Design, syntheses, theoretical calculations, MM-GBSA, potential anti-cancer and enzyme activities of novel Schiff base compounds

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dc.authoridTaslimi, Parham/0000-0002-3171-0633
dc.authoridSadeghian, nastaran/0009-0004-2966-9231
dc.authoridAydin Kose, Fadime/0000-0001-5222-7555
dc.authoridTUZUN, BURAK/0000-0002-0420-2043
dc.contributor.authorYalazan, Halise
dc.contributor.authorKoc, Damla
dc.contributor.authorKose, Fadime Aydin
dc.contributor.authorFandakli, Seda
dc.contributor.authorTuzun, Burak
dc.contributor.authorAkgul, Muhammed Ismail
dc.contributor.authorSadeghian, Nastaran
dc.date.accessioned2024-10-26T18:10:54Z
dc.date.available2024-10-26T18:10:54Z
dc.date.issued2023
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractIn this study, new Schiff base compounds (SB-F-OH, SB-Cl-OH and SB-Br-OH) were derived from chalcone-derived amine compounds containing halogen groups and 4-hydroxybenzaldehyde. Also, their phthalonitrile compounds (SB-F-CN, SB-Cl-CN and SB-Br-CN) have been synthesized. The structures of these compounds were elucidated by NMR, FT-IR and Mass spectroscopic methods. The quantum chemical parameters were calculated at B3LYP/6-31++g(d,p), HF/6-31++g(d,p) and M062X/6-31++g(d,p) levels. As the biological application of the synthesized compounds, (i) their inhibition properties of the synthesized compounds on Acetylcholinesterase (AChE) and Butyrylcholinesterase (BChE) metabolic enzymes were investigated, and their potential anticancer activities against neuroblastoma (NB; SH-SY5Y) and healthy fibroblast (NIH-3T3) cell lines were determined by in vitro assays. All compounds showed inhibition at nanomolar level with the Ki values in the range of 97.86 +/- 30.51-516.82 +/- 31.42 nM for AChE, 33.21 +/- 4.45-78.50 +/- 8.91 nM for BChE, respectively. It has been determined that all tested compounds have a remarkable cytotoxic effect against SH-SY5Y, and IC50 values were significantly lower than NIH-3T3 cells. The lowest IC50 value was observed in SB-Cl-OH (7.48 +/- 0.86 mu M) and SB-Cl-CN (7.31 +/- 0.69 mu M). The molecular docking of the molecules was also investigated using crystal structure of AChE enzyme protein (PDB ID: 4M0E), crystal structure of BChE protein (PDB ID: 6R6V) and SH-SY5Y cancer protein (PDB ID: 2F3F, 3PBL and 5WIV). The ADME properties of the compounds were investigated. MM/GBSA method is calculated binding free energy. Afterwards, ADME/T analysis was performed to examine the some properties of the molecules.Communicated by Ramaswamy H. Sarma
dc.description.sponsorshipThe numerical calculations reported in this article were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.description.sponsorshipThe numerical calculations reported in this article were fully/partially performed at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TRUBA resources).
dc.identifier.doi10.1080/07391102.2023.2274972
dc.identifier.issn0739-1102
dc.identifier.issn1538-0254
dc.identifier.pmid37921706
dc.identifier.scopus2-s2.0-85176085565
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1080/07391102.2023.2274972
dc.identifier.urihttps://hdl.handle.net/20.500.12418/30439
dc.identifier.wosWOS:001093474000001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherTaylor & Francis Inc
dc.relation.ispartofJournal of Biomolecular Structure & Dynamics
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.subjectCell culture
dc.subjectenzyme inhibition
dc.subject4-hydroxybenzaldehyde
dc.subjectmolecular docking
dc.subjectMM-GBSA
dc.titleDesign, syntheses, theoretical calculations, MM-GBSA, potential anti-cancer and enzyme activities of novel Schiff base compounds
dc.typeArticle

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