Synthesis, G-quadruplex binding properties and cytotoxicity of naphthalimide–thiourea conjugates

Ou, Zhize; Xu, Moheng; Gao, Yunyan; Hu, Rui; Li, Qingqing; Cai, Wenjiao; Wang, Ziji; Qian, Yimeng; Yang, Guoqiang

doi:10.1039/c7nj02366a

Cited by 11 publications

(3 citation statements)

References 75 publications

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“…Yield: 87.3% (2.40 g, 8.94 mmol). 1 25 4-Bromo-1,8-naphthalic anhydride (1.39 g, 5.02 mmol) and N,N-dimethylethylenediamine (0.50 g, 5.70 mmol) were added to DMF (25 mL), and the solution was stirred at 120 °C for 2 h. The reaction solution was cooled to room temperature, and then the product was precipitated out. The precipitated product was corrected by filtration, washed with water, and dried under reduced pressure.…”

Section: Methodsmentioning

confidence: 99%

Unique Photophysical Properties of 1,8-Naphthalimide Derivatives: Generation of Semi-stable Radical Anion Species by Photo-Induced Electron Transfer from a Carboxy Group

et al. 2021

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The development of anion sensors for selective detection of a specific anion is a crucial research topic. We previously reported a selective photo-induced colorimetric reaction of 1-methyl-3-(N-(1,8-naphthalimidyl)ethyl)imidazolium (MNEI) having a cationic receptor in the presence of molecules having multiple carboxy groups, such as succinate, citrate, and polyacrylate. However, the mechanism underlying this reaction was not clarified. Here, we investigate the photo-induced colorimetric reaction of N-[2-(trimethylammonium)ethyl]-1,8-naphthalimide (TENI), which has a different cationic receptor from MNEI and undergoes the photo-induced colorimetric reaction, and its analogues to clarify the reaction mechanism. The TENI analogues having substituents on the naphthalene ring provide important evidence, suggesting that the colorimetric chemical species were radical anions generated via photo-induced electron transfer from carboxylate to the naphthalimide derivative. The generation of the naphthalimide-based radical anion is verified by 1H NMR and cyclic voltammetry analyses, and photo-reduction of methylene blue is mediated by TENI. In addition, the role of the cationic receptor for the photo-induced colorimetric reaction is investigated with TENI analogues having different hydrophilic groups instead of the trimethylammonium group. Interestingly, the photo-induced colorimetric reaction is observed in a nonionic analogue having a polyethylene glycol group, indicating that the colorimetric reaction does not require a cationic receptor. On the other hand, we reveal that the trimethylammonium group stabilizes the radical anion species. These generation and stabilization phenomena of naphthalimide-based radical anion species will contribute to the development of sophisticated detection systems specific for carboxylate.

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Section: Methodsmentioning

confidence: 99%

Unique Photophysical Properties of 1,8-Naphthalimide Derivatives: Generation of Semi-stable Radical Anion Species by Photo-Induced Electron Transfer from a Carboxy Group

et al. 2021

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“…The naphthalimide based compounds have potential applications in fluorescent bioprobes, [44–45] in solar energy collectors, [46–47] and laser dyes [48–49] . The 1,8‐naphthalimides have also been used as anion (e. g. F − , AcO − , H 2 PO 4 ) [50–52] and cation sensors (e. g. Cu(II), Zn(II)) [53–54] . The two naphthalimide classes of drugs, amonafide(3‐amino‐1,8‐naphthalimide), mitonafide (3‐nitro‐1,8‐naphthalimide), have reached clinical trials as antitumor agents [55–56] .…”

Section: Introductionmentioning

confidence: 99%

Fluorophore Tagged Mixed Ligand Copper(II) Complexes: Synthesis, Structural Characterization, Protein Binding, DNA Cleavage and Anticancer Activity

