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Thiophene-Derived Schiff Base Complexes: Synthesis, Characterization, Antimicrobial Properties, and Molecular Docking.

ABSTRACT: Novel thiophene-derived Schiff base ligand DE, where DE is (E)-N¹,N¹-diethyl-N²-(thiophen-2-ylmethylene)ethane-1,2-diamine, and the corresponding M(II) complexes, [M(DE)X₂] (M = Cu or Zn, X = Cl; M = Cd, X = Br), were prepared and structurally characterized. X-ray diffraction studies revealed that the geometry around the center of the M(II) complexes, [Zn(DE)Cl₂] and [Cd(DE)Br₂], could be best described as a distorted tetrahedral. In vitro antimicrobial screening of DE and its corresponding M(II) complexes, [M(DE)X₂], was performed. The complexes were more potent and showed higher activities against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa, fungi Candida albicans, and protozoa Leishmania major compared to the ligand. Among the studied complexes, [Cd(DE)Br₂] exhibited the most promising antimicrobial activity against all the tested microbes compared to its analogs. These results were further supported by molecular docking studies. We believe that these complexes may significantly contribute to the efficient designing of metal-derived agents to treat microbial infections.

SUBMITTER: Nayab S

PROVIDER: S-EPMC10210233 | biostudies-literature | 2023 May

REPOSITORIES: biostudies-literature

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Thiophene-Derived Schiff Base Complexes: Synthesis, Characterization, Antimicrobial Properties, and Molecular Docking.

Nayab Saira S Alam Aftab A Ahmad Nasir N Khan Sher Wali SW Khan Waliullah W Shams Dilawar Farhan DF Shah Muhammad Ishaq Ali MIA Ateeq Muhammad M Shah Said Karim SK Lee Hyosun H

ACS omega 20230512 20

Novel thiophene-derived Schiff base ligand DE, where DE is (E)-N1,N1-diethyl-N2-(thiophen-2-ylmethylene)ethane-1,2-diamine, and the corresponding M(II) complexes, [M(DE)X2] (M = Cu or Zn, X = Cl; M = Cd, X = Br), were prepared and structurally characterized. X-ray diffraction studies revealed that the geometry around the center of the M(II) complexes, [Zn(DE)Cl2] and [Cd(DE)Br2< ...[more]

PMID: 37251197

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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

Thiophene-Derived Schiff Base Complexes: Synthesis, Characterization, Antimicrobial Properties, and Molecular Docking.

Publications

Thiophene-Derived Schiff Base Complexes: Synthesis, Characterization, Antimicrobial Properties, and Molecular Docking.

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