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dc.contributor.authorMorak-Młodawska, Beata
dc.contributor.authorPluta, Krystian
dc.contributor.authorLatocha, Małgorzata
dc.contributor.authorJeleń, Małgorzata
dc.contributor.authorKuśmierz, Dariusz
dc.contributor.authorSuwińska, Kinga
dc.contributor.authorShkurenko, Aleksander
dc.contributor.authorCzuba, Zenon
dc.contributor.authorJurzak, Magdalena
dc.date.accessioned2019-08-19T08:04:04Z
dc.date.available2019-08-19T08:04:04Z
dc.date.issued2019-07-16
dc.identifier.citationMorak-Młodawska, B., Pluta, K., Latocha, M., Jeleń, M., Kuśmierz, D., Suwińska, K., … Jurzak, M. (2019). 10H-1,9-diazaphenothiazine and its 10-derivatives: synthesis, characterisation and biological evaluation as potential anticancer agents. Journal of Enzyme Inhibition and Medicinal Chemistry, 34(1), 1298–1306. doi:10.1080/14756366.2019.1639695
dc.identifier.doi10.1080/14756366.2019.1639695
dc.identifier.urihttp://hdl.handle.net/10754/656498
dc.description.abstract10H-1,9-diazaphenothiazine was obtained in the sulphurisation reaction of diphenylamine with elemental sulphur and transformed into new 10-substituted derivatives, containing alkyl and dialkylaminoalkyl groups at the thiazine nitrogen atom. The 1,9-diazaphenothiazine ring system was identified with advanced 1H and 13C NMR techniques (COSY, NOESY, HSQC and HMBC) and confirmed by X-ray diffraction analysis of the methyl derivative. The compounds exhibited significant anticancer activities against the human glioblastoma SNB-19, melanoma C-32 and breast cancer MDA-MB-231 cell lines. The most active 1,9-diazaphenothiazines were the derivatives with the propynyl and N, N-diethylaminoethyl groups being more potent than cisplatin. For those two compounds, the expression of H3, TP53, CDKN1A, BCL-2 and BAX genes was detected by the RT-QPCR method. The proteome profiling study showed the most probable compound action on SNB-19 cells through the intrinsic mitochondrial pathway of apoptosis. The 1,9-diazaphenotiazine system seems to be more potent than known isomeric ones (1,6-diaza-, 1,8-diaza-, 2,7-diaza- and 3,6-diazaphenothiazine).
dc.description.sponsorshipThe work was supported by the Medical University of Silesia [grant KNW-1–072/K/8/O].
dc.publisherInforma UK Limited
dc.relation.urlhttps://www.tandfonline.com/doi/full/10.1080/14756366.2019.1639695
dc.rightsThis is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectPhenothiazines
dc.subjectdipyridothiazines
dc.subjectanticancer activity
dc.subjectgene expressions
dc.subject2D NMR spectra
dc.title10H-1,9-diazaphenothiazine and its 10-derivatives: synthesis, characterisation and biological evaluation as potential anticancer agents
dc.typeArticle
dc.contributor.departmentAdvanced Membranes and Porous Materials Research Center
dc.identifier.journalJournal of Enzyme Inhibition and Medicinal Chemistry
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionDepartment of Organic Chemistry, School of Pharmacy with the Division of Laboratory Medicine, The Medical University of Silesia, Sosnowiec, Poland
dc.contributor.institutionDepartment of Cell Biology, School of Pharmacy with the Division of Laboratory Medicine, The Medical University of Silesia, Sosnowiec, Poland
dc.contributor.institutionFaculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University, Warszawa, Poland
dc.contributor.institutionA. M. Butlerov Institute of Chemistry, Kazan Federal University, Kazan, Russia
dc.contributor.institutionDepartment of Microbiology and Immunology, Medical University of Silesia in Katowice, Zabrze, Poland
kaust.personShkurenko, Aleksander
dc.relation.issupplementedbyDOI:10.6084/m9.figshare.8874593.v1
refterms.dateFOA2019-08-19T08:04:49Z
display.relations<b>Is Supplemented By:</b><br/> <ul><li><i>[Dataset]</i> <br/> Morak-Młodawska, B., Pluta, K., Małgorzata Latocha, Małgorzata Jeleń, Kuśmierz, D., Suwińska, K., Shkurenko, A., Czuba, Z., &amp; Jurzak, M. (2019). 10<i>H</i>-1,9-diazaphenothiazine and its 10-derivatives: synthesis, characterisation and biological evaluation as potential anticancer agents. <i>Taylor &amp; Francis</i>. https://doi.org/10.6084/M9.FIGSHARE.8874593.V1. DOI: <a href="https://doi.org/10.6084/m9.figshare.8874593.v1" >10.6084/m9.figshare.8874593.v1</a> Handle: <a href="http://hdl.handle.net/10754/664763" >10754/664763</a></a></li></ul>
dc.date.published-online2019-07-16
dc.date.published-print2019-01


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This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Except where otherwise noted, this item's license is described as This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.