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.citationcount 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.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.scopus.citedbyCount 7
dc.subject Apoptosis en_US
dc.subject Naproxen
dc.subject Naproxen en_US
dc.subject Thioether en_US
dc.subject Naproxen En_Us
dc.subject Breast cancer cell line en_US
dc.subject Anticancer
dc.subject Triple negative cancer en_US
dc.subject Anticancer En_Us
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
dc.wos.citedbyCount 7
dspace.entity.type Publication

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