New fluoroquinolones/nitric oxide donor hybrids: design, synthesis and antitubercular activity
New fluoroquinolones/nitric oxide donor hybrids: design, synthesis and antitubercular activity
New nitric oxide (NO) donating fluoroquinolones/nitrate ester hybrids were prepared and their structures were characterized
by various spectroscopic and analytical tools. The release of NO from the prepared nitrate esters was measured using the modified Griess colorimetric method. Evaluation of antitubercular activity showed that most of tested compounds exhibited comparable or higher activity than the parent fluoroquinolones. Compounds 2b, 3a, 4a, 5a, and 2d showed better activity than ciprofloxacin. Nevertheless, none of the new compounds were superior to the parent fluoroquinolones in terms of DNA cleavage stimulation in mycobacteria. The additional growth inhibition effect that is distinct from gyrase poisoning may be due to release of NO or enhancement of lipophilicity. These data are augmented by docking results where the docked compounds did not exert additional significant bindings over the parent fluoroquinolones.
Aziz, Hossameldin
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Moustafa, Gamal
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Abbas, Samar H.
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Hauk, Glenn
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Siva Krishna, Vagolu
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Sriram, Dharmarajan
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Berger, James M.
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A. Abuo-Rahma, Gamal El-Din
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10 June 2019
Aziz, Hossameldin
c5507861-a494-42b2-941b-9d3776ddfda0
Moustafa, Gamal
1a452cdc-4856-4243-9864-b391fb115f07
Abbas, Samar H.
49885b77-3fed-42e2-9d75-e3359e3cb8cc
Hauk, Glenn
ed8a0f28-ee9b-4cf0-b2a0-241d3b467331
Siva Krishna, Vagolu
cacefa79-78ce-4d1d-8e65-e0a420c6a2c7
Sriram, Dharmarajan
ef0f17ba-4104-44ee-a165-d628ca33323d
Berger, James M.
12dcfffa-b794-4fd6-894a-5ba42a5728ed
A. Abuo-Rahma, Gamal El-Din
a5a04748-6df5-460f-8449-65a9c91168f0
Aziz, Hossameldin, Moustafa, Gamal, Abbas, Samar H., Hauk, Glenn, Siva Krishna, Vagolu, Sriram, Dharmarajan, Berger, James M. and A. Abuo-Rahma, Gamal El-Din
(2019)
New fluoroquinolones/nitric oxide donor hybrids: design, synthesis and antitubercular activity.
Medicinal Chemistry Research.
(doi:10.1007/s00044-019-02372-y).
Abstract
New nitric oxide (NO) donating fluoroquinolones/nitrate ester hybrids were prepared and their structures were characterized
by various spectroscopic and analytical tools. The release of NO from the prepared nitrate esters was measured using the modified Griess colorimetric method. Evaluation of antitubercular activity showed that most of tested compounds exhibited comparable or higher activity than the parent fluoroquinolones. Compounds 2b, 3a, 4a, 5a, and 2d showed better activity than ciprofloxacin. Nevertheless, none of the new compounds were superior to the parent fluoroquinolones in terms of DNA cleavage stimulation in mycobacteria. The additional growth inhibition effect that is distinct from gyrase poisoning may be due to release of NO or enhancement of lipophilicity. These data are augmented by docking results where the docked compounds did not exert additional significant bindings over the parent fluoroquinolones.
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Aziz2019_Article_NewFluoroquinolonesNitricOxide
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e-pub ahead of print date: 6 June 2019
Published date: 10 June 2019
Identifiers
Local EPrints ID: 434190
URI: http://eprints.soton.ac.uk/id/eprint/434190
ISSN: 1054-2523
PURE UUID: 1c89e61d-4f4d-4c97-b74c-75a733f08663
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Date deposited: 13 Sep 2019 16:30
Last modified: 16 Mar 2024 04:40
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Author:
Hossameldin Aziz
Author:
Samar H. Abbas
Author:
Glenn Hauk
Author:
Vagolu Siva Krishna
Author:
Dharmarajan Sriram
Author:
James M. Berger
Author:
Gamal El-Din A. Abuo-Rahma
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