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N'-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling.

ABSTRACT: The ligand, N'-(furan-2-ylmethylene)-2-hydroxybenzohydrazide (H₂L), was synthesized characterized through various spectral studies which cleared out that the free ligand existed in keto form. The ligand upon reaction with Cu(II), Co(II), Ni(II) and Zn(II) acetates yielded complexes with stoichiometric ratio 1:2 (M:L) which has been validated through the elemental and mass spectral measurements. The IR and NMR spectral studies of the isolated complexes disclosed that the ligand chelated to metal ion in mononegative bidentate fashion via the azomethine nitrogen and deprotonated enolized carbonyl oxygen. Moreover, the DFT quantum chemical calculations designated that the ligand and Ni(II) complex exhibited the highest and lowest values of HOMO, LUMO energies and HOMO-LUMO energy gap, respectively. Furthermore, the in vitro cytotoxic activity towards HePG-2 and HCT-116 cell lines of the isolated compounds was investigated and the data cleared out that the ligand was more potent than the metal complexes.

SUBMITTER: Hosny NM

PROVIDER: S-EPMC10823611 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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N'-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling.

Hosny Nasser M NM Samir Ghada G Abdel-Rhman Mohamed H MH

BMC chemistry 20240128 1

The ligand, N'-(furan-2-ylmethylene)-2-hydroxybenzohydrazide (H<sub>2</sub>L), was synthesized characterized through various spectral studies which cleared out that the free ligand existed in keto form. The ligand upon reaction with Cu(II), Co(II), Ni(II) and Zn(II) acetates yielded complexes with stoichiometric ratio 1:2 (M:L) which has been validated through the elemental and mass spectral measurements. The IR and NMR spectral studies of the isolated complexes disclosed that the ligand chelate ...[more]

PMID: 38281963

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Project description:Despite the common use of salens and hydroxyquinolines as therapeutic and bioactive agents, their metal complexes are still under development. Here, we report the synthesis of novel mixed-ligand metal complexes (MSQ) comprising salen (S), derived from (2,2'-{1,2-ethanediylbis[nitrilo(E) methylylidene]}diphenol, and 8-hydroxyquinoline (Q) with Co(II), Ni(II), Cd(II), Al(III), and La(III). The structures and properties of these MSQ metal complexes were investigated using molar conductivity, melting point, FTIR, 1H NMR, 13C NMR, UV-VIS, mass spectra, and thermal analysis. Quantum calculation, analytical, and experimental measurements seem to suggest the proposed structure of the compounds and its uncommon monobasic tridentate binding mode of salen via phenolic oxygen, azomethine group, and the NH group. The general molecular formula of MSQ metal complexes is [M(S)(Q)(H2O)] for M (II) = Co, Ni, and Cd or [M(S)(Q)(Cl)] and [M(S)(Q)(H2O)]Cl for M(III) = La and Al, respectively. Importantly, all prepared metal complexes were evaluated for their antimicrobial and anticancer activities. The metal complexes exhibited high cytotoxic potency against human breast cancer (MDA-MB231) and liver cancer (Hep-G2) cell lines. Among all MSQ metal complexes, CoSQ and LaSQ produced IC50 values (1.49 and 1.95 µM, respectively) that were comparable to that of cisplatin (1.55 µM) against Hep-G2 cells, whereas CdSQ and LaSQ had best potency against MDA-MB231 with IC50 values of 1.95 and 1.43 µM, respectively. Furthermore, the metal complexes exhibited significant antimicrobial activities against a wide spectrum of both Gram-positive and -negative bacterial and fungal strains. The antibacterial and antifungal efficacies for the MSQ metal complexes, the free S and Q ligands, and the standard drugs gentamycin and ketoconazole decreased in the order AlSQ > LaSQ > CdSQ > gentamycin > NiSQ > CoSQ > Q > S for antibacterial activity, and for antifungal activity followed the trend of LaSQ > AlSQ > CdSQ > ketoconazole > NiSQ > CoSQ > Q > S. Molecular docking studies were performed to investigate the binding of the synthesized compounds with breast cancer oxidoreductase (PDB ID: 3HB5). According to the data obtained, the most probable coordination geometry is octahedral for all the metal complexes. The molecular and electronic structures of the metal complexes were optimized theoretically, and their quantum chemical parameters were calculated. PXRD results for the Cd(II) and La(III) metal complexes indicated that they were crystalline in nature.

Dataset Information

N'-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling.

Publications

N'-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling.

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