Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening
Isatin–quinoline conjugates <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> were assembled by the reaction of N-(bromobutyl) isatin derivatives <b>3a</b>, <b>b</b> with aminoquinolines <b>6a</b>–<b>c</b> and...
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| Format: | Article |
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MDPI AG
2022-10-01
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| Series: | Antibiotics |
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| Online Access: | https://www.mdpi.com/2079-6382/11/11/1507 |
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| author | Elshaymaa I. Elmongy Abdullah A. S. Ahmed Ibrahim El Tantawy El Sayed Ghady Fathy Hanem M. Awad Ayah Usama Salman Mohamed A. Hamed |
| author_facet | Elshaymaa I. Elmongy Abdullah A. S. Ahmed Ibrahim El Tantawy El Sayed Ghady Fathy Hanem M. Awad Ayah Usama Salman Mohamed A. Hamed |
| author_sort | Elshaymaa I. Elmongy |
| collection | DOAJ |
| description | Isatin–quinoline conjugates <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> were assembled by the reaction of N-(bromobutyl) isatin derivatives <b>3a</b>, <b>b</b> with aminoquinolines <b>6a</b>–<b>c</b> and their corresponding hydrazinyl <b>9a</b>–<b>c</b> in good yields. The structures of the resulting conjugates were established by spectroscopic tools and showed data consistent with the proposed structures. In vitro antibacterial activity against different bacterial strains was evaluated. All tested conjugates showed significant biocidal activity with lower MIC than the first line drugs chloramphenicol and ampicillin. Conjugates <b>10a</b>, <b>10b</b> and <b>10f</b> displayed the most potent activity against all clinical isolates. The antibiofilm activity for all tested conjugates was screened against the reference drug vancomycin using the <i>MRSA</i> strain. The results revealed that all conjugates had an inhibitory activity against biofilm formation and conjugate. Conjugate <b>11a</b> showed 83.60% inhibition at 10 mg/mL. In addition, TEM studies were used to prove the mechanism of antibacterial action of conjugates <b>10a</b> and <b>11a</b> against (<i>MRSA</i>). Modeling procedures were performed on <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> and interestingly the results were nearly consistent with the biological activities. In addition, in silico pharmacokinetic evaluation was performed and revealed that the synthesized compounds <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> were considered drug-like molecules with promising bioavailability and high GI absorption. The results confirmed that the title compounds caused the disruption of bacterial cell membranes and could be used as potential leads for the further development and optimization of antibacterial agents. |
| first_indexed | 2024-03-09T19:19:48Z |
| format | Article |
| id | doaj.art-23aecc3cbddc43339eb5065ecb2ccbf5 |
| institution | Directory Open Access Journal |
| issn | 2079-6382 |
| language | English |
| last_indexed | 2024-03-09T19:19:48Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Antibiotics |
| spelling | doaj.art-23aecc3cbddc43339eb5065ecb2ccbf52023-11-24T03:27:30ZengMDPI AGAntibiotics2079-63822022-10-011111150710.3390/antibiotics11111507Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico ScreeningElshaymaa I. Elmongy0Abdullah A. S. Ahmed1Ibrahim El Tantawy El Sayed2Ghady Fathy3Hanem M. Awad4Ayah Usama Salman5Mohamed A. Hamed6Department of Pharmaceutical Sciences, College of Pharmacy, Princess Nourah bint Abdulrahman University, P.O. Box 84428, Riyadh 11671, Saudi ArabiaChemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom 32511, EgyptChemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom 32511, EgyptChemistry Department, Faculty of Science, Menoufia University, Shebin El-Kom 32511, EgyptDepartment of Tanning Materials and Leather Technology, National Research Centre, Dokki, Giza 12611, EgyptDepartment of Botany and Microbiology, Faculty of Science, Menoufia University, Shebin El-Kom 32511, EgyptChemistry Department, Faculty of Science, Tanta University, Tanta 31511, EgyptIsatin–quinoline conjugates <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> were assembled by the reaction of N-(bromobutyl) isatin derivatives <b>3a</b>, <b>b</b> with aminoquinolines <b>6a</b>–<b>c</b> and their corresponding hydrazinyl <b>9a</b>–<b>c</b> in good yields. The structures of the resulting conjugates were established by spectroscopic tools and showed data consistent with the proposed structures. In vitro antibacterial activity against different bacterial strains was evaluated. All tested conjugates showed significant biocidal activity with lower MIC than the first line drugs chloramphenicol and ampicillin. Conjugates <b>10a</b>, <b>10b</b> and <b>10f</b> displayed the most potent activity against all clinical isolates. The antibiofilm activity for all tested conjugates was screened against the reference drug vancomycin using the <i>MRSA</i> strain. The results revealed that all conjugates had an inhibitory activity against biofilm formation and conjugate. Conjugate <b>11a</b> showed 83.60% inhibition at 10 mg/mL. In addition, TEM studies were used to prove the mechanism of antibacterial action of conjugates <b>10a</b> and <b>11a</b> against (<i>MRSA</i>). Modeling procedures were performed on <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> and interestingly the results were nearly consistent with the biological activities. In addition, in silico pharmacokinetic evaluation was performed and revealed that the synthesized compounds <b>10a</b>–<b>f</b> and <b>11a</b>–<b>f</b> were considered drug-like molecules with promising bioavailability and high GI absorption. The results confirmed that the title compounds caused the disruption of bacterial cell membranes and could be used as potential leads for the further development and optimization of antibacterial agents.https://www.mdpi.com/2079-6382/11/11/1507isatinaminoquinolineconjugatesbactericidal activityantibiofilmTEM |
| spellingShingle | Elshaymaa I. Elmongy Abdullah A. S. Ahmed Ibrahim El Tantawy El Sayed Ghady Fathy Hanem M. Awad Ayah Usama Salman Mohamed A. Hamed Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening Antibiotics isatin aminoquinoline conjugates bactericidal activity antibiofilm TEM |
| title | Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening |
| title_full | Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening |
| title_fullStr | Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening |
| title_full_unstemmed | Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening |
| title_short | Synthesis, Biocidal and Antibiofilm Activities of New Isatin–Quinoline Conjugates against Multidrug-Resistant Bacterial Pathogens along with Their In Silico Screening |
| title_sort | synthesis biocidal and antibiofilm activities of new isatin quinoline conjugates against multidrug resistant bacterial pathogens along with their in silico screening |
| topic | isatin aminoquinoline conjugates bactericidal activity antibiofilm TEM |
| url | https://www.mdpi.com/2079-6382/11/11/1507 |
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