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Bioorthogonal Self-Immolative Linker Based on Grob Fragmentation.

Xhenti Ferhati1, Marina Salas-Cubero1, Pablo Garrido2

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Researchers developed a novel self-immolative linker using Grob fragmentation. This linker releases compounds in aqueous media and acidic conditions, showing potential for bioorthogonal applications in living cells.

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Area of Science:

  • Organic Chemistry
  • Bioconjugation Chemistry
  • Chemical Biology

Background:

  • Bioorthogonal chemistry enables selective reactions within biological systems.
  • Conditional linkers are crucial for controlled release of payloads.
  • Grob fragmentation is a known chemical transformation.

Purpose of the Study:

  • To describe a novel self-immolative bioorthogonal linker.
  • To enable conditional release of sulfonate-containing compounds.
  • To explore the linker's utility in acidic tumor microenvironments and physiological conditions.

Main Methods:

  • Synthesis of a linker derived from 1,3-aminocyclohexanols.
  • Investigation of Grob fragmentation mechanism.
  • Assessment of linker cleavage in aqueous media and varying pH.
  • Evaluation of linker performance in living cells.

Main Results:

  • A self-immolative linker based on Grob fragmentation was successfully synthesized.
  • The linker releases sulfonate-containing compounds in aqueous media.
  • Fragmentation is promoted at slightly acidic pH, mimicking tumor environments.
  • The Grob fragmentation proceeds under physiological conditions in living cells.

Conclusions:

  • The developed linker is a promising tool for bioorthogonal chemistry.
  • Its conditional cleavage at acidic pH and physiological conditions offers significant potential for targeted drug delivery and imaging.
  • This work expands the toolbox for controlled chemical modifications in biological systems.