Exploring the antimicrobial potential of new selenium- N-heterocyclic carbene complexes and their benzimidazolium salts: synthesis, characterization, biological evaluation, and docking insights
Boutheina Boualia, Abd el-Krim Sandeli, Houssem Boulebd, Hüseyin Karci, Muhammed Dundar, İlknur Özdemir, Nevin Gürbüz, Ahmet Koç, Rafik Menacer, İsmail Özdemir
{"title":"Exploring the antimicrobial potential of new selenium- N-heterocyclic carbene complexes and their benzimidazolium salts: synthesis, characterization, biological evaluation, and docking insights","authors":"Boutheina Boualia, Abd el-Krim Sandeli, Houssem Boulebd, Hüseyin Karci, Muhammed Dundar, İlknur Özdemir, Nevin Gürbüz, Ahmet Koç, Rafik Menacer, İsmail Özdemir","doi":"10.1007/s11696-024-03866-9","DOIUrl":null,"url":null,"abstract":"<div><p>The present work, describes the synthesis and antimicrobial evaluation of new selenium-NHC adducts (<b>3a-e)</b> and their corresponding benzimidazolium salts (<b>2a-e)</b>. 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 IC<sub>50</sub> value of 6.25 µg/mL against <i>Candida albicans</i>, which was comparable to the reference Caspofungin (6.25 µg/mL). Similarly, compound 2e demonstrated strong antibacterial activity against <i>Staphylococcus aureus</i>, with an IC<sub>50</sub> 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 IC<sub>50</sub> value of 25 µg/mL against <i>Staphylococcus aureus</i>, but failing to surpass the activity of the reference agent. To explore the potential mechanism of action, molecular docking studies were conducted against <i>Escherichia coli</i> 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.</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":513,"journal":{"name":"Chemical Papers","volume":"79 3","pages":"1439 - 1454"},"PeriodicalIF":2.2000,"publicationDate":"2024-12-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Papers","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11696-024-03866-9","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Engineering","Score":null,"Total":0}
引用次数: 0
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.
Chemical PapersChemical 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.