Coumarin functionalized metallo phthalocyanines shows increased singlet oxygen quantum yields when included lipophilic groups.

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In this study, 7‐hydroxy‐3,4‐cyclohexenecoumarin (1), two new phthalonitriles, 7‐(2,3‐dicyanophenoxy)‐3,4‐cyclohexene‐coumarin (2), 7‐(3,4‐dicyanophenoxy)‐3,4‐cyclohexenecoumarin (3), were prepared. The phthalonitrile derivatives 2 and 3 were converted to the respective non‐peripheral tetra, peripheral tetra 7‐oxy‐3,4‐cyclohexenecoumarin substituted zinc(II) (4,6) and indium(III)acetate phthalocyanine (5,7) derivatives. All novel purified compounds (2‐7) were characterized by elemental analysis, FT‐IR, UV‐vis, 1H NMR, 13C NMR, MALDI‐TOF mass data. The spectral, photophysical (fluorescence quantum yields and lifetimes), and photochemical (singlet oxygen generation and photodegradation under light irradiation) properties of the synthesized Pcs (4‐7) were studied in DMF, and the results were compared to determine the effects of the locations of substituents and the diversity of the central metal atom on these properties. The 7‐oxy‐3,4‐cyclohexenecoumarin bearing phthalocyaninatozinc(II) and indium(III)acetate complexes showed good solubility in organic solvents such as chloroform, dichloromethane, tetrahydrofuran, acetone, DMF and DMSO. The fluorescence quenching behavior were investigated using 1,4‐benzoquinone as a quencher. They have an acceptable level of singlet oxygen production, which determines the usability of phthalocyanines in photodynamic therapy applications and demonstrated appropriate photodegradation. The thermal properties of Pcs (4‐7) were also investigated.

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There are many studies in the literature on thymoquinone (TQ)-related cancer cells and models, and there is no relevant study investigating the efficacy of the oxime derivative of TQ (TQ-Ox). This study synthesized TQ-Ox and examined its cytotoxic, genotoxic, and apoptotic properties in ovarian cancer cells. The structure TQ-Ox was confirmed with NMR. The cytotoxicity by luminometric ATP, intracellular reactive oxygen species (iROS) by fluorometric, intracellular calcium (iCa 2+ ) by fluorometric, mitochondrial membrane potential (MMP) by flow cytometry, glutathione (GSH) levels with GSH/GSSG-Glo assay, DNA damage by comet assay, and apoptosis by acridine orange/ethidium bromide dye were determined. Concentrations of TQ-Ox was statistically increased cytotoxicity, DNA damage, apoptosis, iROS, and iCa 2+ in a concentration-dependent manner (p<0.001). Besides, MMP and GSH levels also decreased statistically significantly (p<0.001) with increasing concentrations. TQ-Ox would be an effective treatment option by increasing cytotoxicity, genotoxicity, and apoptosis in ovarian carcinoma.

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The new emerging coronavirus (SARS-CoV-2) has become a global health problem with very rapid transmission from person to person, causing severe acute respiratory problems. In the circumstance, the discovery of vaccines or drugs to eradicate or reduce the impact of the COVID-19 has made it imperative to develop new approaches. In the current situation, many drugs on the drug bank have been researched computationally, and there has not been an emphasis on synthetic effort. We tested 42 coumarin derivatives (1a-14c) containing 14 different substituents, which are secondary metabolites of plants, and the anticoagulant Coumadin (warfarin) drug as a reference by Molecular Docking calculation technique on 6LU7 main protease of the coronavirus. Optimized geometries, electron motions and energy values of all coumarins were also determined using the Density Functional Theory (DFT) method. The drug properties of coumarins were estimated using the ADME-Tox test method. Coumarins formed strong interactions with HIS41, CYS145, and other amino acids in the active site of the main protease. In general, 6,7-dihydroxy-3-phenylcoumarin derivatives gave relatively higher scores, and for all coumarins, biphenyl (for 10a, -8.6 kcal/mol; 10b, -8.3 kcal/mol; 10c, -7.9 kcal/mol) and 4-trifluoromethylphenyl (for 13a, -8.1 kcal/mol; 13b, -8.1 kcal/mol; 13c -8.3 kcal/mol) substituted coumarin had the highest score. The coumarins data reported in this study serves as a stepping stone for in vitro and in vivo experimental research for vaccine development purposes.