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Open AccessArticle

Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines

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The Research Center on Fundamental and Applied Heterochemistry, Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeş-Bolyai University, 11 Arany Janos street, RO-400028 Cluj-Napoca, Romania
2
Department of Radiobiology and Tumor Biology, Institute of Oncology “Prof.Dr. Ion Chiricuta”, 34-36 Republicii street, RO-400015 Cluj-Napoca, Romania
3
Medfuture Research Center for Advanced Medicine, University of Medicine and Pharmacy Iuliu Hatieganu, 8 Babes street, RO-400012 Cluj-Napoca, Romania
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Department of Surgery, Institute of Oncology “Prof.Dr. Ion Chiricuta”, 34-36 Republicii street, 400015 Cluj-Napoca, Romania
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Department of Surgery and Gynecological Oncology, University of Medicine and Pharmacy Iuliu Hatieganu, 23 Marinescu street, 400337 Cluj-Napoca, Romania
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Institute for Interdisciplinary Experimental Research in Bionanoscience, Nanobiophotonics Laboratory, Babeş-Bolyai University, 42 Laurian street, 400271 Cluj-Napoca, Romania
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(9), 3178; https://doi.org/10.3390/ijms21093178
Received: 26 March 2020 / Revised: 24 April 2020 / Accepted: 26 April 2020 / Published: 30 April 2020
(This article belongs to the Special Issue Advances in the Chemistry of Porphyrins and Related Macrocycles)
We report here the synthetic procedure applied for the preparation of new AB3-type and trans-A2B2 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. View Full-Text
Keywords: meso-aryl-porphyrin; metal-porphyrin; phenothiazine; carbazole; UV–Vis spectroscopy; cytotoxicity; fluorescence imaging; TPE-FLIM meso-aryl-porphyrin; metal-porphyrin; phenothiazine; carbazole; UV–Vis spectroscopy; cytotoxicity; fluorescence imaging; TPE-FLIM
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MDPI and ACS Style

Molnar, E.; Gal, E.; Gaina, L.; Cristea, C.; Fischer-Fodor, E.; Perde-Schrepler, M.; Achimas-Cadariu, P.; Focsan, M.; Silaghi-Dumitrescu, L. Novel Phenothiazine-Bridged Porphyrin-(Hetero)aryl dyads: Synthesis, Optical Properties, In Vitro Cytotoxicity and Staining of Human Ovarian Tumor Cell Lines. Int. J. Mol. Sci. 2020, 21, 3178.

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