Imiquimod/β-Cyclodextrin Inclusion Complex: Experimental and Theoretical Studies
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , |
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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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) |
instacron_str |
SBQ |
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 |
_version_ |
1750318183410040832 |