Related Experiment Video

Updated: Jun 14, 2026

Genetically-encoded Molecular Probes to Study G Protein-coupled Receptors
16:16

Genetically-encoded Molecular Probes to Study G Protein-coupled Receptors

Published on: September 13, 2013

15.2K

Harnessing Light for G-Quadruplex Modulation: Dual Isomeric Effects of an Ortho-Fluoroazobenzene Derivative

Marta Dudek1, Lucía López-Pacios2, Nasim Sabouri3

  • 1Institute of Advanced Materials, Faculty of Chemistry, Wrocław University of Science and Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland.

The Journal of Physical Chemistry Letters
|September 17, 2024
PubMed

Insights

Researchers developed a novel light-responsive molecule, Py-Azo4F-3N, to target G-quadruplexes (G4s) in cancer. The trans isomer effectively stabilizes G4s, offering a new strategy for cancer therapy.

Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Cancer Research

Background:

  • G-quadruplexes (G4s) are crucial targets for cancer therapeutics and photopharmacology.
  • Small-molecule ligands targeting G4s can disrupt DNA transactions and induce cancer cell instability.
  • Few G4-ligands offer light-modulated binding properties for precise therapeutic control.

Purpose of the Study:

  • To photophysically characterize a novel ortho-fluoroazobenzene derivative, Py-Azo4F-3N, for its G4-interactive binding properties.
  • To evaluate the potential of light-responsive G4 ligands in cancer treatment strategies.
  • To identify the optimal isomer of Py-Azo4F-3N for G4 stabilization and cancer cell ablation.

Main Methods:

  • Photophysical characterization of Py-Azo4F-3N isomers.
  • Biophysical techniques including affinity and selectivity assays.
  • Structural and computational analysis, cytotoxicity experiments in cancer cell lines.

Main Results:

  • Py-Azo4F-3N exhibits reversible two-way isomerization upon visible light exposure.
  • The trans isomer demonstrates significant G4-interactive binding and stabilization capabilities.
  • Enhanced G4 ablation was observed in cancer cells using the trans isomer.

Conclusions:

  • Py-Azo4F-3N is a promising light-responsive molecule for targeting G-quadruplexes.
  • The trans isomer shows potential for innovative anticancer strategies through precise G4 structure control.
  • This research underscores the value of photo-switchable ligands in cancer therapy.

More Related Videos

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes07:44

Synthesis of Wavelength-shifting DNA Hybridization Probes by Using Photostable Cyanine Dyes

Published on: July 6, 2016

11.1K
Single-Molecule Fluorescence Visualization of DNA Polymerase Dynamics at G-Quadruplexes05:37

Single-Molecule Fluorescence Visualization of DNA Polymerase Dynamics at G-Quadruplexes

Published on: April 4, 2025

384

Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.