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Mechanism and Application of One-Photon Blue or Two-Photon Near-Infrared Light-Gated Hydroxyl Radical Photocage

Mechanism and Application of One-Photon Blue or Two-Photon N...

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中国化学会第十六届全国光化学学术讨论会（2019）

作者： Ming-De Li Nai-Kei Wong Guanheng Huang Xuebo Chen Weihai Fang Dan Yang David Lee Phillips Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province Shantou University State Key Discipline of Infectious Diseases Shenzhen Third People's Hospital Department of Chemistry Beijing Normal University Department of Chemistry The University of Hong Kong

Development of versatile, chemically tunable photocages for photoactivated chemotherapy（PACT） represents an excellent opportunity to address the technical drawbacks of conventional photodynamic therapy（PDT） whose oxygen-dependent nature renders it inadequate in certain therapy contexts such as hypoxic tumors. As an alternative to PDT, oxygen free mechanisms to generate cytotoxic reactive oxygen species（ROS） by visible light cleavable photocages are in demand. Here, we report the detailed mechanisms by which the small molecule blebbistatin acts as a one-photon blue light-gated or two-photon nearinfrared light-gated photocage to directly release a hydroxyl radical in the absence of oxygen. By using femtosecond transient absorption spectroscopy, resonance Raman and chemoselective ROS fluorescent probes, we analyze the dynamics and fate of blebbistatin during photolysis under blue light. Water-dependent photochemistry reveals a critical process of water-assisted protonation and excited state intramolecular proton transfer（ESIPT） that drives the formation of short-lived intermediates, which surprisingly culminates in the release of hydroxyl radical but not superoxide or singlet oxygen from blebbistatin. CASPT2//CASSCF calculations confirm that hydrogen bonding between water and blebbistatin underpins this process. We further determine that blue light enables blebbistatin to induce mitochondria-dependent apoptosis, an attribute conducive to PACT development. Our work demonstrates blebbistatin as a controllable photocage for hydroxyl radical generation and provides insight into the potential development of novel PACT agents.

关键词： photoactivated chemotherapy hydroxyl radical photocage ESIPT

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