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A Photoresponsive Stiff-Stilbene Ligand Fuels the Reversible Unfolding of G-Quadruplex DNA

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A Photoresponsive Stiff-Stilbene Ligand Fuels the Reversible Unfolding of G-Quadruplex DNA. / O'Hagan, Michael; Haldar, Susanta; Duchi, Marta; Oliver, Thomas A. A.; Mulholland, Adrian; Morales, Juan C; Galan, Carmen.

In: Angewandte Chemie - International Edition, Vol. 58, No. 13, 22.03.2019, p. 4334-4338.

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@article{13a0f3e3f53745e1875fc6201ab04850,
title = "A Photoresponsive Stiff-Stilbene Ligand Fuels the Reversible Unfolding of G-Quadruplex DNA",
abstract = "The polymorphic nature of G-quadruplex (G4) DNA structures points to a range of potential applications in nanodevices and an opportunity to control G4 in biological settings. Light is an attractive means for the regulation of oligonucleotide structure as it can be delivered with high spatiotemporal precision. However, surprisingly little attention has been devoted towards the development of ligands for G4 that allow photoregulation of G4 folding. We report a novel G4-binding chemotype derived from stiff-stilbene. Surprisingly however, whilst the ligand induces high stabilization in the potassium form of human telomeric DNA, it causes the unfolding of the same G4 sequence in sodium buffer. This effect can be reversed on demand by irradiation with 400 nm light through deactivation of the ligand by photo-oxidation. By fuelling the system with the photolabile ligand, the conformation of G4 DNA was switched five times.",
keywords = "circular dichroism, DNA, G-quadruplexes, oligonucleotides, photoregulation",
author = "Michael O'Hagan and Susanta Haldar and Marta Duchi and Oliver, {Thomas A. A.} and Adrian Mulholland and Morales, {Juan C} and Carmen Galan",
year = "2019",
month = "3",
day = "22",
doi = "10.1002/anie.201900740",
language = "English",
volume = "58",
pages = "4334--4338",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "Wiley-VCH Verlag",
number = "13",

}

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TY - JOUR

T1 - A Photoresponsive Stiff-Stilbene Ligand Fuels the Reversible Unfolding of G-Quadruplex DNA

AU - O'Hagan, Michael

AU - Haldar, Susanta

AU - Duchi, Marta

AU - Oliver, Thomas A. A.

AU - Mulholland, Adrian

AU - Morales, Juan C

AU - Galan, Carmen

PY - 2019/3/22

Y1 - 2019/3/22

N2 - The polymorphic nature of G-quadruplex (G4) DNA structures points to a range of potential applications in nanodevices and an opportunity to control G4 in biological settings. Light is an attractive means for the regulation of oligonucleotide structure as it can be delivered with high spatiotemporal precision. However, surprisingly little attention has been devoted towards the development of ligands for G4 that allow photoregulation of G4 folding. We report a novel G4-binding chemotype derived from stiff-stilbene. Surprisingly however, whilst the ligand induces high stabilization in the potassium form of human telomeric DNA, it causes the unfolding of the same G4 sequence in sodium buffer. This effect can be reversed on demand by irradiation with 400 nm light through deactivation of the ligand by photo-oxidation. By fuelling the system with the photolabile ligand, the conformation of G4 DNA was switched five times.

AB - The polymorphic nature of G-quadruplex (G4) DNA structures points to a range of potential applications in nanodevices and an opportunity to control G4 in biological settings. Light is an attractive means for the regulation of oligonucleotide structure as it can be delivered with high spatiotemporal precision. However, surprisingly little attention has been devoted towards the development of ligands for G4 that allow photoregulation of G4 folding. We report a novel G4-binding chemotype derived from stiff-stilbene. Surprisingly however, whilst the ligand induces high stabilization in the potassium form of human telomeric DNA, it causes the unfolding of the same G4 sequence in sodium buffer. This effect can be reversed on demand by irradiation with 400 nm light through deactivation of the ligand by photo-oxidation. By fuelling the system with the photolabile ligand, the conformation of G4 DNA was switched five times.

KW - circular dichroism

KW - DNA

KW - G-quadruplexes

KW - oligonucleotides

KW - photoregulation

UR - http://www.scopus.com/inward/record.url?scp=85061792919&partnerID=8YFLogxK

U2 - 10.1002/anie.201900740

DO - 10.1002/anie.201900740

M3 - Article

VL - 58

SP - 4334

EP - 4338

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 13

ER -