Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.

Detalhes bibliográficos
Autor(a) principal: Januário, Jaqueline Pereira
Data de Publicação: 2018
Outros Autores: Souza, Thiago Belarmino de, Lavorato, Stefânia Neiva, Maiolini, Tatiane Cristina Silva, Domingos, Olívia da Silva, Zanin, João Luiz Baldim, Folquitto, Laís Regina dos Santos, Soares, Marisi Gomes, Paula, Daniela Aparecida Chagas de, Dias, Danielle Ferreira, Santos, Marcelo Henrique dos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UFOP
Texto Completo: http://www.repositorio.ufop.br/handle/123456789/11077
Resumo: A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C40 -OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action
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spelling Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.Molecular dockingHydrazinothiazoleTiosemicarbazoneEar edemaStructure activity relationshipA series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C40 -OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action2019-04-22T11:59:10Z2019-04-22T11:59:10Z2018info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfJANUÁRIO, J. P. et al. Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment. Molecules, v. 23, n. 8, p. 1-23, jul. 2018. Disponível em: <https://www.mdpi.com/1420-3049/23/8/1859>. Acesso em: 7 mar. 2019.1420-3049http://www.repositorio.ufop.br/handle/123456789/11077This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/) wich permits copy and redistribute the material in any medium or format provided the original work is properly cited. Fonte: o próprio artigo.info:eu-repo/semantics/openAccessJanuário, Jaqueline PereiraSouza, Thiago Belarmino deLavorato, Stefânia NeivaMaiolini, Tatiane Cristina SilvaDomingos, Olívia da SilvaZanin, João Luiz BaldimFolquitto, Laís Regina dos SantosSoares, Marisi GomesPaula, Daniela Aparecida Chagas deDias, Danielle FerreiraSantos, Marcelo Henrique dosengreponame:Repositório Institucional da UFOPinstname:Universidade Federal de Ouro Preto (UFOP)instacron:UFOP2019-04-22T11:59:10Zoai:repositorio.ufop.br:123456789/11077Repositório InstitucionalPUBhttp://www.repositorio.ufop.br/oai/requestrepositorio@ufop.edu.bropendoar:32332019-04-22T11:59:10Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)false
dc.title.none.fl_str_mv Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
title Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
spellingShingle Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
Januário, Jaqueline Pereira
Molecular docking
Hydrazinothiazole
Tiosemicarbazone
Ear edema
Structure activity relationship
title_short Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
title_full Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
title_fullStr Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
title_full_unstemmed Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
title_sort Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment.
author Januário, Jaqueline Pereira
author_facet Januário, Jaqueline Pereira
Souza, Thiago Belarmino de
Lavorato, Stefânia Neiva
Maiolini, Tatiane Cristina Silva
Domingos, Olívia da Silva
Zanin, João Luiz Baldim
Folquitto, Laís Regina dos Santos
Soares, Marisi Gomes
Paula, Daniela Aparecida Chagas de
Dias, Danielle Ferreira
Santos, Marcelo Henrique dos
author_role author
author2 Souza, Thiago Belarmino de
Lavorato, Stefânia Neiva
Maiolini, Tatiane Cristina Silva
Domingos, Olívia da Silva
Zanin, João Luiz Baldim
Folquitto, Laís Regina dos Santos
Soares, Marisi Gomes
Paula, Daniela Aparecida Chagas de
Dias, Danielle Ferreira
Santos, Marcelo Henrique dos
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Januário, Jaqueline Pereira
Souza, Thiago Belarmino de
Lavorato, Stefânia Neiva
Maiolini, Tatiane Cristina Silva
Domingos, Olívia da Silva
Zanin, João Luiz Baldim
Folquitto, Laís Regina dos Santos
Soares, Marisi Gomes
Paula, Daniela Aparecida Chagas de
Dias, Danielle Ferreira
Santos, Marcelo Henrique dos
dc.subject.por.fl_str_mv Molecular docking
Hydrazinothiazole
Tiosemicarbazone
Ear edema
Structure activity relationship
topic Molecular docking
Hydrazinothiazole
Tiosemicarbazone
Ear edema
Structure activity relationship
description A series of novel benzophenone derivatives containing a thiazole heterocyclic nucleus were designed by molecular hybridization. Molecular docking studies have demonstrated the inhibitory potential of the designed compounds against cyclooxygenase (COX) isoenzymes. These compounds were synthesized, characterized, and evaluated for their anti-inflammatory properties by the croton oil-induced ear edema assay to examine their effect on both prostaglandin (PG) production and neutrophils recruitment. The thiazole derivatives displayed a potent effect in terms of reducing ear edema. The analysis suggested that the presence of 4-phenyl-2-hydrazinothiazole and the absence of C40 -OCH3 on the benzophenone derivative structure are strongly related to the inhibition of PG production. In addition, the derivatives 2e, 3a and 3c concomitantly inhibit PG production and neutrophil recruitment, which may be a mechanism of action better than of common NSAIDs due to their inability to inhibit the neutrophil recruitment. Thus, these compounds can be considered as potential lead compounds toward the development of new anti-inflammatory drugs with an innovating mechanism of action
publishDate 2018
dc.date.none.fl_str_mv 2018
2019-04-22T11:59:10Z
2019-04-22T11:59:10Z
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 JANUÁRIO, J. P. et al. Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment. Molecules, v. 23, n. 8, p. 1-23, jul. 2018. Disponível em: <https://www.mdpi.com/1420-3049/23/8/1859>. Acesso em: 7 mar. 2019.
1420-3049
http://www.repositorio.ufop.br/handle/123456789/11077
identifier_str_mv JANUÁRIO, J. P. et al. Design and synthesis of new benzophenone derivatives with in vivo anti-inflammatory activity through dual inhibition of edema and neutrophil recruitment. Molecules, v. 23, n. 8, p. 1-23, jul. 2018. Disponível em: <https://www.mdpi.com/1420-3049/23/8/1859>. Acesso em: 7 mar. 2019.
1420-3049
url http://www.repositorio.ufop.br/handle/123456789/11077
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFOP
instname:Universidade Federal de Ouro Preto (UFOP)
instacron:UFOP
instname_str Universidade Federal de Ouro Preto (UFOP)
instacron_str UFOP
institution UFOP
reponame_str Repositório Institucional da UFOP
collection Repositório Institucional da UFOP
repository.name.fl_str_mv Repositório Institucional da UFOP - Universidade Federal de Ouro Preto (UFOP)
repository.mail.fl_str_mv repositorio@ufop.edu.br
_version_ 1813002834473385984

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