Synthesis and molecular modeling of MetAP2 of thiosemicarbazides, 1,2,4-triazoles, thioethers derived from (S)-Naproxen as possible breast cancer agents
dc.authorid | YILMAZ, ÖZGÜR/0000-0003-3892-2775 | |
dc.authorid | Küçükgüzel, Ş.Güniz/0000-0001-9405-8905 | |
dc.authorid | Uba, Abdullahi Ibrahim/0000-0002-0853-108X | |
dc.authorid | Mega Tiber, Pinar/0000-0003-0819-0702 | |
dc.authorid | Yelekci, Kemal/0000-0002-0052-4926 | |
dc.authorid | Birgul, Kaan/0000-0003-3963-4687 | |
dc.authorid | Tiryaki, Selen/0000-0002-2940-7678 | |
dc.authorwosid | YILMAZ, ÖZGÜR/AAG-2472-2021 | |
dc.authorwosid | Küçükgüzel, Ş.Güniz/AAQ-8954-2021 | |
dc.authorwosid | Uba, Abdullahi Ibrahim/P-3971-2019 | |
dc.authorwosid | Mega Tiber, Pinar/HJZ-3019-2023 | |
dc.authorwosid | KOCYIGIT SEVINC, SEVGİ/ITT-5404-2023 | |
dc.authorwosid | Yelekci, Kemal/B-1431-2019 | |
dc.contributor.author | Birgul, Kaan | |
dc.contributor.author | Uba, Abdullah Ibrahim | |
dc.contributor.author | Cuhadar, Ozan | |
dc.contributor.author | Sevinc, Sevgi Kocyigit | |
dc.contributor.author | Tiryaki, Selen | |
dc.contributor.author | Tiber, Pinar Mega | |
dc.contributor.author | Orun, Oya | |
dc.date.accessioned | 2023-10-19T15:11:39Z | |
dc.date.available | 2023-10-19T15:11:39Z | |
dc.date.issued | 2022 | |
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, Turkey | en_US |
dc.description.abstract | New 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.sponsorship | Scientific and Technical Research Council of Turkey (TUBITAK) [215S009] | en_US |
dc.description.sponsorship | The 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.citation | 4 | |
dc.identifier.doi | 10.1016/j.molstruc.2022.132739 | en_US |
dc.identifier.issn | 0022-2860 | |
dc.identifier.issn | 1872-8014 | |
dc.identifier.scopus | 2-s2.0-85125952901 | en_US |
dc.identifier.scopusquality | Q2 | |
dc.identifier.uri | https://doi.org/10.1016/j.molstruc.2022.132739 | |
dc.identifier.uri | https://hdl.handle.net/20.500.12469/5150 | |
dc.identifier.volume | 1259 | en_US |
dc.identifier.wos | WOS:000820364800009 | en_US |
dc.identifier.wosquality | N/A | |
dc.khas | 20231019-WoS | en_US |
dc.language.iso | en | en_US |
dc.publisher | Elsevier | en_US |
dc.relation.ispartof | Journal of Molecular Structure | en_US |
dc.relation.publicationcategory | Makale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı | en_US |
dc.rights | info:eu-repo/semantics/closedAccess | en_US |
dc.subject | Naproxen | En_Us |
dc.subject | Apoptosis | en_US |
dc.subject | Naproxen | en_US |
dc.subject | Anticancer | En_Us |
dc.subject | Thioether | en_US |
dc.subject | Breast cancer cell line | en_US |
dc.subject | Naproxen | |
dc.subject | Triple negative cancer | en_US |
dc.subject | Anticancer | |
dc.subject | MetAP2 | en_US |
dc.title | Synthesis and molecular modeling of MetAP2 of thiosemicarbazides, 1,2,4-triazoles, thioethers derived from (S)-Naproxen as possible breast cancer agents | en_US |
dc.type | Article | en_US |
dspace.entity.type | Publication |
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