Please use this identifier to cite or link to this item: https://www.arca.fiocruz.br/handle/icict/11532
Title: Antileishmanial activity of amides from Piper amalago and synthetic analogs
Authors: 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
Affilliation: Universidade 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.
Abstract: 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.
Keywords: Amides
Antileishmanial activity
Piper amalago
Synthetic analogs
DeCS: Amidas
Compostos Orgânicos
Leishmania amazonensis
Issue Date: 2013
Publisher: Universidade Federal do Paraná, Laboratório de Farmacognosia
Citation: 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.
DOI: 10.1590/S0102-695X2013005000022
ISSN: 0102-695X
Copyright: open access
Appears in Collections:IOC - Artigos de Periódicos

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