Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone

Detalhes bibliográficos
Autor(a) principal: Sousa,Iran L.
Data de Publicação: 2020
Outros Autores: Porto,Caio M., Bassani,Kátia C., Martins,Milene H., Pessine,Francisco B. T., Morgon,Nelson H.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801585
Resumo: Benzbromarone (BZB) is a drug that has diuretic activity and is used in the gout treatment. Its therapeutic efficiency is decreased by its low water solubility (11.8 mg L-1) and highly hydrophobic aspect (logP 2.7), which are responsible for affecting its intestinal absorption and bioavailability. BZB inclusion complex (IC) aims at increasing the drug solubility in water and reduce adverse effects resulting in more efficient formulations. The coprecipitation encapsulating method was used to obtain the IC of BZB in β-cyclodextrin (β-CD) and the complex (BZB@β-CD) was characterized via physical-chemical analysis. A comparative study of time-dependent density functional theory (TD-DFT) and configuration interaction singles (CIS), along with “our own N-layered integrated molecular orbital and molecular mechanics” (ONIOM) method, has been carried out on the UV-Vis absorption of BZB and BZB@β-CD. The qualitative description of the simulated spectrum, given by ONIOM(CIS:PM6), is in accord with the formation of BZB@β-CD. It only became possible when phosphate buffer (pH 7.4) was used to prepare the solutions, since the complex formation did not occur in deionized water or buffered acid. Furthermore, by using the Job plot, the Scatchard method and fluorescence, it was possible to conclude that the complex molecular stoichiometry was 1:1 (1 BZB to 1 β-CD).
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spelling Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromaronebenzbromaroneinclusion complexβ-cyclodextrinfluorescenceONIOM(TD-DFT:PM6)ONIOM(CIS:PM6)Benzbromarone (BZB) is a drug that has diuretic activity and is used in the gout treatment. Its therapeutic efficiency is decreased by its low water solubility (11.8 mg L-1) and highly hydrophobic aspect (logP 2.7), which are responsible for affecting its intestinal absorption and bioavailability. BZB inclusion complex (IC) aims at increasing the drug solubility in water and reduce adverse effects resulting in more efficient formulations. The coprecipitation encapsulating method was used to obtain the IC of BZB in β-cyclodextrin (β-CD) and the complex (BZB@β-CD) was characterized via physical-chemical analysis. A comparative study of time-dependent density functional theory (TD-DFT) and configuration interaction singles (CIS), along with “our own N-layered integrated molecular orbital and molecular mechanics” (ONIOM) method, has been carried out on the UV-Vis absorption of BZB and BZB@β-CD. The qualitative description of the simulated spectrum, given by ONIOM(CIS:PM6), is in accord with the formation of BZB@β-CD. It only became possible when phosphate buffer (pH 7.4) was used to prepare the solutions, since the complex formation did not occur in deionized water or buffered acid. Furthermore, by using the Job plot, the Scatchard method and fluorescence, it was possible to conclude that the complex molecular stoichiometry was 1:1 (1 BZB to 1 β-CD).Sociedade Brasileira de Química2020-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801585Journal of the Brazilian Chemical Society v.31 n.8 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200044info:eu-repo/semantics/openAccessSousa,Iran L.Porto,Caio M.Bassani,Kátia C.Martins,Milene H.Pessine,Francisco B. T.Morgon,Nelson H.eng2020-07-23T00:00:00Zoai:scielo:S0103-50532020000801585Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2020-07-23T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
title Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
spellingShingle Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
Sousa,Iran L.
benzbromarone
inclusion complex
β-cyclodextrin
fluorescence
ONIOM(TD-DFT:PM6)
ONIOM(CIS:PM6)
title_short Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
title_full Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
title_fullStr Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
title_full_unstemmed Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
title_sort Preparation and Characterization of the β-Cyclodextrin Inclusion Complex with Benzbromarone
author Sousa,Iran L.
author_facet Sousa,Iran L.
Porto,Caio M.
Bassani,Kátia C.
Martins,Milene H.
Pessine,Francisco B. T.
Morgon,Nelson H.
author_role author
author2 Porto,Caio M.
Bassani,Kátia C.
Martins,Milene H.
Pessine,Francisco B. T.
Morgon,Nelson H.
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Sousa,Iran L.
Porto,Caio M.
Bassani,Kátia C.
Martins,Milene H.
Pessine,Francisco B. T.
Morgon,Nelson H.
dc.subject.por.fl_str_mv benzbromarone
inclusion complex
β-cyclodextrin
fluorescence
ONIOM(TD-DFT:PM6)
ONIOM(CIS:PM6)
topic benzbromarone
inclusion complex
β-cyclodextrin
fluorescence
ONIOM(TD-DFT:PM6)
ONIOM(CIS:PM6)
description Benzbromarone (BZB) is a drug that has diuretic activity and is used in the gout treatment. Its therapeutic efficiency is decreased by its low water solubility (11.8 mg L-1) and highly hydrophobic aspect (logP 2.7), which are responsible for affecting its intestinal absorption and bioavailability. BZB inclusion complex (IC) aims at increasing the drug solubility in water and reduce adverse effects resulting in more efficient formulations. The coprecipitation encapsulating method was used to obtain the IC of BZB in β-cyclodextrin (β-CD) and the complex (BZB@β-CD) was characterized via physical-chemical analysis. A comparative study of time-dependent density functional theory (TD-DFT) and configuration interaction singles (CIS), along with “our own N-layered integrated molecular orbital and molecular mechanics” (ONIOM) method, has been carried out on the UV-Vis absorption of BZB and BZB@β-CD. The qualitative description of the simulated spectrum, given by ONIOM(CIS:PM6), is in accord with the formation of BZB@β-CD. It only became possible when phosphate buffer (pH 7.4) was used to prepare the solutions, since the complex formation did not occur in deionized water or buffered acid. Furthermore, by using the Job plot, the Scatchard method and fluorescence, it was possible to conclude that the complex molecular stoichiometry was 1:1 (1 BZB to 1 β-CD).
publishDate 2020
dc.date.none.fl_str_mv 2020-08-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801585
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dc.language.iso.fl_str_mv eng
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dc.relation.none.fl_str_mv 10.21577/0103-5053.20200044
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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 Journal of the Brazilian Chemical Society v.31 n.8 2020
reponame:Journal of the Brazilian Chemical Society (Online)
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