Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents
| Autor: | Monica Focsan, Castelia Cristea, Luiza Gaina, Mǎdǎlina Nistor, Simion Astilean, Dumitrita Rugina, Alexandru Turza, Bianca Stoean, Tamas Lovasz, Ioan-Dan Porumb, Luminita Silaghi-Dumitrescu, Ana-Maria Craciun, Emese Gal |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Fluorescence-lifetime imaging microscopy
Iodide Pyridinium Compounds 010402 general chemistry Photochemistry 01 natural sciences cellular staining Article Catalysis epi-fluorescence imaging lcsh:Chemistry Inorganic Chemistry Mice chemistry.chemical_compound Phenothiazines Microscopy Animals Physical and Theoretical Chemistry two-photon excited fluorescence lifetime imaging lcsh:QH301-705.5 Molecular Biology HOMO/LUMO Spectroscopy (phenothiazinyl)vinyl-pyridinium (PVP) dyes Fluorescent Dyes chemistry.chemical_classification Photons Staining and Labeling 010405 organic chemistry Chemistry Organic Chemistry Solvatochromism General Medicine Fluorescence 0104 chemical sciences Computer Science Applications Solvent Spectrometry Fluorescence lcsh:Biology (General) lcsh:QD1-999 Microscopy Fluorescence Solvents Pyridinium sonochemistry melanoma cells |
| Zdroj: | International Journal of Molecular Sciences Volume 22 Issue 6 International Journal of Molecular Sciences, Vol 22, Iss 2985, p 2985 (2021) |
| ISSN: | 1422-0067 |
| DOI: | 10.3390/ijms22062985 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|