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photocaged activity-based probes for improved monitoring of protein S-sulfenylation in living cells

Chinese Chemical Letters 2024年第2期35卷 451-454页

作者： Jiahao Zhang Haiyue Peng Zi'an Chen Guorui Li Jing Huang State Key Laboratory of Chemo/Biosensing and Chemometrics Hunan Provincial Key Laboratory of Animal Models and Molecular MedicineSchool of Biomedical SciencesHunan UniversityChangsha 410082China

Protein S-sulfenylation(protein sulfenic acid),as one of the most significant oxidative post-translational modifications(OxiPTMs),plays a vital role in regulating protein function.A variety of activity-based probes have been developed to profile sulfenic acid in living ***,due to the transient presence and low content of sulfenic acid in living cell,high doses of probes are needed to achieve efficient *** importantly,current probes have no temporal control over sulfenic acid *** overcome these limitations,two caged cysteine sulfenic acid probes DYn-2-ONB and DYn-2-Cou with either an o-nitrobenzyl or coumarin protecting group were developed in this *** probes can be efficiently uncaged via irradiation to produce the active C-nucleophile probe *** assay in living cells demonstrated DYn-2-ONB exhibited better labeling capacity compared with DYn-2,providing it as a powerful tool for improved monitoring of protein S-sulfenylation in living cells.

关键词： Cysteine Sulfenic acid Activity-based probe photocage Light activation Protein S-sulfenylation

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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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Light-triggered release of insecticidally active spirotetramat-enol

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Chinese Chemical Letters 2018年第11期29卷 1648-1650页

作者： Zhiping Xu Zhenhong Gao Xusheng Shao Shanghai Key Laboratory of Chemical Biology School of PharmacyEast China University of Science and Technology State Key Laboratory of Bioreactor Engineering East China University of Science and Technology

Spirotetramat metabolizes to its active enol form in the plant. We described here a photocaged pesticide delivery system that can release insecticidal spirotetramat enol form upon light irradiation. Covalently linking spirotetramat-enol with photoresponsive coumarin generated the caged insecticide. The photophysical and photochemical properties, deprotection photolysis and insecticidal activities of the caged spirotetramat enol were studied. This light-triggered system can undergo cleavage to release free spirotetramat enol form at the presence of blue light （420 nm） or sunlight, Bioassays indicated that the triggered molecule has no obvious insecticidal activity against Aphis craccivora Koch at dark and could be activated by light to release the insecticidal ingredients, which provides precise control over insecticide delivery.

关键词： photocage Spirotetramat enol Coumarin Insecticide Light

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