent probes
macrocyclic ligands
DNA
G-quadruplex
aggregation-induced emission
fluorescent probes
triphenylamine polyamines
03 Chemical Sciences
General Chemistry
Publication Status: Published
Conference Place: Germany
Online Publication Date: 2018-06-27
Appears in Collections:Chemistry
Biological and Biophysical Chemistry
Faculty of Natural Sciences



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