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Please use this identifier to cite or link to this item: http://hdl.handle.net/1843/76543
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dc.creatorRicardo de Araujo Marquespt_BR
dc.creatorCláudia Do Ó Pessoapt_BR
dc.creatorManoel Odorico de Moraes Filhopt_BR
dc.creatorÂngelo de Fátimapt_BR
dc.creatorLucas Lopardi Francopt_BR
dc.creatorMarina de Magalhães Silvapt_BR
dc.creatorMaria Dayanne de Araújo Dantaspt_BR
dc.creatorJosué Carinhanha Caldas Santospt_BR
dc.creatorIsis Martins Figueiredopt_BR
dc.creatorEdeildo Ferreira da Silva-Júniorpt_BR
dc.creatorThiago Mendonça de Aquinopt_BR
dc.creatorAkenaton Onassis Cardoso Viana Gomespt_BR
dc.creatorJoão Xavier de Araújo-Júniorpt_BR
dc.creatorMaria da Conceição Ferreira de Oliveirapt_BR
dc.creatorAbeysinghe Aleslie Gunatilakapt_BR
dc.creatorMaria Vieira de Britopt_BR
dc.creatorAna L. P. dos Santospt_BR
dc.creatorGladyane Santos da Silvapt_BR
dc.creatorLeandro Bezerra de Limapt_BR
dc.creatorFátima Miranda Nunespt_BR
dc.creatorMarcos Carlos de Mattospt_BR
dc.creatorFátima de Cássia Evangelista de Oliveirapt_BR
dc.date.accessioned2024-09-17T15:03:51Z-
dc.date.available2024-09-17T15:03:51Z-
dc.date.issued2018-
dc.citation.volume179pt_BR
dc.citation.spage156pt_BR
dc.citation.epage166pt_BR
dc.identifier.doihttps://doi.org/10.1016/j.jphotobiol.2018.01.016pt_BR
dc.identifier.issn1011-1344pt_BR
dc.identifier.urihttp://hdl.handle.net/1843/76543-
dc.description.resumoThe cytotoxic activity of the pimarane diterpene annonalide (1) and nine of its semisynthetic derivatives (2–10) was investigated against the human tumor cell lines HL-60 (leukemia), PC-3 (prostate adenocarcinoma), HepG2 (hepatocellular carcinoma), SF-295 (glioblastoma) and HCT-116 (colon cancer), and normal mouse fibroblast (L929) cells. The preparation of 2–10 involved derivatization of the side chain of 1 at C-13. Except for 2, all derivatives are being reported for the first time. Most of the tested compounds presented IC50s below 4.0 μM, being considered potential antitumor agents. The structures of all new compounds were elucidated by spectroscopic analyses including 2D NMR and HRMS. Additionally, the interaction of annonalide (1) with ctDNA was evaluated using spectroscopic techniques, and the formation of a supramolecular complex with the macromolecule was confirmed. Competition assays with fluorescent probes (Hoechst and ethidium bromide) and theoretical studies confirmed that 1 interacts preferentially via DNA intercalation with stoichiometric ratio of 1:1 (1:ctDNA). The ΔG value was calculated as −28.24 kJ mol−1, and indicated that the interaction process occurs spontaneously. Docking studies revealed that van der Walls is the most important interaction in 1-DNA and EB-DNA complexes, and that both ligands (1 and EB) interact with the same DNA residues (DA6, DA17 and DT19).pt_BR
dc.languageengpt_BR
dc.publisherUniversidade Federal de Minas Geraispt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentICX - DEPARTAMENTO DE QUÍMICApt_BR
dc.publisher.initialsUFMGpt_BR
dc.relation.ispartofJournal of Photochemistry and Photobiology B: Biologypt_BR
dc.rightsAcesso Restritopt_BR
dc.subjectAnnonalidept_BR
dc.subjectSemisynthesispt_BR
dc.subjectCasimirella amplapt_BR
dc.subjectPimarane diterpenept_BR
dc.subjectCytotoxic activitypt_BR
dc.subjectDNA interactionpt_BR
dc.subject.otherDNApt_BR
dc.subject.otherDiterpenospt_BR
dc.subject.otherAgentes antineoplásicospt_BR
dc.subject.otherCitotoxidade de mediação celularpt_BR
dc.subject.otherFuncionais de densidadept_BR
dc.titleAnnonalide and derivatives: semisynthesis, cytotoxic activities and studies on interaction of annonalide with DNApt_BR
dc.typeArtigo de Periódicopt_BR
dc.url.externahttps://www.sciencedirect.com/science/article/pii/S1011134417313441pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-5197-6749pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-6515-0577pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-4344-4336pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-3378-8722pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-2344-5590pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-5196-9845pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-1087-4639pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-2616-6538pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-9525-5123pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-1873-5342pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-1527-4501pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-9138-8466pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0001-6515-0577pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-3187-183Xpt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-7445-2347pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-3194-3314pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-7658-5901pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0003-4291-5199pt_BR
dc.identifier.orcidhttps://orcid.org/0000-0002-4737-5008pt_BR
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