A highly sensitive and selective fluorescent probe for determination of Cu (II) and application in live cell imaging

Fu, Ying; Pang, Xiaoyan; Wang, Zhiqiang; Chai, Qiong; Ye, Fei

doi:10.1016/j.saa.2018.10.005

Cited by 70 publications

(29 citation statements)

References 34 publications

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“…The calculations showed high association constant of azo 4c to Fe 3+ as 4.63 × 10 8 M −1 indicated that Fe 3+ showed high binding affinity toward azo 4c comparable with reported receptors that show high selectivity toward Fe 3+ [30,31]. For instance, rhodamine B with thiocarbonyl moieties showed a binding constant of 2.75 × 10 4 M −1 [32], another rhodamine B derivative showed 1.52 × 10 4 M −1 [33]. Furthermore, azo-Schiff base receptors containing azo and azomethine groups showed 7.72 × 10 4 -1.21 × 10 5 M −1 [33].…”

Section: Association Constantsupporting

confidence: 75%

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

2020

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This research includes the design and synthesis of new derivatives for rhodanine azo compounds (4a–c) containing a naphthalene ring. Physiochemical properties of the synthesized compounds were determined by their melting points, FTIR, 1H-NMR, 13C-NMR, and elemental analysis spectroscopic techniques. The biological activities of the newly prepared azo rhodanine compounds were evaluated against some pathogenic bacteria using three different bacterial species including (Escherichia coli., Pseudomonas aeruginosa, Staphylococcus aureus) and compared with amoxicillin as a reference drug. The results showed that our compounds have moderate-to-good vital activity against the mentioned pathogenic bacteria. The selectivity and sensitivity of the newly prepared rhodanine azo compounds with transition metals Co2+, Cu2+, Zn2+, Ni2+, and Fe3+ were studied using UV–vis and fluorescence spectroscopy techniques. Among the synthesized azos, azo 4c showed affinity toward Fe3+ ions with an association constant of 4.63 × 108 M−1. Furthermore, this azo showed high sensitivity toward Fe3+ ions with detection limits of 5.14 µM. The molar ratio and Benesi–Hildebrand methods confirmed the formation of complexes between azo 4c and Fe3+ with 1:2 binding stoichiometry. Therefore, azo 4c showed excellent potential for developing efficient Fe3+ chemosensors.

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Section: Association Constantsupporting

confidence: 75%

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

2020

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“…The final product PCN was synthesized on the basis of the previous literatures (Malkondu and Erdemir, 2015 ; Fu et al, 2019a ). Compound 2 (0.46 g, 1 mmol) was suspended first in MeOH/CHCl 3 (1:1, 160 mL) followed by adding 0.7 g, 5 mmol p -chlorobenzaldehyde, and then the mixture was stirred at 50°C for 48 h. After cooling to room temperature, the precipitated solid was obtained and washed with methanol.…”

Section: Methodsmentioning

confidence: 99%

A Highly Selective Perylenediimide-Based Chemosensor: “Naked-Eye” Colorimetric and Fluorescent Turn-On Recognition for Al3+

et al. 2020

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A novel "turn-on" fluorescent probe (PCN) was designed, synthesized, and characterized with perylene tetracarboxylic disimide as the fluorophore and Schiff base subunit as the metal ion receptor. The probe demonstrated a considerable fluorescence enhancement in the presence of Al 3+ in DMF with high selectivity and sensitivity. Furthermore, the considerably "off-on" fluorescence response simultaneously led to the apparent color change from colorless to brilliant yellow, which could also be identified by naked eye easily. The sensing capability of PCN to Al 3+ was evaluated by the changes in ultraviolet-visible, fluorescence, Fourier transform-infrared, proton nuclear magnetic resonance, and high-resolution mass spectrometry spectroscopies. The linear concentration range for Al 3+ was 0-63 µM with a detection limit of 0.16 µM, which allowed for the quantitative determination of Al 3+ .

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“… 22 − 24 So far, many fluorescent probes for Cu 2+ ions have been reported. The development of new fluorescent probes is, however, still being concerned due to the limitations of reported probes such as low sensitivity and selectivity, 25 , 26 a narrow range of pH, 20 , 27 − 29 working in solutions with a high proportion of organic solvents, 26 , 30 and excitation wavelength in the ultraviolet region. 26 , 28 , 31 , 32 These limitations reduce the application of probes to monitor Cu 2+ ions in living cells.…”

Section: Introductionmentioning

confidence: 99%

Coumarin-Based Dual Chemosensor for Colorimetric and Fluorescent Detection of Cu²⁺in Water Media

et al. 2020

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A novel coumarin derivative ( 5 ) was synthesized and used as a colorimetric and fluorescent probe for selective detection of Cu 2+ ions in the presence of other metal ions, with the detection limits of 5.7 and 4.0 ppb, respectively. Cu 2+ ion reacts with probe 5 to form a 1:1 stoichiometry complex, resulting in a remarkable redshift of absorption maximum from 460 to 510 nm, as well as almost completely quenching fluorescence intensity of probe 5 at the wavelength of 536 nm. These changes can be distinctly observed by naked eyes. In addition, the working pH range of probe 5 is wide and suitable for physiological conditions, thus probe 5 may be used for detection of Cu 2+ ions in living cells. The stable structures of probe 5 and its 1:1 complex with Cu 2+ ion were optimized at the PBE0/6-31+G(d) level of theory. The presence and characteristics of bonds in compounds were studied through atoms in a molecule and natural bond orbital analysis. The formation of the complex led to a strong transfer of electron density from probe 5 as a ligand to Cu 2+ ion, resulting in breaking the π-electron conjugated system, which is the cause of fluorescence quenching and color change of 5- Cu 2+ complex.

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A highly sensitive and selective fluorescent probe for determination of Cu (II) and application in live cell imaging

Cited by 70 publications

References 34 publications

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

A Highly Selective Perylenediimide-Based Chemosensor: “Naked-Eye” Colorimetric and Fluorescent Turn-On Recognition for Al3+

Coumarin-Based Dual Chemosensor for Colorimetric and Fluorescent Detection of Cu²⁺in Water Media

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A highly sensitive and selective fluorescent probe for determination of Cu (II) and application in live cell imaging

Cited by 70 publications

References 34 publications

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

Synthesis and Antibacterial Activity of Rhodanine-Based Azo Dyes and Their Use as Spectrophotometric Chemosensor for Fe3+ Ions

A Highly Selective Perylenediimide-Based Chemosensor: “Naked-Eye” Colorimetric and Fluorescent Turn-On Recognition for Al3+

Coumarin-Based Dual Chemosensor for Colorimetric and Fluorescent Detection of Cu2+in Water Media

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Product

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Coumarin-Based Dual Chemosensor for Colorimetric and Fluorescent Detection of Cu²⁺in Water Media