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Synthesis and characterization of different complexes derived from Schiff base and evaluation as a potential anticancer, antimicrobial, and insecticide agent.

ABSTRACT: The condensation of (1H-benzimidazole-2-yl) methanamine, with 2-hydroxy naphthaldehyde lead to Schiff base ligand (H2L) (1). This was later reacted with metal salts (ZnCl₂, CrCl₃·6H₂O, and MnCl₂·4H₂O) to afford the corresponding metal complexes. Biological activity findings indicate that the metal complexes have promising activity against Escherichia coli and Bacillus subtilis and modest activity against Aspergillus niger. The in vitro anticancer activities of Zn (II), Cr (III), and Mn (II) complexes were investigated and the best results were observed with Mn (II) complex as the most potent cytotoxic agent toward human cell lines colorectal adenocarcinoma HCT 116, hepatocellular carcinoma HepG₂ and breast adenocarcinoma MCF-7 with 0.7, 1.1 and 6.7 μg of inhibitory concentration IC₅₀ values respectively. Consequently, the Mn (II) complex and ligand were docked inside the energetic site of ERK2 and exhibited favorable energy for binding. The investigation of biological tests towards mosquito larvae indicates that Cr (III) and Mn (II) complexes manifest strong toxicity against Aedes aegypti larvae with 3.458 and 4.764 ppm values of lethal concentration LC₅₀, respectively.

SUBMITTER: Aroua LM

PROVIDER: S-EPMC9982043 | biostudies-literature | 2023 Mar

REPOSITORIES: biostudies-literature

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Synthesis and characterization of different complexes derived from Schiff base and evaluation as a potential anticancer, antimicrobial, and insecticide agent.

Aroua Lotfi M LM Alhag Sadeq K SK Al-Shuraym Laila A LA Messaoudi Sabri S Mahyoub Jazem A JA Alfaifi Mohammad Y MY Al-Otaibi Wafa Mohammed WM

Saudi journal of biological sciences 20230214 3

The condensation of (1H-benzimidazole-2-yl) methanamine, with 2-hydroxy naphthaldehyde lead to Schiff base ligand (H2L) (1). This was later reacted with metal salts (ZnCl2, CrCl3·6H2O, and MnCl2·4H2O) to afford the corresponding metal complexes. Biological activity findings indicate that the metal complexes have promising activity against Escherichia coli and Bacillus subtilis and modest activity against Aspergillus niger</i ...[more]

PMID: 36874197

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Project description:A series of Schiff bases (3.a-f) bearing benzimidazole moiety was successfully synthesized in ethanol by refluxing Oct-2-ynoic acid (1,3-dihydrobenzimidazole-2-ylidene)amide with substituted amines. Fourier transform infrared (FTIR), ultra violet light (UV-VIS), elemental analysis, proton (1H) and carbon (13C) nuclear magnetic resonance spectroscopy were used to characterize the newly synthesized Schiff bases. Micro dilution method was used to determine the minimum inhibitory concentration (MIC) and minimum fungicidal concentration (MFC) of the Schiff bases, against 14 human pathogenic bacteria (8 Gram negative and 6 Gram positive) and against 7 fungal strains (5 Aspergillus and 2 Fusarium) representatives. Antimalarial activity against Plasmodium falciparum and antitrypanosomal property against Trypanosoma brucei was studied in vitro at a single dose concentration of the Schiff bases. Cytotoxicity of the Schiff bases was assessed against human cervix adenocarcinoma (HeLa) cells. Results obtained show that the newly synthesized Schiff bases are very potent antimicrobial agents. Gram negative bacteria Klebsiella pneumonia and Escherichia coli were more affected on exposure to Compounds 3.c-f (MIC 7.8 µg/mL) which in turn exhibited more antibacterial potency than nalidixic acid reference drug that displayed MICs between 64 and 512 µg/mL against K. pneumonia and E. coli respectively. The test compounds also demonstrated high cytotoxic effect against Aspergillus flavus and Aspergillus carbonarius as they displayed MFC 7.8 and 15.6 µg/mL. Compound 3.c exhibited the highest fungicidal property from this series with MFC alternating between 7.8 and 15.6 µg/mL against the investigated strains. The malarial activity revealed Compounds 3.c and 3.d as the more potent antiplasmodial compounds in this group exhibiting 95% and 85% growth inhibition respectively. The IC50 of Compounds 3.c and 3.d were determined and found to be IC50 26.96 and 28.31 µg/mL respectively. Compound 3.a was the most cytotoxic agent against HeLa cells in this group with 48% cell growth inhibition. Compounds 3.c, 3.d and 3.f were biocompatible with HeLa cells and displayed low toxicity. With a very low cytotoxic effect against HeLa, compound 3.c stands out to be a very good antiparasitic agent and consideration to further evaluate the candidate drug against others cell lines is necessary.

Dataset Information

Synthesis and characterization of different complexes derived from Schiff base and evaluation as a potential anticancer, antimicrobial, and insecticide agent.

Publications

Synthesis and characterization of different complexes derived from Schiff base and evaluation as a potential anticancer, antimicrobial, and insecticide agent.

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