Design, synthesis, spectroscopic characterizations, single crystal X-ray analysis, in vitro xanthine oxidase and acetylcholinesterase inhibitory evaluation as well as in silico evaluation of selenium-based N-heterocyclic carbene compounds

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dc.authoridAktaş, Aydın/0000-0001-8496-6782
dc.authoridAygün, Muhittin/0000-0001-9670-9062
dc.authoridTezcan, Burcu/0000-0001-5630-5522
dc.authoridTASKIN TOK, Tugba/0000-0002-0064-8400
dc.authoridAtes, Burhan/0000-0001-6080-229X
dc.authorwosidAktaş, Aydın/J-6194-2019
dc.authorwosidAygün, Muhittin/P-3605-2019
dc.authorwosidBarut Celepci, Duygu/M-6189-2017
dc.authorwosidTezcan, Burcu/GSN-1194-2022
dc.authorwosidTASKIN TOK, Tugba/A-8885-2016
dc.contributor.authorKaya, Guelsen
dc.contributor.authorNoma, Samir Abbas Ali
dc.contributor.authorCelepci, Duygu Barut
dc.contributor.authorBayil, Imren
dc.contributor.authorTaskin-Tok, Tugba
dc.contributor.authorGok, Yetkin
dc.contributor.authorAtes, Burhan
dc.date.accessioned2024-08-04T20:53:22Z
dc.date.available2024-08-04T20:53:22Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractHerein, eight new NHC-based selenourea derivatives were synthesized and characterized by using spectroscopic method (H-1, F-19, and C-13 NMR, FT-IR), and elemental analysis techniques. These compounds were synthesized by mixing benzimidazolium salts, potassium carbonate, and selenium powder in ethyl alcohol. Additionally, the molecular and crystal structures of the three compounds (1c, 2b, and 2c) were determined using the single-crystal x-ray diffraction (XRD) method. Diffraction analysis demonstrated the partial carbon-selenium double-bond character of these compounds. All compounds were determined to be highly potent inhibitors for AChE and XO enzymes. The IC(50 )values for the compounds were found in the range of 0.361-0.754 mu M for XO and from 0.995 to 1.746 mu M for AChE. The DNA binding properties of the compounds were investigated. These compounds did not have a remarkable DNA binding property. Also, DPPH radical scavenging activities of the compounds were also investigated. Compounds (1c), (2a), (3a), and (3b) exhibited more pronounced DPPH radical scavenging activity when compared to other compounds. Docking studies were applied by using AutoDock 4 to determine interaction mechanism of the selected compounds (1a), (1b), and (3b). The compound (1b) has good binding affinity (-9.78 kcal/mol) against AChE, and (-6.86 kcal/mol) for XO target. Drug similarity properties of these compounds compared to positive controls were estimated and evaluated by ADMET analysis. Furthermore, molecular dynamics simulations have been applied to understand the accuracy of docking studies. These findings and the defined compounds could be potential candidates for the discovery and progress of effective medicine(s) for AChE and XO in the future.In this study, we synthesized selenourea derivatives from N-heterocyclic carbene (NHC) precursors. All compounds were characterized by using NMR, FTIR spectroscopic method, and elemental analysis technique. In addition, the crystal structure of the three compounds was determined using the single-crystal X-ray diffraction method. New selenoura derivatives were tested for their effect to inhibit the xanthine oxidase and acetylcholinesterase enzymes. The DNA binding properties of the Se-NHC compounds were investigated and the compounds did not have significant DNA binding properties. In addition, DPPH radical scavenging activities of Se-NHC compounds were also investigated. All compounds exhibited DPPH radical scavenging activity. Molecular Docking studies using AutoDock 4 were used to determine the interaction mechanism of selected compounds (1a, 1b, and 3b) Drug similarity properties of these compounds compared to positive controls were estimated and evaluated by ADMET analysis. Furthermore, molecular dynamics simulations have been applied to understand the accuracy of docking studies.en_US
dc.description.sponsorshipDokuz Eyluel University [2010.KB.FEN.13]en_US
dc.description.sponsorshipThe authors thank the Inoenue University Faculty of Science Department of Chemistry for the spectroscopy data and characterization of compounds. The authors acknowledge Dokuz Eyluel University for the use of the Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No.: 2010.KB.FEN.13).en_US
dc.identifier.doi10.1080/07391102.2022.2163696
dc.identifier.endpage11747en_US
dc.identifier.issn0739-1102
dc.identifier.issn1538-0254
dc.identifier.issue21en_US
dc.identifier.pmid36622368en_US
dc.identifier.scopus2-s2.0-85146656658en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage11728en_US
dc.identifier.urihttps://doi.org/10.1080/07391102.2022.2163696
dc.identifier.urihttps://hdl.handle.net/11616/101126
dc.identifier.volume41en_US
dc.identifier.wosWOS:000911273900001en_US
dc.identifier.wosqualityQ1en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.indekslendigikaynakPubMeden_US
dc.language.isoenen_US
dc.publisherTaylor & Francis Incen_US
dc.relation.ispartofJournal of Biomolecular Structure & Dynamicsen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectEnzyme inhibitionen_US
dc.subjectmolecular dynamic simulationen_US
dc.subjectN-heterocyclic carbeneen_US
dc.subjectselenoureaen_US
dc.subjectsingle-crystalen_US
dc.titleDesign, synthesis, spectroscopic characterizations, single crystal X-ray analysis, in vitro xanthine oxidase and acetylcholinesterase inhibitory evaluation as well as in silico evaluation of selenium-based N-heterocyclic carbene compoundsen_US
dc.typeArticleen_US

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