Synthesis, Characterization and Biological Activities of Tolfenamic Acid Alkaline Earth Metal Complexes

IF 3.7 2区化学 Q2 CHEMISTRY, APPLIED

Applied Organometallic Chemistry Pub Date : 2024-09-30 DOI:10.1002/aoc.7779

Shamima Akther, Saiful Islam, Md. Shahidur Rahman, Hasina Akhter Simol, A. H. M. Shofiul Islam Molla Jamal, Dipa Islam, Pradip K. Bakshi

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Abstract

Solid complexes of tolfenamic acid (tolfH) with Mg(II), Ca(II), Sr(II), and Ba(II) have been synthesized and characterized by CHN, metal contents analysis, FTIR, UV, ¹H-NMR spectroscopy, thermal (TGA, DTG, DTA, and DSC) analysis, molar conductance, powder X-ray diffraction (XRD), and scanning electron microscopy (SEM–EDX). Based on these studies, the probable formulae for the complexes are [Mg(tolf)Cl(H₂O)₃].4H₂O, [Ca(tolf)₂(H₂O)₂], [Sr₂(tolf)₄(H₂O)₄], and [Ba₂(tolf)₄(H₂O)₄]. The ligand tolfenamate ion (tolf) exhibited different modes of coordination, including bidentate and chelating. The ¹H-NMR displayed the presence of tolfenamato ions in the coordination sphere, the purity and stability of the complexes in solution. The average crystallite sizes of the complexes were determined by XRD and ranged from 55 to 70 nm. SEM micrographs showed the rod- or plate-like morphology of the prepared complexes. The complexes showed promising antioxidant activity in the DPPH radical scavenging method, with an IC₅₀ value of 12–15 μg/mL. Against gram-positive and gram-negative bacteria, as well as fungi, the metal complexes also demonstrated significant antimicrobial activity. In the brine shrimp lethality bioassay, the metal complexes exhibited significantly highest cytotoxicity with the range of 15.25–24.57 μg/mL. All the complexes showed cytotoxicity against human cervical carcinoma HeLa cell lines, while the ligand itself did not show any cytotoxicity to these cancer cells. Furthermore, the metal complexes exhibited improved central and peripheral analgesic activity compared to tolfenamic acid.

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甲苯胺酸-碱土金属配合物的合成、表征及生物活性研究

合成了甲苯胺酸（tolfH）与Mg（II）、Ca（II）、Sr（II）和Ba（II）的固体配合物，并用CHN、金属含量分析、FTIR、UV、1H-NMR、热分析（TGA、DTG、DTA和DSC）、摩尔电导、粉末x射线衍射（XRD）和扫描电子显微镜（SEM-EDX）对其进行了表征。根据这些研究，配合物的可能分子式为[Mg(tolf)Cl(H2O)3]。4水,Ca (tolf) 2 (H2O)], [Sr2 (tolf) 4 (H2O)],和[Ba2 (tolf) 4 (H2O)]。配体tolfenamate ion （tolf）表现出不同的配位模式，包括双齿配位和螯合配位。1H-NMR表征了配合物在配位球中的存在以及配合物在溶液中的纯度和稳定性。用XRD测定了配合物的平均晶粒尺寸为55 ~ 70 nm。SEM显微照片显示了所制备的配合物的棒状或片状形态。该配合物在DPPH自由基清除方法中显示出良好的抗氧化活性，IC50值为12 ~ 15 μg/mL。对革兰氏阳性和革兰氏阴性细菌以及真菌，金属配合物也显示出显著的抗菌活性。在盐水对虾致死性生物测定中，金属配合物的细胞毒性最高，范围为15.25 ~ 24.57 μg/mL。所有复合物对人宫颈癌HeLa细胞系均有细胞毒性，而配体本身对宫颈癌HeLa细胞无细胞毒性。此外，与苯胺酸相比，金属配合物表现出更好的中枢和外周镇痛活性。

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来源期刊

Applied Organometallic Chemistry 化学-无机化学与核化学

CiteScore

7.80

自引率

10.30%

发文量

408

审稿时长

2.2 months

期刊介绍： All new compounds should be satisfactorily identified and proof of their structure given according to generally accepted standards. Structural reports, such as papers exclusively dealing with synthesis and characterization, analytical techniques, or X-ray diffraction studies of metal-organic or organometallic compounds will not be considered. The editors reserve the right to refuse without peer review any manuscript that does not comply with the aims and scope of the journal. Applied Organometallic Chemistry publishes Full Papers, Reviews, Mini Reviews and Communications of scientific research in all areas of organometallic and metal-organic chemistry involving main group metals, transition metals, lanthanides and actinides. All contributions should contain an explicit application of novel compounds, for instance in materials science, nano science, catalysis, chemical vapour deposition, metal-mediated organic synthesis, polymers, bio-organometallics, metallo-therapy, metallo-diagnostics and medicine. Reviews of books covering aspects of the fields of focus are also published.