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Semi-coordination Cu–O bond on a copper complex featuring O,O-donor ligand as potential antibacterial agent: green synthesis, characterization, DFT, in-silico ADMET profiling and molecular docking studies

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Abstract

The synthesis of 2-((5-methyl-pyridin-2-yl)amino)acetic acid (MPAA) and its copper complex (Cu-MPAA) has been performed. The new ligand, MPAA, was obtained via a catalyst-free reaction at room temperature by mixing a solution of 2-amino-5-methylpyridine (AMPy) with chloroacetic acid (CA) in a short time. The characterization of MPAA has been carried out using NMR and FTIR spectroscopies, while the complex has been characterized using UV–Vis spectroscopy, AAS, FTIR, molar conductivity, TGA–DSC, and magnetic moments. According to the DFT calculation, Cu(II) forms both coordination and semi-coordination bonds through the carboxylate group of MPAA. Antibacterial activity has been performed using the disk diffusion method against Staphylococcus aureus, Escherichia coli, Salmonella typhi, Staphylococcus epidermidis, and Pseudomonas aeruginosa. The Cu-MPAA complex exhibited the highest activity compared to other tested compounds. Furthermore, molecular docking studies provided additional evidence in favor of these findings. Moreover, through in silico studies, the synthesized complex adhered to acceptable predictive ADMET features and drug-likeness rules. Collectively, we believe that this complex could make a significant contribution to the efficient design of metal-derived agents to treat microbial infections.

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Funding

S.B.R express gratitude to the Institute for Research and Community Service of Sebelas Maret University for research funding support with grant number 228/UN27.22/PT.01.03/2023.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Mulawarman University, Jl. Barong Tongkok, Gunung Kelua, Samarinda, 75242, Indonesia

    Husna Syaima

  2. College of Pharmacy and Research Institute of Drug Development, Chonnam National University, Gwangju, 61186, Korea

    Wahyu Eko Prasetyo

  3. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Sebelas Maret University, Jl. Ir. Sutami No.36A, Surakarta, 57126, Indonesia

    Sentot Budi Rahardjo & Venty Suryanti

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  1. Husna Syaima
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  2. Wahyu Eko Prasetyo
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  4. Venty Suryanti
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Contributions

Husna Syaima: Conceptualization, Investigation, Methodology, Formal analysis, Writing – original draft. Wahyu Eko Prasetyo: Investigation, Methodology, Formal analysis, Writing – original draft. Sentot Budi Rahardjo: Project administration, Funding acquisition, and Supervision. Venty Suryanti: Supervision.

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Correspondence to Sentot Budi Rahardjo.

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Syaima, H., Prasetyo, W.E., Rahardjo, S.B. et al. Semi-coordination Cu–O bond on a copper complex featuring O,O-donor ligand as potential antibacterial agent: green synthesis, characterization, DFT, in-silico ADMET profiling and molecular docking studies. Struct Chem 35, 721–737 (2024). https://doi.org/10.1007/s11224-023-02224-x

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