Annonalide and derivatives: semisynthesis, cytotoxic activities and studies on interaction of annonalide with DNA

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dc.creatorRicardo de Araujo Marques
dc.creatorCláudia Do Ó Pessoa
dc.creatorManoel Odorico de Moraes Filho
dc.creatorÂngelo de Fátima
dc.creatorLucas Lopardi Franco
dc.creatorMarina de Magalhães Silva
dc.creatorMaria Dayanne de Araújo Dantas
dc.creatorJosué Carinhanha Caldas Santos
dc.creatorIsis Martins Figueiredo
dc.creatorEdeildo Ferreira da Silva-Júnior
dc.creatorThiago Mendonça de Aquino
dc.creatorAkenaton Onassis Cardoso Viana Gomes
dc.creatorJoão Xavier de Araújo-Júnior
dc.creatorMaria da Conceição Ferreira de Oliveira
dc.creatorAbeysinghe Aleslie Gunatilaka
dc.creatorMaria Vieira de Brito
dc.creatorAna L. P. dos Santos
dc.creatorGladyane Santos da Silva
dc.creatorLeandro Bezerra de Lima
dc.creatorFátima Miranda Nunes
dc.creatorMarcos Carlos de Mattos
dc.creatorFátima de Cássia Evangelista de Oliveira
dc.date.accessioned2024-09-17T15:03:51Z
dc.date.accessioned2025-09-09T01:25:02Z
dc.date.available2024-09-17T15:03:51Z
dc.date.issued2018
dc.identifier.doihttps://doi.org/10.1016/j.jphotobiol.2018.01.016
dc.identifier.issn1011-1344
dc.identifier.urihttps://hdl.handle.net/1843/76543
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Photochemistry and Photobiology B: Biology
dc.rightsAcesso Restrito
dc.subjectDNA
dc.subjectDiterpenos
dc.subjectAgentes antineoplásicos
dc.subjectCitotoxidade de mediação celular
dc.subjectFuncionais de densidade
dc.subject.otherAnnonalide
dc.subject.otherSemisynthesis
dc.subject.otherCasimirella ampla
dc.subject.otherPimarane diterpene
dc.subject.otherCytotoxic activity
dc.subject.otherDNA interaction
dc.titleAnnonalide and derivatives: semisynthesis, cytotoxic activities and studies on interaction of annonalide with DNA
dc.typeArtigo de periódico
local.citation.epage166
local.citation.spage156
local.citation.volume179
local.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).
local.identifier.orcidhttps://orcid.org/0000-0001-5197-6749
local.identifier.orcidhttps://orcid.org/0000-0001-6515-0577
local.identifier.orcidhttps://orcid.org/0000-0002-4344-4336
local.identifier.orcidhttps://orcid.org/0000-0003-3378-8722
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0002-5196-9845
local.identifier.orcidhttps://orcid.org/0000-0002-1087-4639
local.identifier.orcidhttps://orcid.org/0000-0003-2616-6538
local.identifier.orcidhttps://orcid.org/0000-0002-9525-5123
local.identifier.orcidhttps://orcid.org/0000-0002-1873-5342
local.identifier.orcidhttps://orcid.org/0000-0002-1527-4501
local.identifier.orcidhttps://orcid.org/0000-0001-9138-8466
local.identifier.orcidhttps://orcid.org/0000-0001-6515-0577
local.identifier.orcidhttps://orcid.org/0000-0003-3187-183X
local.identifier.orcidhttps://orcid.org/0000-0002-7445-2347
local.identifier.orcidhttps://orcid.org/0000-0002-3194-3314
local.identifier.orcidhttps://orcid.org/0000-0002-7658-5901
local.identifier.orcidhttps://orcid.org/0000-0003-4291-5199
local.identifier.orcidhttps://orcid.org/0000-0002-4737-5008
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S1011134417313441

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