Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina

Detalhes bibliográficos
Autor(a) principal: Carvalho Neto, Antonio Guilherme de
Data de Publicação: 2017
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da UFS
Texto Completo: http://ri.ufs.br/jspui/handle/riufs/8904
Resumo: The essential oils (EOs) are compounds extracted from plants that have a great variety of biological activities reported in the literature. In this class, carvone, an unsaturated ketone monoterpene, is found in nature under two enantiomeric forms: S-(+)-carvone and R-(-)-carvone. Carvone has several pharmacological properties such as anticancer, anticonvulsant, anxiolytic, antidepressant and anti-inflammatory. R-(-)-carvone has some physico-chemical characteristics that limit its use, such as low solubility in water, high volatilization and easy oxidation. In this perspective, the formation of inclusion complexes (ICs) with cyclodextrins (CDs) have been one of the main strategies to increase the solubility in water of poorly soluble drugs, bypassing their physico-chemical limitations. In this way, the present study aimed to prepare the R-(-)-carvone/β-CD complexes in the 1: 1 molar ratio by different complexation methods: physical mixture (PM), paste complex (PC), slurry complex (SC), ultrasound (US) and freeze drying (FD), characterized by differential scanning calorimetry (DSC), thermogravimetry/derivative thermogravimetry (TG/DTG), Karl Fischer Moisture Determination (KF), Fourier transform infrared spectrophotometry (FTIR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). In addition, the analytical method for quantification of R-(-)-carvone was developed by high performance liquid chromatography (HPLC) and complexation efficiency (CE%) was determined from this method. DSC and TG/DTG curves of the SC and FD methods showed, respectively, the disappearance of the R-(-)-carvone melting characteristic event, and the considerable reduction of mass loss in the first step (Δm1 6.87% and 5.18% between 34-150 °C), indicating the complexation. XRD results of the ICs (PC, SC and FD) showed the disappearance of spectral characteristic lines of β-CD and the emergence of new peaks, suggesting a change of β-CD crystalline phase. SEM images of ICs exhibited relevant changes in morphology compared to free β-CD and PM, showing a decrease in particle size, especially in the US and FD methods. FTIR results showed that there were displacements and reduction in the intensity of the R-(-)-carvone characteristic bands in the ICs spectra. HPLC analysis showed that the higher CE% were obtained by SC and FD methods (70.93% and 84.26%). Thus, it is concluded that the SC and FD complexation methods presented the best host-guest interaction profiles, suggesting IC's formation between R-(-)-carvone and β-CD.
id UFS-2_44286bd4ef9124b194323d5647d501de
oai_identifier_str oai:ufs.br:riufs/8904
network_acronym_str UFS-2
network_name_str Repositório Institucional da UFS
repository_id_str
spelling Carvalho Neto, Antonio Guilherme deSerafini, Mairim Russo2018-09-12T20:42:04Z2018-09-12T20:42:04Z2017-03-06CARVALHO NETO, Antonio Guilherme de. Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina. 2017. 70 f. Dissertação (Mestrado em Ciências Farmacêuticas) – Universidade Federal de Sergipe, São Cristóvão, SE, 2017.http://ri.ufs.br/jspui/handle/riufs/8904The essential oils (EOs) are compounds extracted from plants that have a great variety of biological activities reported in the literature. In this class, carvone, an unsaturated ketone monoterpene, is found in nature under two enantiomeric forms: S-(+)-carvone and R-(-)-carvone. Carvone has several pharmacological properties such as anticancer, anticonvulsant, anxiolytic, antidepressant and anti-inflammatory. R-(-)-carvone has some physico-chemical characteristics that limit its use, such as low solubility in water, high volatilization and easy oxidation. In this perspective, the formation of inclusion complexes (ICs) with cyclodextrins (CDs) have been one of the main strategies to increase the solubility in water of poorly soluble drugs, bypassing their physico-chemical limitations. In this way, the present