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

International Journal of Molecular Sciences

卷:21

Eva Fischer-Fodor¹  Maria Perde-Schrepler¹  Patriciu Achimas-Cadariu²  Monica Focsan³  Eva Molnar⁴  Emese Gal⁴  Luminita Silaghi-Dumitrescu⁴  Castelia Cristea⁴  Luiza Gaina⁴ 

[1] Department of Radiobiology and Tumor Biology, Institute of Oncology “Prof.Dr. Ion Chiricuta”, 34-36 Republicii street, RO-400015 Cluj-Napoca, Romania;

[2] Department of Surgery, Institute of Oncology “Prof.Dr. Ion Chiricuta”, 34-36 Republicii street, 400015 Cluj-Napoca, Romania;

[3] Institute for Interdisciplinary Experimental Research in Bionanoscience, Nanobiophotonics Laboratory, Babeş-Bolyai University, 42 Laurian street, 400271 Cluj-Napoca, Romania;

[4] 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;

关键词: meso-aryl-porphyrin;    metal-porphyrin;    phenothiazine;    carbazole;    UV–Vis spectroscopy;    cytotoxicity;   

DOI  :  10.3390/ijms21093178

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown