Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jddst.2020.101767 http://hdl.handle.net/11449/200382 |
Resumo: | The purpose of this work was to evaluate the inclusion complexes (ICs) of 2-(2-nitrovinyl) furan (G-0) with hydroxypropyl and sulfobutylether-β-cyclodextrin intended for drug stabilization. The freeze-dried ICs were subjected to an accelerated stability study, monitored by HPLC-DAD and GC-MS methods. Drug sublimation/volatility has been analyzed through Thermogravimetric Analysis and Headspace Gas Chromatography. Drug dissolution profile in Simulated Vaginal Fluid (SVF) and permeation/retention in bovine vaginal mucosa were also evaluated. The influence of ICs on the “in vitro” antifungal activity against Candida spp. was investigated through Broth Microdilution Method and the cytotoxicity on fibroblasts and keratinocytes, through MTT assay protocol. ICs ensured an optimum drug chemical stability under accelerated conditions and significantly decreased the drug sublimation/volatilization compared with free G-0 and physical mixtures. Both complexes allowed a fast drug release in SVF, but G-0 was not quantified in the receptor compartment, although it was recovery from the mucosa, without significant influence on the complex formation. ICs maintained the antifungal activity against Candida albicans but improved the drug activity against a Candida krusei resistant strain (ICs MIC = 12.5 μg mL−1, G-0 MIC = 25 μg mL−1, Amphotericin B MIC = 20 μg mL−1). Cytotoxicity on fibroblast and keratinocytes followed the ranking order: G-0 > FD G-0/HP-β-CD > FD G-0/SBE-β-CD. |
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Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives2-(2-nitrovinyl) furanCandida sppCyclodextrins inclusion complexesDrug stabilizationHead space- gas chromatographyThe purpose of this work was to evaluate the inclusion complexes (ICs) of 2-(2-nitrovinyl) furan (G-0) with hydroxypropyl and sulfobutylether-β-cyclodextrin intended for drug stabilization. The freeze-dried ICs were subjected to an accelerated stability study, monitored by HPLC-DAD and GC-MS methods. Drug sublimation/volatility has been analyzed through Thermogravimetric Analysis and Headspace Gas Chromatography. Drug dissolution profile in Simulated Vaginal Fluid (SVF) and permeation/retention in bovine vaginal mucosa were also evaluated. The influence of ICs on the “in vitro” antifungal activity against Candida spp. was investigated through Broth Microdilution Method and the cytotoxicity on fibroblasts and keratinocytes, through MTT assay protocol. ICs ensured an optimum drug chemical stability under accelerated conditions and significantly decreased the drug sublimation/volatilization compared with free G-0 and physical mixtures. Both complexes allowed a fast drug release in SVF, but G-0 was not quantified in the receptor compartment, although it was recovery from the mucosa, without significant influence on the complex formation. ICs maintained the antifungal activity against Candida albicans but improved the drug activity against a Candida krusei resistant strain (ICs MIC = 12.5 μg mL−1, G-0 MIC = 25 μg mL−1, Amphotericin B MIC = 20 μg mL−1). Cytotoxicity on fibroblast and keratinocytes followed the ranking order: G-0 > FD G-0/HP-β-CD > FD G-0/SBE-β-CD.Universidad Nacional de SaltaCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)São Paulo State University (UNESP) School of Pharmaceutical Sciences, Rodovia Araraquara-Jau, km 01Drug Delivery and Disposition Department of Pharmaceutical and Pharmacological Sciences University of Leuven (KULeuven), O&N2 Herestraat 49-Box 921São Paulo State University (UNESP) Center for Monitoring and Research Quality of Fuels Biofuels Petroleum and Derivatives (CEMPEQC) Chemistry Institute, Rua Prof. Francisco Degni 55Pharmacy Department Chemistry and Pharmacy Faculty Central University of Las Villas, Carretera a Camajuaní km 5 ½São Paulo State University (UNESP) School of Pharmaceutical Sciences, Rodovia Araraquara-Jau, km 01São Paulo State University (UNESP) Center for Monitoring and Research Quality of Fuels Biofuels Petroleum and Derivatives (CEMPEQC) Chemistry Institute, Rua Prof. Francisco Degni 55CAPES: 001Universidade Estadual Paulista (Unesp)University of Leuven (KULeuven)Central University of Las VillasRuz Sanjuan, Vivian [UNESP]Van den Mooter, GuyCarlos, Iracilda Zeppone [UNESP]dos Santos Ramos, Matheus Aparecido [UNESP]Bauab, Taís Maria [UNESP]Tercini, Antonio Carlos Bergamaschi [UNESP]González Bedia, Mirtha MayraGomes de Oliveira, Anselmo [UNESP]2020-12-12T02:05:08Z2020-12-12T02:05:08Z2020-08-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.jddst.2020.101767Journal of Drug Delivery Science and Technology, v. 58.1773-2247http://hdl.handle.net/11449/20038210.1016/j.jddst.2020.1017672-s2.0-85084363709Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Drug Delivery Science and Technologyinfo:eu-repo/semantics/openAccess2021-10-23T12:39:37Zoai:repositorio.unesp.br:11449/200382Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T22:19:49.766629Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
