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dc.contributor.author
de Brito, Maria R.M.  
dc.contributor.author
Peláez, Walter José  
dc.contributor.author
Faillace, Martín Sebastián  
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Militão, Gardenia C.G.  
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Almeida, Jackson R.G.S.  
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Argüello, Gustavo Alejandro  
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Szakonyi, Zsolt  
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Fülöp, Ferenc  
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Salvadori, Maria C.  
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Teixeira, Fernanda S.  
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Freitas, Rivelilson M.  
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Pinto, Pedro L.S.  
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Mengarda, Ana C.  
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Silva, Marcos P.N.  
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Da Silva Filho, Ademar A.  
dc.contributor.author
de Moraes, Josué  
dc.date.available
2018-11-13T17:48:24Z  
dc.date.issued
2017-10  
dc.identifier.citation
de Brito, Maria R.M.; Peláez, Walter José; Faillace, Martín Sebastián; Militão, Gardenia C.G.; Almeida, Jackson R.G.S.; et al.; Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects; Pergamon-Elsevier Science Ltd; Toxicology in Vitro; 44; 10-2017; 273-279  
dc.identifier.issn
0887-2333  
dc.identifier.uri
http://hdl.handle.net/11336/64335  
dc.description.abstract
Oxazine derivatives, a class of heterocyclic compounds, exhibit a variety of biological properties, such as anticonvulsant and antitumor activities. In this study, we evaluated the effect of two cyclohexene-fused 1,3-oxazines (cis‑1-benzyl-N-phenyl-1,4,4a,5,8,8a-hexahydro-3,1-benzoxazin-2-imine (1) and trans‑N-phenyl-1,4,4a,5,8,8a-hexahydro-3,1-benzoxazin-2-imine (2)) in cultures of Bacillus cereus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, Salmonella enterica, Serratia marcescens, Shigella flexneri and Staphylococcus aureus by the Minimum Inhibitory Concentration (MIC) and Minimum Bactericidal Concentration (MBC). Additionally, the ex vivo antiparasitic activity of oxazines was assessed against Schistosoma mansoni, a helminth that is one of the major agents of the disease schistosomiasis Also, oxazines were evaluated on three tumor cell lines, NCI-H292 (human lung carcinoma), MCF-7 (human breast adenocarcinoma) and HEp-2 (human cervix carcinoma), and two normal cell lines (Vero and red blood cells). Bioassays revealed that oxazine 2 is more effective against bacteria than oxazine 1, with the lowest MIC and MBC values of 3.91 and 32.5 μg/mL, respectively. Similarly, compound 2 demonstrated higher antiparasitic activity than 1, and scanning electron microscopy analysis showed several morphological alterations in the tegument of worms in a concentration-dependent manner. In contrast, both oxazines exhibited low cytotoxic effects on cancer and normal cell lines. These results indicated that oxazines exerted direct effects on bacteria and parasite schistosomes. More importantly, since schistosomiasis control programs rely on one drug, praziquantel, oxazines may have the potential to become new antischistosomal agents.  
dc.format
application/pdf  
dc.language.iso
eng  
dc.publisher
Pergamon-Elsevier Science Ltd  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
Anthelmintic Activity  
dc.subject
Antimicrobial Activity  
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Cyclohexene-Fused 1,3-Oxazines  
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Schistosoma Mansoni  
dc.subject.classification
Otras Ciencias Químicas  
dc.subject.classification
Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2018-10-22T18:21:41Z  
dc.journal.volume
44  
dc.journal.pagination
273-279  
dc.journal.pais
Países Bajos  
dc.journal.ciudad
Amsterdam  
dc.description.fil
Fil: de Brito, Maria R.M.. Federal University of Piauí; Brasil  
dc.description.fil
Fil: Peláez, Walter José. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina  
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Fil: Faillace, Martín Sebastián. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina  
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Fil: Militão, Gardenia C.G.. Federal University of Pernambuco; Brasil  
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Fil: Almeida, Jackson R.G.S.. Federal University Of San Francisco Valley; Brasil  
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Fil: Argüello, Gustavo Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto de Investigaciones en Físico-química de Córdoba. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Instituto de Investigaciones en Físico-química de Córdoba; Argentina  
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Fil: Szakonyi, Zsolt. University of Szeged; Hungría  
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Fil: Fülöp, Ferenc. University of Szeged; Hungría  
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Fil: Salvadori, Maria C.. Universidade de Sao Paulo; Brasil  
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Fil: Teixeira, Fernanda S.. Universidade de Sao Paulo; Brasil  
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Fil: Freitas, Rivelilson M.. Federal University of Piauí; Brasil  
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Fil: Pinto, Pedro L.S.. Instituto Adolfo Lutz; Brasil  
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Fil: Mengarda, Ana C.. Universidade Guarulhos; Brasil  
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Fil: Silva, Marcos P.N.. Universidade Guarulhos; Brasil  
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Fil: Da Silva Filho, Ademar A.. Universidade Federal de Juiz de Fora; Brasil  
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Fil: de Moraes, Josué. Universidade Guarulhos; Brasil  
dc.journal.title
Toxicology in Vitro  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/http://linkinghub.elsevier.com/retrieve/pii/S0887233317302072  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/https://doi.org/10.1016/j.tiv.2017.07.021