Synthesis and molecular modeling of MetAP2 of thiosemicarbazides, 1,2,4-triazoles, thioethers derived from (S)-Naproxen as possible breast cancer agents

dc.authoridYILMAZ, ÖZGÜR/0000-0003-3892-2775
dc.authoridKüçükgüzel, Ş.Güniz/0000-0001-9405-8905
dc.authoridUba, Abdullahi Ibrahim/0000-0002-0853-108X
dc.authoridMega Tiber, Pinar/0000-0003-0819-0702
dc.authoridYelekci, Kemal/0000-0002-0052-4926
dc.authoridBirgul, Kaan/0000-0003-3963-4687
dc.authoridTiryaki, Selen/0000-0002-2940-7678
dc.authorwosidYILMAZ, ÖZGÜR/AAG-2472-2021
dc.authorwosidKüçükgüzel, Ş.Güniz/AAQ-8954-2021
dc.authorwosidUba, Abdullahi Ibrahim/P-3971-2019
dc.authorwosidMega Tiber, Pinar/HJZ-3019-2023
dc.authorwosidKOCYIGIT SEVINC, SEVGİ/ITT-5404-2023
dc.authorwosidYelekci, Kemal/B-1431-2019
dc.contributor.authorBirgul, Kaan
dc.contributor.authorUba, Abdullah Ibrahim
dc.contributor.authorCuhadar, Ozan
dc.contributor.authorSevinc, Sevgi Kocyigit
dc.contributor.authorTiryaki, Selen
dc.contributor.authorTiber, Pinar Mega
dc.contributor.authorOrun, Oya
dc.date.accessioned2023-10-19T15:11:39Z
dc.date.available2023-10-19T15:11:39Z
dc.date.issued2022
dc.department-temp[Birgul, Kaan] Altinbas Univ, Fac Pharm, Dept Pharmaceut Chem, TR-34144 Istanbul, Turkey; [Uba, Abdullah Ibrahim; Yelekci, Kemal] Kadir Has Univ, Fac Engn & Nat Sci, Dept Genet & Bioengn, TR-34083 Istanbul, Turkey; [Cuhadar, Ozan; Sevinc, Sevgi Kocyigit; Tiber, Pinar Mega; Orun, Oya] Marmara Univ, Sch Med, Dept Biophys, TR-34854 Istanbul, Turkey; [Tiryaki, Selen; Telci, Dilek] Yeditepe Univ, Fac Engn, Dept Genet & Bioengn, TR-34755 Istanbul, Turkey; [Yilmaz, Ozgur] TUBITAK Marmara Res Ctr, TR-41470 Kocaeli, Turkey; [Kucukguzel, S. Guniz] Fenerbahce Univ, Fac Pharm, Dept Pharmaceut Chem, TR-34758 Istanbul, Turkeyen_US
dc.description.abstractNew thiosemicarbazides (3, 5-6), 1,2,4-triazoles (14-15) and thioethers (22-68) from derived (S)-Naproxen were synthesized in this study. The structure of these compounds were elucidated by spectral (FT-IR, H-1 NMR, C-13 NMR) methods, besides elemental analysis and TLC. The molecular binding of the compounds on MetAP-2 was performed. Anticancer effects of the synthesized compounds were studied by using MTT assay method on MCF-7 (includes oestrogene and progesterone receptors) and MDA-MB-231 (lacks estrogen and progesterone receptors) adenocarcinoma cell lines at 0, 10, 25, 50, 75 and 100 mu M concentrations for 24 h. The IC(50 )values of novel (S)-Naproxen derivatives were determined between from 5 to 100 mu M on MCF-7 breast cancer cell line and MDA-MB-231 cell lines. The apoptotic activity of selected compounds 22 and 42 were first analyzed by Annexin V staining using Tali Image-Based Cytometer. Mitochondrial membrane potential changes determined in fluorescence plate reader following JC-1 stain for compounds 22 and 42 in MCF-7 and MDA-MB-231 cells. The effect of these compounds on the cell viability 4T1 mouse mammary tumor cell line was tested at 1 to 5 times of calculated IC50 value (IC(50)x1, IC(50)x2, IC(50)x3, IC(50)x4, and IC(50)x5). Next in order to determine the toxicity of the combination of compound 51 and Docetaxel, WST-1 cell viability and proliferation assay was performed with 4T1. (C) 2022 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipScientific and Technical Research Council of Turkey (TUBITAK) [215S009]en_US
dc.description.sponsorshipThe synthesis, confirmation and molecular docking of novel compounds were supported by a grant of The Scientific and Technical Research Council of Turkey (TUB.ITAK) Research Fund Project Number : 215S009. (+) (S)-Naproxen, was obtained from Deva. IlacSan. Tic. A.S. The optical rotation angle experiment was done in Onko-Kocsel Ilac.en_US
dc.identifier.citation4
dc.identifier.doi10.1016/j.molstruc.2022.132739en_US
dc.identifier.issn0022-2860
dc.identifier.issn1872-8014
dc.identifier.scopus2-s2.0-85125952901en_US
dc.identifier.scopusqualityQ2
dc.identifier.urihttps://doi.org/10.1016/j.molstruc.2022.132739
dc.identifier.urihttps://hdl.handle.net/20.500.12469/5150
dc.identifier.volume1259en_US
dc.identifier.wosWOS:000820364800009en_US
dc.identifier.wosqualityN/A
dc.khas20231019-WoSen_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.relation.ispartofJournal of Molecular Structureen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectNaproxenEn_Us
dc.subjectApoptosisen_US
dc.subjectNaproxenen_US
dc.subjectAnticancerEn_Us
dc.subjectThioetheren_US
dc.subjectBreast cancer cell lineen_US
dc.subjectNaproxen
dc.subjectTriple negative canceren_US
dc.subjectAnticancer
dc.subjectMetAP2en_US
dc.titleSynthesis and molecular modeling of MetAP2 of thiosemicarbazides, 1,2,4-triazoles, thioethers derived from (S)-Naproxen as possible breast cancer agentsen_US
dc.typeArticleen_US
dspace.entity.typePublication

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