Coumarin Tröger’s base derivatives with cyanine substitution as selective and sensitive fluorescent lysosomal probes

Talianová, Veronika; Břı́za, Tomáš; Krčová, Lucie; Dolenský, Bohumil; Králová, Jarmila; Martásek, Pavel; Král, Vladimír; Havlík, Martin

doi:10.1016/j.bioorg.2019.103447

Cited by 6 publications

(7 citation statements)

References 27 publications

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“…The ligands were fully characterized with 1 H and 13 C NMR and mass spectrometry. The purity of the ligands was determined by HPLC before utilizing in the nucleic acid binding studies and bioassays.…”

Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C NMR spectra were recorded using TMS as the internal standard in CDCl3 or DMSO-d6 with a Bruker BioSpin GmbH spectrometer at 400 MHz and 100 MHz, respectively.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

“…The precipitate collected was further purified with flash column chromatography to afford the pure compounds 1−4. All these compounds were fully characterized with 1 H & 13 C NMR, ESI-MS, HPLC before using for measurements and bioassays. The characterizations of each compound were listed as follows:…”

Section: General Procedures For the Synthesis Of Dna-binding Ligands 1-4mentioning

confidence: 99%

“…Fluorescence imaging is a non-invasive and sensitive tool for the investigation of biological functions of biomolecules and probing the molecular dynamics in live cells with the high brightness and photostability fluorescent compounds. [7][8][9][10][11][12][13][14][15][16][17][18][19][20] Currently, the selective sensing or detection of a particular type of biomolecules in their native environment such as in a living cell is still challenging. [21,22] For example, in the field of nucleic acid research, the discrimination of G-quadruplex DNA (G4-DNA) structures from other types of DNA molecules via fluorescent recognition method remains a challenge.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of fluorescent G-quadruplex DNA binding ligands for the comparison of terminal group effects in molecular interaction: Phenol versus methoxybenzene

Jin

Hou

Long

et al. 2020

Bioorganic Chemistry

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Section: Resultsmentioning

confidence: 99%

“…1 H and 13 C NMR spectra were recorded using TMS as the internal standard in CDCl3 or DMSO-d6 with a Bruker BioSpin GmbH spectrometer at 400 MHz and 100 MHz, respectively.…”

Section: Materials and Instrumentationmentioning

confidence: 99%

Section: General Procedures For the Synthesis Of Dna-binding Ligands 1-4mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of fluorescent G-quadruplex DNA binding ligands for the comparison of terminal group effects in molecular interaction: Phenol versus methoxybenzene

Jin

Hou

Long

et al. 2020

Bioorganic Chemistry

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“…Fluorescent probes, particularly emitting in NIR, based on polymethine dyes [2], polyfluorinated cyanine dyes [3], and cyanine-benzothiazole hybrid system [4] revealed high selectivity towards mitochondria. The lysosomal compartment of different cell lines such as HF-P4, BLM, U-2 OS and A-2058 were selectivity labeled by fluorescent Coumarin Troger's base derivatives with cyanine substituents [5]. The selective staining of the cytoplasm was achieved by using different classes of organic dyes.…”

Section: Introductionmentioning

confidence: 99%

Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents

Stoean

Rugină

Focșan

et al. 2021

IJMS

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We report here the synthesis and structural characterization of novel cationic (phenothiazinyl)vinyl-pyridinium (PVP) dyes, together with optical (absorption/emission) properties and their potential applicability as fluorescent labels. Convective heating, ultrasound irradiation and mechanochemical synthesis were considered as alternative synthetic methodologies proficient for overcoming drawbacks such as long reaction time, nonsatisfactory yields or solvent requirements in the synthesis of novel dye (E)-1-(3-chloropropyl)-4-(2-(10-methyl-10H-phenothiazin-3-yl)vinyl)pyridin-1-ium bromide 3d and its N-alkyl-2-methylpyridinium precursor 1c. The trans geometry of the newly synthesized (E)-4-(2-(7-bromo-10-ethyl-10H-phenothiazin-3-yl)vinyl)-1-methylpyridin-1-ium iodide 3b and (E)-1-methyl-4-(2-(10-methyl-10H-phenothiazin-3-yl)vinyl)pyridin-1-ium tetrafluoroborate 3a’ was confirmed by single crystal X-ray diffraction. A negative solvatochromism of the dyes in polar solvents was highlighted by UV-Vis spectroscopy and explanatory insights were supported by molecular modeling which suggested a better stabilization of the lowest unoccupied molecular orbitals (LUMO). The photostability of the dye 3b was investigated by irradiation at 365 nm in different solvents, while the steady-state and time-resolved fluorescence properties of dye 3b and 3a’ in solid state were evaluated under one-photon excitation at 485 nm. The in vitro cytotoxicity of the new PVP dyes on B16-F10 melanoma cells was evaluated by WST-1 assay, while their intracellular localization was assessed by epi-fluorescence conventional microscopy imaging as well as one- and two-photon excited confocal fluorescence lifetime imaging microscopy (FLIM). PVP dyes displayed low cytotoxicity, good internalization inside melanoma cells and intense fluorescence emission inside the B16-F10 murine melanoma cells, making them suitable staining agents for imaging applications.

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Targeted photoresponsive carbazole–coumarin and drug conjugates for efficient combination therapy in leukemia cancer cells

Wang

Lin

Lai

et al. 2020

Bioorganic Chemistry

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Coumarin Tröger’s base derivatives with cyanine substitution as selective and sensitive fluorescent lysosomal probes

Cited by 6 publications

References 27 publications

Synthesis of fluorescent G-quadruplex DNA binding ligands for the comparison of terminal group effects in molecular interaction: Phenol versus methoxybenzene

Synthesis of fluorescent G-quadruplex DNA binding ligands for the comparison of terminal group effects in molecular interaction: Phenol versus methoxybenzene

Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents

Targeted photoresponsive carbazole–coumarin and drug conjugates for efficient combination therapy in leukemia cancer cells

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