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

Photoclick and release: A cyclopropenone scaffold was employed as a strained alkyne precursor for bioorthogonal prodrug design. Such a photoclick-and-release system not only resolved the stability issues of strained alkynes but also exhibited multiple outputs and relatively fast kinetics.

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.

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