Synthesis, anticancer activity and molecular modeling study of novel substituted triazole linked tetrafluoronaphthalene hybrid derivatives

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dc.authoridERDOGAN, Musa/0000-0001-6097-2862
dc.authoridComert Onder, Ferah/0000-0002-4037-1979
dc.contributor.authorErdogan, Musa
dc.contributor.authorComert Onder, Ferah
dc.date.accessioned2025-01-27T20:16:36Z
dc.date.available2025-01-27T20:16:36Z
dc.date.issued2024
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractTo create some novel anticancer molecules, a library of novel series of various triazoles linked to the hydroxyl group of 5,6,7,8-tetrafluoronaphthalen-1-ol (3) was designed and synthesized via CuAAC reaction 'Click Chemistry' of tetrafluoronaphthalene based terminal alkyne with substituted organic azides. The structural characterizations of the targeted Click products 9-18 were confirmed by FTIR, H-1 NMR, F-19 NMR, C-13 NMR and HRMS spectroscopy. Synthesized compounds were tested in two triple negative breast cancer (TNBC) cell lines to understand their anticancer potentials. According to our findings, compounds 14 and 13 showed high cytotoxicity in BT549 cells at 20 mu M and 30 mu M, respectively. Moreover, these compounds blocked the migration of BT549 cells. In the MDA-MB-231 cell line, compound 18 exhibited high cytotoxicity and can block cell migration for 24 h. Molecular docking study with synthesized novel compounds was performed by Glide/SP method against SphK1 drug target. Furthermore, molecular dynamics (MD) simulation was carried out for the compounds 12-14 and 18. The compounds 13 and 14 may be potential inhibitor candidates in place of a reference inhibitor. A pharmacophore model was generated with the most potent compound 14, and the approved drugs were screened using the modules of Discovery Studio to find similar drugs. Consequently, this comprehensive study encompassing design, synthesis, in vitro and in silico analyses were correlated with the structure-activity relationship between compounds. The findings have the potential to unveil promising drug candidates for future studies.
dc.identifier.doi10.1080/07391102.2023.2252914
dc.identifier.endpage9786
dc.identifier.issn0739-1102
dc.identifier.issn1538-0254
dc.identifier.issue18
dc.identifier.pmid37676264
dc.identifier.scopus2-s2.0-85169881317
dc.identifier.scopusqualityQ1
dc.identifier.startpage9767
dc.identifier.urihttps://doi.org/10.1080/07391102.2023.2252914
dc.identifier.urihttps://hdl.handle.net/20.500.12428/21316
dc.identifier.volume42
dc.identifier.wosWOS:001063991300001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherTaylor & Francis Inc
dc.relation.ispartofJournal of Biomolecular Structure & Dynamics
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WoS_20250125
dc.subjectClick chemistry
dc.subjecttetrafluoronaphthalene
dc.subjecttriazole
dc.subjectanticancer activity
dc.subjectADMET
dc.subjectmolecular docking
dc.subjectmolecular dynamics (MD) simulation
dc.titleSynthesis, anticancer activity and molecular modeling study of novel substituted triazole linked tetrafluoronaphthalene hybrid derivatives
dc.typeArticle

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