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

[Display omitted] • 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 H 2 O 2 detection in tumor cells. 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 H 2 O 2 -activated theranostic prodrugs (CPTSe1-CPTSe7) were developed containing allyl phenyl selenide moieties as H 2 O 2 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 H 2 O 2 inducing experiment. The selectively activated fluorescence signals of CPTSe1 in tumor cells make it useful for real-time monitoring of CPT release and H 2 O 2 detection. Furthermore, excellent selectivity of CPTSe1 was achieved for tumor cells over normal cells. Our results provide a new platform for the development of H 2 O 2 -responsive theranostic prodrugs. [ABSTRACT FROM AUTHOR]