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Insights into the in vitro antitumor mechanism of action of a new pyranoxanthone

2010Journal article Open access
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dc.contributor.authorPalmeira, Andreia
dc.contributor.authorPaiva, Ana
dc.contributor.authorSousa, Emília
dc.contributor.authorSeca, Hugo
dc.contributor.authorAlmeida, Gabriela M.
dc.contributor.authorLima, Raquel T.
dc.contributor.authorFernandes, Miguel X.
dc.contributor.authorPinto, Madalena
dc.contributor.authorVasconcelos, M. Helena
dc.date.accessioned2023-02-08T11:29:22Z
dc.date.available2023-02-08T11:29:22Z
dc.date.issued2010
dc.description.abstractNaturally occurring xanthones have been docu mented as having antitumor properties, with some of them presently undergoing clinical trials. In an attempt to improve the biological activities of dihydroxyxanthones, prenylation and other mole cular modifications were performed. All the com pounds reduced viable cell number in a leukemia cell line K-562, with the fused xanthone 3, 4-dihydro-12-hydroxy-2,2-dimethyl-2H,6H-pyrano[3, 2-b]xanthen-6-one (5) being the most potent. The pyranoxanthone 5 was particularly effective in additional leukemia cell lines (HL-60 and BV-173). Furthermore, the pyranoxanthone 5 decreased cel lular proliferation and induced an S-phase cell cycle arrest. In vitro, the pyranoxanthone 5 increased the percentage of apoptotic cells which was confirmed by an appropriate response at the protein level (e.g., PARP cleavage). Using a com puter screening strategy based on the structure of several anti- and pro-apoptotic proteins, it was verified that the pyranoxanthone 5 may block the binding of anti-apoptotic Bcl-xL to pro-apoptotic Bad and Bim. The structure-based screening revealed the pyranoxanthone 5 as a new scaffold that may guide the design of small molecules with better affinity profile for Bcl-xL.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationPalmeira, A., Paiva, A., Sousa, E., Seca, H., Almeida, G. M., Lima, R. T., ... & Vasconcelos, M. H. (2010). Insights into the in vitro antitumor mechanism of action of a new pyranoxanthone. Chemical biology & drug design, 76(1), 43-58.pt_PT
dc.identifier.doi10.1111/j.1747-0285.2010.00978.xpt_PT
dc.identifier.urihttp://hdl.handle.net/10400.13/5013
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWileypt_PT
dc.relation.publisherversionhttps://onlinelibrary.wiley.com/doi/full/10.1111/j.1747-0285.2010.00978.xpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectAntiproliferationpt_PT
dc.subjectApoptosispt_PT
dc.subjectBcl-xLpt_PT
dc.subjectLeukemiapt_PT
dc.subjectStructure-based screeningpt_PT
dc.subjectXanthonept_PT
dc.subject.pt_PT
dc.subjectFaculdade de Ciências Exatas e da Engenhariapt_PT
dc.titleInsights into the in vitro antitumor mechanism of action of a new pyranoxanthonept_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage58pt_PT
oaire.citation.issue1pt_PT
oaire.citation.startPage43pt_PT
oaire.citation.titleChemical Biology & Drug Designpt_PT
oaire.citation.volume76pt_PT
person.familyNameFernandes
person.givenNameMiguel Xavier
person.identifier.ciencia-idED1D-3C7A-467C
person.identifier.orcid0000-0002-1840-616X
person.identifier.ridA-4373-2013
person.identifier.scopus-author-id35466972500
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication8dab9a0d-f44a-4d2d-b9b1-7b3145162ca3
relation.isAuthorOfPublication.latestForDiscovery8dab9a0d-f44a-4d2d-b9b1-7b3145162ca3

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