期刊
DYES AND PIGMENTS
卷 183, 期 -, 页码 -出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.dyepig.2020.108728
关键词
Porphyrin; Cappingmechanism; Metalcomplex; Antioxidant; Antitumor; Dockingstudies
In this work, we have synthesized a series of novel porphyrin derivatives, 1-5, in high yields. The metal complexes of two of the newly synthesized porphyrin derivatives, 1a-d and 2a-d, have also been synthesized in high yields and characterized. In the synthesis of the new porphyrins and metalloporphrins, we employed our reported strategy in which we utilized N,N-dimethylformamide (DMF) as a capping agent in the reaction of pyrrole with different hetero-aryl aldehydes. The new porphyrin derivatives are equipped with different aromatic substituents and hetero-cycles at the peripheral position. The structures of the new compounds were confirmed by elemental and spectral analyses. The geometry and magnetic properties of the new metalloporphyrins 1a-d and 2a-d have also been studied. Antioxidant and cytotoxic activities of the new compounds were evaluated and structure-activity relationships were performed. Porphyrin derivatives 2a and 4 showed exceptional antioxidant activity compared to ascorbic acid as a reference. While the derivatives 2, 3, and 5 exhibited very strong cytotoxic activity against two human cell lines, HePG-2 and MCF-7. Docking for the most promising antioxidant porphyrins, 2a and 4, into the binding active site of antioxidant protein Human Peroxiredoxin (code: 1HD2) has been carried out to detect the degree of recognition antioxidant activity. Molecular docking of the most cytotoxic active porphyrins, 3 and 5, into the biding site of telomerase inhibitor enzyme has been carried out to assess the degree of recognition cytotoxic activity.
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