Literature DB >> 30682233

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

Michael P O'Hagan1, Susanta Haldar1, Marta Duchi1, Thomas A A Oliver1, Adrian J Mulholland1, Juan C Morales2, M Carmen Galan1.   

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.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  DNA; G-quadruplexes; circular dichroism; oligonucleotides; photoregulation

Mesh:

Substances:

Year:  2019        PMID: 30682233      PMCID: PMC6563076          DOI: 10.1002/anie.201900740

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  33 in total

1.  DNA duplex-quadruplex exchange as the basis for a nanomolecular machine.

Authors:  Patrizia Alberti; Jean-Louis Mergny
Journal:  Proc Natl Acad Sci U S A       Date:  2003-02-06       Impact factor: 11.205

2.  DNA nanomachines and nanostructures involving quadruplexes.

Authors:  Patrizia Alberti; Anne Bourdoncle; Barbara Saccà; Laurent Lacroix; Jean-Louis Mergny
Journal:  Org Biomol Chem       Date:  2006-06-22       Impact factor: 3.876

3.  Reversible photoswitching of a G-quadruplex.

Authors:  Shinzi Ogasawara; Mizuo Maeda
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  pH-triggered switchable Mg2+-dependent DNAzymes.

Authors:  Johann Elbaz; Simcha Shimron; Itamar Willner
Journal:  Chem Commun (Camb)       Date:  2010-01-14       Impact factor: 6.222

5.  Resolution and characterization of the structural polymorphism of a single quadruplex-forming sequence.

Authors:  Magdalena M Dailey; M Clarke Miller; Paula J Bates; Andrew N Lane; John O Trent
Journal:  Nucleic Acids Res       Date:  2010-03-25       Impact factor: 16.971

6.  Energetics and kinetics of a conformational switch in G-quadruplex DNA.

Authors:  Robert D Gray; Jing Li; Jonathan B Chaires
Journal:  J Phys Chem B       Date:  2009-03-05       Impact factor: 2.991

7.  Structural polymorphism of telomeric DNA regulated by pH and divalent cation.

Authors:  Daisuke Miyoshi; Shizuka Matsumura; Wei Li; Naoki Sugimoto
Journal:  Nucleosides Nucleotides Nucleic Acids       Date:  2003-02       Impact factor: 1.381

Review 8.  Polymorphism of human telomeric quadruplex structures.

Authors:  Jixun Dai; Megan Carver; Danzhou Yang
Journal:  Biochimie       Date:  2008-03-08       Impact factor: 4.079

9.  A small molecule that disrupts G-quadruplex DNA structure and enhances gene expression.

Authors:  Zoë A E Waller; Sven A Sewitz; Shang-Te Danny Hsu; Shankar Balasubramanian
Journal:  J Am Chem Soc       Date:  2009-09-09       Impact factor: 15.419

10.  Diarylethynyl amides that recognize the parallel conformation of genomic promoter DNA G-quadruplexes.

Authors:  Jyotirmayee Dash; Pravin S Shirude; Shang-Te Danny Hsu; Shankar Balasubramanian
Journal:  J Am Chem Soc       Date:  2008-11-26       Impact factor: 15.419

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  12 in total

Review 1.  Molecular photoswitches in aqueous environments.

Authors:  Jana Volarić; Wiktor Szymanski; Nadja A Simeth; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2021-11-15       Impact factor: 54.564

2.  Switching G-quadruplex to parallel duplex by molecular rotor clustering.

Authors:  Qiuda Xu; Mujing Yang; Yun Chang; Shuzhen Peng; Dandan Wang; Xiaoshun Zhou; Yong Shao
Journal:  Nucleic Acids Res       Date:  2022-10-14       Impact factor: 19.160

3.  Stiff-Stilbene Ligands Target G-Quadruplex DNA and Exhibit Selective Anticancer and Antiparasitic Activity.

Authors:  Michael P O'Hagan; Pablo Peñalver; Rosina S L Gibson; Juan C Morales; M Carmen Galan
Journal:  Chemistry       Date:  2020-04-28       Impact factor: 5.236

4.  Modulating gene expression in breast cancer via DNA secondary structure and the CRISPR toolbox.

Authors:  Jessica A Kretzmann; Kelly L Irving; Nicole M Smith; Cameron W Evans
Journal:  NAR Cancer       Date:  2021-12-22

5.  Enhanced sampling molecular dynamics simulations correctly predict the diverse activities of a series of stiff-stilbene G-quadruplex DNA ligands.

Authors:  Michael P O'Hagan; Susanta Haldar; Juan C Morales; Adrian J Mulholland; M Carmen Galan
Journal:  Chem Sci       Date:  2020-11-26       Impact factor: 9.825

6.  G-quadruplex targeting chemical nucleases as a nonperturbative tool for analysis of cellular G-quadruplex DNA.

Authors:  Zhen Yu; Amber L Hendricks; James A Cowan
Journal:  iScience       Date:  2021-05-29

7.  Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer.

Authors:  Nadja A Simeth; Shotaro Kobayashi; Piermichele Kobauri; Stefano Crespi; Wiktor Szymanski; Kazuhiko Nakatani; Chikara Dohno; Ben L Feringa
Journal:  Chem Sci       Date:  2021-05-27       Impact factor: 9.825

8.  Selective targeting of mutually exclusive DNA G-quadruplexes: HIV-1 LTR as paradigmatic model.

Authors:  Martina Tassinari; Michela Zuffo; Matteo Nadai; Valentina Pirota; Adriana Carolina Sevilla Montalvo; Filippo Doria; Mauro Freccero; Sara N Richter
Journal:  Nucleic Acids Res       Date:  2020-05-21       Impact factor: 16.971

Review 9.  Stiff-Stilbene Photoswitches: From Fundamental Studies to Emergent Applications.

Authors:  David Villarón; Sander J Wezenberg
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-02       Impact factor: 15.336

10.  Effect of ring rize on photoisomerization properties of stiff stilbene macrocycles.

Authors:  Sandra Olsson; Óscar Benito Pérez; Magnus Blom; Adolf Gogoll
Journal:  Beilstein J Org Chem       Date:  2019-10-11       Impact factor: 2.883

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