Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity
Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity
New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).
Mohammed, Hamada H.H.
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Abdelhafez, El-Shimaa M.N.
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Abbas, Samar H.
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Moustafa, Gamal A. I.
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Hauk, Glenn
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Berger, James M.
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Mitarai, Satoshi
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Arai, Masayoshi
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Abd El-Baky, Rehab M.
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A. Abuo-Rahma, Gamal El-Din
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July 2019
Mohammed, Hamada H.H.
e3894802-1b10-4e51-9f65-cbff9d7fbf70
Abdelhafez, El-Shimaa M.N.
35259872-44ee-4964-a84d-99fc619ada12
Abbas, Samar H.
49885b77-3fed-42e2-9d75-e3359e3cb8cc
Moustafa, Gamal A. I.
1a452cdc-4856-4243-9864-b391fb115f07
Hauk, Glenn
ed8a0f28-ee9b-4cf0-b2a0-241d3b467331
Berger, James M.
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Mitarai, Satoshi
726a3ffd-073b-4eb6-8a6c-a01bd259211f
Arai, Masayoshi
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Abd El-Baky, Rehab M.
8e5f82e4-2b9c-41a9-91b0-dc3b0cbc2ce8
A. Abuo-Rahma, Gamal El-Din
a5a04748-6df5-460f-8449-65a9c91168f0
Mohammed, Hamada H.H., Abdelhafez, El-Shimaa M.N., Abbas, Samar H., Moustafa, Gamal A. I., Hauk, Glenn, Berger, James M., Mitarai, Satoshi, Arai, Masayoshi, Abd El-Baky, Rehab M. and A. Abuo-Rahma, Gamal El-Din
(2019)
Design, synthesis and molecular docking of new N-4-piperazinyl ciprofloxacin-triazole hybrids with potential antimicrobial activity.
Bioorganic Chemistry, 88, [102952].
(doi:10.1016/j.bioorg.2019.102952).
Abstract
New N-4-piperazinyl ciprofloxacin-triazole hybrids 6a-o were prepared and characterized. The in vitro antimycobacterial activity revealed that compound 6a experienced promising antimycobacterial activity against Mycobactrium smegmatis compared with the reference isoniazide (INH). Additionally, compound 6a exhibited broad spectrum antibacterial activity against all the tested strains either Gram-positive or Gram-negative bacteria compared with the reference ciprofloxacin. Also, compounds 6g and 6i displayed considerable antifungal activity compared with the reference ketoconazole. DNA cleavage assay of the highly active compounds 6c and 6h showed a good correlation between the Mycobactrium cleaved DNA gyrase assay and their in vitro antimycobactrial activity. Moreover, molecular modeling studies were done for the designed ciprofloxacin derivatives to predict their binding modes towards Topoisomerase II enzyme (PDB: 5bs8).
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Accepted/In Press date: 24 April 2019
e-pub ahead of print date: 25 April 2019
Published date: July 2019
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Local EPrints ID: 432814
URI: http://eprints.soton.ac.uk/id/eprint/432814
ISSN: 0045-2068
PURE UUID: d5abb21a-b9ea-41b4-b662-df74f4b0d819
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Date deposited: 26 Jul 2019 16:30
Last modified: 16 Mar 2024 04:40
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Contributors
Author:
Hamada H.H. Mohammed
Author:
El-Shimaa M.N. Abdelhafez
Author:
Samar H. Abbas
Author:
Glenn Hauk
Author:
James M. Berger
Author:
Satoshi Mitarai
Author:
Masayoshi Arai
Author:
Rehab M. Abd El-Baky
Author:
Gamal El-Din A. Abuo-Rahma
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