Live cell imaging by 3-imino-(2-phenol)-1,8-naphthalimides: The effect of ex vivo hydrolysis

Korzec, Mateusz; Malarz, Katarzyna; Mrozek-Wilczkiewicz, Anna; Rzycka-Korzec, Roksana; Schab‐Balcerzak, Ewa; Polański, Jarosław

doi:10.1016/j.saa.2020.118442

Cited by 15 publications

(26 citation statements)

References 57 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: Resultssupporting

confidence: 93%

“…Table 4 , Figure 3 ). In turn, the maximum emission for each compound in methanol was redshifted with respect to other solvents in the range of 525–548 nm, which is due to the intermolecular hydrogen bonding with protic solvents [ 28 , 34 ].…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, the amine (substrate for the target compounds) was tested in the same solvents and TFA concentration. This substrate was tested due to the possible hydrolysis of imines [ 25 , 26 , 28 ] as well as the use of an amine in cellular imaging reported in our earlier studies [ 28 ]. The results for amine are shown in Figure S9 .…”

Section: Resultsmentioning

confidence: 99%

“…The spectroscopic tests for the analyzed compounds were performed to determine the properties in the aggregated state and the susceptibility of the compounds to the inhibition of the PET process. The influence of the partial imine hydrolysis, mainly due to its importance in our previous research [ 25 , 26 , 28 ], was also analyzed in this paper, from the point of view of its application, such as for cell imaging. In addition, the electroluminescent properties of the described compounds were tested and compared with the results obtained in previous studies, in which the structure of the device was similar.…”

Section: Introductionmentioning

confidence: 99%

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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: Resultssupporting

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2021

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“…In the first stage, the condensation of commercially available 3-nitro-1,8-naphthalic anhydride with various amines, such as (1) hexylamine, (2) benzylamine, (3) 4-methylbenzylamine, (4) 2-phenethylamine in the ethanol was performed. Next, the nitro group was reduced to the amine by using 10% Pd/C as catalyst and hydrazine in ethanol [ 46 , 57 ]. Then, a reaction was carried out between the synthesized amines and commercially available dialdehydes such as: (a) 4,4′-diformyltriphenylamine, (b) 2,5-diformylthiophene, (c) 4,4′-biphenyldicarbaldehyde, as well as (d) dialdehyde obtained in the Sonogashira reaction.…”

Section: Resultsmentioning

confidence: 99%

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

et al. 2021

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In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about −3.22 eV and HOMO levels above −5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243–415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.

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1,8-Naphthalimides 3-substituted with imine or β-ketoenamine unit evaluated as compounds for organic electronics and cell imaging

et al. 2021

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Live cell imaging by 3-imino-(2-phenol)-1,8-naphthalimides: The effect of ex vivo hydrolysis

Cited by 15 publications

References 57 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

New Acceptor–Donor–Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide)

1,8-Naphthalimides 3-substituted with imine or β-ketoenamine unit evaluated as compounds for organic electronics and cell imaging

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