Synthesis, spectral investigation, biological efficacy, and computational evaluation of the hydroxamic acid chelator and its Zn(II) metal complex with potent anticancer activity

Shubham Sharma; Maridula Thakur; Sohini Sharma; Shamsher Singh Kanwar; Meena Kumari

doi:10.5155/eurjchem.15.2.166-177.2527

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Published: Jun 30, 2024

DOI: https://doi.org/10.5155/eurjchem.15.2.166-177.2527

Keywords:

Chelation, Zinc(II) complex, Bidentate ligand, Molecular docking, Coordination geometry, 3-Methoxybenzohydroxamate

Section

Research Article

Issue

Vol. 15 No. 2 (2024): June 2024

Dates

Received 2024-02-22
Accepted 2024-05-05
Published 2024-06-30

Shubham Sharma

Department of Chemistry, Faculty of Physical Sciences, University of Himachal Pradesh, Shimla-171005, India

https://orcid.org/0000-0003-2483-9524

Maridula Thakur

Department of Chemistry, Faculty of Physical Sciences, University of Himachal Pradesh, Shimla-171005, India

https://orcid.org/0000-0001-9788-5308

Sohini Sharma

Department of Biotechnology, Faculty of Life Sciences, University of Himachal Pradesh, Shimla-171005, India

https://orcid.org/0009-0008-0844-928X

Shamsher Singh Kanwar

Department of Biotechnology, Faculty of Life Sciences, University of Himachal Pradesh, Shimla-171005, India

https://orcid.org/0000-0002-3196-3366

Meena Kumari

Department of Chemistry, Faculty of Physical Sciences, University of Himachal Pradesh, Shimla-171005, India

https://orcid.org/0000-0003-1107-3005

Abstract

The biologically active Zn(II) complex [Zn(HL)₂] (HL = 3-OCH₃C₆H₄-(CO)NHO) has been synthesized by the reaction of ZnSO₄with potassium 3-methoxybenzohydroxamate (KHL, 3-OCH₃C₆H₄CONHOK) in a 1:2 molar ratio in MeOH solvent medium simply stirring, avoiding drastic conditions and hazardous chemicals. Physicochemical (elemental analysis, molar conductivity) and spectroscopic studies (FTIR, UV-visible, ¹H NMR, and ¹³C NMR) were conducted to characterize the complex. The coordination involving the oxygen atoms of carbonyl and hydroxamic groups (O,O coordination) and the presence of a distorted tetrahedral geometry around the complex have been inferred on the basis of computational studies. Computational investigations indicate that the complex exhibits greater stability in comparison to that of the ligand, and additional calculations were conducted to assess various chemical reactivity parameters. The biological efficacy of the complex has been evaluated through investigations of its antimicrobial, cytotoxic, and anticancer properties, complemented by DNA binding and docking analyzes. The antimicrobial activity of the ligand and the complex against selected bacteria (S. aureus, S. typhi, E. coli, S. flexneri) and fungi (R. solani, A. alternata, and F. sambucinum) was also evaluated. The complex was found to be more toxic against the bacterial species S. typhi and E. coli and showed efficient inhibitory activity against the fungi F. sambucinum and A. alternata. The results were compared with the standard antibacterial drug tetracycline and the antifungal drug amphotericin B. In vitro cytotoxicity assessments were performed using L₂₀B cell lines, which are malignant mouse cells expressing the human poliovirus receptor (CD155), and Rhabdomyosarcoma RD cancer cell lines derived from muscle tissue. The findings revealed decreased cell viability, which is correlated with the increase in the concentrations of the test compounds, demonstrating potent anticancer activity specifically against rhabdomyosarcoma cancer cell lines. Additionally, molecular docking investigations were performed to explore the molecular interactions between the ligand, the complex, and the crystal structure of the A. alternata allergen (3V0R), further supporting the efficacy of both the ligand and the complex.

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Sharma, S.; Thakur, M.; Sharma, S.; Kanwar, S. S.; Kumari, M. Synthesis, Spectral Investigation, Biological Efficacy, and Computational Evaluation of the Hydroxamic Acid Chelator and Its Zn(II) Metal Complex With Potent Anticancer Activity. Eur. J. Chem. 2024, 15, 166-177.

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Department of Chemistry, Faculty of Physical Sciences, University of Himachal Pradesh, Shimla-171005, India

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