Allyl phenyl selenides as H2O2 acceptors to develop ROS-responsive theranostic prodrugs

ElsevierVolume 129, December 2022, 106154Bioorganic ChemistryHighlights•

Synthesis of ROS-responsive camptothecin prodrugs containing allyl phenyl selenides (CPTSe1-CPTSe7).

CPTSe1-CPTSe7 showed good selectivity for tumor cells over normal cells.

CPTSe1 was more stable than CPT-B.

CPTSe1 enabled real-time monitoring of CPT release and H2O2 detection in tumor cells.

Abstract

Reactive oxygen species (ROS)-responsive prodrugs have received significant attention due to their capacity to target tumors to relieve the side effects caused by chemotherapy. Herein, a series of novel H2O2-activated theranostic prodrugs (CPTSe1-CPTSe7) were developed containing allyl phenyl selenide moieties as H2O2 acceptors. Compared with conventional boronate ester-based prodrug CPT-B, CPTSe1 was more stable in human plasma and showed a more complete release of camptothecin (CPT) in H2O2 inducing experiment. The selectively activated fluorescence signals of CPTSe1 in tumor cells make it useful for real-time monitoring of CPT release and H2O2 detection. Furthermore, excellent selectivity of CPTSe1 was achieved for tumor cells over normal cells. Our results provide a new platform for the development of H2O2-responsive theranostic prodrugs.

Keywords

ROS-responsive

Theranostic prodrug

Camptothecin

Selenide

Antitumor

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