Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens
Condensation of the reaction between enrofloxacin and ethylenediamine in the existence of glacial acetic acid produced a new N,N-ethylene (bis 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid Schiff base (<b>H<sub>2</sub>Erx-en</b>). <...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-10-01
|
| Series: | Inorganics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2304-6740/10/11/177 |
| _version_ | 1797467858993676288 |
|---|---|
| author | Amira A. Mohamed Fatma M. Ahmed Wael A. Zordok Walaa H. El-Shwiniy Sadeek A. Sadeek Hazem S. Elshafie |
| author_facet | Amira A. Mohamed Fatma M. Ahmed Wael A. Zordok Walaa H. El-Shwiniy Sadeek A. Sadeek Hazem S. Elshafie |
| author_sort | Amira A. Mohamed |
| collection | DOAJ |
| description | Condensation of the reaction between enrofloxacin and ethylenediamine in the existence of glacial acetic acid produced a new N,N-ethylene (bis 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid Schiff base (<b>H<sub>2</sub>Erx-en</b>). <b>H<sub>2</sub>Erx-en</b> was used as a tetra-dentate ligand to produce novel complexes by interacting with metal ions iron(III), yttrium(III), zirconium(IV), and lanthanum(III). The synthetic <b>H<sub>2</sub>Erx-en</b> and its chelates had been detected with elemental analysis, spectroscopic methods, mass spectrometry, thermal studies, conductometric and magnetic measurements experiments. The calculated molar conductance of the complexes in 1 × 10<sup>−3</sup> M DMF solution shows that iron(III), yttrium(III) and lanthanum(III) are 1:1 electrolytes, however the zirconium(IV) complex is non-electrolyte. The infrared spectra of <b>H<sub>2</sub>Erx-en</b> chelates indicated that the carboxylic group is deprotonated and <b>H<sub>2</sub>Erx-en</b> is associated with metals as a tetra-dentate through nitrogen and oxygen atoms. The disappearance of the carboxylic proton in all complexes corroborated information concerning <b>H<sub>2</sub>Erx-en</b> deprotonation and complexation with metal ions, according to <sup>1</sup>H NMR data. Thermal analysis revealed the abundance of H<sub>2</sub>O particles in the chelates’ entrance and outlet spheres, indicating the disintegration pattern of <b>H<sub>2</sub>Erx-en</b> and their chelates. The Coats–Redfern and Horowitz–Metzeger approaches were utilized to calculate the thermodynamic items (E<sub>a</sub>, ΔS *, ΔH *, and ΔG *) at n = 1 and n ≠ 1. The resulting data reveal better organized chelate building activation. Density functional theory (DFT) was created to properly grasp the optimal architecture of the molecules. The chelates are softer than <b>H<sub>2</sub>Erx-en</b>, with estimates varying between 95.23 eV to 400.00 eV, compared to 31.47 eV for <b>H<sub>2</sub>Erx-en</b>. The disc diffusion technique was utilized to assess <b>H<sub>2</sub>Erx-en</b> and their chelates in an antimicrobial assay against various food and phytopathogens. The zirconium(IV) chelate has the most potent antibacterial action and is particularly efficient against <i>Salmonella typhi</i>. |
| first_indexed | 2024-03-09T18:58:43Z |
| format | Article |
| id | doaj.art-85584b5f985d40e5920c6e04c5c562bb |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-09T18:58:43Z |
| publishDate | 2022-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-85584b5f985d40e5920c6e04c5c562bb2023-11-24T05:12:20ZengMDPI AGInorganics2304-67402022-10-01101117710.3390/inorganics10110177Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-PathogensAmira A. Mohamed0Fatma M. Ahmed1Wael A. Zordok2Walaa H. El-Shwiniy3Sadeek A. Sadeek4Hazem S. Elshafie5Department of Basic Science, Zagazig Higher Institute of Engineering and Technology, Zagazig 44519, EgyptRegional Joint Laboratory, Directorate of Health Affairs, Zagazig 44519, EgyptDepartment of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, EgyptDepartment of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, EgyptDepartment of Chemistry, Faculty of Science, Zagazig University, Zagazig 44519, EgyptSchool of Agricultural, Forestry, Food and Environmental Sciences, University of Basilicata, Viale dell’Ateneo Lucano, 85100 