Naphthalimide–coumarin conjugate: ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells

Shiraishi, Yasuhiro; Hayashi, Naoto; Nakahata, Masaki; Sakai, Shinji; Hirai, Takayuki

doi:10.1039/c7ra05423h

Cited by 20 publications

(12 citation statements)

References 35 publications

(6 reference statements)

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“…1,8-Naphthalimide is a motif in compounds with a wide range of applications, for example, organic electronics (e.g., organic light emitting diodes (OLEDs), bulk heterojunction solar cells (BHJs), dye-sensitized solar cells (DSSCs), etc.) and cellular imaging; it also exhibits a broad spectrum of biological activity [ 1 , 2 , 3 , 4 ]. The wide range of applications is mainly considered in compounds substituted in the 4-C position of the naphthalene ring, which may be associated with obtaining a suitable donor-acceptor system.…”

Section: Introductionmentioning

confidence: 99%

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

et al. 2021

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A new series of 1,8-naphtalimides containing an imine bond at the 3-position of the naphthalene ring was synthesized using 1H, 13C NMR, FTIR, and elementary analysis. The impact of the substituent in the imine linkage on the selected properties and bioimaging of the synthesized compounds was studied. They showed a melting temperature in the range of 120–164 °C and underwent thermal decomposition above 280 °C. Based on cyclic and differential pulse voltammetry, the electrochemical behavior of 1,8-naphtalimide derivatives was evaluated. The electrochemical reduction and oxidation processes were observed. The compounds were characterized by a low energy band gap (below 2.60 eV). Their photoluminescence activities were investigated in solution considering the solvent effect, in the aggregated and thin film, and a mixture of poly(N-vinylcarbazole) (PVK) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt.%). They demonstrated low emissions due to photoinduced electron transport (PET) occurring in the solution and aggregation, which caused photoluminescence quenching. Some of them exhibited light emission as thin films. They emitted light in the range of 495 to 535 nm, with photoluminescence quantum yield at 4%. Despite the significant overlapping of its absorption range with emission of the PVK:PBD, incomplete Förster energy transfer from the matrix to the luminophore was found. Moreover, its luminescence ability induced by external voltage was tested in the diode with guest–host configuration. The possibility of compound hydrolysis due to the presence of the imine bond was also discussed, which could be of importance in biological studies that evaluate 3-imino-1,8-naphatalimides as imaging tools and fluorescent materials for diagnostic applications and molecular bioimaging.

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Section: Introductionmentioning

confidence: 99%

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

et al. 2021

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“…The toxicity of cyanide anion, CN – , one of the harmful anions, is associated with binding to the iron in cytochrome c oxidase, which interrupts electron transport and causes hypoxia. , In addition, through lungs, gastrointestinal tract, and skin, cyanide could be absorbed, which results in convulsion and unconsciousness leading to death . Even with its toxicity, cyanide anion is extensively utilized in chemical operations, including manufacture of plastics, extraction of gold and silver, and metallurgy. − Thus, it is very critical to have tactics to selectively and sensitively monitor CN – . − …”

Section: Introductionmentioning

confidence: 99%

Fluorescent Sensor for Sequentially Monitoring Zinc(II) and Cyanide Anion in Near-Perfect Aqueous Media

Jang

Kang

Lee

et al. 2017

Ind. Eng. Chem. Res.

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We report a new sensor, 1, for sequentially detecting Zn 2+ and CN − based on fluorescence. Sensor 1 was prepared through the reaction of 3-aminobenzofuran-2-carboxamide with 4diethylaminosalicylaldehyde. Sensor 1 showed a selective "off−on" fluorescent response toward Zn 2+ , distinguishing Zn 2+ from Cd 2+ . The limit of 1 (0.35 μM) for monitoring Zn 2+ is lower than the World Health Organization (WHO) guideline (76 μM) for water available for drinking. Importantly, sensor 1 could sense Zn 2+ in living cells and aqueous media. In addition, the resulting 1−Zn 2+ complex functioned as an efficient "on−off" sensor for CN − . The mechanisms of 1 for detecting Zn 2+ and CN − were explained by spectroscopic, spectrometric, and theoretical studies.

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“…The cells were washed with PBS and subjected for observation on a fluorescence microscopy (BIOREVE BZ-9000, Keyence Corp., Osaka, Japan) [28]. Cell viability tests were performed as follows [29]: Trypsinized HeLa cells were incubated with PBS/MeCN (8/2 v/v) mixture containing 1 (50 µM) for 20 min at 37 • C in humidified air containing 5% CO 2 . After washing with PBS for three times, a Trypan blue solution was added to the cells.…”

Section: Biological Experimentsmentioning

confidence: 99%

A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite

Shiraishi¹,

Nakatani²,

Takagi³

et al. 2020

Chemosensors

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Hypochlorite anion (ClO−) is a widely-used disinfectant and a microbicidal agent in the immune system. Accurate detection of ClO− in environmental and biological samples by simply prepared chemosensors/chemodosimeters is important. Herein, we report that a naphthalimide–sulfonylhydrazine conjugate with an imine (C = N) linker, prepared via simple condensation, acts as an effective fluorescent chemodosimeter for ClO−. The molecule exhibits a weak emission, but ClO−-selective cleavage of its C = N bond creates a strong green emission. Ab initio calculation showed that the emission enhancement by ClO− originates from the suppression of intramolecular electron transfer from the photoexcited naphthalimide through the C = N linker. This response enables selective and sensitive detection of ClO− at physiological pH range (7–9) and allows fluorometric ClO− imaging in the presence of cells.

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Naphthalimide–coumarin conjugate: ratiometric fluorescent receptor for self-calibrating quantification of cyanide anions in cells

Abstract: Quantitative determination of toxic cyanide anions (CN À ) in biological samples is an important subject. We

Cited by 20 publications

References 35 publications

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives

Fluorescent Sensor for Sequentially Monitoring Zinc(II) and Cyanide Anion in Near-Perfect Aqueous Media

A Naphthalimide–Sulfonylhydrazine Conjugate as a Fluorescent Chemodosimeter for Hypochlorite

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