Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents
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 s...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-03-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/6/2985 |
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| author | Bianca Stoean Dumitrita Rugina Monica Focsan Ana-Maria Craciun Mǎdǎlina Nistor Tamas Lovasz Alexandru Turza Ioan-Dan Porumb Emese Gál Castelia Cristea Luminita Silaghi-Dumitrescu Simion Astilean Luiza Ioana Gaina |
| author_facet | Bianca Stoean Dumitrita Rugina Monica Focsan Ana-Maria Craciun Mǎdǎlina Nistor Tamas Lovasz Alexandru Turza Ioan-Dan Porumb Emese Gál Castelia Cristea Luminita Silaghi-Dumitrescu Simion Astilean Luiza Ioana Gaina |
| author_sort | Bianca Stoean |
| collection | DOAJ |
| description | 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 <b>3d</b> and its <i>N</i>-alkyl-2-methylpyridinium precursor <b>1c</b>. The <i>trans</i> geometry of the newly synthesized (E)-4-(2-(7-bromo-10-ethyl-10H-phenothiazin-3-yl)vinyl)-1-methylpyridin-1-ium iodide <b>3b</b> and (E)-1-methyl-4-(2-(10-methyl-10H-phenothiazin-3-yl)vinyl)pyridin-1-ium tetrafluoroborate <b>3a′</b> 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 <b>3b</b> was investigated by irradiation at 365 nm in different solvents, while the steady-state and time-resolved fluorescence properties of dye <b>3b</b> and <b>3a′</b> 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. |
| first_indexed | 2024-03-10T13:13:34Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T13:13:34Z |
| publishDate | 2021-03-01 |
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| series | International Journal of Molecular Sciences |
| spelling | doaj.art-7cc65091d15e48e7a0ba037403ec38092023-11-21T10:35:50ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-03-01226298510.3390/ijms22062985Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining AgentsBianca Stoean0Dumitrita Rugina1Monica Focsan2Ana-Maria Craciun3Mǎdǎlina Nistor4Tamas Lovasz5Alexandru Turza6Ioan-Dan Porumb7Emese Gál8Castelia Cristea9Luminita Silaghi-Dumitrescu10Simion Astilean11Luiza Ioana Gaina12Research Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaBiochemistry Department, Faculty of Veterinary Medicine, University of Agricultural Science and Veterinary Medicine, 3-5 Calea Manastur Street, 400327 Cluj-Napoca, RomaniaNanobiophotonics and Laser Microspectroscopy Center, Interdisciplinary Research Institute in Bio-Nano-Sciences, Babes-Bolyai University, 42 Treboniu Laurian Street, 400271 Cluj-Napoca, RomaniaNanobiophotonics and Laser Microspectroscopy Center, Interdisciplinary Research Institute in Bio-Nano-Sciences, Babes-Bolyai University, 42 Treboniu Laurian Street, 400271 Cluj-Napoca, RomaniaBiochemistry Department, Faculty of Veterinary Medicine, University of Agricultural Science and Veterinary Medicine, 3-5 Calea Manastur Street, 400327 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaDepartment of Mass Spectrometry, Chromatography and Applied Physics, National Institute for Research and Development of Isotopic and Molecular Technologies, 67-103 Donat Street, 400293 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaNanobiophotonics and Laser Microspectroscopy Center, Interdisciplinary Research Institute in Bio-Nano-Sciences, Babes-Bolyai University, 42 Treboniu Laurian Street, 400271 Cluj-Napoca, RomaniaResearch Center on Fundamental and Applied Heterochemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos Street, 400028 Cluj-Napoca, RomaniaWe 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 <b>3d</b> and its <i>N</i>-alkyl-2-methylpyridinium precursor <b>1c</b>. The <i>trans</i> geometry of the newly synthesized (E)-4-(2-(7-bromo-10-ethyl-10H-phenothiazin-3-yl)vinyl)-1-methylpyridin-1-ium iodide <b>3b</b> and (E)-1-methyl-4-(2-(10-methyl-10H-phenothiazin-3-yl)vinyl)pyridin-1-ium tetrafluoroborate <b>3a′</b> 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 <b>3b</b> was investigated by irradiation at 365 nm in different solvents, while the steady-state and time-resolved fluorescence properties of dye <b>3b</b> and <b>3a′</b> 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.https://www.mdpi.com/1422-0067/22/6/2985(phenothiazinyl)vinyl-pyridinium (PVP) dyessonochemistrycellular stainingmelanoma cellsepi-fluorescence imagingtwo-photon excited fluorescence lifetime imaging |
| spellingShingle | Bianca Stoean Dumitrita Rugina Monica Focsan Ana-Maria Craciun Mǎdǎlina Nistor Tamas Lovasz Alexandru Turza Ioan-Dan Porumb Emese Gál Castelia Cristea Luminita Silaghi-Dumitrescu Simion Astilean Luiza Ioana Gaina Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents International Journal of Molecular Sciences (phenothiazinyl)vinyl-pyridinium (PVP) dyes sonochemistry cellular staining melanoma cells epi-fluorescence imaging two-photon excited fluorescence lifetime imaging |
| title | Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents |
| title_full | Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents |
| title_fullStr | Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents |
| title_full_unstemmed | Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents |
| title_short | Novel (Phenothiazinyl)Vinyl-Pyridinium Dyes and Their Potential Applications as Cellular Staining Agents |
| title_sort | novel phenothiazinyl vinyl pyridinium dyes and their potential applications as cellular staining agents |
| topic | (phenothiazinyl)vinyl-pyridinium (PVP) dyes sonochemistry cellular staining melanoma cells epi-fluorescence imaging two-photon excited fluorescence lifetime imaging |
| url | https://www.mdpi.com/1422-0067/22/6/2985 |
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