A ratiometric fluorescence sensor for Fe<sup>3+</sup> based on FRET and PET processes

Hu, Yongjun; Wang, Jiaoliang; Liu, Liping; Xiao, Xiaoming

doi:10.1002/bio.2915

Cited by 25 publications

(12 citation statements)

References 28 publications

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“…(b) Heteroatoms present in the quinoline-2-carbohydrazide moiety may furnish an additional binding site and could improve the selectivity of the receptor. (c) It is a fluorophore unit that displays outstanding photophysical properties and easy modification. − After having compound 5 in a good amount in hand, we investigated the metal-sensing properties because metals are an absolute requirement for all life and play vital roles in osmotic regulation, enzymatic catalysis, metabolism, and signaling . The designed probe 5 shows excellent selectivity and sensitivity toward Fe 3+ , Cu 2+ , and Cu + ions.…”

Section: Resultsmentioning

confidence: 99%

“…44−46 After having compound 5 in a good amount in hand, we investigated the metal-sensing properties because metals are an absolute requirement for all life and play vital roles in osmotic regulation, enzymatic catalysis, metabolism, and signaling. 47 The designed probe 5 shows excellent selectivity and sensitivity toward Fe 3+ , Cu 2+ , and Cu + ions. Fe 3+ and Cu 2+ are known as efficient quenchers of excited-state fluorophores because of their paramagnetic nature.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

et al. 2020

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Differentially selective molecular sensors that exhibit differential response toward multiple analytes are cost-effective and in high demand for various practical applications. A novel, highly differentially selective electrochemical and fluorescent chemosensor, 5, based on a ferrocene-appended coumarin–quinoline platform has been designed and synthesized. Our designed probe is very specific toward Fe3+ via a reversible redox process, whereas it detects Cu2+ via irreversible oxidation. Interestingly, it exhibits differential affinity toward the Cu+ ion via complexation. High-resolution mass spectrometry, 1H NMR titration, and IR spectral studies revealed the formation of a bidentate Cu+ complex involving an O atom of the amide group attached to the quinoline ring and a N atom of imine unit, and this observation was further supported by quantum-chemical calculations. The metal binding responses were further investigated by UV–vis, fluorescence spectroscopy, and electrochemical analysis. Upon the addition of Fe3+ and Cu2+ ions, the fluorescence emission of probe 5 shows a “turn-on” signal due to inhibition of the photoinduced electron transfer (PET) process from a donor ferrocene unit to an excited-state fluorophore. The addition of sodium l-ascorbate (LAS) as a reducing agent causes fluorescence “turn off” for the Fe3+ ion because of reemergence of the PET process but not for the Cu2+ ion because it oxidizes the ferrocene unit to a ferrocenium ion with its concomitant reduction to Cu+, which further complexes with 5. Thermodynamic calculations using the Weller equation along with density functional theory calculations validate the feasibility of the PET process. A unique combination of Fe3+, LAS, and Cu2+ ions has been used to produce a molecular system demonstrating combinational “AND–OR” logic operation.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

et al. 2020

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“…Rhodamine-coumarin conjugate 149 exhibits a blue fluorescence emission at 465 nm in methanol, originating from the coumarin group. The addition of Fe 3+ induces a slight fluorescence enhancement at 465 nm and the appearance of a new fluorescence emission at 573 nm with 75-fold ratiometric fluorescence enhancement ( F 573 / F 460 ).…”

Section: Fluorescent Chemosensors Based On Coumarin Platform For Meta...mentioning

confidence: 99%

Coumarin-Based Small-Molecule Fluorescent Chemosensors

et al. 2019

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Coumarins are a very large family of compounds containing the unique 2H-chromen-2-one motif, as it is known according to IUPAC nomenclature. Coumarin derivatives are widely found in nature, especially in plants and are constituents of several essential oils. Up to now, thousands of coumarin derivatives have been isolated from nature or produced by chemists. More recently, the coumarin platform has been widely adopted in the design of small-molecule fluorescent chemosensors because of its excellent biocompatibility, strong and stable fluorescence emission, and good structural flexibility. This scaffold has found wide applications in the development of fluorescent chemosensors in the fields of molecular recognition, molecular imaging, bioorganic chemistry, analytical chemistry, materials chemistry, as well as in the biology and medical science communities. This review focuses on the important progress of coumarin-based small-molecule fluorescent chemosensors during the period of 2012− 2018. This comprehensive and critical review may facilitate the development of more powerful fluorescent chemosensors for broad and exciting applications in the future.

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“…The mechanisms of all xanthene-coumarin non-conjugated hybrid fluorophores are relatively similar, and most are related to the binding reaction of the target molecule with the closedloop spirolactone or spirolactam of rhodamine or fluorescein, leading to the opening of spirolactone or spirolactam and fluorescence changes in xanthene. Fluorophores 191, [121] 194, [124] 195 [125] 196-201, [126][127][128][129][130] 205-207, [132] and 209 [134] displayed in Figure 14 and Table 11 operate via such a mechanism. For example, 195 is an Al 3 + sensor developed by Adhikari et al in 2016.…”

Section: Xanthene-coumarin Non-conjugated Hybrid Fluorophoresmentioning

confidence: 99%

Rational Design and Biological Application of Hybrid Fluorophores

Zhang,

Qu,

Zhang

et al. 2024

Chemistry A European J

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Fluorophores are considered powerful tools for not only enabling the visualization of cell structures, substructures, and biological processes, but also making for the quantitative and qualitative measurement of various analytes in living systems. However, most fluorophores do not meet the diverse requirements for biological applications in terms of their photophysical and biological properties. Hybridization is an important strategy in molecular engineering that provides fluorophores with complementarity and multifunctionality. This review summarizes the basic strategies of hybridization with four classes of fluorophores, including xanthene, cyanine, coumarin, and BODIPY with a focus on their structure‐property relationship (SPR) and biological applications. This review aims to provide rational hybrid ideas for expanding the reservoir of knowledge regarding fluorophores and promoting the development of newly produced fluorophores for applications in the field of life sciences.

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A ratiometric fluorescence sensor for Fe³⁺ based on FRET and PET processes

Cited by 25 publications

References 28 publications

Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Rational Design and Biological Application of Hybrid Fluorophores

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A ratiometric fluorescence sensor for Fe3+ based on FRET and PET processes

Cited by 25 publications

References 28 publications

Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

Oxidation-Induced Differentially Selective Turn-On Fluorescence via Photoinduced Electron Transfer Based on a Ferrocene-Appended Coumarin–Quinoline Platform: Application in Cascaded Molecular Logic

Coumarin-Based Small-Molecule Fluorescent Chemosensors

Rational Design and Biological Application of Hybrid Fluorophores

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A ratiometric fluorescence sensor for Fe³⁺ based on FRET and PET processes