Cargando…
Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines
We report here the synthetic procedure applied for the preparation of new AB(3)-type and trans-A(2)B(2) type meso-halogenophenothiazinyl-phenyl-porphyrin derivatives, their metal core complexation and their peripheral modification using Suzuki–Miyaura cross coupling reactions with various (hetero)ar...
Autores principales: | , , , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7246510/ https://www.ncbi.nlm.nih.gov/pubmed/32365924 http://dx.doi.org/10.3390/ijms21093178 |
_version_ | 1783537962939580416 |
---|---|
author | Molnar, Eva Gal, Emese Gaina, Luiza Cristea, Castelia Fischer-Fodor, Eva Perde-Schrepler, Maria Achimas-Cadariu, Patriciu Focsan, Monica Silaghi-Dumitrescu, Luminita |
author_facet | Molnar, Eva Gal, Emese Gaina, Luiza Cristea, Castelia Fischer-Fodor, Eva Perde-Schrepler, Maria Achimas-Cadariu, Patriciu Focsan, Monica Silaghi-Dumitrescu, Luminita |
author_sort | Molnar, Eva |
collection | PubMed |
description | We report here the synthetic procedure applied for the preparation of new AB(3)-type and trans-A(2)B(2) type meso-halogenophenothiazinyl-phenyl-porphyrin derivatives, their metal core complexation and their peripheral modification using Suzuki–Miyaura cross coupling reactions with various (hetero)aryl (phenothiazinyl, 7-formyl-phenothiazinyl, (9-carbazolyl)-phenyl and 4-formyl-phenyl, phenyl) boronic acid derivatives. The meso-phenothiazinyl-phenyl-porphyrin (MPP) dyes family was thus extended by a series of novel phenothiazine-bridged porphyrin-(hetero)aryl dyads characterized by UV–Vis absorption/emission properties typical to the porphyrin chromophore, slightly modulated by increasing the size of peripheral substituents. Three phenothiazine-bridged porphyrin-heteroaryl dyads with fluorescence emission above 655 nm were selected as fluorophores in red spectral region for applications in cellular staining of human ovarian tumors. In vitro experiments of cell metabolic activity displayed a moderate toxicity on human ovarian tumor cell lines (OVCAR-3, cisplatin-sensitive A2780 and cisplatin-resistant A2780cis respectively). Visualization of the stained living cells was performed both by fluorescence microscopy imaging and by fluorescence lifetime imaging under two photon excitation (TPE-FLIM), confirming their cellular uptake and the capability of staining the cell nucleus. |
format | Online Article Text |
id | pubmed-7246510 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-72465102020-06-11 Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines Molnar, Eva Gal, Emese Gaina, Luiza Cristea, Castelia Fischer-Fodor, Eva Perde-Schrepler, Maria Achimas-Cadariu, Patriciu Focsan, Monica Silaghi-Dumitrescu, Luminita Int J Mol Sci Article We report here the synthetic procedure applied for the preparation of new AB(3)-type and trans-A(2)B(2) type meso-halogenophenothiazinyl-phenyl-porphyrin derivatives, their metal core complexation and their peripheral modification using Suzuki–Miyaura cross coupling reactions with various (hetero)aryl (phenothiazinyl, 7-formyl-phenothiazinyl, (9-carbazolyl)-phenyl and 4-formyl-phenyl, phenyl) boronic acid derivatives. The meso-phenothiazinyl-phenyl-porphyrin (MPP) dyes family was thus extended by a series of novel phenothiazine-bridged porphyrin-(hetero)aryl dyads characterized by UV–Vis absorption/emission properties typical to the porphyrin chromophore, slightly modulated by increasing the size of peripheral substituents. Three phenothiazine-bridged porphyrin-heteroaryl dyads with fluorescence emission above 655 nm were selected as fluorophores in red spectral region for applications in cellular staining of human ovarian tumors. In vitro experiments of cell metabolic activity displayed a moderate toxicity on human ovarian tumor cell lines (OVCAR-3, cisplatin-sensitive A2780 and cisplatin-resistant A2780cis respectively). Visualization of the stained living cells was performed both by fluorescence microscopy imaging and by fluorescence lifetime imaging under two photon excitation (TPE-FLIM), confirming their cellular uptake and the capability of staining the cell nucleus. MDPI 2020-04-30 /pmc/articles/PMC7246510/ /pubmed/32365924 http://dx.doi.org/10.3390/ijms21093178 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Molnar, Eva Gal, Emese Gaina, Luiza Cristea, Castelia Fischer-Fodor, Eva Perde-Schrepler, Maria Achimas-Cadariu, Patriciu Focsan, Monica Silaghi-Dumitrescu, Luminita Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title | Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title_full | Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title_fullStr | Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title_full_unstemmed | Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title_short | Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines |
title_sort | novel phenothiazine-bridged porphyrin-(hetero)aryl dyads: synthesis, optical properties, in vitro cytotoxicity and staining of human ovarian tumor cell lines |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7246510/ https://www.ncbi.nlm.nih.gov/pubmed/32365924 http://dx.doi.org/10.3390/ijms21093178 |
work_keys_str_mv | AT molnareva novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT galemese novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT gainaluiza novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT cristeacastelia novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT fischerfodoreva novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT perdeschreplermaria novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT achimascadariupatriciu novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT focsanmonica novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines AT silaghidumitresculuminita novelphenothiazinebridgedporphyrinheteroaryldyadssynthesisopticalpropertiesinvitrocytotoxicityandstainingofhumanovariantumorcelllines |