A Novel Biscarbazole-Xanthene Hybrid Fluorescent Probe for Selective and Sensitive Detection of Cu2+ and Applications in Bioimaging

Huang, Kun; Han, Defang; Li, Xianglin; Peng, Mengni; Qiu, Qi; Qin, Da‐Bin

doi:10.1007/s10895-019-02393-1

Cited by 10 publications

(5 citation statements)

References 61 publications

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“…From this starting point, many similar hydrazide Cu(II) probes that employ rhodamine ring-opening strategies have been developed and applied to detect exogenous addition of Cu(II) in various cell types such as rhodamine B variants with dimethylaminovinylbenzene (252) 412 , ethyl hydroxide (RO1; 253), 413 2-methylpiperidine (254), 414 Furan-2-carbaldehyde (255), 415 3-chloropyridazine (256), 416 or benzyl-methyltriazole (RHT; 257) 417 substitutions, or a bis-spirocyclic configuration (258) 418 ; rhodamine 6G variants with methanethioamide (259), 419 ethyl hydroxide (260), 420 tert-butylpyrrolyl methanimine (261), 421 or trifluoroacetaldehyde substitutions (262); 422 and fluorescein variants with pyridinylmethanimine (FHP; 263) 423 and nitrobenzo-oxadiazole substitutions (NF; 264). 424 Other hydrazide variants have employed rhodamines with extended π-conjugation for a redshifted emission such those with a vinylbenzonitrile (CSCN-Cu; 265), 425 a naphthylamine (BF-Cu; 266), 426 a carbazole (MeCzR-Cu; 267), 427 a biscarbazole (BCX-Cu; 268), 428 a benzimidazole with a six-membered spirocyclic hydrazide (BiF-Cu; 269), 429 a quinazolinone (RQNA; 270), 430 a benzene (FLACu; 271), 431 a diethyl-tetrahydroquinoxaline/julolidine (JRQN; 272), 432 and a quinoline (QFH; 273). 433 Ratiometric Cu(II) sensors have also been developed using the hydrazide reaction (Figure 28, Table 14).…”

Section: Activity-based Cu(ii) Sensors Based On Cu(ii)-mediated Hydro...mentioning

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: Activity-based Cu(ii) Sensors Based On Cu(ii)-mediated Hydro...mentioning

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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“… [50] Based on this mechanism, an increasing number of Cu(II) probes derived from rhodamine have emerged [51] . For example, Huang et al [52] . reported a fluorescent probe 12 ( BCX‐Cu , Figure 8B) based on the scaffold of biscarbazole‐fused xanthene hybrid, which had high selectivity and sensitivity to Cu(II).…”

Section: Fluorescence Turn‐on Probes For Cumentioning

confidence: 99%

“…[50] Based on this mechanism, an increasing number of Cu(II) probes derived from rhodamine have emerged. [51] For example, Huang et al [52] reported a fluorescent probe 12 (BCX-Cu, Figure 8B) based on the scaffold of biscarbazole-fused xanthene hybrid, which had high selectivity and sensitivity to Cu(II). In addition, it had a detection limit of 88.7 nM (Table 2) and a dissociation constant of (19.233 � 0.385)×10 À 6 M. In the absence of Cu(II), probe 12 had absorption bands at 319 nm and 334 nm, which were characteristic of the carbazole moiety.…”

Section: Activity-based Probes For Cu(ii)mentioning

confidence: 99%

Current and Future of “Turn‐On” Based Small‐Molecule Copper Probes for Cuproptosis

Peng,

Qiu,

et al. 2023

ChemistryOpen

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Increasing evidence shows that abnormal copper (Cu) metabolism is highly related to many diseases, such as Alzheimer's disease, Wilson's disease, hematological malignancies and Menkes disease. Very recently, cuproptosis, a Cu‐dependent, programmed cell death was firstly described by Tsvetkov et al. in 2022. Their findings may provide a new perspective for the treatment of related diseases. However, the concrete mechanisms of these diseases, especially cuproptosis, remain completely unclear, the reason of which may be a lack of reliable tools to conduct highly selective, sensitive and high‐resolution imaging of Cu in complex life systems. So far, numerous small‐molecular fluorescent probes have been designed and utilized to explore the Cu signal pathway. Among them, fluorescence turn‐on probes greatly enhance the resolution and accuracy of imaging and may be a promising tool for research of investigation into cuproptosis. This review summarizes the probes developed in the past decade which have the potential to study cuproptosis, focusing on the design strategies, luminescence mechanism and biological‐imaging applications. Besides, we put forward some ideas concerning the design of next‐generation probes for cuproptosis, aiming to tackle the main problems in this new field. Furthermore, the prospect of cuproptosis in the treatment of corresponding diseases is also highlighted.

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“…Over the past few years, a broad range of fluorescent probes based on small organic 38–80 and inorganic molecules, 16,17,81–94 nano-materials, 17,95–97 modified proteins, 98–103 metal–organic frameworks (MOFs) 104–107 and sol-gels 17,108–110 have been developed for the recognition of Cu( i ) and Cu( ii ) ions.…”

Section: Introductionmentioning

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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A Novel Biscarbazole-Xanthene Hybrid Fluorescent Probe for Selective and Sensitive Detection of Cu2+ and Applications in Bioimaging

Cited by 10 publications

References 61 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

Current and Future of “Turn‐On” Based Small‐Molecule Copper Probes for Cuproptosis

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

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