Design, Synthesis, and Bioevaluation of Moxifloxacin Hydrazide Metal Complexes: Integrated Spectroscopic, Computational, Antimicrobial, and Anticancer Investigations

莫西沙星酰肼金属配合物的设计、合成和生物活性评价:光谱学、计算、抗菌和抗癌活性综合研究

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Abstract

This study reports the synthesis, spectroscopic characterization, and biological evaluation of a novel moxifloxacin hydrazide derivative (MOX-H) and its metal complexes with Co(II), Ni(II), Cu(II), VO(IV), and Gd(III). The ligand was synthesized by hydrazinolysis of moxifloxacin hydrochloride, and the resulting hydrazide was subsequently complexed with the respective metal salts. The interaction between MOX-H and the metal ions yielded the corresponding complexes, formulated as [Co(H(2)O)Cl(MOX-H)(2)]Cl·2.5H(2)O, [Ni(H(2)O)Cl(MOX-H)(2)]Cl.4.5H(2)O, [VO(MOX-H)(2)]SO(4).3.5H(2)O, [Gd (H(2)O)(MOX-H)(2)(NO(3))(2)]NO(3).2H(2)O, and [Cu(MOX-H)(2)(H(2)O)Cl]Cl·xH(2)O (where x = 2, 2.5, 0.5, for products synthesized via template, microwave-assisted, and hydrothermal methods, respectively). The synthesized analogues were characterized by elemental analysis (CHN), FT-IR, UV-visible, and (1)H NMR spectroscopy, and mass spectrometry, as well as thermogravimetric (TG/DTG) and magnetic measurements. FT-IR spectra confirmed coordination through the hydrazide carbonyl and amine groups, while UV-visible and magnetic data indicated predominantly octahedral geometries. The thermal behavior exhibited multistep decomposition with activation parameters supporting exothermic processes. When compared to the free ligand, the metal complexes showed increased antimicrobial activity against both Gram-positive and Gram-negative bacteria and fungus species, particularly for the Co(II) and Cu(II) complexes, which showed the largest inhibition zones. The Cu(II)-MOX-H complex exhibited the lowest MIC values (4.88-9.76 µg/mL) among all tested compounds, confirming its outstanding antibacterial potency and high sensitivity compared to the free ligand and standard drug. Cytotoxicity assays demonstrated selective anticancer activity, with the Cu(II)-MOX-H complex showing the highest potency (IC(50) ≈ 2.95 µM against MCF-7 and IC(50) ≈ 0.98 µM against HepG-2), while maintaining minimal toxicity toward normal cells. These findings were corroborated by molecular docking investigations, which showed that the MOX-H complexes had substantial binding affinities (-9 to -10 kcal/mol) toward DNA topoisomerase II, consistent with their observed biological effects.

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