Aza-BODIPY photosensitizer substituted with phthalonitrile groups: Synthesis, photophysical properties and in vitro tests for breast cancer

•A novel aza-BODIPY with phthalonitrile substituents was synthesized.•Spectrophysical and spectrochemical properties were investigated.•Singlet oxygen quantum yield and fluorescence quantum yield were quantified.•Photodynamic efficiency as a photosensitizer for PDT was investigated.•The cytotoxicity...

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Bibliographic Details
Published in:Journal of molecular structure 2023-01, Vol.1271, p.134019, Article 134019
Main Authors: Özçelik, Şennur, Yurttaş, Asiye Gök, Kahveci, Muhammet U., Sevim, Altuğ Mert, Gül, Ahmet
Format: Article
Language:English
Subjects:
Aza-BODIPY
Cancer
Dark toxicity
Light toxicity
Photodynamic therapy (PDT)
Phthalonitrile
Synthesis
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Summary:•A novel aza-BODIPY with phthalonitrile substituents was synthesized.•Spectrophysical and spectrochemical properties were investigated.•Singlet oxygen quantum yield and fluorescence quantum yield were quantified.•Photodynamic efficiency as a photosensitizer for PDT was investigated.•The cytotoxicity towards breast cancer cell line, MCF-7 cells, was investigated. In photodynamic therapy (PDT), reactive oxygen species (ROS) are generated through dynamic interactions between light of a specific wavelength, a photosensitizer (PS) and molecular oxygen. Nowadays, there has been an increment in the number of studies evaluating the possible utilization of BF2 chelated tetraarylazadipyrromethanes (aza-BODIPYs) as photosensitizers in PDT. In this study, a novel aza-BODIPY with phthalonitrile substituents was synthesized by the esterification reaction of a phthalonitrile derivative namely, 4-((3,4-dicyanophenyl)sulphanyl)benzoic acid with an aza-BODIPY bearing hydroxy groups on the para positions of distal phenyl groups. Aza-BODIPY compound bearing phthalonitrile substituents was characterized by using UV–Vis, fluorescence, 1H-NMR and mass spectroscopy techniques. Photophysical and photochemical properties including fluorescence quantum yield and singlet oxygen yield were determined. In order to explore its photodynamic efficacy, it was tested on a breast cancer cell line (MCF-7 cells) and on a normal healthy cell line (L929 cells) through dark and light cytotoxicity. [Display omitted]
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2022.134019