New approach for the synthesis, docking of new porphyrins and their antitumor activity

Abstract

A new methodology for the synthesis of a new series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 5a–5d, 6a–6c, 7 and 8 is presented. Structures of new compounds were established based on both elemental and spectral data. Cytotoxicity activity of the newly synthesized compounds was investigated against two human cell lines MCF-7 and HepG2. Molecular docking was performed to investigate the binding between the most active porphyrin derivatives and Bcl-2 molecular biomarkers in HepG2 cells.

Main Strategies for the Synthesis of meso-Arylporphyrins

“…First of all, the proposed method attracts attention due to high yield and the possibility of direct condensa­tion of aldehyde with pyrrole to afford porphyrins (e.g., tetrahydroxy and tetraamino tetraphenylporphyrins) that cannot be accessed by other methods (Table 2 ). All porphyrins were obtained in 75–82% yield (Table 1 ), and, what is important, the procedure for the isolation of porphyrins by pouring the reaction mixture onto ice largely facilitates the process and simplifies and accel­er­ates purification of the final products [ 131 , 132 ].…”

Metalated porphyrins as versatile visible light and NIR photoinitiators of polymerization

“…All compounds were characterized using the procedures and equipments ( 1 H and 13 C NMR, high resolution mass spectrometry (HRMS),…) reported elsewhere. [39] 4-Dodecylbenzaldehyde [40] , 2-dodecylbenzaldehyde [41] , 2,4-dibutoxybenzaldehyde [42] , 2butoxy-4-diethylaminobenzaldehyde [43] and 9-hexyl-9H-carbazole-3-carbaldehyde [44] , Porph_1 [45][46][47][48][49] , Porph_2 [50] , Porph_3 [51] , Porph_6 [52][53][54] , Porph_7 [55] , Porph_8 [56] , Fe-Porph_1 [57] were synthesized, as previously reported in the literature, without modification and in similar yields.…”

Docking studies, antitumor and antioxidant evaluation of newly synthesized porphyrin and metalloporphyrin derivatives

“…Dimethylformamide (DMF) was used as a solvent and capping reagent (Scheme 3). The DMF-pyrrole intermediate reacts with more pyrrole to keep constructing the corresponding porphorengon, and the DMF molecule would act as good leaving group in each time pyrrole is added [17][18][19].…”

“…We succeeded to prepare a series of mesoporphyrins in high yields using DMF as a capping reagent [17][18][19].…”

“…Therefore, we have also synthesized a novel series of porphyrin metal complexes in high yields and performed an in-vitro study of their protective effects. The new porphyrins have been prepared in high yields by using the previously reported modified one pot mixed solvent method in which DMF is used as capping reagent [17][18][19]. All the synthesized compounds have been characterized and assessed for the antioxidant and antitumor activities.…”