Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | por |
| Título da fonte: | Research, Society and Development |
| Texto Completo: | https://rsdjournal.org/index.php/rsd/article/view/23600 |
Resumo: | The interest in obtaining chalcones is due to the numerous pharmacological activities described in the literature for these compounds that are intermediates in the biosynthesis of flavonoids. Thus, the synthesis and characterization of several chalcones and derivatives become important for the development of compounds with antiproliferative activity. In this work, ten substances were synthesized, seven chalcones and three naphthoflavanones, obtained by the Claisen Schmidt aldol condensation reaction between acetophenones and aldehydes, at room temperature conditions in a basic medium. Yields ranged between 65.35% and 97.45%. Being characterized and confirmed through ¹H and ¹³C NMR spectroscopic techniques in comparison with literature data. All synthesized products were submitted to the cytotoxicity assay of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) bromide, to evaluate the antiproliferative activity in vitro, in gastric tumor lineage (AGP01), compared to the normal lung cell line (MRC-5). The most active substances were chalcones 2, 6, 3, 4 and 1, which showed the greatest reduction in cell viability of AGP01, being greater than 90%. |
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Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cellSíntesis y evaluación biológica de chalconas y derivados in vitro frente a células AGP01Síntese e avaliação biológica de chalconas e derivados in vitro contra célula AGP01ChalconeFlavanonesAntiproliferative.ChalconaFlavanonasAntiproliferativo.ChalconaFlavanonasAntiproliferativa.The interest in obtaining chalcones is due to the numerous pharmacological activities described in the literature for these compounds that are intermediates in the biosynthesis of flavonoids. Thus, the synthesis and characterization of several chalcones and derivatives become important for the development of compounds with antiproliferative activity. In this work, ten substances were synthesized, seven chalcones and three naphthoflavanones, obtained by the Claisen Schmidt aldol condensation reaction between acetophenones and aldehydes, at room temperature conditions in a basic medium. Yields ranged between 65.35% and 97.45%. Being characterized and confirmed through ¹H and ¹³C NMR spectroscopic techniques in comparison with literature data. All synthesized products were submitted to the cytotoxicity assay of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) bromide, to evaluate the antiproliferative activity in vitro, in gastric tumor lineage (AGP01), compared to the normal lung cell line (MRC-5). The most active substances were chalcones 2, 6, 3, 4 and 1, which showed the greatest reduction in cell viability of AGP01, being greater than 90%.El interés en la obtención de calconas se debe a las numerosas actividades farmacológicas descritas en la literatura para estos compuestos que son intermediarios en la biosíntesis de flavonoides. De esta forma, la síntesis y caracterización de varias calconas y derivados adquiere importancia para el desarrollo de compuestos con actividad antiproliferativa. En este trabajo se sintetizaron diez sustancias, siete chalconas y tres naftoflavanonas, obtenidas mediante la reacción de condensación aldólica de Claisen Schmidt entre acetofenonas y aldehídos, a temperatura ambiente en un medio básico. Los rendimientos oscilaron entre el 65,35% y el 97,45%. Estar caracterizado y confirmado mediante técnicas espectroscópicas de RMN ¹H y ¹³C en comparación con los datos de la literatura. Todos los productos sintetizados se sometieron al ensayo de citotoxicidad de bromuro de 3- (4,5-dimetiltiazol-2-il) -2,5-difeniltetrazolio (MTT), para evaluar la actividad antiproliferativa in vitro, en linaje tumoral gástrico (AGP01), en comparación con la línea de células pulmonares normales (MRC-5). Las sustancias más activas fueron las chalconas 2, 6, 3, 4 y 1 que mostraron la mayor reducción en la viabilidad celular de AGP01, siendo superior al 90%.O interesse pela obtenção de chalconas se deve as inúmeras atividades farmacológicas descritas na literatura para esses compostos que são intermediários da biossíntese de flavonoides. Dessa forma, a síntese e caracterização de várias chalconas e derivados se tornam importantes para o desenvolvimento de compostos com atividade antiproliferativa. Neste trabalho foram sintetizadas dez substâncias, sendo sete chalconas e três naftoflavanonas, obtidas pela reação de condensação aldólica de Claisen Schmidt entre acetofenonas e aldeídos, em condições de temperatura ambiente em meio básico. Os rendimentos variaram entre 65,35% e 97,45%. Sendo caracterizadas e confirmadas por meio de técnicas espectroscópicas de RMN de ¹H e ¹³C em comparação com os dados da literatura. Todos os produtos sintetizados foram submetidos ao ensaio de citotoxicidade do brometo de 3- (4,5-dimetiltiazol-2-il) -2,5-difeniltetrazólio (MTT), para a avaliação da atividade antiproliferativa in vitro, em linhagem tumoral gástrica (AGP01), com comparação à linhagem celular normal de pulmão (MRC-5). As substancias mais ativas, foram as chalconas 2, 6, 3, 4 e 1 que apresentaram maior redução na viabilidade celular de AGP01, sendo maior que 90%.Research, Society and Development2021-12-13info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://rsdjournal.org/index.php/rsd/article/view/2360010.33448/rsd-v10i16.23600Research, Society and Development; Vol. 10 No. 16; e332101623600Research, Society and Development; Vol. 10 Núm. 16; e332101623600Research, Society and Development; v. 10 n. 16; e3321016236002525-3409reponame:Research, Society and Developmentinstname:Universidade Federal de Itajubá (UNIFEI)instacron:UNIFEIporhttps://rsdjournal.org/index.php/rsd/article/view/23600/20980Copyright (c) 2021 Maricelia Lopes dos Anjos; Herald Souza dos Reis; Heriberto Rodrigues Bitencourt ; Natasha Costa da Rocha Galucio; André Salim Khayat; Antônio Pedro da Silva Souza Filho; Marta Chagas Monteirohttps://creativecommons.org/licenses/by/4.0info:eu-repo/semantics/openAccessAnjos, Maricelia Lopes dos Reis, Herald Souza dos Bitencourt , Heriberto Rodrigues Galucio, Natasha Costa da Rocha Khayat, André Salim Souza Filho, Antônio Pedro da Silva Monteiro, Marta Chagas 2021-12-20T11:03:07Zoai:ojs.pkp.sfu.ca:article/23600Revistahttps://rsdjournal.org/index.php/rsd/indexPUBhttps://rsdjournal.org/index.php/rsd/oairsd.articles@gmail.com2525-34092525-3409opendoar:2024-01-17T09:42:24.831455Research, Society and Development - Universidade Federal de Itajubá (UNIFEI)false |
