Antileishmanial activity of amides from Piper amalago and synthetic analogs
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2013 |
| 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/11532 |
Resumo: | Universidade Estadual de Maringá. Departamento de Farmácia. Maringá, PR, Brasil. |
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Carrara, Vanessa da SilvaCunha Júnior, Edézio FerreiraSantos, Eduardo Caio TorresCorrêa, Arlene GonçalvesMonteiro, Júlia L.Demarchi, Izabel GalhardoLonardoni, Maria Valdinez CampanaCortez, Diógenes Aparício Garcia2015-08-19T13:49:28Z2015-08-19T13:49:28Z2013CARRARA, Vanessa da Silva; Antileishmanial activity of amides from Piper 23(3): 447-454, May/Jun. 2013 amalago and synthetic analogs. Revista Brasileira de Farmacognosia, v.23, n.3, p.447-454, maio/jun. 2013.0102-695Xhttps://www.arca.fiocruz.br/handle/icict/1153210.1590/S0102-695X2013005000022engUniversidade Federal do Paraná, Laboratório de FarmacognosiaAntileishmanial activity of amides from Piper amalago and synthetic analogsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Estadual de Maringá. Departamento de Farmácia. Maringá, PR, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Bioquímica de Tripanossomatídeos. Rio de Janeiro, RJ, Brasil.Fundação Oswaldo Cruz. Instituto Oswaldo Cruz. Laboratório de Bioquímica de Tripanossomatídeos. Rio de Janeiro, RJ, Brasil.Universidade Federal de São Carlos. Departamento de Química. São Carlos, SP, Brasil.Universidade Federal de São Carlos. Departamento de Química. São Carlos, SP, Brasil.Universidade Estadual de Maringá. Departamento de Análises Clínicas. Maringá, PR, Brasil.Universidade Estadual de Maringá. Departamento de Análises Clínicas. Maringá, PR, Brasil.Universidade Estadual de Maringá. Departamento de Farmácia. Maringá, PR, Brasil.Two natural amides isolated from the chloroform extract of Piper amalago L., Piperaceae, leaves, a hydrogenated derivative and seven synthetic analogs were tested against the promastigote and intracellular amastigote forms of Leishmania amazonensis. The antileishmanial activity was evaluated in terms of growth inhibitory concentration for 50% of protozoa (IC50). The cytotoxicity toward the J774A1 macrophages was evaluated in terms of the cytotoxic concentrations for 50% of macrophages (CC50). The ability to induce nitric oxide production was also investigated for all compounds. The saturated amide 7-(1,3-benzodioxol-5-yl)-1-(1-pyrrolidinyl)- 1-heptanone was obtained by hydrogenation of the natural compound N-[7-(3’,4’- methylenedioxyphenyl)-2(Z),4(Z)-heptadienoyl]pyrrolidine. Synthetic amides were prepared by addition of the appropriate amine to the corresponding acyl chloride. The natural compound, N-[7-(3’,4’-methylenedioxyphenyl)-2(E),4(E)-heptadienoyl] pyrrolidine, was the most active of all tested compounds against the promastigote and intracellular amastigote forms with IC50 values of 15 μM and 14.5 μM, respectively. None of the compounds modulated the production of nitric oxide.AmidesAntileishmanial activityPiper amalagoSynthetic analogsAmidasCompostos OrgânicosLeishmania amazonensisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txttext/plain1914https://www.arca.fiocruz.br/bitstream/icict/11532/1/license.txt7d48279ffeed55da8dfe2f8e81f3b81fMD51ORIGINALedesio_cunhajr_etal_IOC_2103.pdfapplication/pdf741888https://www.arca.fiocruz.br/bitstream/icict/11532/2/edesio_cunhajr_etal_IOC_2103.pdfde13dfba4adc71601959b53ed0b7df86MD52TEXTedesio_cunhajr_etal_IOC_2103.pdf.txtedesio_cunhajr_etal_IOC_2103.pdf.txtExtracted texttext/plain36841https://www.arca.fiocruz.br/bitstream/icict/11532/3/edesio_cunhajr_etal_IOC_2103.pdf.txte0f65a1c10431348e4eaa16c0bb49158MD53icict/115322022-06-24 12:17:44.662oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352022-06-24T15:17:44Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.pt_BR.fl_str_mv |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| title |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| spellingShingle |
Antileishmanial activity of amides from Piper amalago and synthetic analogs Carrara, Vanessa da Silva Amides Antileishmanial activity Piper amalago Synthetic analogs Amidas Compostos Orgânicos Leishmania amazonensis |
| title_short |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| title_full |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| title_fullStr |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| title_full_unstemmed |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| title_sort |
Antileishmanial activity of amides from Piper amalago and synthetic analogs |
| author |
Carrara, Vanessa da Silva |
| author_facet |
Carrara, Vanessa da Silva Cunha Júnior, Edézio Ferreira Santos, Eduardo Caio Torres Corrêa, Arlene Gonçalves Monteiro, Júlia L. Demarchi, Izabel Galhardo Lonardoni, Maria Valdinez Campana Cortez, Diógenes Aparício Garcia |
| author_role |
author |
| author2 |
Cunha Júnior, Edézio Ferreira Santos, Eduardo Caio Torres Corrêa, Arlene Gonçalves Monteiro, Júlia L. Demarchi, Izabel Galhardo Lonardoni, Maria Valdinez Campana Cortez, Diógenes Aparício Garcia |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Carrara, Vanessa da Silva Cunha Júnior, Edézio Ferreira Santos, Eduardo Caio Torres Corrêa, Arlene Gonçalves Monteiro, Júlia L. Demarchi, Izabel Galhardo Lonardoni, Maria Valdinez Campana Cortez, Diógenes Aparício Garcia |
| dc.subject.en.pt_BR.fl_str_mv |
Amides Antileishmanial activity Piper amalago Synthetic analogs |
| topic |
Amides Antileishmanial activity Piper amalago Synthetic analogs Amidas Compostos Orgânicos Leishmania amazonensis |
| dc.subject.decs.pt_BR.fl_str_mv |
Amidas Compostos Orgânicos Leishmania amazonensis |
| description |
Universidade Estadual de Maringá. Departamento de Farmácia. Maringá, PR, Brasil. |
| publishDate |
2013 |
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2013 |
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2015-08-19T13:49:28Z |
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2015-08-19T13:49:28Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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CARRARA, Vanessa da Silva; Antileishmanial activity of amides from Piper 23(3): 447-454, May/Jun. 2013 amalago and synthetic analogs. Revista Brasileira de Farmacognosia, v.23, n.3, p.447-454, maio/jun. 2013. |
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https://www.arca.fiocruz.br/handle/icict/11532 |
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0102-695X |
| dc.identifier.doi.pt_BR.fl_str_mv |
10.1590/S0102-695X2013005000022 |
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CARRARA, Vanessa da Silva; Antileishmanial activity of amides from Piper 23(3): 447-454, May/Jun. 2013 amalago and synthetic analogs. Revista Brasileira de Farmacognosia, v.23, n.3, p.447-454, maio/jun. 2013. 0102-695X 10.1590/S0102-695X2013005000022 |
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Universidade Federal do Paraná, Laboratório de Farmacognosia |
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Universidade Federal do Paraná, Laboratório de Farmacognosia |
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