Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery

Detalhes bibliográficos
Autor(a) principal: Moreira, Dmitriy
Data de Publicação: 2023
Outros Autores: Regev, Oren, Basílio, Nuno, Marques, Eduardo F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/162657
Resumo: The authors acknowledge Fundação para a Ciência e Tecnologia (FCT), FEDER/COMPETE and P2020|COMPETE for financial support through projects POCI-01-0145-FEDER-032351 (PhotoSAN) Publisher Copyright: © 2023 The Authors
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spelling Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug deliveryFrom molecular design to the controlled release of doxorubicinAnticancer drugCatanionic vesiclesLiposomal deliveryPhotoresponsive surfactantSmart drug deliveryStimuli-responsive nanocarriersSustained releaseElectronic, Optical and Magnetic MaterialsBiomaterialsSurfaces, Coatings and FilmsColloid and Surface ChemistrySDG 3 - Good Health and Well-beingThe authors acknowledge Fundação para a Ciência e Tecnologia (FCT), FEDER/COMPETE and P2020|COMPETE for financial support through projects POCI-01-0145-FEDER-032351 (PhotoSAN) Publisher Copyright: © 2023 The AuthorsSpatially and temporally localized delivery is a promising strategy to circumvent adverse effects of traditional drug therapy such as drug toxicity and prolonged treatments. Stimuli-responsive colloidal nanocarriers can be crucial to attain such goals. Here, we develop a delivery system based on dual light and pH responsive vesicles having a cationic bis-quat gemini surfactant, 12–2-12, and a negatively charged amphiphilic chalcone, C4SCh. The premise is to exploit the chalcone/flavylium interconversion to elicit a morphological change of the vesicles leading to the controlled release of an encapsulated drug. First, the phase behavior of the catanionic system is studied and the desirable composition yielding stable unilamellar vesicles identified and selected for further studies. The solutions containing vesicles (Dh ≈ 200 nm, ζ-potential ≈ 80 mV) are in-depth characterized by light microscopy, cryo-transmission electron microscopy (cryo-TEM), dynamic light scattering (DLS) and surface tension measurements. Upon subjecting the vesicles to UV irradiation (λ = 365 nm) at near neutral pH (≈ 6.0), no morphological effects are observed, yet when irradiation is coupled with pH = 3.0, the majority of the vesicles are disrupted into bilayer fragments. The anticancer drug doxorubicin (DOX) is successfully entrapped in the non-irradiated vesicles, yielding an encapsulation efficiency of ≈ 25% and a loading capacity of ≈ 3%. The release profile of the drug-loaded vesicles is then studied in vitro in four conditions: i) no stimuli (pH = 6.0); ii) irradiation, pH = 6.0; iii) no irradiation and adjusted pH = 3.0; iv) irradiation and adjusted pH = 3.0 Crucially, irradiation at pH = 3.0 leads to a sustained release of DOX to ca. 80% (within 4 h), whereas cases i) and ii) lead to only ≈ 25 % release and case iii) to 50% release but precipitation of the vesicles. Thus, our initial hypothesis is confirmed: we present a proof of concept delivery system where light and pH act as inputs of an AND logic gate mechanism for the controlled release of a relevant biomedical drug (output). This may prove useful if the irradiated nanocarriers meet acidified physiological environments such as tumors sites, endosomes or lysosomes.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNMoreira, DmitriyRegev, OrenBasílio, NunoMarques, Eduardo F.2024-01-22T22:59:51Z2023-11-152023-11-15T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article11application/pdfhttp://hdl.handle.net/10362/162657eng0021-9797PURE: 82138635https://doi.org/10.1016/j.jcis.2023.07.129info: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:RCAAP2024-05-22T18:17:40Zoai:run.unl.pt:10362/162657Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-22T18:17:40Repositório 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 Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
From molecular design to the controlled release of doxorubicin
title Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
spellingShingle Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
Moreira, Dmitriy
Anticancer drug
Catanionic vesicles
Liposomal delivery
Photoresponsive surfactant
Smart drug delivery
Stimuli-responsive nanocarriers
Sustained release
Electronic, Optical and Magnetic Materials
Biomaterials
Surfaces, Coatings and Films
Colloid and Surface Chemistry
SDG 3 - Good Health and Well-being
title_short Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
title_full Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
title_fullStr Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
title_full_unstemmed Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
title_sort Light and pH responsive catanionic vesicles based on a chalcone/flavylium photoswitch for smart drug delivery
author Moreira, Dmitriy
author_facet Moreira, Dmitriy
Regev, Oren
Basílio, Nuno
Marques, Eduardo F.
author_role author
author2 Regev, Oren
Basílio, Nuno
Marques, Eduardo F.
author2_role author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Moreira, Dmitriy
Regev, Oren
Basílio, Nuno
Marques, Eduardo F.
dc.subject.por.fl_str_mv Anticancer drug
Catanionic vesicles
Liposomal delivery
Photoresponsive surfactant
Smart drug delivery
Stimuli-responsive nanocarriers
Sustained release
Electronic, Optical and Magnetic Materials
Biomaterials
Surfaces, Coatings and Films
Colloid and Surface Chemistry
SDG 3 - Good Health and Well-being
topic Anticancer drug
Catanionic vesicles
Liposomal delivery
Photoresponsive surfactant
Smart drug delivery
Stimuli-responsive nanocarriers
Sustained release
Electronic, Optical and Magnetic Materials
Biomaterials
Surfaces, Coatings and Films
Colloid and Surface Chemistry
SDG 3 - Good Health and Well-being
description The authors acknowledge Fundação para a Ciência e Tecnologia (FCT), FEDER/COMPETE and P2020|COMPETE for financial support through projects POCI-01-0145-FEDER-032351 (PhotoSAN) Publisher Copyright: © 2023 The Authors
publishDate 2023
dc.date.none.fl_str_mv 2023-11-15
2023-11-15T00:00:00Z
2024-01-22T22:59:51Z
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/10362/162657
url http://hdl.handle.net/10362/162657
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0021-9797
PURE: 82138635
https://doi.org/10.1016/j.jcis.2023.07.129
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 11
application/pdf
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
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
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
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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