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Synthesis, Structural Investigations, Molecular Docking, and Anticancer Activity of Some Novel Schiff Bases and Their Uranyl Complexes.

ABSTRACT: Three novel 2-aminopyrazine Schiff bases derived from salicylaldehyde derivatives and their uranyl complexes were synthesized and characterized by elemental analysis, UV-vis, FTIR, molar conductance, and thermal gravimetric analysis (TGA). The proposed structures were optimized using density functional theory (DFT/B3LYP) and 6-311G ∗(d,p) basis sets. All uranyl complexes are soluble in DMSO and have low molar conductance, which indicates that all the complexes are nonelectrolytes. The DNA binding of those Schiff bases and their uranyl complexes was studied using UV-vis spectroscopy, and screening of their ability to bind to calf thymus DNA (CT-DNA) showed that the complexes interact with CT-DNA through an intercalation mode, for which the K_b values ranged from 1 × 10⁶ to 3.33 × 10⁵ M^-1. The anticancer activities of the Schiff base ligands and their uranyl complexes against two ovarian (Ovcar-3) and melanoma cell lines (M14) were investigated, and the results indicated that uranyl complexes exhibit better results than the Schiff base ligands. Molecular docking identified the distance, energy account, type, and position of links contributing to the interactions between these complexes and two different cancer proteins (3W2S and 2OPZ).

SUBMITTER: Howsaui HB

PROVIDER: S-EPMC8391876 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:In this contribution, five Ni(II) complexes have been synthesized from sulfonamide-based Schiff bases (SB1-SB5) that comprise bromo or iodo substituents in the salicylidene moiety. The chemical structures of these compounds were extensively elucidated by different analytical and physicochemical studies. All ligands act as bidentate chelators with ON binding mode yielding octahedral, square planar, or tetrahedral geometries. The phenolic OH at δ 12.80 ppm in the free Schiff base SB2 vanishes in the 1H NMRspectrum of diamagnetic complex [Ni(SB2-H)2] favoring the OH deprotonation prior to the chelation with Ni(II) ion. The appearance of twin molecular ion peaks ([M - 1]+ and [M + 1]+) is due to the presence of bromine isotopes (79Br and 81Br) in the mass spectra of most cases. Also, the thermal decomposition stages of all complexes confirmed their high thermal stability and ended with the formation of NiO residue of mass 6.42% to 14.18%. Besides, antimicrobial activity and cytotoxicity of the ligands and some selected complexes were evaluated. Among the ligands, SB4 showed superior antimicrobial efficacy with MIC values of 0.46, 7.54, and 0.95 µM against B. subtilis, E. coli, and A. fumigatus strains, respectively. The consortium of different substituents as two bromine atoms either at positions 3 and/or 5 on the phenyl ring and a thiazole ring is one of the reasons behind the recorded optimal activity. Moreover, there is a good correlation between the cytotoxicity screening (IC50) and molecular docking simulation outcomes that predicted a strong binding of SB2 (16.0 μM), SB4 (18.8 μM), and SB5 (6.32 μM) to the breast cancer protein (3s7s). Additionally, [Ni(SB4-H)2] (4.33 µM) has nearly fourfold potency in comparison with cisplatin (19.0 μM) against breast carcinoma cells (MCF-7) and is highly recommended as a promising, potent, as well as low-cost non-platinum antiproliferative agent after further drug authorization processes.

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Synthesis, Structural Investigations, Molecular Docking, and Anticancer Activity of Some Novel Schiff Bases and Their Uranyl Complexes.

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