| dc.title.none.fl_str_mv |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell Síntesis y evaluación biológica de chalconas y derivados in vitro frente a células AGP01 Síntese e avaliação biológica de chalconas e derivados in vitro contra célula AGP01 |
| title |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| spellingShingle |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell Anjos, Maricelia Lopes dos Chalcone Flavanones Antiproliferative. Chalcona Flavanonas Antiproliferativo. Chalcona Flavanonas Antiproliferativa. |
| title_short |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| title_full |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| title_fullStr |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| title_full_unstemmed |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| title_sort |
Synthesis and biological evaluation of chalcones and derivatives in vitro against AGP01 cell |
| author |
Anjos, Maricelia Lopes dos |
| author_facet |
Anjos, Maricelia Lopes dos Reis, Herald Souza dos Bitencourt , Heriberto Rodrigues Galucio, Natasha Costa da Rocha Khayat, André Salim Souza Filho, Antônio Pedro da Silva Monteiro, Marta Chagas |
| author_role |
author |
| author2 |
Reis, Herald Souza dos Bitencourt , Heriberto Rodrigues Galucio, Natasha Costa da Rocha Khayat, André Salim Souza Filho, Antônio Pedro da Silva Monteiro, Marta Chagas |
| author2_role |
author author author author author author |
| dc.contributor.author.fl_str_mv |
Anjos, Maricelia Lopes dos Reis, Herald Souza dos Bitencourt , Heriberto Rodrigues Galucio, Natasha Costa da Rocha Khayat, André Salim Souza Filho, Antônio Pedro da Silva Monteiro, Marta Chagas |
| dc.subject.por.fl_str_mv |
Chalcone Flavanones Antiproliferative. Chalcona Flavanonas Antiproliferativo. Chalcona Flavanonas Antiproliferativa. |
| topic |
Chalcone Flavanones Antiproliferative. Chalcona Flavanonas Antiproliferativo. Chalcona Flavanonas Antiproliferativa. |
| description |
The interest in obtaining chalcones is due to the numerous pharmacological activities described in the literature for these compounds that are intermediates in the biosynthesis of flavonoids. Thus, the synthesis and characterization of several chalcones and derivatives become important for the development of compounds with antiproliferative activity. In this work, ten substances were synthesized, seven chalcones and three naphthoflavanones, obtained by the Claisen Schmidt aldol condensation reaction between acetophenones and aldehydes, at room temperature conditions in a basic medium. Yields ranged between 65.35% and 97.45%. Being characterized and confirmed through ¹H and ¹³C NMR spectroscopic techniques in comparison with literature data. All synthesized products were submitted to the cytotoxicity assay of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) bromide, to evaluate the antiproliferative activity in vitro, in gastric tumor lineage (AGP01), compared to the normal lung cell line (MRC-5). The most active substances were chalcones 2, 6, 3, 4 and 1, which showed the greatest reduction in cell viability of AGP01, being greater than 90%. |
| publishDate |
2021 |
| dc.date.none.fl_str_mv |
2021-12-13 |
| dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion |
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publishedVersion |
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https://rsdjournal.org/index.php/rsd/article/view/23600 10.33448/rsd-v10i16.23600 |
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https://rsdjournal.org/index.php/rsd/article/view/23600 |
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10.33448/rsd-v10i16.23600 |
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por |
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por |
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https://rsdjournal.org/index.php/rsd/article/view/23600/20980 |
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https://creativecommons.org/licenses/by/4.0 info:eu-repo/semantics/openAccess |
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https://creativecommons.org/licenses/by/4.0 |
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openAccess |
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application/pdf |
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Research, Society and Development |
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Research, Society and Development |
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Research, Society and Development; Vol. 10 No. 16; e332101623600 Research, Society and Development; Vol. 10 Núm. 16; e332101623600 Research, Society and Development; v. 10 n. 16; e332101623600 2525-3409 reponame:Research, Society and Development instname:Universidade Federal de Itajubá (UNIFEI) instacron:UNIFEI |
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Research, Society and Development |
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Research, Society and Development - Universidade Federal de Itajubá (UNIFEI) |
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rsd.articles@gmail.com |
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1797052834605170688 |