Cyclodextrin modulation of gallic acid in vitro antibacterial activity

Detalhes bibliográficos
Autor(a) principal: Pinho, Eva
Data de Publicação: 2015
Outros Autores: Soares, Graça M. B., Henriques, Mariana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/33101
Resumo: The substitution of large spectrum antibiotics for natural bioactive molecules (especially polyphenolics) for the treatment of wound infections has come into prominence in the pharmaceutical industry. However, the use of such molecules depends on their stability during environmental stress and on their ability to reach the action site without losing biological properties. The application of cyclodextrins as a vehicle for polyphenolics protection has been documented and appears to enhance the properties of bioactive molecules. Therefore, the encapsulation of gallic acid, an antibacterial agent with low stability, by -cyclodextrin, (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin, was investigated. Encapsulation by -cyclodextrin was confirmed for pH 3 and 5, with similar stability parameters. The (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin interactions with gallic acid were only confirmed at pH 3. Among the three cyclodextrins, better gallic acid encapsulation were observed for (2-hydroxy) propyl--cyclodextrin, followed by -cyclodextrin and methyl--cyclodextrin. The effect of cyclodextrin encapsulation on the gallic acid antibacterial activity was also analysed. The antibacterial activity of the inclusion complexes was investigated here for the first time. According to the results, encapsulation of gallic acid by (2-hydroxy) propyl--cyclodextrin seems to be a viable option for the treatment of skin and soft tissue infections, since this inclusion complex has good stability and antibacterial activity.
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spelling Cyclodextrin modulation of gallic acid in vitro antibacterial activityGallic acidß-cyclodextrin(2-hydroxy) propyl-ß-cyclodextrinMethyl-ß-cyclodextrinBenesi-Hildebrand equationAntibacterial activity(2-hydroxy) propyl-β-cyclodextrinMethyl-β-cyclodextrinβ-cyclodextrinScience & TechnologyThe substitution of large spectrum antibiotics for natural bioactive molecules (especially polyphenolics) for the treatment of wound infections has come into prominence in the pharmaceutical industry. However, the use of such molecules depends on their stability during environmental stress and on their ability to reach the action site without losing biological properties. The application of cyclodextrins as a vehicle for polyphenolics protection has been documented and appears to enhance the properties of bioactive molecules. Therefore, the encapsulation of gallic acid, an antibacterial agent with low stability, by -cyclodextrin, (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin, was investigated. Encapsulation by -cyclodextrin was confirmed for pH 3 and 5, with similar stability parameters. The (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin interactions with gallic acid were only confirmed at pH 3. Among the three cyclodextrins, better gallic acid encapsulation were observed for (2-hydroxy) propyl--cyclodextrin, followed by -cyclodextrin and methyl--cyclodextrin. The effect of cyclodextrin encapsulation on the gallic acid antibacterial activity was also analysed. The antibacterial activity of the inclusion complexes was investigated here for the first time. According to the results, encapsulation of gallic acid by (2-hydroxy) propyl--cyclodextrin seems to be a viable option for the treatment of skin and soft tissue infections, since this inclusion complex has good stability and antibacterial activity.The authors are grateful for the FCT Strategic Project PEst-OE/EQB/LA0023/2013 and the Project "BioHealth-Biotechnology and Bioengineering approaches to improve health quality", Ref. NORTE-07-0124-FEDER-000027, co-funded by the "Programa Operacional Regional do Norte" (ON.2-O Novo Norte), QREN, FEDER. The authors also acknowledge the project "Consolidating Research Expertise and Resources on Cellular and Molecular Biotechnology at CEB/IBB", Ref. FCOMP-01-0124-FEDER-027462. This work is, also, funded by FEDER funds through the Operational Programme for Competitiveness Factors-COMPETE and National Funds through FCT-Foundation for Science and Technology under the project PEst-C/CTM/UI0264/2011. Additionally, the authors would like to thank the FCT for the grant for E. Pinho (SFRH/BD/62665/2009).SpringerUniversidade do MinhoPinho, EvaSoares, Graça M. B.Henriques, Mariana20152015-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/33101engPinho, Eva; Soares, Graça M. B.; Henriques, Mariana, Cyclodextrin modulation of gallic acid in vitro antibacterial activity. