Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα)
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UFRN |
Texto Completo: | https://repositorio.ufrn.br/jspui/handle/123456789/29787 |
Resumo: | Quinoxaline derivatives have attracted considerable attention due to their vast range of applications that includes electroluminescence and biomedicine. Concerning the latter, the literature has shown that compounds with a quinoxaline motif bind quite efficiently to phosphatidylinositol-4,5-bisphosphate 3-kinases (PI3Ks), which are enzymes found to be overexpressed in some types of neoplasms. In the present study, gold nanoparticles (AuNPs) were easily functionalized with 2,3-diethanolminoquinoxaline (DEQX) and 2-(2,3-dihydro-[1,4]oxazino[2,3-b]quinoxalin-4-yl)ethanol (OAQX). We made use of glycerol in alkaline media as reducing agent and the quinoxalines served as capping ligands to stabilize the AuNPs. This is the first report on the modification of a nanostructure with quinoxalines. Functionalization confers nanoparticles the required specificity to target only cancer cells, which opens possibilities for phototherapy since the modified AuNPs would concentrate in the tumor tissue as a consequence of PI3Kα overexpression. Molecular dynamics simulations have shown that DEQX and OAQX are potential inhibitors of PI3Kα since they bind to the active site of the enzyme in a way similar to other known inhibitors. |
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Silva, Janine de AraújoMenezes, Fabrício GavaAthayde, Heloiza Fernanda Oliveira da SilvaVieira, Davi SerradellaSilva, Sérgio Ruschi BergamachiBortoluzzi, Adailton J.Sant’Anna, CelsoEugenio, MateusNeri, Jannyely MoreiraGasparotto, Luiz Henrique da Silva2020-08-06T14:55:23Z2020-08-06T14:55:23Z2018-12-17ARAÚJO, Janine; MENEZES, Fabrício G.; SILVA, Heloiza F. O.; VIEIRA, Davi S.; SILVA, Sergio R. B.; BORTOLUZZI, Adailton J.; SANT’ANNA, Celso; EUGENIO, Mateus; NERI, Jannyely M.; GASPAROTTO, Luiz H. S. Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα). New Journal Of Chemistry, [S.l.], v. 43, n. 4, p. 1803-1811, 2019. http://dx.doi.org/10.1039/c8nj04314k. Disponível em: https://pubs.rsc.org/en/content/articlelanding/2019/nj/c8nj04314k#!divAbstract. Acesso em: 6 ago. 2020.https://repositorio.ufrn.br/jspui/handle/123456789/2978710.1039/C8NJ04314KRoyal Society of Chemistry (RSC)QuinoxalinesPhosphoinositide-3 kinase inhibitorsFunctionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα)info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleQuinoxaline derivatives have attracted considerable attention due to their vast range of applications that includes electroluminescence and biomedicine. Concerning the latter, the literature has shown that compounds with a quinoxaline motif bind quite efficiently to phosphatidylinositol-4,5-bisphosphate 3-kinases (PI3Ks), which are enzymes found to be overexpressed in some types of neoplasms. In the present study, gold nanoparticles (AuNPs) were easily functionalized with 2,3-diethanolminoquinoxaline (DEQX) and 2-(2,3-dihydro-[1,4]oxazino[2,3-b]quinoxalin-4-yl)ethanol (OAQX). We made use of glycerol in alkaline media as reducing agent and the quinoxalines served as capping ligands to stabilize the AuNPs. This is the first report on the modification of a nanostructure with quinoxalines. Functionalization confers nanoparticles the required specificity to target only cancer cells, which opens possibilities for phototherapy since the modified AuNPs would concentrate in the tumor tissue as a consequence of PI3Kα overexpression. Molecular dynamics simulations have shown that DEQX and OAQX are potential inhibitors of PI3Kα since they bind to the active site of the enzyme in a way similar to other known inhibitors.engreponame:Repositório Institucional da UFRNinstname:Universidade Federal do Rio Grande do Norte (UFRN)instacron:UFRNinfo:eu-repo/semantics/openAccessORIGINALFunctionalizationGoldNanoparticles_Silva_2019.pdfFunctionalizationGoldNanoparticles_Silva_2019.pdfFunctionalizationGoldNanoparticles_Silva_2019application/pdf1255952https://repositorio.ufrn.br/bitstream/123456789/29787/1/FunctionalizationGoldNanoparticles_Silva_2019.pdf99ef505cbf919f5e25510db95bbf54f1MD51LICENSElicense.txtlicense.txttext/plain; charset=utf-81484https://repositorio.ufrn.br/bitstream/123456789/29787/2/license.txte9597aa2854d128fd968be5edc8a28d9MD52TEXTFunctionalizationGoldNanoparticles_Silva_2019.pdf.txtFunctionalizationGoldNanoparticles_Silva_2019.pdf.txtExtracted texttext/plain38794https://repositorio.ufrn.br/bitstream/123456789/29787/3/FunctionalizationGoldNanoparticles_Silva_2019.pdf.txtee0b1ba43634a7fc04d943e3326d266aMD53THUMBNAILFunctionalizationGoldNanoparticles_Silva_2019.pdf.jpgFunctionalizationGoldNanoparticles_Silva_2019.pdf.jpgGenerated Thumbnailimage/jpeg1507https://repositorio.ufrn.br/bitstream/123456789/29787/4/FunctionalizationGoldNanoparticles_Silva_2019.pdf.jpg5ed5b54333a767a70570c8b646afa009MD54123456789/297872020-08-09 04:51:51.442oai:https://repositorio.ufrn.br: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Repositório de PublicaçõesPUBhttp://repositorio.ufrn.br/oai/opendoar:2020-08-09T07:51:51Repositório Institucional da UFRN - Universidade Federal do Rio Grande do Norte (UFRN)false |