study aimed to prepare the R-(-)-carvone/β-CD complexes in the 1: 1 molar ratio by different complexation methods: physical mixture (PM), paste complex (PC), slurry complex (SC), ultrasound (US) and freeze drying (FD), characterized by differential scanning calorimetry (DSC), thermogravimetry/derivative thermogravimetry (TG/DTG), Karl Fischer Moisture Determination (KF), Fourier transform infrared spectrophotometry (FTIR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). In addition, the analytical method for quantification of R-(-)-carvone was developed by high performance liquid chromatography (HPLC) and complexation efficiency (CE%) was determined from this method. DSC and TG/DTG curves of the SC and FD methods showed, respectively, the disappearance of the R-(-)-carvone melting characteristic event, and the considerable reduction of mass loss in the first step (Δm1 6.87% and 5.18% between 34-150 °C), indicating the complexation. XRD results of the ICs (PC, SC and FD) showed the disappearance of spectral characteristic lines of β-CD and the emergence of new peaks, suggesting a change of β-CD crystalline phase. SEM images of ICs exhibited relevant changes in morphology compared to free β-CD and PM, showing a decrease in particle size, especially in the US and FD methods. FTIR results showed that there were displacements and reduction in the intensity of the R-(-)-carvone characteristic bands in the ICs spectra. HPLC analysis showed that the higher CE% were obtained by SC and FD methods (70.93% and 84.26%). Thus, it is concluded that the SC and FD complexation methods presented the best host-guest interaction profiles, suggesting IC's formation between R-(-)-carvone and β-CD.Os óleos essenciais (OEs) são compostos extraídos de plantas que dispõem de uma grande variedade de atividades biológicas relatadas na literatura. Nessa classe, destaca-se a carvona, monoterpeno cetônico insaturado, encontrado na natureza sob duas formas enantioméricas, a S-(+)-carvona e R-(-)-carvona. A carvona possui diversas propriedades farmacológicas tais como: anticancerígena, anticonvulsivante, ansiolítica, antidepressiva e anti-inflamatória. A R-(-)-carvona apresenta algumas características físico-químicas que limitam sua utilização, como por exemplo, baixa solubilidade em água, elevada volatilização e fácil oxidação. Nessa perspectiva, a formação de complexos de inclusão (CIs) com ciclodextrinas (CDs) têm sido uma das principais estratégias para aumentar a solubilidade em água de fármacos fracamente solúveis contornando suas limitações físico-químicas. Dessa forma, o presente estudo teve como objetivo preparar os complexos R-(-)-carvona/β-CD na razão molar 1:1 por diferentes métodos de complexação: mistura física (MF), malaxagem (MA), coevaporação (CE), ultrassom (US) e liofilização (LF) caracterizando-os por calorimetria exploratória diferencial (DSC), termogravimetria /termogravimetria derivada (TG/DTG), determinação de umidade por Karl Fischer (KF), espectrofotometria de absorção na região do infravermelho com transformada de Fourier (FTIR), difração de raios X (DRX) e microscopia eletrônica de varredura (MEV). Além disso, o método analítico para quantificação da R-(-)-carvona foi desenvolvido por cromatografia líquida de alta eficiência (CLAE) e a eficiência de complexação (EC%) foi determinada a partir desse método. As curvas DSC e TG/DTG dos métodos de CE e LF mostraram respectivamente, o desaparecimento do evento característico de fusão da R-(-)-carvona, e a redução considerável de perda de massa na primeira etapa (Δm1 6,87% e 5,18% entre 34-150 °C), indicando a complexação. Os resultados de DRX dos CIs (MA, CE e LF) apresentaram o desaparecimento de linhas espectrais características da β-CD e o surgimento de novos picos, sugerindo mudanças na fase cristalina da β-CD. As imagens de MEV dos CIs exibiram mudanças relevantes na morfologia em comparação com a β-CD livre e a MF, apresentando uma diminuição no tamanho das partículas, principalmente nos métodos US e LF. Os resultados de FTIR demonstrou que houve deslocamentos e redução na intensidade das bandas características da R-(-)-carvona nos espectros dos CIs. As