Natural chromenes and chromene derivatives as potential anti-trypanosomal agents
Autor(a) principal: | |
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Data de Publicação: | 2008 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1248/bpb.31.538 http://hdl.handle.net/11449/70323 |
Resumo: | The aim of the study was to investigate the anti-trypanocidal activities of natural chromene and chromene derivatives. Five chromenes were isolated from Piper gaudichaudianum and P. aduncum, and a further seven derivatives were prepared using standard reduction, methylation and acetylation procedures. These compounds were assayed in vitro against epimastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. The results showed that the most of the compounds, especially those possessing electron-donating groups as substituents on the aromatic ring, showed potent trypanocidal activity. The most active compound, [(2S)-methyl-2-methyl-8-(3″-methylbut-2″-enyl)-2- (4′-methylpent-3′-enyl)-2H-chromene-6-carboxylate], was almost four times more potent than benznidazole (the positive control) and showed an IC 50 of 2.82 μM. The results reveal that chromenes exhibit significant anti-trypanocidal activities and indicate that this class of natural product should be considered further in the development of new and more potent drugs for use in the treatment of Chagas disease. © 2008 Pharmaceutical Society of Japan. |
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Natural chromenes and chromene derivatives as potential anti-trypanosomal agentsChromenePiper aduncumPiper gaudichaudianumPiperaceaeTrypanosoma cruziantitrypanosomal agentbenznidazolechromene derivativemethyl 2 methyl 8 (3'' methylbut 2'' enyl) 2 (4' methylpent 3' enyl)2h chromene 6 carboxylic acidunclassified drugacetylationChagas diseasecontrolled studydrug activitydrug isolationdrug potencyelectronIC 50in vitro studymethylationnonhumanAnimalsBenzopyransParasitic Sensitivity TestsPiperStructure-Activity RelationshipTrypanocidal AgentsThe aim of the study was to investigate the anti-trypanocidal activities of natural chromene and chromene derivatives. Five chromenes were isolated from Piper gaudichaudianum and P. aduncum, and a further seven derivatives were prepared using standard reduction, methylation and acetylation procedures. These compounds were assayed in vitro against epimastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. The results showed that the most of the compounds, especially those possessing electron-donating groups as substituents on the aromatic ring, showed potent trypanocidal activity. The most active compound, [(2S)-methyl-2-methyl-8-(3″-methylbut-2″-enyl)-2- (4′-methylpent-3′-enyl)-2H-chromene-6-carboxylate], was almost four times more potent than benznidazole (the positive control) and showed an IC 50 of 2.82 μM. The results reveal that chromenes exhibit significant anti-trypanocidal activities and indicate that this class of natural product should be considered further in the development of new and more potent drugs for use in the treatment of Chagas disease. © 2008 Pharmaceutical Society of Japan.Instituto de Química Universidade Estadual Paulista (UNESP), Prof. Francisco Degni, 14801-970, Araraquara, SPFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP), Rodovia Araraquara/Jaú Km 1, 14801-902, Araraquara, SPInstituto de Química Universidade de São Paulo, Av. Prof. Lineu Prestes 748, 05508-900, São Paulo, SPInstituto de Química Universidade Estadual Paulista (UNESP), Prof. Francisco Degni, 14801-970, Araraquara, SPFaculdade de Ciências Farmacêuticas Universidade Estadual Paulista (UNESP), Rodovia Araraquara/Jaú Km 1, 14801-902, Araraquara, SPUniversidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Batista Jr., João Marcos [UNESP]Lopes, Adriana Aparecida [UNESP]Ambrósio, Daniela Luz [UNESP]Regasini, Luis Octávio [UNESP]Kato, Massuo JorgeBolzani, Vanderlan da Silva [UNESP]Cicarelli, Regina Maria Barreto [UNESP]Furlan, Maysa [UNESP]2014-05-27T11:22:49Z2014-05-27T11:22:49Z2008-03-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article538-540http://dx.doi.org/10.1248/bpb.31.538Biological and Pharmaceutical Bulletin, v. 31, n. 3, p. 538-540, 2008.0918-61581347-5215http://hdl.handle.net/11449/7032310.1248/bpb.31.5382-s2.0-41149159074448408368525167313080427947868720992736452764550Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengBiological and Pharmaceutical Bulletin1.6940,6260,626info:eu-repo/semantics/openAccess2024-06-24T13:06:52Zoai:repositorio.unesp.br:11449/70323Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T14:21:15.710023Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
title |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