Potenza, ItalyCondensation of the reaction between enrofloxacin and ethylenediamine in the existence of glacial acetic acid produced a new N,N-ethylene (bis 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6-fluoro-1,4-dihydroquinoline-3-carboxylic acid Schiff base (<b>H<sub>2</sub>Erx-en</b>). <b>H<sub>2</sub>Erx-en</b> was used as a tetra-dentate ligand to produce novel complexes by interacting with metal ions iron(III), yttrium(III), zirconium(IV), and lanthanum(III). The synthetic <b>H<sub>2</sub>Erx-en</b> and its chelates had been detected with elemental analysis, spectroscopic methods, mass spectrometry, thermal studies, conductometric and magnetic measurements experiments. The calculated molar conductance of the complexes in 1 × 10<sup>−3</sup> M DMF solution shows that iron(III), yttrium(III) and lanthanum(III) are 1:1 electrolytes, however the zirconium(IV) complex is non-electrolyte. The infrared spectra of <b>H<sub>2</sub>Erx-en</b> chelates indicated that the carboxylic group is deprotonated and <b>H<sub>2</sub>Erx-en</b> is associated with metals as a tetra-dentate through nitrogen and oxygen atoms. The disappearance of the carboxylic proton in all complexes corroborated information concerning <b>H<sub>2</sub>Erx-en</b> deprotonation and complexation with metal ions, according to <sup>1</sup>H NMR data. Thermal analysis revealed the abundance of H<sub>2</sub>O particles in the chelates’ entrance and outlet spheres, indicating the disintegration pattern of <b>H<sub>2</sub>Erx-en</b> and their chelates. The Coats–Redfern and Horowitz–Metzeger approaches were utilized to calculate the thermodynamic items (E<sub>a</sub>, ΔS *, ΔH *, and ΔG *) at n = 1 and n ≠ 1. The resulting data reveal better organized chelate building activation. Density functional theory (DFT) was created to properly grasp the optimal architecture of the molecules. The chelates are softer than <b>H<sub>2</sub>Erx-en</b>, with estimates varying between 95.23 eV to 400.00 eV, compared to 31.47 eV for <b>H<sub>2</sub>Erx-en</b>. The disc diffusion technique was utilized to assess <b>H<sub>2</sub>Erx-en</b> and their chelates in an antimicrobial assay against various food and phytopathogens. The zirconium(IV) chelate has the most potent antibacterial action and is particularly efficient against <i>Salmonella typhi</i>.https://www.mdpi.com/2304-6740/10/11/177enrofloxacin schiff basemetal complexesspectrathermalantimicrobial activityphytopathogens |
| spellingShingle | Amira A. Mohamed Fatma M. Ahmed Wael A. Zordok Walaa H. El-Shwiniy Sadeek A. Sadeek Hazem S. Elshafie Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens Inorganics enrofloxacin schiff base metal complexes spectra thermal antimicrobial activity phytopathogens |
| title | Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens |
| title_full | Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens |
| title_fullStr | Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens |
| title_full_unstemmed | Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens |
| title_short | Novel Enrofloxacin Schiff Base Metal Complexes: Synthesis, Spectroscopic Characterization, Computational Simulation and Antimicrobial Investigation against Some Food and Phyto-Pathogens |
| title_sort | novel enrofloxacin schiff base metal complexes synthesis spectroscopic characterization computational simulation and antimicrobial investigation against some food and phyto pathogens |
| topic | enrofloxacin schiff base metal complexes spectra thermal antimicrobial activity phytopathogens |
| url | https://www.mdpi.com/2304-6740/10/11/177 |
| work_keys_str_mv | AT amiraamohamed novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens AT fatmamahmed novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens AT waelazordok novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens AT walaahelshwiniy novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens AT sadeekasadeek novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens AT hazemselshafie novelenrofloxacinschiffbasemetalcomplexessynthesisspectroscopiccharacterizationcomputationalsimulationandantimicrobialinvestigationagainstsomefoodandphytopathogens |