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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Bioorthogonal Engineering of Cellular Microenvironments Using Isonitrile Ligations.

Ping Zhou1, Lauren Brown2, Christopher M Madl1

  • 1Department of Materials Science & Engineering, University of Pennsylvania, Philadelphia, PA 19104, USA.

Advanced Functional Materials
|August 21, 2025
PubMed
Summary
This summary is machine-generated.

New bioorthogonal isonitrile ligations offer advanced hydrogel crosslinking for tissue engineering. This expands material properties control, enabling precise regulation of cell behavior and long-term cell culture.

Keywords:
bioorthogonal chemistryengineered extracellular matriceshydrogelsisonitrile ligationrecombinant protein materials

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Area of Science:

  • Biomaterials Science
  • Tissue Engineering
  • Polymer Chemistry

Background:

  • Hydrogels are crucial scaffolds in tissue engineering, mimicking the extracellular matrix.
  • Current crosslinking methods often involve reactive conditions, limiting control over material properties and cell fate.
  • Existing bioorthogonal chemistries for hydrogel formation are limited, restricting independent tuning of material characteristics.

Purpose of the Study:

  • To introduce isonitrile ligations as a novel, bioorthogonal strategy for hydrogel crosslinking.
  • To expand the available bioorthogonal toolkit for precise control over hydrogel properties.
  • To develop advanced hydrogels for regenerative medicine applications.

Main Methods:

  • Investigated isonitrile ligations with chlorooxime (ChO), tetrazine (Tz), and azomethine imine (AMI) functional groups.
  • Synthesized poly(ethylene glycol) (PEG) hydrogels using isonitrile-ChO ligation.
  • Combined ChO-functionalized PEGs with isonitrile-functionalized elastin-like proteins (ELPs).
  • Assessed hydrogel properties including gelation kinetics, mechanical stability, and biocompatibility.
  • Evaluated the orthogonality of isonitrile-ChO ligation with azide-alkyne cycloaddition.

Main Results:

  • Demonstrated hydrogel formation using isonitrile-ChO, isonitrile-Tz, and isonitrile-AMI ligations.
  • Isonitrile-ChO ligation exhibited optimal gelation kinetics and mechanical properties.
  • PEG hydrogels crosslinked via isonitrile-ChO ligation showed rapid gelation, elasticity, stability, and biocompatibility.
  • Simultaneous control over network connectivity and ligand presentation was achieved using PEG-ELP hydrogels, regulating cell spreading.
  • Confirmed orthogonality of isonitrile-ChO ligation to azide-alkyne cycloaddition for independent hydrogel functionalization.

Conclusions:

  • Isonitrile ligations represent a versatile and biocompatible platform for hydrogel crosslinking.
  • Isonitrile-ChO ligation provides a robust method for creating advanced hydrogels with tunable properties.
  • These hydrogels support long-term culture of diverse human cell types for regenerative medicine.
  • The demonstrated orthogonality allows for sequential, bioorthogonal modification of hydrogels within live cell environments.