Synthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity

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dc.contributor.authorPoslu, Ayşe Halıç
dc.contributor.authorAslan, Şafak Esra
dc.contributor.authorKoz, Gamze
dc.contributor.authorŞentürk, Esra
dc.contributor.authorKoz, Omer
dc.contributor.authorŞentürk, Murat
dc.contributor.authorNalbantsoy, A. Ş.
dc.date.accessioned2026-02-08T15:11:02Z
dc.date.available2026-02-08T15:11:02Z
dc.date.issued2024
dc.departmentBursa Teknik Üniversitesi
dc.description.abstractA series of salicylidene uracil (1–18) derived from 5-aminouracil and substituted salicylaldehydes were analyzed for cytotoxic activity and enzyme inhibitory potency. Nine out of eighteen derivatives (6–8, 10, 12–15, 18) are novel molecules synthesized for the first time in this work, and other derivatives were previously synthesized by our group. The compounds were characterized by Proton nuclear magnetic resonance, carbon nuclear magnetic resonance, fourier transform infrared spectroscopy, and elemental analysis. All compounds were tested for their in vitro cytotoxicity against PC-3 (human prostate adenocarcinoma), A549 (human alveolar adenocarcinoma), and SHSY-5Y (human neuroblastoma) cancer cell lines and the nontumorigenic HEK293 (human embryonic kidney cells) cell line. The 3,5-di-tert-butylsalicylaldehyde derived compound (8) was toxic to PC-3 human prostate adenocarcinoma cells, showing a promising IC<inf>50</inf> value at 7.05 ± 0.76 ?M. The present study also aimed to evaluate the inhibitory effects of the compounds against several key enzymes, namely carbonic anhydrase I and II (CA I and CA II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and glutathione reductase (GR), which are implicated in various global disorders, such as Alzheimer's disease, epilepsy, cancer, malaria, diabetes, and glaucoma. The inhibitory profiles of the tested compounds were assessed by determining their K<inf>i</inf> values, which ranged from 2.96 to 9.24 nM for AChE, 3.78 to 12.57 nM for BChE, 8.42 to 25.74 nM for CA I, 7.24 to 19.74 nM for CA II, and 0.541 to 1.124 ?M for GR. Molecular docking studies were also performed for all compounds. Most derivatives exhibited much more effective inhibitory action compared with clinically used standards. Thus, our findings indicate that the salicylidene derivatives presented in this study are promising drug candidates that need further evaluation. © 2023 The Authors. Archiv der Pharmazie published by Wiley-VCH GmbH on behalf of Deutsche Pharmazeutische Gesellschaft.
dc.description.sponsorship(182L14); Türkiye Bilimsel ve Teknolojik Araştırma Kurumu, TÜBİTAK, (217Z221)
dc.identifier.doi10.1002/ardp.202300374
dc.identifier.issn0365-6233
dc.identifier.issue1
dc.identifier.pmid37902389
dc.identifier.scopus2-s2.0-85175378700
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1002/ardp.202300374
dc.identifier.urihttps://hdl.handle.net/20.500.12885/5196
dc.identifier.volume357
dc.identifier.wosWOS:001095045700001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.indekslendigikaynakWeb of Science
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc
dc.relation.ispartofArchiv der Pharmazie
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzScopus_KA_20260207
dc.subjectcarbonic anhydrase
dc.subjectcholinesterases
dc.subjectcytotoxicity
dc.subjectglutathione reductase
dc.subjectsalicylidene uracil
dc.titleSynthesis and biological evaluation of novel salicylidene uracils: Cytotoxic activity on human cancer cell lines and inhibitory action on enzymatic activity
dc.typeArticle

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