A single-chromophore-based agent enables rapid sensing of intracellular hypochlorous acid and in-situ photodynamic therapy to cancer cells

A single-chromophore-based photoactive agent (MB-DOPA) capable of rapid sensing of nanomolar hypochlorous acid (HOCl) and in-situ generating photocytotoxicity to cancer cells was developed using dopamine moiety as the recognition unit and methylene blue (MB) moiety as the fluorescence signaling unit. Specifically, HOCl triggered conversion of the nonfluorescent MB-DOPA to MB enabling far-red fluorescence emission (lambda(max) similar to 683 nm) and additional ability to photogenerate O-1(2) species. Owing to the catechol nature of dopamine characterized with strong electron-donating property, MB-DOPA underwent HOCl-mediated conversion with response time of similar to 20 s and a strong fluorescence OFF-to-ON contrast by a factor of more than 3000. The preliminary bioimaging results confirmed the intracellular HOCl sensing ability of MB-DOPA and the in-situ photodynamic therapy (PDT) effectiveness for inducing massive apoptosis of cancer cells. The figure of merits of MB-DOPA, including ability for sensing of nanomolar HOCl with high specificity, rapid response, practicality for intracellular fluorescence imaging, and the in-situ generation of O-1(2) for killing tumor cells, is expected to enable diagnosis of early-stage oncogenesis based on the highly specific detection of abnormal HOCl levels in the transformed cells and the simultaneous treatment in biomedical applications. (C) 2019 Elsevier B.V. All rights reserved.