Selective Fluorescence Sensing of Copper(II) and Water via Competing Imine Hydrolysis and Alcohol Oxidation Pathways Sensitive to Water Content in Aqueous Acetonitrile Mixtures

Mariappan, Kadarkaraisamy; Alaparthi, Madhubabu; Caple, G.; Balasubramanian, V.; Hoffman, Mariah M.; Hudspeth, Mikaela; Sykes, Andrew G.

doi:10.1021/ic402723c

Cited by 51 publications

(16 citation statements)

References 55 publications

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“…The researchers have demonstrated that Zn 2+ ion possesses strong affinity toward Pi, which could be used as secondary probes for Pi, so that it is reasonable using Pi snatching Zn 2+ ion from the formed complex and releasing the free probe, leading a recovery optical signal of free probe. The major deficiencies of Zn 2+ probes reported are the interference from other transition metal ions, especially Cd 2+ , due to in the same group of the Periodic table and similar properties . Although a small amount of fluorescent probe is enhanced, its fluorescence excitation and emission wavelengths (usually less than 350 and 500 nm) are shorter, which suffers from background interference and low collection efficiency in deep‐tissue imaging .…”

Section: Introductionmentioning

confidence: 95%

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

Chang

Bai

et al. 2019

Applied Organom Chemis

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A novel fluorescent probe 5‐(diethylamino)‐2‐(((2‐(hydroxymethyl)quinolin‐8‐yl)imino)methyl)phenol (QS) was synthesized by condensation reaction of 8‐aminoquinoline derivative and 4‐(diethylamino)salicylaldehyde. It was found that the probe QS was capable of high selectivity and sensitivity about specific color and fluorescence changes towards Zn2+ ion in EtOH‐H2O (v/v = 4/1, 0.01 M, Tris–HCl buffer, pH = 7.30) solution. The interaction of QS with Zn2+ ion illustrated a “turn‐on” fluorescence response at 550 nm (λex: 458 nm), moreover, after the subsequent addition of inorganic phosphate (Pi) into the solution above, a “turn‐off” fluorescence response was observed. The sensing ability of the probe QS towards Zn2+ was confirmed by fluorescence titration, UV–Vis titration and HRMS analysis. Besides, the intracellular sensing behavior of QS with Zn2+ and Pi were captured in living PC12 cells. The limit of detection (LOD) for Zn2+ and Pi sensing was found to be 0.03 μM and 0.08 μM, respectively.

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Section: Introductionmentioning

confidence: 95%

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

Chang

Bai

et al. 2019

Applied Organom Chemis

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“…Consequently, the proposed mechanism is depicted as follows (Scheme 2): Cu 2+ firstly coordinates with two adjacent nitrogen of diaminomaleonitrile moiety followed by the cleavage of the C=N bond to yield aldehyde-BODIPY 3, which was further oxidized into 4 by Cu 2+ in acetonitrile. [68][69][70] Job's plot experiment was carried out to determine the binding stoichiometry of the reaction. As shown in Fig.…”

Section: Mechanism Studymentioning

confidence: 99%

Diaminomaleonitrile-based Fluorophores as Highly Selective Sensing Platform for Cu2+

et al. 2019

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A colorimetric and turn-on fluorescent chemodosimeter 1 based on diaminomaleonitrile was synthesized for Cu 2+ detection. It showed high selectivity and sensitivity towards Cu 2+ over the other tested metal ions. Probe 1 in acetonitrile exhibited a strong absorption band at 530 nm and weak fluorescence emission when excited at 480 nm, while the addition of Cu 2+ could lead to a 30-nm blue shift of the absorption band and a remarkable fluorescence enhancement. Moreover, the detection limit of probe 1 for Cu 2+ was calculated to be 28 nM. Quite different from the reported mechanism based on a metal-complexation induced fluorescence enhancement, the sensing mechanism was proved to be based on the Cu 2+-promoted hydrolysis reaction, which was confirmed by 1 H NMR, 13 C NMR and mass spectrum analysis. Studies on probe 2 were carried out to verify the universality of this sensing mechanism.

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“…From the fluorescence titration experiment, the association constant of the receptor 64 toward the Pb 2+ , Zn 2+ and Cu 2+ were calculated to be 8800, 510 and 55000 M −1 , respectively revealed the highest tendency of the receptor 64 toward the copper ion in comparison to the Pb 2+ and Zn 2+ due to highest value of association constant. Mariappan et al 150 reported the selective fluorescence sensing of copper(II) and water via competing imine hydrolysis and alcohol oxidation pathways sensitive to water content in aqueous acetonitrile mixtures (Fig. 55.…”

Section: Bodipy Based Cu 2+ Sensormentioning

confidence: 99%

Optical sensor: a promising strategy for environmental and biomedical monitoring of ionic species

2015

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There is fast growing research on designing and improving the metal recognition methodologies in the ecosystems and biological media. The fluorescent based techniques proved a mile stones for non-invasive metal sensation and quantification in the multichannel environment. Metals as the natural components of Earth's crust are generally present in trace concentrations in the environmental samples where the humic substances have complexation affinity toward them. Iron, zinc and copper are the 1 st , 2 nd and 3 rd adequate elements indispensable to the body in trace playing the crucial roles in many biological processes. However, the unregulated amounts either as excess or deficient may exacerbate deterioration to the vital organs and triggered the progression of complications. Beside these three essential elements, mercury is widely considered to be one of the most hazardous pollutants and highly dangerous elements due to its recognized accumulative and toxic characters in the environment and the ecosystem. In the current scenario, we have tried to summarize the maximum amount of recently developed fluorescent signaling materials for the Cu 2+ , Fe 2+ / Fe 3+ , Zn 2+ and Hg 2+ . The spectral shifting in the molecules on metal chelation, mode of complexation and stoichiometries of resulting adducts have been discussed in detail. Furthermore, the molecules which have been reported as intracellular metal detector via bioimaging are specifically highlighted that might be useful for the design and development of cell viable and membrane permeable molecular probes in the future perspective.

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Selective Fluorescence Sensing of Copper(II) and Water via Competing Imine Hydrolysis and Alcohol Oxidation Pathways Sensitive to Water Content in Aqueous Acetonitrile Mixtures

Cited by 51 publications

References 55 publications

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

An aminoquinoline based fluorescent probe for sequential detection of Znic (II) and inorganic phosphate and application in living cell imaging

Diaminomaleonitrile-based Fluorophores as Highly Selective Sensing Platform for Cu2+

Optical sensor: a promising strategy for environmental and biomedical monitoring of ionic species

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