3-Hydroxy-2-methylene-3-(4-nitrophenylpropanenitrile): A new highly active compound against epimastigote and trypomastigote form of Trypanosoma cruzi

dc.creatorSandes, Jana M.
dc.creatorBorges, Andrezza R.
dc.creatorJunior, Cláudio G. L.
dc.creatorSilva, Fábio P. L.
dc.creatorCarvalho, Gabriel A. U.
dc.creatorRocha, Gerd B.
dc.creatorVasconcellos, Mário L. A. A.
dc.creatorFigueiredo, Regina C. B. Q.
dc.date2018-04-27T13:11:09Z
dc.date2018-04-27T13:11:09Z
dc.date2010
dc.date.accessioned2023-09-26T22:21:01Z
dc.date.available2023-09-26T22:21:01Z
dc.identifierSANDES, J. M. et al. 3-Hydroxy-2-methylene-3-(4-nitrophenylpropanenitrile): A new highly active compound against epimastigote and trypomastigote form of Trypanosoma cruzi. Bioorganic Chemistry, v. 38, n. 5, p. 190–195, out. 2010.
dc.identifier1090-2120
dc.identifierhttps://www.arca.fiocruz.br/handle/icict/26169
dc.identifier10.1016/j.bioorg.2010.06.003
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8878194
dc.descriptionEste trabalho contou com o apoio do CNPq, CAPES, FAPESQ-PB, FIOCRUZ.
dc.descriptionWe have synthesized the Morita-Baylis-Hillman adduct (MBHA) 3-hydroxy-2-methylene-3-(4-nitrophenyl)-propanenitrile (3) in quantitative yield and evaluated on Trypanosoma cruzi epimastigote and bloodstream trypomastigote forms. Compound 3 strongly inhibited epimastigote growth, with IC(50)/72hof 28.5 microM and also caused intense trypomastigotes lysis, with an IC(50)/24h of 25.5 microM. Ultrastructural analysis showed significant morphological changes on both parasite forms treated with 3, including increase of cell volume and rounding of cell body as well as intense intracellular disorganization. Morphological changes indicative of apoptosis, autophagy or necrosis were observed in most affected cells. Docking calculations of 1, 2 and 3 pointed out the possibility of T. cruzi Farnesyl Pyrophosphate Synthase (TcFPPS) enzyme inhibition in 3 mechanism of action.
dc.description2050-01-01
dc.formatapplication/pdf
dc.languageeng
dc.publisherElsevier
dc.rightsrestricted access
dc.subjectAdutos de Morita-Baylis-Hillman
dc.subjectAtividade de Anti- Trypanosoma cruzi
dc.subjectMorita–Baylis–Hillman adducts
dc.subjectAnti-Trypanosoma cruzi activity
dc.subjectAcrilonitrila / análogos e derivados
dc.subjectAcrilonitrila / síntese química
dc.subjectAcrilonitrila / farmacologia
dc.subjectÁlcoois benzílicos / síntese química
dc.subjectÁlcoois benzílicos / farmacologia
dc.subjectDoença de Chagas / quimioterapia
dc.subjectHumanos
dc.subjectConcentração Inibidora 50
dc.subjectModelos, Molecular
dc.subjectAgentes Tripanocidas / síntese química
dc.subjectTripanocidas Agentes / Farmacologia
dc.subjectTrypanosoma cruzi / efeitos de drogas
dc.subjectTrypanosoma cruzi / crescimento & desenvolvimento
dc.title3-Hydroxy-2-methylene-3-(4-nitrophenylpropanenitrile): A new highly active compound against epimastigote and trypomastigote form of Trypanosoma cruzi
dc.typeArticle


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