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<p>Malaria, an ancient and persistent global health threat, continues to afflict millions, particularly in resource-limited regions with vulnerable populations. Despite notable progress in antimalarial strategies, the emergence of drug resistance underscores the urgent need for novel therapeutic agents. In this context, transition metal chelates derived from hydrazone ligands have shown promise due to their enhanced biological activity.&#xa0;Two hydrazone ligands were synthesized from 5-bromovanillin and benzohydrazide (1–2), along with their Co(II), Ni(II), Cu(II), and Zn(II) complexes (3–10). The synthesized compounds were characterized using spectroscopic and physical methods, confirming the octahedral geometry of the metal chelates with a 1:1 molar ratio by coordination through the O<sub>enolic</sub>, N<sub>azomethine</sub>, and O<sub>water</sub> molecules. The biological activities such as antimalarial, antimicrobial, and antioxidant studies were evaluated using micro-assay, serial dilution, and DPPH methods, respectively. Additionally, molecular docking against PDB ID: 1U5A and ADMET analysis were conducted to assess binding affinity and drug-like properties.&#xa0;Biological evaluation revealed that the metal chelates exhibited superior activity compared to the free ligands. Among them, the Cu(II) and Zn(II) complexes (9, 10) displayed the highest antimalarial potency, with IC<sub>50</sub> values of 0.87 ± 0.045 and 0.91 ± 0.027 µM, respectively. The same complexes also showed significant antioxidant activity, with IC<sub>50</sub> values of 6.2 ± 0.037 and 6.4 ± 0.056 µM. Complexes (5, 6, 9, and 10) exhibited remarkable antimicrobial activity, with MIC values ranging from 0.0075 to 0.0158 µmol/mL. Molecular docking results indicated strong binding affinities of complexes 9 and 10, with binding energies of -9.7 and − 9.8&#xa0;kcal/mol, respectively, corroborating their experimental antimalarial efficacy. This study highlights the potential of vanillin-derived hydrazone metal chelates, particularly Cu(II) and Zn(II) complexes, as promising candidates for combating malaria, microbial infections, and oxidative stress. The combined experimental and computational results, including ADMET analysis, suggest that these complexes possess favorable drug-like properties and warrant further investigation as potential therapeutic agents.</p>

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Vanillin Derived Hydrazone Ligands and Their Transition Metal Complexes: Synthesis, Characterization, Biological Activity and Molecular Docking Studies

  • 期刊论文

  • 发表日期：

    2025年1月27日

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  • Jai Devi,
  • Tanisha Arora

摘要

Malaria, an ancient and persistent global health threat, continues to afflict millions, particularly in resource-limited regions with vulnerable populations. Despite notable progress in antimalarial strategies, the emergence of drug resistance underscores the urgent need for novel therapeutic agents. In this context, transition metal chelates derived from hydrazone ligands have shown promise due to their enhanced biological activity. Two hydrazone ligands were synthesized from 5-bromovanillin and benzohydrazide (1–2), along with their Co(II), Ni(II), Cu(II), and Zn(II) complexes (3–10). The synthesized compounds were characterized using spectroscopic and physical methods, confirming the octahedral geometry of the metal chelates with a 1:1 molar ratio by coordination through the Oenolic, Nazomethine, and Owater molecules. The biological activities such as antimalarial, antimicrobial, and antioxidant studies were evaluated using micro-assay, serial dilution, and DPPH methods, respectively. Additionally, molecular docking against PDB ID: 1U5A and ADMET analysis were conducted to assess binding affinity and drug-like properties. Biological evaluation revealed that the metal chelates exhibited superior activity compared to the free ligands. Among them, the Cu(II) and Zn(II) complexes (9, 10) displayed the highest antimalarial potency, with IC50 values of 0.87 ± 0.045 and 0.91 ± 0.027 µM, respectively. The same complexes also showed significant antioxidant activity, with IC50 values of 6.2 ± 0.037 and 6.4 ± 0.056 µM. Complexes (5, 6, 9, and 10) exhibited remarkable antimicrobial activity, with MIC values ranging from 0.0075 to 0.0158 µmol/mL. Molecular docking results indicated strong binding affinities of complexes 9 and 10, with binding energies of -9.7 and − 9.8 kcal/mol, respectively, corroborating their experimental antimalarial efficacy. This study highlights the potential of vanillin-derived hydrazone metal chelates, particularly Cu(II) and Zn(II) complexes, as promising candidates for combating malaria, microbial infections, and oxidative stress. The combined experimental and computational results, including ADMET analysis, suggest that these complexes possess favorable drug-like properties and warrant further investigation as potential therapeutic agents.