Natural chromenes and chromene derivatives as potential anti-trypanosomal agents

Detalhes bibliográficos
Autor(a) principal: Batista Jr., João Marcos [UNESP]
Data de Publicação: 2008
Outros Autores: 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]
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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spelling 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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