Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i>
Two subseries of aminated quinolinequinones (AQQs, <b>AQQ1</b>–<b>16</b>) containing electron-withdrawing group (EWG) or electron-donating group (EDG) in aryl amine moiety were successfully synthesized. Antimicrobial activity assessment indicates that some of the AQQs (<b&...
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MDPI AG
2022-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/9/2923 |
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| author | Hatice Yıldırım Nilüfer Bayrak Mahmut Yıldız Fatıma Nur Yılmaz Emel Mataracı-Kara Deepak Shilkar Venkatesan Jayaprakash Amaç Fatih TuYuN |
| author_facet | Hatice Yıldırım Nilüfer Bayrak Mahmut Yıldız Fatıma Nur Yılmaz Emel Mataracı-Kara Deepak Shilkar Venkatesan Jayaprakash Amaç Fatih TuYuN |
| author_sort | Hatice Yıldırım |
| collection | DOAJ |
| description | Two subseries of aminated quinolinequinones (AQQs, <b>AQQ1</b>–<b>16</b>) containing electron-withdrawing group (EWG) or electron-donating group (EDG) in aryl amine moiety were successfully synthesized. Antimicrobial activity assessment indicates that some of the AQQs (<b>AQQ8</b>–<b>10</b> and <b>AQQ12</b>–<b>14</b>) with an EDG in aryl amine exhibited strong antibacterial activity against Gram-positive bacterial strains, including Staphylococcus aureus (ATCC<sup>®</sup> 29213) and Enterococcus faecalis (ATCC<sup>®</sup> 29212). In contrast, <b>AQQ4</b> with an EWG in aryl amine displayed excellent antifungal activity against fungi Candida albicans (ATCC<sup>®</sup> 10231) with a MIC value of 1.22 μg/mL. To explore the mode of action, the selected AQQs (<b>AQQ4</b> and <b>AQQ9</b>) were further evaluated in vitro to determine their antimicrobial activity against each of 20 clinically obtained resistant strains of Gram-positive bacteria by performing antibiofilm activity assay and time-kill curve assay. In addition, in silico studies were carried out to determine the possible mechanism of action observed in vitro. The data obtained from these experiments suggests that these molecules could be used to target pathogens in different modes of growth, such as planktonic and biofilm. |
| first_indexed | 2024-03-10T03:53:22Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:53:22Z |
| publishDate | 2022-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1e1dae92a0dc47e4a340e8e04f37195d2023-11-23T08:51:39ZengMDPI AGMolecules1420-30492022-05-01279292310.3390/molecules27092923Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i>Hatice Yıldırım0Nilüfer Bayrak1Mahmut Yıldız2Fatıma Nur Yılmaz3Emel Mataracı-Kara4Deepak Shilkar5Venkatesan Jayaprakash6Amaç Fatih TuYuN7Department of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Avcilar, Istanbul 34320, TurkeyDepartment of Chemistry, Engineering Faculty, Istanbul University-Cerrahpasa, Avcilar, Istanbul 34320, TurkeyDepartment of Chemistry, Gebze Technical University, Gebze, Kocaeli 41400, TurkeyDepartment of Pharmaceutical Microbiology, Pharmacy Faculty, Istanbul University, Beyazit, Istanbul 34116, TurkeyDepartment of Pharmaceutical Microbiology, Pharmacy Faculty, Istanbul University, Beyazit, Istanbul 34116, TurkeyDepartment of Pharmaceutical Sciences & Technology, Birla Institute of Technology, Mesra, Ranchi 835 215, Jharkhand, IndiaDepartment of Pharmaceutical Sciences & Technology, Birla Institute of Technology, Mesra, Ranchi 835 215, Jharkhand, IndiaDepartment of Chemistry, Faculty of Science, Istanbul University, Fatih, Istanbul 34116, TurkeyTwo subseries of aminated quinolinequinones (AQQs, <b>AQQ1</b>–<b>16</b>) containing electron-withdrawing group (EWG) or electron-donating group (EDG) in aryl amine moiety were successfully synthesized. Antimicrobial activity assessment indicates that some of the AQQs (<b>AQQ8</b>–<b>10</b> and <b>AQQ12</b>–<b>14</b>) with an EDG in aryl amine exhibited strong antibacterial activity against Gram-positive bacterial strains, including Staphylococcus aureus (ATCC<sup>®</sup> 29213) and Enterococcus faecalis (ATCC<sup>®</sup> 29212). In contrast, <b>AQQ4</b> with an EWG in aryl amine displayed excellent antifungal activity against fungi Candida albicans (ATCC<sup>®</sup> 10231) with a MIC value of 1.22 μg/mL. To explore the mode of action, the selected AQQs (<b>AQQ4</b> and <b>AQQ9</b>) were further evaluated in vitro to determine their antimicrobial activity against each of 20 clinically obtained resistant strains of Gram-positive bacteria by performing antibiofilm activity assay and time-kill curve assay. In addition, in silico studies were carried out to determine the possible mechanism of action observed in vitro. The data obtained from these experiments suggests that these molecules could be used to target pathogens in different modes of growth, such as planktonic and biofilm.https://www.mdpi.com/1420-3049/27/9/2923antibacterial activityantibiofilm activityantifungal activitybactericidal effectkinetic studyquinolinequinones |
| spellingShingle | Hatice Yıldırım Nilüfer Bayrak Mahmut Yıldız Fatıma Nur Yılmaz Emel Mataracı-Kara Deepak Shilkar Venkatesan Jayaprakash Amaç Fatih TuYuN Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> Molecules antibacterial activity antibiofilm activity antifungal activity bactericidal effect kinetic study quinolinequinones |
| title | Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> |
| title_full | Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> |
| title_fullStr | Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> |
| title_full_unstemmed | Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> |
| title_short | Highly Active Small Aminated Quinolinequinones against Drug-Resistant <i>Staphylococcus aureus</i> and <i>Candida albicans</i> |
| title_sort | highly active small aminated quinolinequinones against drug resistant i staphylococcus aureus i and i candida albicans i |
| topic | antibacterial activity antibiofilm activity antifungal activity bactericidal effect kinetic study quinolinequinones |
| url | https://www.mdpi.com/1420-3049/27/9/2923 |
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