Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets
The structure assignment and conformational analysis of thiosemicarbazone <b>KKI15</b> and thiocarbohydrazone <b>KKI18</b> were performed through homonuclear and heteronuclear 2D Nuclear Magnetic Resonance (NMR) spectroscopy (2D-COSY, 2D-NOESY, 2D-HSQC, and 2D-HMBC) and quant...
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MDPI AG
2022-04-01
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| author | Nikitas Georgiou Aikaterini Katsogiannou Dimitrios Skourtis Hermis Iatrou Demeter Tzeli Stamatia Vassiliou Uroš Javornik Janez Plavec Thomas Mavromoustakos |
| author_facet | Nikitas Georgiou Aikaterini Katsogiannou Dimitrios Skourtis Hermis Iatrou Demeter Tzeli Stamatia Vassiliou Uroš Javornik Janez Plavec Thomas Mavromoustakos |
| author_sort | Nikitas Georgiou |
| collection | DOAJ |
| description | The structure assignment and conformational analysis of thiosemicarbazone <b>KKI15</b> and thiocarbohydrazone <b>KKI18</b> were performed through homonuclear and heteronuclear 2D Nuclear Magnetic Resonance (NMR) spectroscopy (2D-COSY, 2D-NOESY, 2D-HSQC, and 2D-HMBC) and quantum mechanics (QM) calculations using Functional Density Theory (DFT). After the structure identification of the compounds, various conformations of the two compounds were calculated using DFT. The two molecules showed the most energy-favorable values when their two double bonds adopted the <i>E</i> configuration. These configurations were compatible with the spatial correlations observed in the 2D-NOESY spectrum. In addition, due to the various isomers that occurred, the energy of the transition states from one isomer to another was calculated. Finally, molecular binding experiments were performed to detect potential targets for <b>KKI15</b> and <b>KKI18</b> derived from SwissAdme. In silico molecular binding experiments showed favorable binding energy values for all four enzymes studied. The strongest binding energy was observed in the enzyme butyrylcholinesterase. ADMET calculations using the preADMET and pKCSm software showed that the two molecules appear as possible drug leads. |
| first_indexed | 2024-03-09T13:14:07Z |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T13:14:07Z |
| publishDate | 2022-04-01 |
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| series | Molecules |
| spelling | doaj.art-ff1848becdff4b1f9565eadcf1beb0c92023-11-30T21:38:17ZengMDPI AGMolecules1420-30492022-04-01278253710.3390/molecules27082537Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible TargetsNikitas Georgiou0Aikaterini Katsogiannou1Dimitrios Skourtis2Hermis Iatrou3Demeter Tzeli4Stamatia Vassiliou5Uroš Javornik6Janez Plavec7Thomas Mavromoustakos8Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceLaboratory of Polymer Chemistry, Department of Chemistry, National and Kapodistrian Nikitas Georgiou University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceLaboratory of Polymer Chemistry, Department of Chemistry, National and Kapodistrian Nikitas Georgiou University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceLaboratory of Physical Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceSlovenian NMR Centre, National Institute of Chemistry, SI-1001 Ljubljana, SloveniaSlovenian NMR Centre, National Institute of Chemistry, SI-1001 Ljubljana, SloveniaLaboratory of Organic Chemistry, Department of Chemistry, National and Kapodistrian University of Athens, Panepistimioupolis Zografou, 11571 Athens, GreeceThe structure assignment and conformational analysis of thiosemicarbazone <b>KKI15</b> and thiocarbohydrazone <b>KKI18</b> were performed through homonuclear and heteronuclear 2D Nuclear Magnetic Resonance (NMR) spectroscopy (2D-COSY, 2D-NOESY, 2D-HSQC, and 2D-HMBC) and quantum mechanics (QM) calculations using Functional Density Theory (DFT). After the structure identification of the compounds, various conformations of the two compounds were calculated using DFT. The two molecules showed the most energy-favorable values when their two double bonds adopted the <i>E</i> configuration. These configurations were compatible with the spatial correlations observed in the 2D-NOESY spectrum. In addition, due to the various isomers that occurred, the energy of the transition states from one isomer to another was calculated. Finally, molecular binding experiments were performed to detect potential targets for <b>KKI15</b> and <b>KKI18</b> derived from SwissAdme. In silico molecular binding experiments showed favorable binding energy values for all four enzymes studied. The strongest binding energy was observed in the enzyme butyrylcholinesterase. ADMET calculations using the preADMET and pKCSm software showed that the two molecules appear as possible drug leads.https://www.mdpi.com/1420-3049/27/8/2537thiosemicarbazonesthiocarbohydrazonesNMR spectroscopyquantum mechanicsmolecular bindingDFT |
| spellingShingle | Nikitas Georgiou Aikaterini Katsogiannou Dimitrios Skourtis Hermis Iatrou Demeter Tzeli Stamatia Vassiliou Uroš Javornik Janez Plavec Thomas Mavromoustakos Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets Molecules thiosemicarbazones thiocarbohydrazones NMR spectroscopy quantum mechanics molecular binding DFT |
| title | Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets |
| title_full | Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets |
| title_fullStr | Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets |
| title_full_unstemmed | Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets |
| title_short | Conformational Properties of New Thiosemicarbazone and Thiocarbohydrazone Derivatives and Their Possible Targets |
| title_sort | conformational properties of new thiosemicarbazone and thiocarbohydrazone derivatives and their possible targets |
| topic | thiosemicarbazones thiocarbohydrazones NMR spectroscopy quantum mechanics molecular binding DFT |
| url | https://www.mdpi.com/1420-3049/27/8/2537 |
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