Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα)

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-bisphosp...

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Principais autores: 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
Formato: article
Idioma:English
Publicado em: Royal Society of Chemistry (RSC)
Assuntos:
Quinoxalines
Phosphoinositide-3 kinase inhibitors
Endereço do item:https://repositorio.ufrn.br/jspui/handle/123456789/29787
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spelling ri-123456789-297872020-08-09T07:51:51Z Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα) 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 Quinoxalines Phosphoinositide-3 kinase inhibitors 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. 2020-08-06T14:55:23Z 2020-08-06T14:55:23Z 2018-12-17 article 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. https://repositorio.ufrn.br/jspui/handle/123456789/29787 10.1039/C8NJ04314K en application/pdf Royal Society of Chemistry (RSC)
institution Repositório Institucional
collection RI - UFRN
language English
topic Quinoxalines
Phosphoinositide-3 kinase inhibitors
spellingShingle Quinoxalines
Phosphoinositide-3 kinase inhibitors
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
Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα)
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.
format article
author 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_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_sort Silva, Janine de Araújo
title Functionalization of gold nanoparticles with two aminoalcohol-based quinoxaline derivatives for targeting phosphoinositide 3-kinases (PI3Kα)
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)
publisher Royal Society of Chemistry (RSC)
publishDate 2020
url https://repositorio.ufrn.br/jspui/handle/123456789/29787
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