Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies

Detalhes bibliográficos
Autor(a) principal: Guedes,Luciana S.
Data de Publicação: 2020
Outros Autores: Morgon,Nelson H., Martins,Milene H., Pessine,Francisco B. T.
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=S0103-50532020000801732
Resumo: Imiquimod (IMQ), an immune response modifier, is used for topical treatment of basal cell carcinoma and actinic keratosis. The very poor aqueous solubility of imiquimod gives rise to difficulties in designing aqueous formulations with this drug. One approach that is widely used to enhance drug solubility is complexation with cyclodextrins. The formation of the inclusion complex between IMQ and β-cyclodextrin was investigated in solution and in solid state. IMQ aqueous solubility was improved in the presence of citric acid. The experimental results and molecular modeling indicated the formation of the inclusion complex in aqueous solution of citric acid pH 3.0; however, the low apparent stability constant suggested weak interaction between β-cyclodextrin and IMQ which hampered the use of this approach to improve imiquimod aqueous solubility and the development of an aqueous formulation containing IMQ in the same concentration as in the commercial product.
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spelling Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studiesimiquimodβ-cyclodextrincitric acidinclusion complexphysicochemical characterizationmolecular modelingImiquimod (IMQ), an immune response modifier, is used for topical treatment of basal cell carcinoma and actinic keratosis. The very poor aqueous solubility of imiquimod gives rise to difficulties in designing aqueous formulations with this drug. One approach that is widely used to enhance drug solubility is complexation with cyclodextrins. The formation of the inclusion complex between IMQ and β-cyclodextrin was investigated in solution and in solid state. IMQ aqueous solubility was improved in the presence of citric acid. The experimental results and molecular modeling indicated the formation of the inclusion complex in aqueous solution of citric acid pH 3.0; however, the low apparent stability constant suggested weak interaction between β-cyclodextrin and IMQ which hampered the use of this approach to improve imiquimod aqueous solubility and the development of an aqueous formulation containing IMQ in the same concentration as in the commercial product.Sociedade Brasileira de Química2020-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801732Journal of the Brazilian Chemical Society v.31 n.8 2020reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20200060info:eu-repo/semantics/openAccessGuedes,Luciana S.Morgon,Nelson H.Martins,Milene H.Pessine,Francisco B. T.eng2020-07-23T00:00:00Zoai:scielo:S0103-50532020000801732Revistahttp://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 Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
title Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
spellingShingle Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
Guedes,Luciana S.
imiquimod
β-cyclodextrin
citric acid
inclusion complex
physicochemical characterization
molecular modeling
title_short Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
title_full Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
title_fullStr Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
title_full_unstemmed Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
title_sort Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
author Guedes,Luciana S.
author_facet Guedes,Luciana S.
Morgon,Nelson H.
Martins,Milene H.
Pessine,Francisco B. T.
author_role author
author2 Morgon,Nelson H.
Martins,Milene H.
Pessine,Francisco B. T.
author2_role author
author
author
dc.contributor.author.fl_str_mv Guedes,Luciana S.
Morgon,Nelson H.
Martins,Milene H.
Pessine,Francisco B. T.
dc.subject.por.fl_str_mv imiquimod
β-cyclodextrin
citric acid
inclusion complex
physicochemical characterization
molecular modeling
topic imiquimod
β-cyclodextrin
citric acid
inclusion complex
physicochemical characterization
molecular modeling
description Imiquimod (IMQ), an immune response modifier, is used for topical treatment of basal cell carcinoma and actinic keratosis. The very poor aqueous solubility of imiquimod gives rise to difficulties in designing aqueous formulations with this drug. One approach that is widely used to enhance drug solubility is complexation with cyclodextrins. The formation of the inclusion complex between IMQ and β-cyclodextrin was investigated in solution and in solid state. IMQ aqueous solubility was improved in the presence of citric acid. The experimental results and molecular modeling indicated the formation of the inclusion complex in aqueous solution of citric acid pH 3.0; however, the low apparent stability constant suggested weak interaction between β-cyclodextrin and IMQ which hampered the use of this approach to improve imiquimod aqueous solubility and the development of an aqueous formulation containing IMQ in the same concentration as in the commercial product.
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
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801732
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532020000801732
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20200060
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 Journal of the Brazilian Chemical Society v.31 n.8 2020
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
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institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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