et al. 2021

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Two fluorophore tagged copper(II) complexes [Cu(phen)(L)(ClO4)2] (1) and [Cu(bpy)(L)(H2O)(ClO4)](ClO4) (2), (where L=2‐amino‐1H‐benzo[de]isoquinoline‐1,3‐(2H)dione (L), phen=1,10‐phenanthroline and bpy=2,2′‐bipyridine) have been synthesized and structurally characterized. Structures of the copper complexes 1 and 2 were confirmed by single‐crystal X‐ray structure determination. The coordination geometry around the copper center of complexes 1 and 2 is distorted octahedral. The plasmid DNA cleavage activity of the complexes has been investigated by agarose gel electrophoresis and the study reveals that both the complexes have high plasmid DNA photo‐cleavage activity. The binding interaction ability of the metal complexes with bovine serum albumin (BSA) was investigated using fluorescence spectroscopy. The cytotoxicity of the complexes has been evaluated by MTT (3‐[4,5‐dimethylthiazole‐2‐yl]‐2,5‐diphenyltetrazolium bromide) assay against A549 (adenocarcinoma human alveolar basal epithelial cells) and MCF‐7 (breast cancer cell line) cell lines in comparison with cis‐platin. Complexes 1 and 2 have exhibited better cytotoxic activity than cis‐platin against A549 and MCF‐7 cell lines. The cellular uptake study and localization of the complexes within the cells have been investigated by fluorescence microscopy. The cell staining and flow cytometry experiments suggest that complexes induce an apoptotic mode of cell death.

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“…Interestingly, G4-DNA-binding NI derivatives, such as mitonafide, amonafide, elinafide, and bisnafide, have enhanced anticancer activity . A broad variety of NI derivatives and their anticancer properties have been reported. − The modifications of NI with polyamines as space linkers have attained considerable interest due to high DNA affinity and good anticancer activity of the compounds. ,, However, the space linker modifications of bis-NIs have rarely been reported. Inspired by these findings, we rationally designed and synthesized a series of bis-NI derivatives (bis-NI1 tobis-NI6) that consist of various space linkers (phenyl dialkyne, triazole, and alkyne) and side chains (2,6-diisopropyl and 2,4,6-trimethylaniline).…”

Section: Introductionmentioning

confidence: 99%

Side-Chain-Dependent Binding of bis-Naphthalimide Self-Assembled Nanoparticles to G-Quadruplex DNA for Potential Anticancer Therapy

Kulsi

Samson

Purushothaman

et al. 2020

ACS Appl. Nano Mater.

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Novel bis-naphthalimide (NI)-based molecules composed of space linkers of phenyl dialkyne (bis-NI1 and bis-NI2), triazole (bis-NI3 and bis-NI4), and alkyne (bis-NI5 and bis-NI6) with the distinctive side chain of 2,6-diisopropylaniline or 2,4,6-trimethylaniline were designed and synthesized as nanoparticles (NPs) that bind to Gquadruplex (G4) DNA. The supramolecular assemblies of the bis-NIs were found to form isolated spheres (bis-NI1, bis-NI3), dumbbells with or without a cylindrical bridge (bis-NI2, bis-NI4), and needle-like structures (bis-NI6). The side chain of 2,4,6-trimethylaniline is suggested to play a key role in the self-assembly of the bridge-connected shape such as dumbbells or needle in bis-NIs with three different space linkers. The small sphere shaped NP formed by bis-NI1 displayed both intercalation and groove binding to G4-DNAs, while a larger sphere shaped NP of bis-NI3 represented binding to the G4-DNA groove. The dumbbells of bis-NI2 showed both intercalation and groove binding to G4-DNAs, whereas the dumbbells of bis-NI4 represented binding to the G4-DNA groove. The needle-shaped bis-NI6 exhibited both intercalation and groove binding to G4-DNAs. Different morphologies of self-assembled bis-NIs provided different IC 50 values. Furthermore, bis-NI1, bis-NI4, and bis-NI6 induced cell cycle arrest (G1/S phase) and apoptosis in cancer cells. This suggests bis-NI1, bis-NI4, and bis-NI6 are potential anticancer agents.

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Synthesis, G-quadruplex binding properties and cytotoxicity of naphthalimide–thiourea conjugates

Abstract: The hydrogen bonding between a thiourea moiety and a G-quadruplex plays a crucial role in the sequence-specific DNA binding of naphthalimide–thiourea conjugates.

Cited by 11 publications

References 75 publications

Unique Photophysical Properties of 1,8-Naphthalimide Derivatives: Generation of Semi-stable Radical Anion Species by Photo-Induced Electron Transfer from a Carboxy Group

Unique Photophysical Properties of 1,8-Naphthalimide Derivatives: Generation of Semi-stable Radical Anion Species by Photo-Induced Electron Transfer from a Carboxy Group

Fluorophore Tagged Mixed Ligand Copper(II) Complexes: Synthesis, Structural Characterization, Protein Binding, DNA Cleavage and Anticancer Activity

Side-Chain-Dependent Binding of bis-Naphthalimide Self-Assembled Nanoparticles to G-Quadruplex DNA for Potential Anticancer Therapy

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