Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives

Detalhes bibliográficos
Autor(a) principal: Soares, Milena Botelho Pereira
Data de Publicação: 2010
Outros Autores: Costa, José Fernando Oliveira, Sá, Matheus Santos de, Santos, Ricardo Ribeiro dos, Pigeon, Pascal, Jaouen, Gérard, Santana, Antônio Euzébio Goulart, Goulart, Marilia Oliveira Fonseca, Hillard, Elizabeth
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/9025
Resumo: Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil
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spelling Soares, Milena Botelho PereiraCosta, José Fernando OliveiraSá, Matheus Santos deSantos, Ricardo Ribeiro dosPigeon, PascalJaouen, GérardSantana, Antônio Euzébio GoulartGoulart, Marilia Oliveira FonsecaHillard, Elizabeth2014-12-02T12:46:58Z2014-12-02T12:46:58Z2010SOARES, M. B. P. et al. Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives. Drug Development Research, v. 71, p. 69–75, 2010.0272-4391https://www.arca.fiocruz.br/handle/icict/902510.1002/ddr.20349engWiley-Liss, INCAntiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivativesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, BrasilÉcole Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, FranceÉcole Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, FranceInstituto de Química e Biotecnologia. UFAL. Maceió, Al, BrasilInstituto de Química e Biotecnologia. UFAL. Maceió, Al, BrasilÉcole Nationale Supérieure de Chimie de Paris. Laboratoire Charles Friedel. Paris, FranceThe ferrocenyl diphenol 1 [1,1-bis(4-hydroxyphenyl)-2-ferrocenyl-but-1-ene] displays strong cytotoxic effects against a variety of cancer cells. In the present study we have evaluated the immunomodulatory and antiparasitic activities of compound 1 and its protected dipalmitate analogue 2. We have furthermore compared the antiparasitic results of 1 and 2 with the organic analogue, 3 [1,1-bis(4- hydroxyphenyl)-2-phenyl-but-1-ene], where the ferrocenyl group has been replaced by a phenyl ring. When assayed against normal (noncancerous) splenocytes, all compounds were considered nontoxic. Compound 1 inhibited NO production by macrophages, inhibited concanavalin A-induced lymphoproliferation, and was active against Leishmania amazonensis and Trypanosoma cruzi. Compound 2 had lower activity in all assays performed. Surprisingly, compounds 1 and 2 exhibited similar and significant activity against Plasmodium falciparum, with IC50 values of 3.50 and 1.33 mM, respectively. Compound 3 showed an inverse activity profile, being active against T. cruzi but far less active against P. falciparum.FerroceneMalariaBioorganometallic chemistryImmunomodulatoryNitric oxideChagas diseaseinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-81914https://www.arca.fiocruz.br/bitstream/icict/9025/1/license.txt7d48279ffeed55da8dfe2f8e81f3b81fMD51ORIGINALSoares MBP Antiparasitic and....pdfSoares MBP Antiparasitic and....pdfapplication/pdf117652https://www.arca.fiocruz.br/bitstream/icict/9025/2/Soares%20MBP%20Antiparasitic%20and....pdf4a98f792abe5cce85a6ebdd002cba4b1MD52TEXTSoares MBP Antiparasitic and....pdf.txtSoares MBP Antiparasitic and....pdf.txtExtracted texttext/plain32145https://www.arca.fiocruz.br/bitstream/icict/9025/3/Soares%20MBP%20Antiparasitic%20and....pdf.txt8a2ce1aafd3ddf04654ffd0926312a63MD53icict/90252023-03-15 14:32:59.196oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:32:59Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false
dc.title.pt_BR.fl_str_mv Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
title Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
spellingShingle Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
Soares, Milena Botelho Pereira
Ferrocene
Malaria
Bioorganometallic chemistry
Immunomodulatory
Nitric oxide
Chagas disease
title_short Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
title_full Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
title_fullStr Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
title_full_unstemmed Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
title_sort Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives
author Soares, Milena Botelho Pereira
author_facet Soares, Milena Botelho Pereira
Costa, José Fernando Oliveira
Sá, Matheus Santos de
Santos, Ricardo Ribeiro dos
Pigeon, Pascal
Jaouen, Gérard
Santana, Antônio Euzébio Goulart
Goulart, Marilia Oliveira Fonseca
Hillard, Elizabeth
author_role author
author2 Costa, José Fernando Oliveira
Sá, Matheus Santos de
Santos, Ricardo Ribeiro dos
Pigeon, Pascal
Jaouen, Gérard
Santana, Antônio Euzébio Goulart
Goulart, Marilia Oliveira Fonseca
Hillard, Elizabeth
author2_role author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Soares, Milena Botelho Pereira
Costa, José Fernando Oliveira
Sá, Matheus Santos de
Santos, Ricardo Ribeiro dos
Pigeon, Pascal
Jaouen, Gérard
Santana, Antônio Euzébio Goulart
Goulart, Marilia Oliveira Fonseca
Hillard, Elizabeth
dc.subject.en.pt_BR.fl_str_mv Ferrocene
Malaria
Bioorganometallic chemistry
Immunomodulatory
Nitric oxide
Chagas disease
topic Ferrocene
Malaria
Bioorganometallic chemistry
Immunomodulatory
Nitric oxide
Chagas disease
description Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia Salvador, BA, Brasil / Hospital São Rafael. Salvador, BA, Brasil
publishDate 2010
dc.date.issued.fl_str_mv 2010
dc.date.accessioned.fl_str_mv 2014-12-02T12:46:58Z
dc.date.available.fl_str_mv 2014-12-02T12:46:58Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.citation.fl_str_mv SOARES, M. B. P. et al. Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives. Drug Development Research, v. 71, p. 69–75, 2010.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/9025
dc.identifier.issn.none.fl_str_mv 0272-4391
dc.identifier.doi.none.fl_str_mv 10.1002/ddr.20349
identifier_str_mv SOARES, M. B. P. et al. Antiparasitic and immunomodulatory activities of 1,1-bis(4-Hydroxyphenyl)-2-Phenyl-but-1-ene and Its protected and free 2-Ferrocenyl derivatives. Drug Development Research, v. 71, p. 69–75, 2010.
0272-4391
10.1002/ddr.20349
url https://www.arca.fiocruz.br/handle/icict/9025
dc.language.iso.fl_str_mv eng
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dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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