Fluorescent probes based 1,8-naphthalimide-nitrogen heterocyclic for monitoring the fluctuation of mitochondrial viscosity

Wei, Yu-Fang; Zhang, Xiaoqing; Sun, Rong; Xu, Yu-Jie; Ge, Jian‐Feng

doi:10.1016/j.dyepig.2021.109559

Cited by 17 publications

(7 citation statements)

References 38 publications

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“…All of the tested 1,8-napthalimides displayed a tendency to bind to the negatively charged mitochondrial membrane. These results are consistent with numerous reports of the high affinity of 1,8-naphthalimide derivatives for staining the mitochondria of the cell [28,35,53]. Additionally, the AzNI-3 containing a bromophenol group seemed to have an affinity to the endoplasmatic reticulum (Figure S18 in the SI).…”

Section: Cell Imagingsupporting

confidence: 91%

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: Cell Imagingsupporting

confidence: 91%

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

et al. 2021

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“…For example, recently Wei et al prepared three 1,8-naphthalimides 16a-c bounded to different nitrogen-containing heterocycles ( Figure 17 ) [ 82 ]. These compounds showed only very weak fluorescence emissions due to non-radiative decay through a twisted intramolecular charge transfer.…”

Section: Fluorescent Probes Based On Twisted Intramolecular Charge Tr...mentioning

confidence: 99%

“…Cells incubated with the probe (10 μM) for 20 min (upper panel) and incubated with monensin (10 μM) for 30 min and probe 16a (10 μM) for another 20 min (lower panel). Adapted with permission from [ 82 ]. Copyright (2021) Elsevier.…”

Section: Figures and Schemementioning

confidence: 99%

Fluorescent Probes as a Tool in Diagnostic and Drug Delivery Systems

et al. 2023

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Over the last few years, the development of fluorescent probes has received considerable attention. Fluorescence signaling allows noninvasive and harmless real-time imaging with great spectral resolution in living objects, which is extremely useful for modern biomedical applications. This review presents the basic photophysical principles and strategies for the rational design of fluorescent probes as visualization agents in medical diagnosis and drug delivery systems. Common photophysical phenomena, such as Intramolecular Charge Transfer (ICT), Twisted Intramolecular Charge Transfer (TICT), Photoinduced Electron Transfer (PET), Excited-State Intramolecular Proton Transfer (ESIPT), Fluorescent Resonance Energy Transfer (FRET), and Aggregation-Induced Emission (AIE), are described as platforms for fluorescence sensing and imaging in vivo and in vitro. The presented examples are focused on the visualization of pH, biologically important cations and anions, reactive oxygen species (ROS), viscosity, biomolecules, and enzymes that find application for diagnostic purposes. The general strategies regarding fluorescence probes as molecular logic devices and fluorescence–drug conjugates for theranostic and drug delivery systems are discussed. This work could be of help for researchers working in the field of fluorescence sensing compounds, molecular logic gates, and drug delivery.

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“…The compound presented in Scheme 1 under study is a TICT (twisted intramolecular charge transfer) molecular rotor with fluorescence-sensing properties focusing on pH and viscosity. The rapid analysis of pH and viscosity plays a critical role in large areas of industrial production, food processing, and environmental monitoring [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ]; also, the abnormal values of intracellular pH and viscosity could be associated with several diseases, such as atherosclerosis, Alzheimer’s disease, diabetes, and cancer [ 38 , 39 , 40 , 41 , 42 ]; hence, the synthesis of fluorescent probes for both pH and viscosity currently could be of significant importance. In order to simultaneously achieve pH- and viscosity-switchable fluorescence, the novel probe was based on a TICT molecular rotor platform.…”

Section: Introductionmentioning

confidence: 99%

A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor

2022

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A novel highly water-soluble 1,8-naphthalimide with pH and viscosity-sensing fluorescence was synthesized and investigated. The synthesized compound was designed as a molecular device in which a molecular rotor and molecular “off-on” switcher were integrated. In order to obtain a TICT driven molecular motion at C-4 position of the 1,8-naphthalimide fluorophore, a 4-methylpiperazinyl fragment was introduced. The molecular motion was confirmed after photophysical investigation in solvents with different viscosity; furthermore, the fluorescence-sensing properties of the examined compound were investigated in 100% aqueous medium and it was found that it could be used as an efficient fluorescent probe for pH. Due to the non-emissive deexcitation nature of the TICT fluorophore, the novel system showed low yellow–green emission, which represented “power-on”/“rotor-on” state. The protonation of the methylpiperazine amine destabilized the TICT process, which was accompanied by fluorescence enhancement indicating a “power-on”/“rotor-off” state of the system. The results obtained clearly illustrated the great potential of the synthesized compound to serve as pH- and viscosity-sensing material in aqueous solution.

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Fluorescent probes based 1,8-naphthalimide-nitrogen heterocyclic for monitoring the fluctuation of mitochondrial viscosity

Cited by 17 publications

References 38 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 Probes as a Tool in Diagnostic and Drug Delivery Systems

A Novel Fluorescent Probe for Determination of pH and Viscosity Based on a Highly Water-Soluble 1,8-Naphthalimide Rotor

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