análises de CLAE demonstraram que as maiores EC% foram obtidas pelos métodos de CE e LF (70,93% e 84,26%). Assim, conclui-se que os métodos de complexação CE e LF apresentaram os melhores perfis de interação hóspede-hospedeiro, sugerindo a formação dos CIs entre a R-(-)-carvona e a β-CD.Fundação de Apoio a Pesquisa e à Inovação Tecnológica do Estado de Sergipe - FAPITEC/SESão Cristóvão, SEporEssências e óleos essenciaisMonoterpenosCiclodextrinasCarvonaÓleos essenciaisβ-ciclodextrinaComplexos de inclusãoEssential oilsMonoterpeneCarvoneβ-cyclodextrinInclusion complexesCIENCIAS BIOLOGICAS::FARMACOLOGIAElucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrinainfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisPós-Graduação em Ciências FarmacêuticasUniversidade Federal de Sergipereponame:Repositório Institucional da UFSinstname:Universidade Federal de Sergipe (UFS)instacron:UFSinfo:eu-repo/semantics/openAccessTEXTANTONIO_GUILHERME_CARVALHO_NETO.pdf.txtANTONIO_GUILHERME_CARVALHO_NETO.pdf.txtExtracted texttext/plain116670https://ri.ufs.br/jspui/bitstream/riufs/8904/3/ANTONIO_GUILHERME_CARVALHO_NETO.pdf.txt8e2be49d20aba6dff23741c342690affMD53THUMBNAILANTONIO_GUILHERME_CARVALHO_NETO.pdf.jpgANTONIO_GUILHERME_CARVALHO_NETO.pdf.jpgGenerated Thumbnailimage/jpeg1356https://ri.ufs.br/jspui/bitstream/riufs/8904/4/ANTONIO_GUILHERME_CARVALHO_NETO.pdf.jpg94372f3f8de66642db34cc936f316bf0MD54LICENSElicense.txtlicense.txttext/plain; charset=utf-81475https://ri.ufs.br/jspui/bitstream/riufs/8904/1/license.txt098cbbf65c2c15e1fb2e49c5d306a44cMD51ORIGINALANTONIO_GUILHERME_CARVALHO_NETO.pdfANTONIO_GUILHERME_CARVALHO_NETO.pdfapplication/pdf1803095https://ri.ufs.br/jspui/bitstream/riufs/8904/2/ANTONIO_GUILHERME_CARVALHO_NETO.pdfb1d9c657eb02f198e798f0aa6a4af8feMD52riufs/89042018-09-12 17:42:05.059oai:ufs.br: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Repositório InstitucionalPUBhttps://ri.ufs.br/oai/requestrepositorio@academico.ufs.bropendoar:2018-09-12T20:42:05Repositório Institucional da UFS - Universidade Federal de Sergipe (UFS)false
dc.title.pt_BR.fl_str_mv Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
title Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
spellingShingle Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
Carvalho Neto, Antonio Guilherme de
Essências e óleos essenciais
Monoterpenos
Ciclodextrinas
Carvona
Óleos essenciais
β-ciclodextrina
Complexos de inclusão
Essential oils
Monoterpene
Carvone
β-cyclodextrin
Inclusion complexes
CIENCIAS BIOLOGICAS::FARMACOLOGIA
title_short Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
title_full Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
title_fullStr Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
title_full_unstemmed Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
title_sort Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina
author Carvalho Neto, Antonio Guilherme de
author_facet Carvalho Neto, Antonio Guilherme de
author_role author
dc.contributor.author.fl_str_mv Carvalho Neto, Antonio Guilherme de
dc.contributor.advisor1.fl_str_mv Serafini, Mairim Russo
contributor_str_mv Serafini, Mairim Russo
dc.subject.por.fl_str_mv Essências e óleos essenciais
Monoterpenos
Ciclodextrinas
Carvona
Óleos essenciais
β-ciclodextrina
Complexos de inclusão
topic Essências e óleos essenciais
Monoterpenos
Ciclodextrinas
Carvona
Óleos essenciais
β-ciclodextrina
Complexos de inclusão
Essential oils
Monoterpene
Carvone
β-cyclodextrin
Inclusion complexes
CIENCIAS BIOLOGICAS::FARMACOLOGIA
dc.subject.eng.fl_str_mv Essential oils
Monoterpene
Carvone
β-cyclodextrin
Inclusion complexes
dc.subject.cnpq.fl_str_mv CIENCIAS BIOLOGICAS::FARMACOLOGIA