dc.title.pt_BR.fl_str_mv |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
title |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
spellingShingle |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) Silva, Janine de Araújo Quinoxalines Phosphoinositide-3 kinase inhibitors |
title_short |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
title_full |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
title_fullStr |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
title_full_unstemmed |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
title_sort |
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) |
author |
Silva, Janine de Araújo |
author_facet |
Silva, Janine de Araújo Menezes, Fabrício Gava Athayde, Heloiza Fernanda Oliveira da Silva Vieira, Davi Serradella Silva, Sérgio Ruschi Bergamachi Bortoluzzi, Adailton J. Sant’Anna, Celso Eugenio, Mateus Neri, Jannyely Moreira Gasparotto, Luiz Henrique da Silva |
author_role |
author |
author2 |
Menezes, Fabrício Gava Athayde, Heloiza Fernanda Oliveira da Silva Vieira, Davi Serradella Silva, Sérgio Ruschi Bergamachi Bortoluzzi, Adailton J. Sant’Anna, Celso Eugenio, Mateus Neri, Jannyely Moreira Gasparotto, Luiz Henrique da Silva |
author2_role |
author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Silva, Janine de Araújo Menezes, Fabrício Gava Athayde, Heloiza Fernanda Oliveira da Silva Vieira, Davi Serradella Silva, Sérgio Ruschi Bergamachi Bortoluzzi, Adailton J. Sant’Anna, Celso Eugenio, Mateus Neri, Jannyely Moreira Gasparotto, Luiz Henrique da Silva |
dc.subject.por.fl_str_mv |
Quinoxalines Phosphoinositide-3 kinase inhibitors |
topic |
Quinoxalines Phosphoinositide-3 kinase inhibitors |
description |
Quinoxaline derivatives have attracted considerable attention due to their vast range of applications that includes electroluminescence and biomedicine. Concerning the latter, the literature has shown that compounds with a quinoxaline motif bind quite efficiently to phosphatidylinositol-4,5-bisphosphate 3-kinases (PI3Ks), which are enzymes found to be overexpressed in some types of neoplasms. In the present study, gold nanoparticles (AuNPs) were easily functionalized with 2,3-diethanolminoquinoxaline (DEQX) and 2-(2,3-dihydro-[1,4]oxazino[2,3-b]quinoxalin-4-yl)ethanol (OAQX). We made use of glycerol in alkaline media as reducing agent and the quinoxalines served as capping ligands to stabilize the AuNPs. This is the first report on the modification of a nanostructure with quinoxalines. Functionalization confers nanoparticles the required specificity to target only cancer cells, which opens possibilities for phototherapy since the modified AuNPs would concentrate in the tumor tissue as a consequence of PI3Kα overexpression. Molecular dynamics simulations have shown that DEQX and OAQX are potential inhibitors of PI3Kα since they bind to the active site of the enzyme in a way similar to other known inhibitors. |
publishDate |
2018 |
dc.date.issued.fl_str_mv |
2018-12-17 |
dc.date.accessioned.fl_str_mv |
2020-08-06T14:55:23Z |
dc.date.available.fl_str_mv |
2020-08-06T14:55:23Z |
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.citation.fl_str_mv |
ARAÚJO, Janine; MENEZES, Fabrício G.; SILVA, Heloiza F. O.; VIEIRA, Davi S.; SILVA, Sergio R. B.; BORTOLUZZI, Adailton J.; SANT’ANNA, Celso; EUGENIO, Mateus; NERI, Jannyely M.; GASPAROTTO, Luiz H. S. Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα). New Journal Of Chemistry, [S.l.], v. 43, n. 4, p. 1803-1811, 2019. http://dx.doi.org/10.1039/c8nj04314k. Disponível em: https://pubs.rsc.org/en/content/articlelanding/2019/nj/c8nj04314k#!divAbstract. Acesso em: 6 ago. 2020. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufrn.br/jspui/handle/123456789/29787 |
dc.identifier.doi.none.fl_str_mv |
10.1039/C8NJ04314K |
identifier_str_mv |
ARAÚJO, Janine; MENEZES, Fabrício G.; SILVA, Heloiza F. O.; VIEIRA, Davi S.; SILVA, Sergio R. B.; BORTOLUZZI, Adailton J.; SANT’ANNA, Celso; EUGENIO, Mateus; NERI, Jannyely M.; GASPAROTTO, Luiz H. S. Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα). New Journal Of Chemistry, [S.l.], v. 43, n. 4, p. 1803-1811, 2019. http://dx.doi.org/10.1039/c8nj04314k. Disponível em: https://pubs.rsc.org/en/content/articlelanding/2019/nj/c8nj04314k#!divAbstract. Acesso em: 6 ago. 2020. 10.1039/C8NJ04314K |
url |
https://repositorio.ufrn.br/jspui/handle/123456789/29787 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
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openAccess |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry (RSC) |
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Royal Society of Chemistry (RSC) |
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reponame:Repositório Institucional da UFRN instname:Universidade Federal do Rio Grande do Norte (UFRN) instacron:UFRN |
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Universidade Federal do Rio Grande do Norte (UFRN) |
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UFRN |
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UFRN |
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