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https://www.arca.fiocruz.br/handle/icict/45838
PRODUCTION OF HIGHLY ACTIVE ANTIPARASITIC COMPOUNDS FROM THE CONTROLLED HALOGENATION OF THE ARRABIDAEA BRACHYPODA CRUDE PLANT EXTRACT
Raizes de plantas
Leishmania amazonensis
Trypanosoma cruzi
Halogenação
Author
Affilliation
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Centro de Ciência Exatas e Tecnologia. Departamento de Química. Laboratório de Produtos Naturais. São Luis, MA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Centro de Ciência Exatas e Tecnologia. Departamento de Química. Laboratório de Produtos Naturais. São Luis, MA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Laboratório de Engenharia Tecidual e Imunofarmacologia. Salvador, BA, Brasil.
University of Geneva. School of Pharmaceutical Sciences and Institute of Pharmaceutical Sciences of Western Switzerland. Geneva, Switzerland .
Abstract
Direct halogenation of phenolic compounds present
in the CH2Cl2 extract of the roots of Arrabidaea brachypoda was
investigated to enhance chemodiversity. The approach is based on
eco-friendly reactions using NaBr, NaI, and NaCl in aqueous
media to generate multiple “unnatural” halogenated natural
products from crude extracts. The halogenation reactions,
monitored by UHPLC-PDA-ELSD-MS, were optimized to
generate mono-, di-, or trihalogenated derivatives. To isolate
these compounds, the reactions were scaled up and the
halogenated analogues were isolated by semipreparative HPLCUV
and fully characterized by NMR and HR-MS data. All of the
original 16 halogenated derivatives were evaluated for their
antiparasitic activities against the parasites Leishmania amazonensis
and Trypanosoma cruzi. Compounds presenting selective antiparasitic activities against one or both parasites with IC50 values
comparable to the reference were identified.
Keywords in Portuguese
AntiparasitáriosRaizes de plantas
Leishmania amazonensis
Trypanosoma cruzi
Halogenação
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