spellingShingle |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents Batista Jr., João Marcos [UNESP] Chromene Piper aduncum Piper gaudichaudianum Piperaceae Trypanosoma cruzi antitrypanosomal agent benznidazole chromene derivative methyl 2 methyl 8 (3'' methylbut 2'' enyl) 2 (4' methylpent 3' enyl)2h chromene 6 carboxylic acid unclassified drug acetylation Chagas disease controlled study drug activity drug isolation drug potency electron IC 50 in vitro study methylation nonhuman Animals Benzopyrans Parasitic Sensitivity Tests Piper Structure-Activity Relationship Trypanocidal Agents |
title_short |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
title_full |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
title_fullStr |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
title_full_unstemmed |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
title_sort |
Natural chromenes and chromene derivatives as potential anti-trypanosomal agents |
author |
Batista Jr., João Marcos [UNESP] |
author_facet |
Batista Jr., João Marcos [UNESP] Lopes, Adriana Aparecida [UNESP] Ambrósio, Daniela Luz [UNESP] Regasini, Luis Octávio [UNESP] Kato, Massuo Jorge Bolzani, Vanderlan da Silva [UNESP] Cicarelli, Regina Maria Barreto [UNESP] Furlan, Maysa [UNESP] |
author_role |
author |
author2 |
Lopes, Adriana Aparecida [UNESP] Ambrósio, Daniela Luz [UNESP] Regasini, Luis Octávio [UNESP] Kato, Massuo Jorge Bolzani, Vanderlan da Silva [UNESP] Cicarelli, Regina Maria Barreto [UNESP] Furlan, Maysa [UNESP] |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) Universidade de São Paulo (USP) |
dc.contributor.author.fl_str_mv |
Batista Jr., João Marcos [UNESP] Lopes, Adriana Aparecida [UNESP] Ambrósio, Daniela Luz [UNESP] Regasini, Luis Octávio [UNESP] Kato, Massuo Jorge Bolzani, Vanderlan da Silva [UNESP] Cicarelli, Regina Maria Barreto [UNESP] Furlan, Maysa [UNESP] |
dc.subject.por.fl_str_mv |
Chromene Piper aduncum Piper gaudichaudianum Piperaceae Trypanosoma cruzi antitrypanosomal agent benznidazole chromene derivative methyl 2 methyl 8 (3'' methylbut 2'' enyl) 2 (4' methylpent 3' enyl)2h chromene 6 carboxylic acid unclassified drug acetylation Chagas disease controlled study drug activity drug isolation drug potency electron IC 50 in vitro study methylation nonhuman Animals Benzopyrans Parasitic Sensitivity Tests Piper Structure-Activity Relationship Trypanocidal Agents |
topic |
Chromene Piper aduncum Piper gaudichaudianum Piperaceae Trypanosoma cruzi antitrypanosomal agent benznidazole chromene derivative methyl 2 methyl 8 (3'' methylbut 2'' enyl) 2 (4' methylpent 3' enyl)2h chromene 6 carboxylic acid unclassified drug acetylation Chagas disease controlled study drug activity drug isolation drug potency electron IC 50 in vitro study methylation nonhuman Animals Benzopyrans Parasitic Sensitivity Tests Piper Structure-Activity Relationship Trypanocidal Agents |
description |
The aim of the study was to investigate the anti-trypanocidal activities of natural chromene and chromene derivatives. Five chromenes were isolated from Piper gaudichaudianum and P. aduncum, and a further seven derivatives were prepared using standard reduction, methylation and acetylation procedures. These compounds were assayed in vitro against epimastigote forms of Trypanosoma cruzi, the causative agent of Chagas disease. The results showed that the most of the compounds, especially those possessing electron-donating groups as substituents on the aromatic ring, showed potent trypanocidal activity. The most active compound, [(2S)-methyl-2-methyl-8-(3″-methylbut-2″-enyl)-2- (4′-methylpent-3′-enyl)-2H-chromene-6-carboxylate], was almost four times more potent than benznidazole (the positive control) and showed an IC 50 of 2.82 μM. The results reveal that chromenes exhibit significant anti-trypanocidal activities and indicate that this class of natural product should be considered further in the development of new and more potent drugs for use in the treatment of Chagas disease. © 2008 Pharmaceutical Society of Japan. |
publishDate |
2008 |
dc.date.none.fl_str_mv |
2008-03-01 2014-05-27T11:22:49Z 2014-05-27T11:22:49Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1248/bpb.31.538 Biological and Pharmaceutical Bulletin, v. 31, n. 3, p. 538-540, 2008. 0918-6158 1347-5215 http://hdl.handle.net/11449/70323 10.1248/bpb.31.538 2-s2.0-41149159074 4484083685251673 1308042794786872 0992736452764550 |
url |
http://dx.doi.org/10.1248/bpb.31.538 http://hdl.handle.net/11449/70323 |
identifier_str_mv |
Biological and Pharmaceutical Bulletin, v. 31, n. 3, p. 538-540, 2008. 0918-6158 1347-5215 10.1248/bpb.31.538 2-s2.0-41149159074 4484083685251673 1308042794786872 0992736452764550 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Biological and Pharmaceutical Bulletin 1.694 0,626 0,626 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
538-540 |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
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_version_ |
1808128350799003648 |