A TPA-caged precursor of (imino)coumarin for “turn-on” fluorogenic detection of Cu+

Hu, Zhangjun; Hu, Jiwen; Wang, Hui; Zhang, Qiong; Zhao, Meng; Brommesson, Caroline; Tian, Yupeng; Gao, Hongwen; Zhang, Xuanjun

doi:10.1016/j.aca.2016.05.031

Cited by 25 publications

(21 citation statements)

References 31 publications

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“…6A ). 55 Through the complexation of the analyte cuprous ion, the carbon–oxygen bond is broken, and the fluorophore precursor is covalently assembled through Pinner cyclization to form a fluorophore with strong fluorescence signal. The probe CU-01 made according to this strategy not only showed excellent solubility in aqueous solution and living cells, but also had a low fluorescence background and rapid response to analytes in living cells, which are worthy of recognition.…”

Section: Rational Design Of Covalent Assembly-based Fluorescent Probesmentioning

confidence: 99%

Small-molecule fluorescent probes based on covalent assembly strategy for chemoselective bioimaging

Chen

Huang

et al. 2022

RSC Adv.

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Section: Rational Design Of Covalent Assembly-based Fluorescent Probesmentioning

confidence: 99%

Small-molecule fluorescent probes based on covalent assembly strategy for chemoselective bioimaging

Chen

Huang

et al. 2022

RSC Adv.

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“…Alternatively, in the reaction-based pathway, the binding of cation first induces a chemical transformation in the probe, which eventually leads to the production of an optical signal due to the formation of a fluorescent product. 48,[73][74][75][76][77][78][79][80] The selectivity of a particular probe is determined by its specificity for chemical reactions (Scheme 1(B)).…”

Section: Fluorescent Probe Designmentioning

confidence: 99%

Recent progress on synthetic and protein-based genetically encoded sensors for fluorimetric Cu(i) recognition: binding and reaction-based approaches

et al. 2022

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“…After establishing that CD probes are sensitive to copper with high metal selectivity and can label a model protein by SDS-PAGE analysis with a fluorogenic readout, we next tested the ability of this 63 Cu levels in microglia under various inflammatory stimuli (with normalization of different cell numbers by total cellular 31 P level). Error bars denote standard derivation (SD; n = 2).…”

Section: Live-cell Imaging Of Labile Copper Pools With Cd649 Under Simentioning

confidence: 99%

Activity-Based Sensing with a Metal-Directed Acyl Imidazole Strategy Reveals Cell Type-Dependent Pools of Labile Brain Copper

et al. 2020

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Copper is a required nutrient for life and particularly important to the brain and central nervous system. Indeed, copper redox activity is essential to maintaining normal physiological responses spanning neural signaling to metabolism, but at the same time copper misregulation is associated with inflammation and neurodegeneration. As such, chemical probes that can track dynamic changes in copper with spatial resolution, especially in loosely-bound, labile forms, are valuable tools to identify and characterize its contributions to healthy and disease states. In this report, we present an activity-based sensing (ABS) strategy for copper detection in live cells that preserves spatial information by a copper-dependent bioconjugation reaction. Specifically, we designed copper-directed acyl imidazole (CD) dyes that operate through copper-mediated activation of acyl imidazole electrophiles for subsequent labeling of proximal proteins at sites of elevated labile copper to provide a permanent stain that resists washing and fixation. To showcase the utility of this new ABS platform, we sought to characterize labile copper pools in the three main cell types in the brain: neurons, astrocytes, and microglia. Exposure of each of these cell types to physiologically relevant stimuli shows distinct changes in labile copper pools. Neurons display translocation of labile copper from somatic cell bodies to peripheral processes upon activation, whereas astrocytes and microglia exhibit global decreases and increases in intracellular labile copper pools, respectively, after exposure to inflam-matory stimuli. This work provides foundational information on cell type-dependent homeostasis of copper, an essential metal in the brain, as well as a starting point for the design of new activity-based probes for metals and other dynamic signaling and stress analytes in biology. File list (2) download file view on ChemRxiv CJC Copper DAI Main Text ChemRxiv.pdf (837.74 KiB) download file view on ChemRxiv CJC Copper DAI SI Rev Clean Final.pdf (760.44 KiB)

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A TPA-caged precursor of (imino)coumarin for “turn-on” fluorogenic detection of Cu+

Cited by 25 publications

References 31 publications

Small-molecule fluorescent probes based on covalent assembly strategy for chemoselective bioimaging

Small-molecule fluorescent probes based on covalent assembly strategy for chemoselective bioimaging

Recent progress on synthetic and protein-based genetically encoded sensors for fluorimetric Cu(i) recognition: binding and reaction-based approaches

Activity-Based Sensing with a Metal-Directed Acyl Imidazole Strategy Reveals Cell Type-Dependent Pools of Labile Brain Copper

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