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Light Switchable Bioorthogonal Reaction Manifold for Modulation of Hydrogel Properties.

Wai Lean Koay1, Chang Gao2, Quyen Thi Vu1

  • 1Institute of Sustainability for Chemicals, Energy and Environment (ISCE2), Agency for Science, Technology and Research (A*STAR), 1 Pesek Road, Jurong Island, Singapore 627833, Republic of Singapore.

Biomacromolecules
|August 20, 2024
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Summary

Researchers developed a versatile chalcone pyrene (CPyr) system for controllable polymer modifications. This bioorthogonal manifold enables light-induced dimerization/cleavage and rapid thiol-ene click reactions for advanced materials and biomaterials.

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Area of Science:

  • Polymer Chemistry
  • Bioorthogonal Chemistry
  • Materials Science

Background:

  • Controllable multi-pathway chemical reaction systems are crucial for advanced materials and biological research.
  • Bioorthogonal reactions offer precise chemical modifications within biological systems.
  • Chalcone derivatives are known for their photoreactivity.

Purpose of the Study:

  • To introduce a novel bioorthogonal reaction manifold based on a chalcone pyrene (CPyr) moiety.
  • To demonstrate the controllable dual-reactivity of CPyr for polymer functionalization and hydrogel formation.
  • To explore the potential of this system in biomaterials applications.

Main Methods:

  • Synthesis of a chalcone pyrene (CPyr) moiety coupled to poly(ethylene glycol).
  • Photoreversible [2 + 2] cycloaddition triggered by blue and UV light for polymer dimerization and cleavage.
  • Thiol-Michael addition click reaction for rapid polymer end-group functionalization.
  • Preparation and characterization of hydrogels via polymer cross-linking.

Main Results:

  • Efficient polymer dimerization and cleavage achieved using blue light (450 nm) and UV light (340 nm).
  • Rapid polymer end-group functionalization demonstrated via thiol-Michael addition in aqueous environments.
  • Hydrogel formation with tunable stiffness and morphology achieved through light or thiol cross-linking.
  • Successful spatial and temporal conjugation of streptavidin protein using both reaction pathways.
  • Demonstrated non-toxicity of cross-linking conditions to various cell lines.

Conclusions:

  • The CPyr moiety provides a versatile bioorthogonal reaction manifold with dual-reactivity.
  • This system allows for precise control over polymer assembly, functionalization, and hydrogel properties.
  • The demonstrated biocompatibility and controllability highlight its significant potential for advanced biomaterials applications.