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Caging of Bodipy Photosensitizers through Hydrazone Bond Formation and their Activation Dynamics

Von Wiley-VCH zur Verfügung gestellt

Intersystem crossing, to produce cytotoxic singlet oxygen, was quenched with a new mechanism, through hydrazone bond formation. Under biologically relevant conditions and low pH of the tumor microenvironment, hydrolysis took place and switched singlet oxygen formation back on, as well as fluorescence.


Abstract

Three unique hydrazone-based small-molecule-activatable photosensitizers were designed and synthesized. Two of them work efficiently in a low-pH environment, resembling the microenvironment of the cancerous tissues. The activation pathway is unique and based on hydrazone bond cleavage. They were investigated through in vitro cellular studies in aggressive cancer lines, and tumor-specific culture conditions successfully initiated the cleavage and activation of the cytotoxic singlet oxygen generation in the relevant time period. The interesting photophysical characteristics of the α- and β-substituted hydrazone derivatives of the Bodipy structures and their mild hydrolysis methodologies were also investigated successfully.

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