title |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
spellingShingle |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives Ruz Sanjuan, Vivian [UNESP] 2-(2-nitrovinyl) furan Candida spp Cyclodextrins inclusion complexes Drug stabilization Head space- gas chromatography |
title_short |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
title_full |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
title_fullStr |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
title_full_unstemmed |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
title_sort |
Stability, biological and biopharmaceutical evaluation of the inclusion complexes of the antifungal and antiprotozoal drug candidate 2-(2-nitrovinyl) furan (G-0) with beta cyclodextrin derivatives |
author |
Ruz Sanjuan, Vivian [UNESP] |
author_facet |
Ruz Sanjuan, Vivian [UNESP] Van den Mooter, Guy Carlos, Iracilda Zeppone [UNESP] dos Santos Ramos, Matheus Aparecido [UNESP] Bauab, Taís Maria [UNESP] Tercini, Antonio Carlos Bergamaschi [UNESP] González Bedia, Mirtha Mayra Gomes de Oliveira, Anselmo [UNESP] |
author_role |
author |
author2 |
Van den Mooter, Guy Carlos, Iracilda Zeppone [UNESP] dos Santos Ramos, Matheus Aparecido [UNESP] Bauab, Taís Maria [UNESP] Tercini, Antonio Carlos Bergamaschi [UNESP] González Bedia, Mirtha Mayra Gomes de Oliveira, Anselmo [UNESP] |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Estadual Paulista (Unesp) University of Leuven (KULeuven) Central University of Las Villas |
dc.contributor.author.fl_str_mv |
Ruz Sanjuan, Vivian [UNESP] Van den Mooter, Guy Carlos, Iracilda Zeppone [UNESP] dos Santos Ramos, Matheus Aparecido [UNESP] Bauab, Taís Maria [UNESP] Tercini, Antonio Carlos Bergamaschi [UNESP] González Bedia, Mirtha Mayra Gomes de Oliveira, Anselmo [UNESP] |
dc.subject.por.fl_str_mv |
2-(2-nitrovinyl) furan Candida spp Cyclodextrins inclusion complexes Drug stabilization Head space- gas chromatography |
topic |
2-(2-nitrovinyl) furan Candida spp Cyclodextrins inclusion complexes Drug stabilization Head space- gas chromatography |
description |
The purpose of this work was to evaluate the inclusion complexes (ICs) of 2-(2-nitrovinyl) furan (G-0) with hydroxypropyl and sulfobutylether-β-cyclodextrin intended for drug stabilization. The freeze-dried ICs were subjected to an accelerated stability study, monitored by HPLC-DAD and GC-MS methods. Drug sublimation/volatility has been analyzed through Thermogravimetric Analysis and Headspace Gas Chromatography. Drug dissolution profile in Simulated Vaginal Fluid (SVF) and permeation/retention in bovine vaginal mucosa were also evaluated. The influence of ICs on the “in vitro” antifungal activity against Candida spp. was investigated through Broth Microdilution Method and the cytotoxicity on fibroblasts and keratinocytes, through MTT assay protocol. ICs ensured an optimum drug chemical stability under accelerated conditions and significantly decreased the drug sublimation/volatilization compared with free G-0 and physical mixtures. Both complexes allowed a fast drug release in SVF, but G-0 was not quantified in the receptor compartment, although it was recovery from the mucosa, without significant influence on the complex formation. ICs maintained the antifungal activity against Candida albicans but improved the drug activity against a Candida krusei resistant strain (ICs MIC = 12.5 μg mL−1, G-0 MIC = 25 μg mL−1, Amphotericin B MIC = 20 μg mL−1). Cytotoxicity on fibroblast and keratinocytes followed the ranking order: G-0 > FD G-0/HP-β-CD > FD G-0/SBE-β-CD. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-12-12T02:05:08Z 2020-12-12T02:05:08Z 2020-08-01 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.jddst.2020.101767 Journal of Drug Delivery Science and Technology, v. 58. 1773-2247 http://hdl.handle.net/11449/200382 10.1016/j.jddst.2020.101767 2-s2.0-85084363709 |
url |
http://dx.doi.org/10.1016/j.jddst.2020.101767 http://hdl.handle.net/11449/200382 |
identifier_str_mv |
Journal of Drug Delivery Science and Technology, v. 58. 1773-2247 10.1016/j.jddst.2020.101767 2-s2.0-85084363709 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Drug Delivery Science and Technology |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129416225619968 |