Synthesis and Anticancer Activity of Novel Derivatives of ?,?-Unsaturated Ketones Based on Oleanolic Acid: in Vitro and in Silico Studies against Prostate Cancer Cells

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dc.contributor.authorŞenol, Halil
dc.contributor.authorGhaffari-Moghaddam, Mansour
dc.contributor.authorBulut, Şeyma
dc.contributor.authorAkbaş, Fahri
dc.contributor.authorTopçu, Gülaçtı
dc.date.accessioned2023-09-28T06:11:02Z
dc.date.available2023-09-28T06:11:02Z
dc.date.issued2023
dc.departmentSabire Yazıcı Fen Edebiyat Fakültesi
dc.description.abstractHerein, new derivatives of ?,?-unsaturated ketones based on oleanolic acid (4 a–i) were designed, synthesized, characterized, and tested against human prostate cancer (PC3). According to the in vitro cytotoxic study, title compounds (4 a–i) showed significantly lower toxicity toward healthy cells (HUVEC) in comparison with the reference drug doxorubicin. The compounds with the lowest IC50 values on PC3 cell lines were 4 b (7.785 ?M), 4 c (8.869 ?M), and 4 e (8.765 ?M). The results of the ADME calculations showed that the drug-likeness parameters were within the defined ranges according to Lipinski's and Jorgensen's rules. For the most potent compounds 4 b, 4 c, and 4 e, a molecular docking analysis using the induced fit docking (IFD) protocol was performed against three protein targets (PARP, PI3K, and mTOR). Based on the IFD scores, compound 4 b had the highest calculated affinity for PARP1, while compound 4 c had higher affinities for mTOR and PI3K. The MM-GBSA calculations showed that the most potent compounds had high binding affinities and formed stable complexes with the protein targets. Finally, a 50 ns molecular dynamics simulation was performed to study the behavior of protein target complexes under in silico physiological conditions.
dc.identifier.doi10.1002/cbdv.202301089
dc.identifier.issn1612-1872
dc.identifier.issue9en_US
dc.identifier.pmid37596247
dc.identifier.scopusqualityQ3
dc.identifier.urihttps:/dx.doi.org10.1002/cbdv.202301089
dc.identifier.urihttps://hdl.handle.net/20.500.12451/10992
dc.identifier.volume20en_US
dc.identifier.wosWOS:001061625500001
dc.identifier.wosqualityQ3
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherJohn Wiley and Sons Inc
dc.relation.ispartofChemistry and Biodiversity
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/embargoedAccess
dc.subjectChalcone
dc.subjectIn Silico
dc.subjectOleanolic Acid
dc.subjectProstate Cancer
dc.subjectSemi-Synthesis
dc.titleSynthesis and Anticancer Activity of Novel Derivatives of ?,?-Unsaturated Ketones Based on Oleanolic Acid: in Vitro and in Silico Studies against Prostate Cancer Cells
dc.typeArticle

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