A lysosome-targeted near-infrared fluorescent probe for cell imaging of Cu2+

Chen, Yin; Long, Zhiqing; Wang, Yuming; Zhu, Jingjing; Wang, Shasha; Liu, Yan; Wei, Peng; Yi, Tao

doi:10.1016/j.dyepig.2022.110472

Cited by 21 publications

(4 citation statements)

References 53 publications

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“…454 The Chan group also used this same reactive trigger to develop photoacoustic probes for Cu(II). 462 Other analogous Cu(II)-mediated hydrolysis reactions have also been employed for sensing exogenous Cu(II) in various cell types: hydrazone hydrolysis to release a BODIPY (300); 463 2picolinyl hydrazide hydrolysis to release a carbazole (CuCM; 301); 464 imine hydrolysis to release a coumarin (CuCIN; 302 and MGM; 303); 465,466 thiohydrazide hydrolysis to release a coumarin (CuFS; 304); 467 1,8-diaminonaphthalene hydrolysis to release a rhodamine B (305); 468 hydrazone-pyrrole elimination to yield a naphthalimide (306); 469 2-aminoimidazolyl hydrolysis to release a rhodamine B (307); 470 urea hydrolysis and subsequent decarboxylation to yield a phenoxazine (PZ-N; 308); 471 hydrazide hydrolysis and subsequent cyclization to yield an oxadiazole (OAHP; 309); 472 hydrazide hydrolysis and subsequent decarboxylation to yield methylene blue (DHUCu-1; 310); 473 and thiosemicarbazone hydrolysis to yield a quinoline (GT-TSC; 311). 474 4.2.2.2.…”

Section: Chemicalmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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Although transition metals constitute less than 0.1% of the total mass within a human body, they have a substantial impact on fundamental biological processes across all kingdoms of life. Indeed, these nutrients play crucial roles in the physiological functions of enzymes, with the redox properties of many of these metals being essential to their activity. At the same time, imbalances in transition metal pools can be detrimental to health. Modern analytical techniques are helping to illuminate the workings of metal homeostasis at a molecular and atomic level, their spatial localization in real time, and the implications of metal dysregulation in disease pathogenesis. Fluorescence microscopy has proven to be one of the most promising non-invasive methods for studying metal pools in biological samples. The accuracy and sensitivity of bioimaging experiments are predominantly determined by the fluorescent metal-responsive sensor, highlighting the importance of rational probe design for such measurements. This review covers activity-and binding-based fluorescent metal sensors that have been applied to cellular studies. We focus on the essential redox-active metals: iron, copper, manganese, cobalt, chromium, and nickel. We aim to encourage further targeted efforts in developing innovative approaches to understanding the biological chemistry of redox-active metals. CONTENTS5908 8.2. Activity-Based Fluorescent Sensors for Ni(II) 5911 9. Outlook 5911 Author Information 5912 Corresponding Authors 5912

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Section: Chemicalmentioning

confidence: 99%

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Grover,

Koblova,

Pezacki

et al. 2024

Chem. Rev.

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show abstract

“…Cu 2+ in lysosomes is reported to relate to Munk’s syndrome, Wilson’s disease, Alzheimer’s disease, and other diseases [ 150 ]. Chen et al designed and synthesized a lysosome-targeted fluorescence probe, DHUCu-1 ( 45 , Scheme 6 ), with near-infrared emission using methylene blue as the fluorescence carrier [ 151 ]. It can detect and image Cu 2+ in lysosomes, in addition to having the advantages of good water solubility and low toxicity.…”

Section: Design Of Molecular Probes For Organelle-targeted Cell Imagingmentioning

confidence: 99%

Recent Development of Advanced Fluorescent Molecular Probes for Organelle-Targeted Cell Imaging

Dai

Cui

et al. 2023

Biosensors

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Fluorescent molecular probes are very powerful tools that have been generally applied in cell imaging in the research fields of biology, pathology, pharmacology, biochemistry, and medical science. In the last couple of decades, numerous molecular probes endowed with high specificity to particular organelles have been designed to illustrate intracellular images in more detail at the subcellular level. Nowadays, the development of cell biology has enabled the investigation process to go deeply into cells, even at the molecular level. Therefore, probes that can sketch a particular organelle’s location while responding to certain parameters to evaluate intracellular bioprocesses are under urgent demand. It is significant to understand the basic ideas of organelle properties, as well as the vital substances related to each unique organelle, for the design of probes with high specificity and efficiency. In this review, we summarize representative multifunctional fluorescent molecular probes developed in the last decade. We focus on probes that can specially target nuclei, mitochondria, endoplasmic reticulums, and lysosomes. In each section, we first briefly introduce the significance and properties of different organelles. We then discuss how probes are designed to make them highly organelle-specific. Finally, we also consider how probes are constructed to endow them with additional functions to recognize particular physical/chemical signals of targeted organelles. Moreover, a perspective on the challenges in future applications of highly specific molecular probes in cell imaging is also proposed. We hope that this review can provide researchers with additional conceptual information about developing probes for cell imaging, assisting scientists interested in molecular biology, cell biology, and biochemistry to accelerate their scientific studies.

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“…Moreover, recent investigations into their photophysical properties have unveiled new avenues for the advancement of sensors in biological environments. The literature reports that conventional organic sensors face a low bioavailability disadvantage related to the low sensor biopermeability and poor water solubility [68][69][70], making their application as sensors in biological media unfeasible. To deepen our comprehension of the interplay between metal ions and the chiral ionic liquid, we conducted titration experiments with a metal ion and calculated Stern-Volmer quenching constant (K SV ).…”

Section: Optical Sensingmentioning

confidence: 99%

Thiazolidine-Based Fluorescent Chiral Ionic Liquids for Trace Copper(II) Ion Sensing

Griebeler,

Bach,

Silva

et al. 2023

Compounds

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This study presents a comprehensive analysis of the synthesis and photophysical properties of thiazolidine-functionalized chiral ionic liquids (CILs) derived from L-cysteine. The synthesis involves a four-step route, encompassing N-protection, coupling reactions with bromoalcohols, and ionic liquid formation. The optical properties of the compounds were evaluated using UV–Vis absorption and fluorescence emission spectroscopies, revealing distinct behavior for different heterocycles and counter-ions. Notably, the investigation reveals that thiazolidine-based CILs exhibit unconventional intrinsic luminescence characteristics. Building upon these photophysical properties, an interaction study was conducted between copper (II) and the CILs. The findings exhibit a robust linear relationship between the optical response and the concentration of the metal ion. Through the calculation of the Stern–Volmer quenching constant, it was determined that the 1:1 binding model is applicable. This research underscores the potential of UV–Vis absorption spectroscopy as a highly sensitive method for detecting metal ions. By elucidating the synthesis, photophysical behavior, and metal ion interaction of thiazolidine-based CILs, this study contributes valuable insights into the field of functionalized ionic liquids and their potential applications in various areas.

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A lysosome-targeted near-infrared fluorescent probe for cell imaging of Cu2+

Cited by 21 publications

References 53 publications

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Small-Molecule Fluorescent Probes for Binding- and Activity-Based Sensing of Redox-Active Biological Metals

Recent Development of Advanced Fluorescent Molecular Probes for Organelle-Targeted Cell Imaging

Thiazolidine-Based Fluorescent Chiral Ionic Liquids for Trace Copper(II) Ion Sensing

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