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Fully Reversible Photocontrol over DNA Intercalation with Visible Light.

David E Grantz1, Christophe Lachance-Brais1, Giuseppe Giangreco1,2

  • 1Stratingh Institute for Chemistry, Faculty for Science and Engineering, University of Groningen, Nijenborgh 3, 9747 AG Groningen, The Netherlands.

Journal of the American Chemical Society
|June 5, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed novel photoswitchable DNA intercalators that reversibly bind DNA. These diazocine compounds offer unprecedented light-controlled "on-off" binding, enabling precise photopharmacology applications.

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Area of Science:

  • Medicinal Chemistry
  • Molecular Biology
  • Photochemistry

Background:

  • DNA intercalators are crucial in molecular biology and medicine.
  • Developing controllable DNA-binding agents is a key challenge.
  • Photoswitchable molecules offer potential for spatiotemporal control.

Purpose of the Study:

  • To synthesize and characterize novel photoswitchable DNA intercalators.
  • To investigate their DNA binding properties and light-responsive behavior.
  • To evaluate their potential in photopharmacology.

Main Methods:

  • Synthesis of diazocine-based photoswitchable compounds.
  • B-DNA binding affinity measurements (KD) in trans and cis states.
  • Reversibility and fatigue testing under visible light.
  • Cytotoxicity assays (EC50) in HeLa cells with and without irradiation.

Main Results:

  • Three novel photoswitchable DNA intercalators based on the diazocine scaffold were synthesized.
  • Compounds exhibit reversible "on-off" DNA binding upon visible light irradiation.
  • The trans state shows high affinity (KD ~10-4 M), with >1000-fold lower affinity in the cis state.
  • Negligible dark toxicity for compound 3 (EC50 > 100 μM), with photo-induced toxicity upon 395 nm irradiation (EC50 = 45.4 μM).

Conclusions:

  • The developed diazocine intercalators demonstrate efficient and reversible light-controlled DNA binding.
  • This photoswitchable binding is superior to existing literature methods.
  • The compounds show potential for spatiotemporal control in photopharmacology due to their tunable activity.