苯并咪唑基 N-杂环碳烯和硒加合物的制备、表征、DFT 计算、生物评估和分子对接研究

IF 2.7 3区 化学 Q2 CHEMISTRY, INORGANIC & NUCLEAR Inorganica Chimica Acta Pub Date : 2024-08-30 DOI:10.1016/j.ica.2024.122348
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引用次数: 0

摘要

本研究通过 DFT 设计、合成和表征了三种苯并咪唑盐(AL1-AL3)及其相应的硒加合物(AC1-AC3)。通过傅立叶变换红外光谱和 1H & 13C NMR 对这些化合物进行了理论和实验表征。采用 B3LYP/6-31 G (d, p) 理论水平进行了理论计算,以确定所设计分子的各种光学和化学特性。还计算了 HOMO/LUMO 能量及其能隙,以评估结构-活性关系。使用 MTT 法对人类乳腺腺癌细胞株(MCF-7)进行了体外测试,并使用 5-氟尿嘧啶(标准)进行结果比较。配体 AL3 显示出最大的抑制潜力(66.51 ± 0.82),甚至接近标准的 5FU,而复合物 AC3 则显示出最大的存活率,对 MCF7 细胞株的抑制值最小(21.7 ± 0.73)。此外,还评估了清除 DPPH 自由基的抗氧化潜力,结果显示 AL1 的潜力最大,为 62.01 ± 0.9。还通过分子对接研究评估了复合物与各种蛋白质的相互作用,结果显示,复合物与血管生成因子(如 VEGF-A、EGF、HIF 和 COX-1)具有很强的结合能和配体亲和力。这表明 AC1-AC3 复合物的抗癌活性可能归因于其强大的抗血管生成作用。此外,与配体相比,硒-NHC 加合物具有更显著的抗癌潜力。此外,还对 AC1-AC3 化合物的抗菌和抗真菌潜力进行了评估。值得注意的是,配体 AL2 对大肠杆菌具有显著的抗菌活性,抑制区(ZI)值为 17.5 ± 0.29 mm,而 AL3 对多杀性白喉杆菌的活性最高,抑制区(ZOI)值为 18.5 ± 0.38。在所有合成化合物中,AL1 对 F. avenaceum 的抗真菌活性最为显著(27 ± 0.51 mm),甚至超过了在相同条件下测试的标准药物庆大霉素(13 ± 0.23 mm)。然而,其相应的 Se-NHC 加合物 AC1 却没有活性。总之,AL3 及其相应的 Se-NHC 加合物(AC3)对大多数受试菌株都具有卓越的生物潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

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Preparation, Characterization, DFT Calculations, biological evaluations and Molecular docking studies of benzimidazolium-based N-heterocyclic carbenes and selenium-adducts

This study involves designing through DFT, synthesis, and characterization of three benzimidazolium salts (AL1-AL3) and their corresponding selenium adducts (AC1-AC3). The compounds were characterized theoretically as well as experimentally through FT-IR and 1H & 13C NMR. Theoretical calculations were performed using the B3LYP/6–31 G (d, p) levels of theory to determine various optical and chemical properties of the designed molecules. The HOMO/LUMO energies and their energy gaps were also calculated to assess the structure–activity relationships. In vitro testing against the Human breast Adenocarcinoma cell line (MCF-7) was conducted using the MTT assay and 5-Fluorouracil (standard) was used for the comparison of results. The ligand AL3 showed maximum inhibitory potential (66.51 ± 0.82) even approaching the standard 5FU while the complex AC3 showed maximum viability with the least inhibition value as (21.7 ± 0.73) against MCF7 cell line. The antioxidant potential for scavenging DPPH radicals was also assessed, revealing that AL1 has the greatest potential, with a value of 62.01 ± 0.9. The interactions of the complexes with various proteins were also assessed via molecular docking studies, revealing strong binding energies and ligand affinities towards angiogenic factors such as VEGF-A, EGF, HIF, and COX-1. This suggests that the anticancer activities of the complexes AC1-AC3 may be attributed to their potent anti-angiogenic effects. Moreover, selenium-NHC adducts exhibited more significant anticancer potential as compared to their ligands. Furthermore, the antibacterial and antifungal potential of compounds AC1-AC3 was assessed. Notably, the ligand AL2 exhibited significant antibacterial activity against E. coli, as evidenced by a zone of inhibition (ZI) value of 17.5 ± 0.29 mm, whereas AL3 demonstrated the highest activity against P. multocida showing the ZOI value of 18.5 ± 0.38. Among all the synthesized compounds, AL1 displayed the most significant antifungal activity against F. avenaceum (27 ± 0.51 mm), surpassing even the standard drug gentamycin (13 ± 0.23 mm), which was tested under the same conditions. However, its corresponding Se-NHC, AC1, adduct was found to be inactive. Overall, AL3 and its corresponding Se-NHC adduct (AC3), demonstrated superior biological potential against the majority of the tested strains.

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来源期刊
Inorganica Chimica Acta
Inorganica Chimica Acta 化学-无机化学与核化学
CiteScore
6.00
自引率
3.60%
发文量
440
审稿时长
35 days
期刊介绍: Inorganica Chimica Acta is an established international forum for all aspects of advanced Inorganic Chemistry. Original papers of high scientific level and interest are published in the form of Articles and Reviews. Topics covered include: • chemistry of the main group elements and the d- and f-block metals, including the synthesis, characterization and reactivity of coordination, organometallic, biomimetic, supramolecular coordination compounds, including associated computational studies; • synthesis, physico-chemical properties, applications of molecule-based nano-scaled clusters and nanomaterials designed using the principles of coordination chemistry, as well as coordination polymers (CPs), metal-organic frameworks (MOFs), metal-organic polyhedra (MPOs); • reaction mechanisms and physico-chemical investigations computational studies of metalloenzymes and their models; • applications of inorganic compounds, metallodrugs and molecule-based materials. Papers composed primarily of structural reports will typically not be considered for publication.
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