Issue 36, 2017

A two-photon-activated prodrug for therapy and drug release monitoring

Abstract

A light-activated cleavage strategy for the concomitant release of active drugs and generation of fluorescence changes is highly desirable. Herein a molecular prodrug featuring real-time monitoring of drug localization and release by manipulating fluorophores has been created by constructing a cleavable structure which comprises a photoremovable coumarinyl, an anticancer drug camptothecin, a cleavable linker and a near infrared fluorescent dye dicyanomethylene-4H-pyran (DCM). The fluorescence of coumarinyl and CPT is completely quenched by the DCM moiety via fluorescence resonance energy transfer (FRET). The internalization of the prodrug by cells and its subsequent intracellular location can be tracked by collecting the red fluorescence of DCM; while the release of active CPT as a result of one- or two-photon irradiation can be monitored by observing the newly emerged fluorescence of CPT under one- or two-photon excitation. The prodrug also shows highly controllable cytotoxicity toward HeLa cells and A549 cells, with low IC50 values of 4.01 and 2.53 μM, respectively, upon light irradiation and with much higher IC50 values (>40 μM) without light irradiation. This strategy may provide an approach for the development of light-activatable theranostic anticancer therapeutics.

Graphical abstract: A two-photon-activated prodrug for therapy and drug release monitoring

Supplementary files

Article information

Article type
Paper
Submitted
24 May 2017
Accepted
14 Aug 2017
First published
15 Aug 2017

J. Mater. Chem. B, 2017,5, 7538-7546

A two-photon-activated prodrug for therapy and drug release monitoring

P. Liu, B. Li, C. Zhan, F. Zeng and S. Wu, J. Mater. Chem. B, 2017, 5, 7538 DOI: 10.1039/C7TB01408B

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