A near-infrared colorimetric and fluorometric chemodosimeter for Cu2+ based on a bis-spirocyclic rhodamine and its application in imagings

Gao, Guangqin; Hao, Changming; Ding, Chuanxian; Zheng, Xiaohui; Liu, Lijie; Xie, Puhui; Guo, Fengqi

doi:10.1007/s11164-022-04920-5

Cited by 6 publications

(1 citation statement)

References 38 publications

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“…The sensor was applied to detect changes in Cu(II) in HeLa cells incubated in growth medium supplemented with 50 μM CuCl 2 . 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 ), ethyl hydroxide (RO1; 253 ), 2-methylpiperidine ( 254 ), Furan-2-carbaldehyde ( 255 ), 3-chloropyridazine ( 256 ), or benzyl-methyl-triazole (RHT; 257 ) substitutions, or a bis-spirocyclic configuration ( 258 ); rhodamine 6G variants with methanethioamide ( 259 ), ethyl hydroxide ( 260 ), tert -butylpyrrolyl methanimine ( 261 ), or trifluoroacetaldehyde substitutions ( 262 ); and fluorescein variants with pyridinylmethanimine (FHP; 263 ) and nitrobenzo-oxadiazole substitutions (NF; 264 ) . Other hydrazide variants have employed rhodamines with extended π-conjugation for a red-shifted emission such those with a vinylbenzonitrile (CSCN-Cu; 265 ), a naphthylamine (BF-Cu; 266 ), a carbazole (MeCzR-Cu; 267 ), a biscarbazole (BCX-Cu; 268 ), a benzimidazole with a six-membered spirocyclic hydrazide (BiF-Cu; 269 ), a quinazolinone (RQNA; 270 ), a benzene (FLACu; 271 ), a diethyl-tetrahydroquinoxaline/julolidine (JRQN; 272 ), and a quinoline (QFH; 273 ) …”

Section: Fluorescent Sensors For Coppermentioning

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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