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 81(1-2), 205-214, 20151388-31271573-111110.1007/s10847-014-0449-8info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:01:05Zoai:repositorium.sdum.uminho.pt:1822/33101Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:51:00.558498Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Cyclodextrin modulation of gallic acid in vitro antibacterial activity
title Cyclodextrin modulation of gallic acid in vitro antibacterial activity
spellingShingle Cyclodextrin modulation of gallic acid in vitro antibacterial activity
Pinho, Eva
Gallic acid
ß-cyclodextrin
(2-hydroxy) propyl-ß-cyclodextrin
Methyl-ß-cyclodextrin
Benesi-Hildebrand equation
Antibacterial activity
(2-hydroxy) propyl-β-cyclodextrin
Methyl-β-cyclodextrin
β-cyclodextrin
Science & Technology
title_short Cyclodextrin modulation of gallic acid in vitro antibacterial activity
title_full Cyclodextrin modulation of gallic acid in vitro antibacterial activity
title_fullStr Cyclodextrin modulation of gallic acid in vitro antibacterial activity
title_full_unstemmed Cyclodextrin modulation of gallic acid in vitro antibacterial activity
title_sort Cyclodextrin modulation of gallic acid in vitro antibacterial activity
author Pinho, Eva
author_facet Pinho, Eva
Soares, Graça M. B.
Henriques, Mariana
author_role author
author2 Soares, Graça M. B.
Henriques, Mariana
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Pinho, Eva
Soares, Graça M. B.
Henriques, Mariana
dc.subject.por.fl_str_mv Gallic acid
ß-cyclodextrin
(2-hydroxy) propyl-ß-cyclodextrin
Methyl-ß-cyclodextrin
Benesi-Hildebrand equation
Antibacterial activity
(2-hydroxy) propyl-β-cyclodextrin
Methyl-β-cyclodextrin
β-cyclodextrin
Science & Technology
topic Gallic acid
ß-cyclodextrin
(2-hydroxy) propyl-ß-cyclodextrin
Methyl-ß-cyclodextrin
Benesi-Hildebrand equation
Antibacterial activity
(2-hydroxy) propyl-β-cyclodextrin
Methyl-β-cyclodextrin
β-cyclodextrin
Science & Technology
description The substitution of large spectrum antibiotics for natural bioactive molecules (especially polyphenolics) for the treatment of wound infections has come into prominence in the pharmaceutical industry. However, the use of such molecules depends on their stability during environmental stress and on their ability to reach the action site without losing biological properties. The application of cyclodextrins as a vehicle for polyphenolics protection has been documented and appears to enhance the properties of bioactive molecules. Therefore, the encapsulation of gallic acid, an antibacterial agent with low stability, by -cyclodextrin, (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin, was investigated. Encapsulation by -cyclodextrin was confirmed for pH 3 and 5, with similar stability parameters. The (2-hydroxy) propyl--cyclodextrin and methyl--cyclodextrin interactions with gallic acid were only confirmed at pH 3. Among the three cyclodextrins, better gallic acid encapsulation were observed for (2-hydroxy) propyl--cyclodextrin, followed by -cyclodextrin and methyl--cyclodextrin. The effect of cyclodextrin encapsulation on the gallic acid antibacterial activity was also analysed. The antibacterial activity of the inclusion complexes was investigated here for the first time. According to the results, encapsulation of gallic acid by (2-hydroxy) propyl--cyclodextrin seems to be a viable option for the treatment of skin and soft tissue infections, since this inclusion complex has good stability and antibacterial activity.
publishDate 2015
dc.date.none.fl_str_mv 2015
2015-01-01T00:00:00Z
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://hdl.handle.net/1822/33101
url http://hdl.handle.net/1822/33101
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Pinho, Eva; Soares, Graça M. B.; Henriques, Mariana, Cyclodextrin modulation of gallic acid in vitro antibacterial activity. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 81(1-2), 205-214, 2015
1388-3127
1573-1111
10.1007/s10847-014-0449-8
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Springer
publisher.none.fl_str_mv Springer
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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