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

ABSTRACT: 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.

SUBMITTER: Molnar E

PROVIDER: S-EPMC7246510 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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

Molnar Eva E Gal Emese E Gaina Luiza L Gaina Luiza L Cristea Castelia C Fischer-Fodor Eva E Perde-Schrepler Maria M Achimas-Cadariu Patriciu P Focsan Monica M Silaghi-Dumitrescu Luminita L

International journal of molecular sciences 20200430 9

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 ...[more]

PMID: 32365924

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Project description:A series of 1,8-naphthalimide (NI)-phenothiazine (PTZ) electron donor-acceptor dyads were prepared to study the thermally activated delayed fluorescence (TADF) properties of the dyads, from a point of view of detection of the various transient species. The photophysical properties of the dyads were tuned by changing the electron-donating and the electron-withdrawing capability of the PTZ and NI moieties, respectively, by oxidation of the PTZ unit, or by using different aryl substituents attached to the NI unit. This tuning effect was manifested in the UV-vis absorption and fluorescence emission spectra, e.g., in the change of the charge transfer absorption bands. TADF was observed for the dyads containing the native PTZ unit, and the prompt and delayed fluorescence lifetimes changed with different aryl substituents on the imide part. In polar solvents, no TADF was observed. For the dyads with the PTZ unit oxidized, no TADF was observed as well. Femtosecond transient absorption spectra showed that the charge separation takes ca. 0.6 ps, and admixtures of locally excited (3LE) state and charge separated (1CS/3CS) states formed (in n-hexane). The subsequent charge recombination from the 1CS state takes ca. 7.92 ns. Upon oxidation of the PTZ unit, the beginning of charge separation is at 178 fs and formation of 3LE state takes 4.53 ns. Nanosecond transient absorption (ns-TA) spectra showed that both 3CS and 3LE states were observed for the dyads showing TADF, whereas only 3LE or 3CS states were observed for the systems lacking TADF. This is a rare but unambiguous experimental evidence that the spin-vibronic coupling of 3CS/3LE states is crucial for TADF. Without the mediating effect of the 3LE state, no TADF is resulted, even if the long-lived 3CS state is populated (lifetime τCS ≈ 140 ns). This experimental result confirms the 3CS → 1CS reverse intersystem crossing (rISC) is slow, without coupling with an approximate 3LE state. These studies are useful for an in-depth understanding of the photophysical mechanisms of the TADF emitters, as well as for molecular structure design of new electron donor-acceptor TADF emitters.

Dataset Information

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

Publications

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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