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

Miao Liu, Yuhan Wang, Zhicheng Yan, Jiabin Yang, Yongyou Wu, Dawei Ding, Xingyue Ji

2022ChemBioChem21 citationsDOI

Abstract

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.

Topics & Concepts

KineticsChemistrySulfonamideCarbon monoxideBioorthogonal chemistryFluorescenceCombinatorial chemistryChemical kineticsProdrugBiophysicsCatalysisClick chemistryStereochemistryOrganic chemistryBiochemistryPhysicsBiologyQuantum mechanicsNanoplatforms for cancer theranosticsClick Chemistry and ApplicationsAdenosine and Purinergic Signaling
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