Exploring the antimicrobial potential of new selenium- N-heterocyclic carbene complexes and their benzimidazolium salts: synthesis, characterization, biological evaluation, and docking insights

IF 2.2 4区 化学 Q2 Engineering
Boutheina Boualia, Abd el-Krim Sandeli, Houssem Boulebd, Hüseyin Karci, Muhammed Dundar, İlknur Özdemir, Nevin Gürbüz, Ahmet Koç, Rafik Menacer, İsmail Özdemir
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Abstract

The present work, describes the synthesis and antimicrobial evaluation of new selenium-NHC adducts (3a-e) and their corresponding benzimidazolium salts (2a-e). Specific synthetic approaches were employed, resulting in compounds with satisfactory stability under humid and aerated conditions. Characterization by spectroscopic methods confirmed structural changes upon selenium incorporation. Biological evaluations revealed varying antimicrobial and antifungal activities among the synthesized compounds. The results indicated that the benzimidazolium salts exhibited significantly enhanced antimicrobial and antifungal activities compared to reference agents. For instance, compound 2a demonstrated an IC50 value of 6.25 µg/mL against Candida albicans, which was comparable to the reference Caspofungin (6.25 µg/mL). Similarly, compound 2e demonstrated strong antibacterial activity against Staphylococcus aureus, with an IC50 value of 0.8 µg/mL, significantly outperforming the reference Ampicillin (1.56 µg/mL). In contrast, the selenium-NHC adducts exhibited moderate to minimal activity, with compound 3e showing the highest IC50 value of 25 µg/mL against Staphylococcus aureus, but failing to surpass the activity of the reference agent. To explore the potential mechanism of action, molecular docking studies were conducted against Escherichia coli DNA gyrase and CYP51. The molecular docking results demonstrate that synthesized compounds exhibit significant binding affinity against both enzymes, indicating antibacterial and antifungal potential. These binding affinities suggest that these molecules could be effective dual-action antimicrobial agents.

Graphical abstract

Abstract Image

探索新型硒-N-杂环碳烯配合物及其苯并咪唑盐的抗菌潜力:合成、表征、生物学评价和对接研究的启示
本研究介绍了新型硒-NHC 加合物(3a-e)及其相应的苯并咪唑盐(2a-e)的合成和抗菌评估。这些化合物采用了特定的合成方法,在潮湿和通气条件下具有令人满意的稳定性。通过光谱方法进行的表征证实了硒元素加入后的结构变化。生物学评价显示,合成的化合物具有不同的抗菌和抗真菌活性。结果表明,与参考制剂相比,苯并咪唑盐的抗菌和抗真菌活性明显增强。例如,化合物 2a 对白色念珠菌的 IC50 值为 6.25 µg/mL,与参考药物卡泊芬净(6.25 µg/mL)相当。同样,化合物 2e 对金黄色葡萄球菌具有很强的抗菌活性,其 IC50 值为 0.8 µg/mL,明显优于参考药物氨苄西林(1.56 µg/mL)。相比之下,硒-NHC 加合物表现出中等到最低程度的活性,其中化合物 3e 对金黄色葡萄球菌的 IC50 值最高,为 25 µg/mL,但未能超过参考制剂的活性。为了探索潜在的作用机制,研究人员针对大肠杆菌 DNA 回旋酶和 CYP51 进行了分子对接研究。分子对接结果表明,合成的化合物对这两种酶都具有显著的结合亲和力,表明其具有抗菌和抗真菌的潜力。这些结合亲和力表明,这些分子可以成为有效的双效抗菌剂。
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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来源期刊
Chemical Papers
Chemical Papers Chemical Engineering-General Chemical Engineering
CiteScore
3.30
自引率
4.50%
发文量
590
期刊介绍: Chemical Papers is a peer-reviewed, international journal devoted to basic and applied chemical research. It has a broad scope covering the chemical sciences, but favors interdisciplinary research and studies that bring chemistry together with other disciplines.
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