Synthesis and molecular docking of new N4-piperazinyl ciprofloxacin hybrids as antimicrobial DNA gyrase inhibitors
© 2022. The Author(s)..
A series of N-4 piperazinyl ciprofloxacin derivatives as urea-tethered ciprofloxacin-chalcone hybrids 2a-j and thioacetyl-linked ciprofloxacin-pyrimidine hybrids 5a-i were synthesized. The target compounds were investigated for their antibacterial activity against S. aureus, P. aeruginosa, E. coli, and C. albicans strains, respectively. Ciprofloxacin derivatives 2a-j and 5a-i revealed broad antibacterial activity against either Gram positive or Gram negative strains, with MIC range of 0.06-42.23 µg/mL compared to ciprofloxacin with an MIC range of 0.15-3.25 µg/mL. Among the tested compounds, hybrids 2b, 2c, 5a, 5b, 5h, and 5i exhibited remarkable antibacterial activity with MIC range of 0.06-1.53 µg/mL against the tested bacterial strains. On the other hand, compounds 2c, 2e, 5c, and 5e showed comparable antifungal activity to ketoconazole against candida albicans with MIC range of 2.03-3.89 µg/mL and 2.6 µg/mL, respectively. Further investigations showed that some ciprofloxacin hybrids have inhibitory activity against DNA gyrase as potential molecular target compared to ciprofloxacin with IC50 range of 0.231 ± 0.01-7.592 ± 0.40 µM and 0.323 ± 0.02 µM, respectively. Docking studies of compounds 2b, 2c, 5b, 5c, 5e, 5h, and 5i on the active site of DNA gyrase (PDB: 2XCT) confirmed their ability to form stable complex with the target enzyme like that of ciprofloxacin.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:27 |
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| Enthalten in: |
Molecular diversity - 27(2023), 4 vom: 24. Aug., Seite 1751-1765 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Mohammed, Hamada H H [VerfasserIn] |
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| Links: |
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| Anmerkungen: |
Date Completed 23.10.2023 Date Revised 23.10.2023 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1007/s11030-022-10528-z |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM34668417X |
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| 041 | |a eng | ||
| 100 | 1 | |a Mohammed, Hamada H H |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Synthesis and molecular docking of new N4-piperazinyl ciprofloxacin hybrids as antimicrobial DNA gyrase inhibitors |
| 264 | 1 | |c 2023 | |
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| 500 | |a Date Completed 23.10.2023 | ||
| 500 | |a Date Revised 23.10.2023 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a © 2022. The Author(s). | ||
| 520 | |a A series of N-4 piperazinyl ciprofloxacin derivatives as urea-tethered ciprofloxacin-chalcone hybrids 2a-j and thioacetyl-linked ciprofloxacin-pyrimidine hybrids 5a-i were synthesized. The target compounds were investigated for their antibacterial activity against S. aureus, P. aeruginosa, E. coli, and C. albicans strains, respectively. Ciprofloxacin derivatives 2a-j and 5a-i revealed broad antibacterial activity against either Gram positive or Gram negative strains, with MIC range of 0.06-42.23 µg/mL compared to ciprofloxacin with an MIC range of 0.15-3.25 µg/mL. Among the tested compounds, hybrids 2b, 2c, 5a, 5b, 5h, and 5i exhibited remarkable antibacterial activity with MIC range of 0.06-1.53 µg/mL against the tested bacterial strains. On the other hand, compounds 2c, 2e, 5c, and 5e showed comparable antifungal activity to ketoconazole against candida albicans with MIC range of 2.03-3.89 µg/mL and 2.6 µg/mL, respectively. Further investigations showed that some ciprofloxacin hybrids have inhibitory activity against DNA gyrase as potential molecular target compared to ciprofloxacin with IC50 range of 0.231 ± 0.01-7.592 ± 0.40 µM and 0.323 ± 0.02 µM, respectively. Docking studies of compounds 2b, 2c, 5b, 5c, 5e, 5h, and 5i on the active site of DNA gyrase (PDB: 2XCT) confirmed their ability to form stable complex with the target enzyme like that of ciprofloxacin | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Antimicrobial | |
| 650 | 4 | |a Ciprofloxacin chalcone | |
| 650 | 4 | |a Ciprofloxacin pyrimidine | |
| 650 | 4 | |a DNA gyrase inhibitors | |
| 650 | 7 | |a Ciprofloxacin |2 NLM | |
| 650 | 7 | |a 5E8K9I0O4U |2 NLM | |
| 650 | 7 | |a Topoisomerase II Inhibitors |2 NLM | |
| 650 | 7 | |a DNA Gyrase |2 NLM | |
| 650 | 7 | |a EC 5.99.1.3 |2 NLM | |
| 650 | 7 | |a Anti-Infective Agents |2 NLM | |
| 650 | 7 | |a Anti-Bacterial Agents |2 NLM | |
| 700 | 1 | |a Ali, Doaa Mohamed Elroby |e verfasserin |4 aut | |
| 700 | 1 | |a Badr, Mohamed |e verfasserin |4 aut | |
| 700 | 1 | |a Habib, Ahmed G K |e verfasserin |4 aut | |
| 700 | 1 | |a Mahmoud, Abobakr Mohamed |e verfasserin |4 aut | |
| 700 | 1 | |a Farhan, Sarah M |e verfasserin |4 aut | |
| 700 | 1 | |a Gany, Shimaa Salah Hassan Abd El |e verfasserin |4 aut | |
| 700 | 1 | |a Mohamad, Soad A |e verfasserin |4 aut | |
| 700 | 1 | |a Hayallah, Alaa M |e verfasserin |4 aut | |
| 700 | 1 | |a Abbas, Samar H |e verfasserin |4 aut | |
| 700 | 1 | |a Abuo-Rahma, Gamal El-Din A |e verfasserin |4 aut | |
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