ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA)
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , |
Tipo de documento: | Artigo |
Idioma: | por |
Título da fonte: | Química Nova (Online) |
Texto Completo: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019000200135 |
Resumo: | Human serum albumin (HSA) plays an important role in the transport of a wide variety of substances, including compounds with pharmacological properties. The dansylglycine (DanG) is a fluorescent amino acid derivative specific for the site II of HSA. This work aimed to elucidate the induction of chirality in the DanG due to its bonding to the HSA. Theoretical electronic circular dichroism spectra (ECDs) were simulated using the Density Functional Theory (DFT) and the implicit Solvation Model based on Density (SMD). The DanG-HSA complexation resulted in the appearance of a positive ECD spectrum centered at 346 nm. Focusing on the dihedral angles between the -N(CH3)2 group bounded to the naphthalene ring, the potential energy surface (PES) of the DanG was obtained. Analysis of the various conformations obtained revealed that the calculated dihedral angle (150º) is in agreed with the experimental ECD spectrum. In addition, we observed that the nitrogen atom of the -N(CH3)2 group presented the greatest contribution to the HOMO-LUMO transition that gives rise to the n→π* electronic transition involved in the generation of the ECD signal. Molecular docking analysis of the complexation between DanG and HSA revealed a conformation with a dihedral angle similar to that obtained by DFT. |
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ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA)human serum albuminDFTelectronic circular dichroismdansylglycineHuman serum albumin (HSA) plays an important role in the transport of a wide variety of substances, including compounds with pharmacological properties. The dansylglycine (DanG) is a fluorescent amino acid derivative specific for the site II of HSA. This work aimed to elucidate the induction of chirality in the DanG due to its bonding to the HSA. Theoretical electronic circular dichroism spectra (ECDs) were simulated using the Density Functional Theory (DFT) and the implicit Solvation Model based on Density (SMD). The DanG-HSA complexation resulted in the appearance of a positive ECD spectrum centered at 346 nm. Focusing on the dihedral angles between the -N(CH3)2 group bounded to the naphthalene ring, the potential energy surface (PES) of the DanG was obtained. Analysis of the various conformations obtained revealed that the calculated dihedral angle (150º) is in agreed with the experimental ECD spectrum. In addition, we observed that the nitrogen atom of the -N(CH3)2 group presented the greatest contribution to the HOMO-LUMO transition that gives rise to the n→π* electronic transition involved in the generation of the ECD signal. Molecular docking analysis of the complexation between DanG and HSA revealed a conformation with a dihedral angle similar to that obtained by DFT.Sociedade Brasileira de Química2019-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019000200135Química Nova v.42 n.2 2019reponame:Química Nova (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0100-4042.20170341info:eu-repo/semantics/openAccessSouza,Aguinaldo Robinson deBoza,Izabelle Amorim FerreiraXimenes,Valdecir FariasYoguin,Maurício IkedaDávila-Rodriguez,María-JoséMorgon,Nelson HenriqueCaracelli,Ignezpor2019-03-25T00:00:00Zoai:scielo:S0100-40422019000200135Revistahttps://www.scielo.br/j/qn/ONGhttps://old.scielo.br/oai/scielo-oai.phpquimicanova@sbq.org.br1678-70640100-4042opendoar:2019-03-25T00:00Química Nova (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
title |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
spellingShingle |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) Souza,Aguinaldo Robinson de human serum albumin DFT electronic circular dichroism dansylglycine |
title_short |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
title_full |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
title_fullStr |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
title_full_unstemmed |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
title_sort |
ELUCIDAÇÃO DA QUIRALIDADE INDUZIDA NA MOLÉCULA DANSILGLICINA NA COMPLEXAÇÃO COM A PROTEÍNA ALBUMINA DO SORO HUMANO (HSA) |
author |
Souza,Aguinaldo Robinson de |
author_facet |
Souza,Aguinaldo Robinson de Boza,Izabelle Amorim Ferreira Ximenes,Valdecir Farias Yoguin,Maurício Ikeda Dávila-Rodriguez,María-José Morgon,Nelson Henrique Caracelli,Ignez |
author_role |
author |
author2 |
Boza,Izabelle Amorim Ferreira Ximenes,Valdecir Farias Yoguin,Maurício Ikeda Dávila-Rodriguez,María-José Morgon,Nelson Henrique Caracelli,Ignez |
author2_role |
author author author author author author |
dc.contributor.author.fl_str_mv |
Souza,Aguinaldo Robinson de Boza,Izabelle Amorim Ferreira Ximenes,Valdecir Farias Yoguin,Maurício Ikeda Dávila-Rodriguez,María-José Morgon,Nelson Henrique Caracelli,Ignez |
dc.subject.por.fl_str_mv |
human serum albumin DFT electronic circular dichroism dansylglycine |
topic |
human serum albumin DFT electronic circular dichroism dansylglycine |
description |
Human serum albumin (HSA) plays an important role in the transport of a wide variety of substances, including compounds with pharmacological properties. The dansylglycine (DanG) is a fluorescent amino acid derivative specific for the site II of HSA. This work aimed to elucidate the induction of chirality in the DanG due to its bonding to the HSA. Theoretical electronic circular dichroism spectra (ECDs) were simulated using the Density Functional Theory (DFT) and the implicit Solvation Model based on Density (SMD). The DanG-HSA complexation resulted in the appearance of a positive ECD spectrum centered at 346 nm. Focusing on the dihedral angles between the -N(CH3)2 group bounded to the naphthalene ring, the potential energy surface (PES) of the DanG was obtained. Analysis of the various conformations obtained revealed that the calculated dihedral angle (150º) is in agreed with the experimental ECD spectrum. In addition, we observed that the nitrogen atom of the -N(CH3)2 group presented the greatest contribution to the HOMO-LUMO transition that gives rise to the n→π* electronic transition involved in the generation of the ECD signal. Molecular docking analysis of the complexation between DanG and HSA revealed a conformation with a dihedral angle similar to that obtained by DFT. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-02-01 |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019000200135 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422019000200135 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.none.fl_str_mv |
10.21577/0100-4042.20170341 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
text/html |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
Química Nova v.42 n.2 2019 reponame:Química Nova (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
instname_str |
Sociedade Brasileira de Química (SBQ) |
instacron_str |
SBQ |
institution |
SBQ |
reponame_str |
Química Nova (Online) |
collection |
Química Nova (Online) |
repository.name.fl_str_mv |
Química Nova (Online) - Sociedade Brasileira de Química (SBQ) |
repository.mail.fl_str_mv |
quimicanova@sbq.org.br |
_version_ |
1750318119591608320 |