Photoclick and Release: Co-activation of Carbon Monoxide and a Fluorescent Self-reporter, COS or Sulfonamide with Fast Kinetics

Chembiochem. 2023 Feb 1;24(3):e202200506. doi: 10.1002/cbic.202200506. Epub 2022 Dec 23.

Abstract

Bioorthogonal prodrugs with both fast reaction kinetics and multiple outputs are highly desirable but are only found sporadically. Herein, we report a novel photoclick-and-release strategy for the co-activation of carbon monoxide and a self-reporter, carbonyl sulfide, or sulfonamide with fast reaction kinetics (k: 1.4-22.6 M-1 s-1 ). Such a photoclick-and-release strategy was successfully applied in live cells to deliver carbon monoxide and a fluorescent self-reporter, both of which exhibited pronounced antiproliferative activity against 4T1 cancer cells. It is conceivable that this photoclick-and-release strategy could find applications in other fields, in which a controlled bond cleavage is preferred.

Keywords: bioorthogonal prodrugs; carbon monoxide; carbonyl sulfide; hydrogen sulfide; photoclick and release.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon Monoxide* / chemistry
  • Coloring Agents
  • Kinetics
  • Molecular Structure
  • Prodrugs* / chemistry
  • Sulfanilamide
  • Sulfonamides

Substances

  • Carbon Monoxide
  • Sulfonamides
  • Coloring Agents
  • Prodrugs
  • Sulfanilamide