description The essential oils (EOs) are compounds extracted from plants that have a great variety of biological activities reported in the literature. In this class, carvone, an unsaturated ketone monoterpene, is found in nature under two enantiomeric forms: S-(+)-carvone and R-(-)-carvone. Carvone has several pharmacological properties such as anticancer, anticonvulsant, anxiolytic, antidepressant and anti-inflammatory. R-(-)-carvone has some physico-chemical characteristics that limit its use, such as low solubility in water, high volatilization and easy oxidation. In this perspective, the formation of inclusion complexes (ICs) with cyclodextrins (CDs) have been one of the main strategies to increase the solubility in water of poorly soluble drugs, bypassing their physico-chemical limitations. In this way, the present study aimed to prepare the R-(-)-carvone/β-CD complexes in the 1: 1 molar ratio by different complexation methods: physical mixture (PM), paste complex (PC), slurry complex (SC), ultrasound (US) and freeze drying (FD), characterized by differential scanning calorimetry (DSC), thermogravimetry/derivative thermogravimetry (TG/DTG), Karl Fischer Moisture Determination (KF), Fourier transform infrared spectrophotometry (FTIR), X-ray diffraction (XRD) and scanning electron microscopy (SEM). In addition, the analytical method for quantification of R-(-)-carvone was developed by high performance liquid chromatography (HPLC) and complexation efficiency (CE%) was determined from this method. DSC and TG/DTG curves of the SC and FD methods showed, respectively, the disappearance of the R-(-)-carvone melting characteristic event, and the considerable reduction of mass loss in the first step (Δm1 6.87% and 5.18% between 34-150 °C), indicating the complexation. XRD results of the ICs (PC, SC and FD) showed the disappearance of spectral characteristic lines of β-CD and the emergence of new peaks, suggesting a change of β-CD crystalline phase. SEM images of ICs exhibited relevant changes in morphology compared to free β-CD and PM, showing a decrease in particle size, especially in the US and FD methods. FTIR results showed that there were displacements and reduction in the intensity of the R-(-)-carvone characteristic bands in the ICs spectra. HPLC analysis showed that the higher CE% were obtained by SC and FD methods (70.93% and 84.26%). Thus, it is concluded that the SC and FD complexation methods presented the best host-guest interaction profiles, suggesting IC's formation between R-(-)-carvone and β-CD.
publishDate 2017
dc.date.issued.fl_str_mv 2017-03-06
dc.date.accessioned.fl_str_mv 2018-09-12T20:42:04Z
dc.date.available.fl_str_mv 2018-09-12T20:42:04Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
format masterThesis
status_str publishedVersion
dc.identifier.citation.fl_str_mv CARVALHO NETO, Antonio Guilherme de. Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina. 2017. 70 f. Dissertação (Mestrado em Ciências Farmacêuticas) – Universidade Federal de Sergipe, São Cristóvão, SE, 2017.
dc.identifier.uri.fl_str_mv http://ri.ufs.br/jspui/handle/riufs/8904
identifier_str_mv CARVALHO NETO, Antonio Guilherme de. Elucidação da interação hóspede-hospedeiro entre R-(-)- carvona e β-ciclodextrina. 2017. 70 f. Dissertação (Mestrado em Ciências Farmacêuticas) – Universidade Federal de Sergipe, São Cristóvão, SE, 2017.
url http://ri.ufs.br/jspui/handle/riufs/8904
dc.language.iso.fl_str_mv por
language por
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.program.fl_str_mv Pós-Graduação em Ciências Farmacêuticas
dc.publisher.initials.fl_str_mv Universidade Federal de Sergipe
dc.source.none.fl_str_mv reponame:Repositório Institucional da UFS
instname:Universidade Federal de Sergipe (UFS)
instacron:UFS
instname_str Universidade Federal de Sergipe (UFS)
instacron_str UFS
institution UFS
reponame_str Repositório Institucional da UFS
collection Repositório Institucional da UFS
bitstream.url.fl_str_mv https://ri.ufs.br/jspui/bitstream/riufs/8904/3/ANTONIO_GUILHERME_CARVALHO_NETO.pdf.txt
https://ri.ufs.br/jspui/bitstream/riufs/8904/4/ANTONIO_GUILHERME_CARVALHO_NETO.pdf.jpg
https://ri.ufs.br/jspui/bitstream/riufs/8904/1/license.txt
https://ri.ufs.br/jspui/bitstream/riufs/8904/2/ANTONIO_GUILHERME_CARVALHO_NETO.pdf
bitstream.checksum.fl_str_mv 8e2be49d20aba6dff23741c342690aff
94372f3f8de66642db34cc936f316bf0
098cbbf65c2c15e1fb2e49c5d306a44c
b1d9c657eb02f198e798f0aa6a4af8fe
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
MD5
repository.name.fl_str_mv Repositório Institucional da UFS - Universidade Federal de Sergipe (UFS)
repository.mail.fl_str_mv repositorio@academico.ufs.br
_version_ 1802110784061308928