Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2017 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| DOI: | 10.1111/cbdd.12951 |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/25491 |
Resumo: | FAPESB, Grant/Award Number: PNX 0009/2009 and RED0010/2012. |
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Moreira, Diogo Rodrigo MagalhaesSantos, Dourivaldo SilvaEspírito Santo, Renan Fernandes doSantos, Flávia Evangelista DosOliveira Filho, Gevanio Bezerra deLeite, Ana Cristina LimaSoares, Milena Botelho PereiraVillarreal, Cristiane Flora2018-03-26T14:02:21Z2018-03-26T14:02:21Z2017MOREIRA, D. R. M. et al. Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy. Chemical Biology and Drug Design, v. 90, p. 297–307, 2017.1747-0277https://www.arca.fiocruz.br/handle/icict/2549110.1111/cbdd.12951FAPESB, Grant/Award Number: PNX 0009/2009 and RED0010/2012.Fundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilUniversidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Universidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, BrasilUniversidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, BrasilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrazilUniversidade Federal de Pernambuco. Centro de Ciências da Saúde. Departamento de Ciências Farmacêuticas. Recife, PE, BrazilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Centro de Biotecnologia e Terapia Celular. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Universidade Federal da Bahia. Faculdade de Farmácia. Salvador, BA, BrasilChemotherapy-induced neuropathy is a disabling pain condition resulting from chemotherapy for cancers. Up to now, no drug is available to cure chemotherapy-induced neuropathy. In the present study, we describe the structural design, synthesis, chemical and pharmacological characterization of 15 thiazolidinones, a class of potential analgesic compounds. The synthesis of new thiazolidinones was achieved by using the thiazolidinone heterocyclic as main structural pharmacophoric group and varying the substituents attached to the phenyl near to the iminic bond. The analgesic potential of the compounds was investigated in a mice model of oxaliplatin-induced neuropathic pain, using von Frey, rota-rod and open-field tests. Except for compound 14, these thiazolidinones exhibited antinociceptive property without causing motor impairment. Thiazolidinones 12, 15 and 16 displayed a dose-dependent antinociceptive effect, with similar efficacy and enhanced potency than gabapentin, the gold standard drug used for neuropathic pain. In addition, the antinociceptive activity of 16 lasted longer than gabapentin. The antinociceptive effect of thiazolidinones was prevented by GW9662, a PPARγ antagonist. The main antinociceptive compounds exhibited positive Lipinski's index, predicting their oral bioavailability. In conclusion, the structural design performed here led to the identification of new compounds endowed with potent antinociceptive activity, potentially useful to treat chemotherapy-induced neuropathic pain.engWileyAnalgésicoGlitazonasDor neuropáticaOxaliplatinaPPARAnalgesicGlitazonesNeuropathic painOxaliplatinPPARStructural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathyinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/25491/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALMoreira DRM Structural improvement of new thiazolidinones....pdfMoreira DRM Structural improvement of new 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| dc.title.pt_BR.fl_str_mv |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| title |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| spellingShingle |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy Moreira, Diogo Rodrigo Magalhaes Analgésico Glitazonas Dor neuropática Oxaliplatina PPAR Analgesic Glitazones Neuropathic pain Oxaliplatin PPAR |
| title_short |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| title_full |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| title_fullStr |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| title_full_unstemmed |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| title_sort |
Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy |
| author |
Moreira, Diogo Rodrigo Magalhaes |
| author_facet |
Moreira, Diogo Rodrigo Magalhaes Santos, Dourivaldo Silva Espírito Santo, Renan Fernandes do Santos, Flávia Evangelista Dos Oliveira Filho, Gevanio Bezerra de Leite, Ana Cristina Lima Soares, Milena Botelho Pereira Villarreal, Cristiane Flora |
| author_role |
author |
| author2 |
Santos, Dourivaldo Silva Espírito Santo, Renan Fernandes do Santos, Flávia Evangelista Dos Oliveira Filho, Gevanio Bezerra de Leite, Ana Cristina Lima Soares, Milena Botelho Pereira Villarreal, Cristiane Flora |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Moreira, Diogo Rodrigo Magalhaes Santos, Dourivaldo Silva Espírito Santo, Renan Fernandes do Santos, Flávia Evangelista Dos Oliveira Filho, Gevanio Bezerra de Leite, Ana Cristina Lima Soares, Milena Botelho Pereira Villarreal, Cristiane Flora |
| dc.subject.other.pt_BR.fl_str_mv |
Analgésico Glitazonas Dor neuropática Oxaliplatina PPAR |
| topic |
Analgésico Glitazonas Dor neuropática Oxaliplatina PPAR Analgesic Glitazones Neuropathic pain Oxaliplatin PPAR |
| dc.subject.en.pt_BR.fl_str_mv |
Analgesic Glitazones Neuropathic pain Oxaliplatin PPAR |
| description |
FAPESB, Grant/Award Number: PNX 0009/2009 and RED0010/2012. |
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2017 |
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2017 |
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2018-03-26T14:02:21Z |
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2018-03-26T14:02:21Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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MOREIRA, D. R. M. et al. Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy. Chemical Biology and Drug Design, v. 90, p. 297–307, 2017. |
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https://www.arca.fiocruz.br/handle/icict/25491 |
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1747-0277 |
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10.1111/cbdd.12951 |
| identifier_str_mv |
MOREIRA, D. R. M. et al. Structural improvement of new thiazolidinones compounds with antinociceptive activity in experimental chemotherapy-induced painful neuropathy. Chemical Biology and Drug Design, v. 90, p. 297–307, 2017. 1747-0277 10.1111/cbdd.12951 |
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