Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2018 |
| Outros Autores: | , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/28466 |
Resumo: | Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil. |
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Oliveira, Luiz Filipe GonçalvesSilva, Franklin SouzaCôrtes, Luzia Monteiro de CastroCysne-Finkelstein, LeaPereira, Mirian Claudia de SouzaOliveira Junior, Francisco Odêncio dePinho, Rosa TeixeiraCorte Real, SuzanaBourguignon, Saulo CabralFerreira, Vitor FranciscoAlves, Carlos Roberto2018-08-30T13:20:18Z2018-08-30T13:20:18Z2018OLIVEIRA, Luiz Felipe Gonçalves; et al. Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,20-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment. Molecules, v.23, n.864,12p, 2018.1420-3049https://www.arca.fiocruz.br/handle/icict/2846610.3390/molecules230408641420-3049engMDPIatividade antileishmanialantimoniato de megluminaLeishamanioseTratamentoantileishmanial activityoxiranesnaphthoquinonesepoxymethoxy-lawsonemeglumine antimoniateCompostos de EpóxiNaftoquinonasAntileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatmentinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleFundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunoparasitologia. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Ultraestrutura Celular. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Ultraestrutura Celular. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Imunologia Clínica. Rio de Janeiro, RJ. Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Estrutural. Rio de Janeiro, RJ. Brasil.Universidade Federal Fluminense. Instituto de Biologia. Departamento de Biologia Celular e Molecular. Laboratório de Interação Celular e Molecular. Niterói, RJ, Brasil.Universidade Federal Fluminense. Faculdade de Farmácia. Departamento de Tecnologia Farmacêutica. Niterói, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil.Epoxymethoxylawsone is a naphthoquinone derivative promising as drug candidate for the treatment of leishmaniases. In the present work the effectiveness of epoxymethoxylawsone, and meglumine antimoniate on Leishmania (Leishmania) amazonensis parasites and on mice paw lesions of infected BALB/c mice was assessed. In an intracellular amastigotes assay, the half-maximal inhibitory concentration (IC50) value for epoxymethoxylawsone was slightly higher (1.7-fold) than that found for meglumine antimoniate. The efficacy of both drugs became more evident after 48 h of exposure when either the oxirane compound and reference drug reached 18-fold and 7.4-fold lower IC50 values (0.40 ± 0.001 µM and 0.60 ± 0.02 µM), respectively. Promastigotes were also affected by epoxymethoxylawsone after 24 h of incubation (IC50 = 45.45 ± 5.0 µM), but with IC50 6-fold higher than those found for intracellular amastigotes. Cytotoxicity analysis revealed that epoxymethoxylawsone (CC50 = 40.05 ± µM) has 1.7-fold higher effects than meglumine antimoniate (CC50 = 24.14 ± 2.6 µM). Treatment of the paw lesion in infected BALB/c mice with epoxymethoxy-lawsone led to a significant 27% reduction (p < 0.05) of the lesion size, for all administrated doses, compared to the control group. Lesion reduction was also detected after mice treatment with meglumine antimoniate, reaching 31.0% (0.23 mg of Sb(V)/Kg/day and 2.27 mg of Sb(V)/Kg/day) and 64.0% (22.7 mg of Sb(V)/Kg/day). In addition, mice lesion ultrastructural changes were evidenced in amastigotes. The set of data gathered here indicate that epoxymethoxylawsone has pronounced effects on parasites and merits furthering to the preclinical stage.info:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/28466/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALluizfelipe_oliveira_etal_IOC_2018.pdfluizfelipe_oliveira_etal_IOC_2018.pdfapplication/pdf26096608https://www.arca.fiocruz.br/bitstream/icict/28466/2/luizfelipe_oliveira_etal_IOC_2018.pdf250a755524c784e4db88bc2cf40e49d1MD52TEXTluizfelipe_oliveira_etal_IOC_2018.pdf.txtluizfelipe_oliveira_etal_IOC_2018.pdf.txtExtracted texttext/plain40066https://www.arca.fiocruz.br/bitstream/icict/28466/3/luizfelipe_oliveira_etal_IOC_2018.pdf.txt030505fd384d07b0e9b91aad51220883MD53icict/284662022-06-24 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| dc.title.pt_BR.fl_str_mv |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| title |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| spellingShingle |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment Oliveira, Luiz Filipe Gonçalves atividade antileishmanial antimoniato de meglumina Leishamaniose Tratamento antileishmanial activity oxiranes naphthoquinones epoxymethoxy-lawsone meglumine antimoniate Compostos de Epóxi Naftoquinonas |
| title_short |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| title_full |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| title_fullStr |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| title_full_unstemmed |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| title_sort |
Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,2'-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment |
| author |
Oliveira, Luiz Filipe Gonçalves |
| author_facet |
Oliveira, Luiz Filipe Gonçalves Silva, Franklin Souza Côrtes, Luzia Monteiro de Castro Cysne-Finkelstein, Lea Pereira, Mirian Claudia de Souza Oliveira Junior, Francisco Odêncio de Pinho, Rosa Teixeira Corte Real, Suzana Bourguignon, Saulo Cabral Ferreira, Vitor Francisco Alves, Carlos Roberto |
| author_role |
author |
| author2 |
Silva, Franklin Souza Côrtes, Luzia Monteiro de Castro Cysne-Finkelstein, Lea Pereira, Mirian Claudia de Souza Oliveira Junior, Francisco Odêncio de Pinho, Rosa Teixeira Corte Real, Suzana Bourguignon, Saulo Cabral Ferreira, Vitor Francisco Alves, Carlos Roberto |
| author2_role |
author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Oliveira, Luiz Filipe Gonçalves Silva, Franklin Souza Côrtes, Luzia Monteiro de Castro Cysne-Finkelstein, Lea Pereira, Mirian Claudia de Souza Oliveira Junior, Francisco Odêncio de Pinho, Rosa Teixeira Corte Real, Suzana Bourguignon, Saulo Cabral Ferreira, Vitor Francisco Alves, Carlos Roberto |
| dc.subject.other.pt_BR.fl_str_mv |
atividade antileishmanial antimoniato de meglumina Leishamaniose Tratamento |
| topic |
atividade antileishmanial antimoniato de meglumina Leishamaniose Tratamento antileishmanial activity oxiranes naphthoquinones epoxymethoxy-lawsone meglumine antimoniate Compostos de Epóxi Naftoquinonas |
| dc.subject.en.pt_BR.fl_str_mv |
antileishmanial activity oxiranes naphthoquinones epoxymethoxy-lawsone meglumine antimoniate |
| dc.subject.decs.pt_BR.fl_str_mv |
Compostos de Epóxi Naftoquinonas |
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Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Biologia Molecular e Doenças Endêmicas. Rio de Janeiro, RJ. Brasil. |
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2018 |
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2018-08-30T13:20:18Z |
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2018-08-30T13:20:18Z |
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2018 |
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OLIVEIRA, Luiz Felipe Gonçalves; et al. Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,20-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment. Molecules, v.23, n.864,12p, 2018. |
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https://www.arca.fiocruz.br/handle/icict/28466 |
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1420-3049 |
| dc.identifier.doi.none.fl_str_mv |
10.3390/molecules23040864 |
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1420-3049 |
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OLIVEIRA, Luiz Felipe Gonçalves; et al. Antileishmanial Activity of 2-Methoxy-4H-spiro-[naphthalene-1,20-oxiran]-4-one (Epoxymethoxy-lawsone): A Promising New Drug Candidate for Leishmaniasis Treatment. Molecules, v.23, n.864,12p, 2018. 1420-3049 10.3390/molecules23040864 |
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