Efficient synthesis of meso‐substituted porphyrins and molecular docking as potential new antioxidant and cytotoxicity agents

Abstract

An improved methodology is reported for the synthesis of new series of mesotetrakis-[aryl]-21H,23H-porphyrin derivatives 2a-h and was considered as a model to study their antioxidant and cytotoxic activities. The structures of the novel compounds were determined in 1 H and 13 C NMR, UV-Vis, and elemental analyses. Among the derivatives, compounds 2c, 2d, and 2h showed strongest radical-scavenging activity.Moreover, according to our results, compounds 2c, 2d, 2g, and 2h have very strong activity against the HepG2 hepatoma cell line, with IC 50 values from 9 to 25 μg/mL.Molecular docking was performed to investigate the binding between the most active porphyrin derivatives 2c, 2d, 2g, 2h and the two molecular targets Bcl-2 and caspase-3.Compounds 2c and 2d seem to have better affinities to both proteins than 2g and 2h.

Design and synthesis of novel phthalocyanines as potential antioxidant and antitumor agents starting with new synthesized phthalonitrile derivatives

“…Compounds 18 and 17 have the strongest radical scavenging activity, owing to their distinct structures and many nitrogen atoms in the hetero-aryl moiety in addition to the presence of the keto–enol form, which enhances the antioxidant activity. 20 As also reported in Table 2 , the deoxyribose assay was used to measure the hydroxyl radical scavenging activity of our synthesized compounds. The synthesized compounds can inhibit the degradation by removing the hydroxyl radicals from the tested solution, which helps us to monitor the protective effect of these compounds.…”

“…These results were found to be similar to those of previously reported compounds that have quinone moieties, which were reported to be good antioxidant agents at lower concentrations. 20 Cytotoxicity (anticancer screening). There are two factors that can be relied upon to study the cytotoxicity activity of synthesized compounds towards any cell line: 21,22 (1) the formation of an intramolecular H-bond with any of one of the nucleotides in DNA; (2) the attraction force between the positive charge on the tested derivatives and the negative charge on the wall of the cell.…”

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

“…Introduction of appropriate donor/acceptor substituents and/or metal complexation contributed to the modification of structural factors, such as molecular symmetry, size and degree of conjugation of the π-electronic system, emphasizing a high impact on the optical performances of the porphyrin-based materials. Among the various heteroaromatic units attached to the porphine chromophore aiming the modulation of its photophysical properties, the introduction of an electron rich phenothiazine unit gave fruitful returns; e.g., fluorescent porphyrins emitting intense red light with high fluorescent quantum yields [1] "push−pull" porphyrin dyes for photon to energy conversion systems [2][3][4][5] as well as potential biologically active compounds [6]. The syntheses, optical properties and electrochemical behaviors of meso-phenothiazinyl-phenyl porphyrin (MPP) dyes were first reported by our group [7] followed by the description of their metal complexation [8].…”

“…UV-Vis linear optical properties of metal complexes of bromoMPP (4, 5) and chloroMPP(6,7) in DCM solution.…”

Macrocycles and Supramolecules as Antioxidants: Excellent Scaffolds for Development of Potential Therapeutic Agents

“…Mn porphyrins that mimic the SOD[98].Tesakova et al reported the tetraphenylporphyrene (93) and evaluation of its antioxidant activity by electrochemistry[99]. Abu-Melha reported the synthesis of meso-substituted porphyrins 94-101 and the evaluation of their antioxidant activity (Figure 16)[100]. Among derivatives 94-101, compounds 96, 98 and 101 exhibited the strongest antioxidant activity.…”