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Azidocoumarin Glycan Probes for Photoinduced Cross-Linking and In Situ Fluorescent Labeling.

Nina Jahnke1, Marc D Driessen2, Georgia Partalidou3

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This study introduces a novel azidocoumarin photo-cross-linker for creating glycan probes. These probes enable visualization and covalent linking of lectins, aiding in the identification of glycan receptors in biological samples.

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Glycobiology

Background:

  • Photoinduced affinity labeling is crucial for identifying biomolecular interactions and biomarkers.
  • Next-generation photo-cross-linkers offer inducible fluorogenic properties for visual readout.
  • Azido-substituted coumarins are nonfluorescent until UV irradiation, generating reactive nitrenes and restoring fluorescence.

Purpose of the Study:

  • To develop a versatile 7-azidocoumarin derivative as a building block for solid-phase synthesis of glycan-based photo affinity probes.
  • To demonstrate the application of these novel probes for targeting and visualizing lectin-glycan interactions.
  • To showcase the potential for identifying and localizing glycan receptors in complex biological systems.

Main Methods:

  • Synthesis of a 7-azidocoumarin derivative suitable for solid-phase synthesis.
  • Development of various glycan-presenting photo affinity probes using the azidocoumarin building block.
  • Application of probes to selectively target and covalently link to lectins, accompanied by fluorescence activation.
  • Demonstration of selective lectin recognition in complex biological environments.

Main Results:

  • A novel 7-azidocoumarin derivative was synthesized and used to create diverse glycan photo affinity probes.
  • These probes successfully achieved selective targeting and covalent linking of specific lectins.
  • A significant turn-on fluorescence activity of the coumarin fluorophore was observed upon cross-linking.
  • Selective lectin recognition was demonstrated in complex biological settings, validating probe efficacy.

Conclusions:

  • The developed azidocoumarin glycan probes are effective tools for studying lectin-glycan interactions.
  • These probes facilitate the identification and localization of known and novel glycan receptors in biological samples.
  • This technology opens new avenues for biomarker discovery and understanding cellular processes involving glycans.