Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy

Photodynamic therapy (PDT) is still hindered by limitations such as poor bioavailability and insufficient selectivity towards tumor cells. To overcome these drawbacks, nanostructured delivery systems have emerged as promising platforms due to their ability to enhance bioavailability and achieve effi...

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Detalles Bibliográficos
Autores: Paramio Calvo, Irene, Dai, Gaole, Torres Cebada, Tomás, Ng, Dennis K.P., Torre Ponce, Gema de la
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad Autónoma de Madrid
Repositorio:Biblos-e Archivo. Repositorio Institucional de la UAM
Idioma:inglés
OAI Identifier:oai:repositorio.uam.es:10486/743320
Acceso en línea:https://hdl.handle.net/10486/743320
https://dx.doi.org/10.1016/j.bioorg.2025.109376
Access Level:acceso abierto
Palabra clave:Photodynamic therapy
Phthalocyanines
Amphiphiles
Self-assembly
Nanoparticles
Glucose transporters
Química
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spelling Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapyParamio Calvo, IreneDai, GaoleTorres Cebada, TomásNg, Dennis K.P.Torre Ponce, Gema de laPhotodynamic therapyPhthalocyaninesAmphiphilesSelf-assemblyNanoparticlesGlucose transportersQuímicaPhotodynamic therapy (PDT) is still hindered by limitations such as poor bioavailability and insufficient selectivity towards tumor cells. To overcome these drawbacks, nanostructured delivery systems have emerged as promising platforms due to their ability to enhance bioavailability and achieve efficient tumor targeting. In this context, nanoparticles (NPs) formed by the self-assembly of highly amphiphilic photosensitizers (PS) in aqueous media are particularly attractive. Among the various PS available, phthalocyanines (Pcs) are especially suitable for constructing nanoassemblies for PDT owing to their outstanding optical and photophysical properties, as well as their ability to form stable nanoaggregates in water through a combination of ππ stacking and hydrophobic interactions. In this work, we describe the design, synthesis, and evaluation of two amphiphilic, glucose- functionalized zinc(II) phthalocyanines (Zn(II)Pcs) as self-assembled PS for PDT. These derivatives are obtained from binaphthyloxy-linked AABB-type Zn(II)Pc synthons previously reported by our group, which are functionalized at the binaphthol ring with glucose units via Sonogashira coupling or copper-catalyzed click reaction. The resulting amphiphiles, GluPc-1 and GluPc-2, spontaneously self-assemble into stable NPs (15–30 nm) that undergo partial disassembly inside cells, which restores the photophysical properties required for efficient PDT. Notably, the glucose moieties exposed on the NP surface enhance selective uptake by tumor cells overexpressing glucose transporters (GLUT-1). Biological studies in cancerous (A549 and HT29) and non- cancerous (HEK293) cell lines confirmed preferential uptake in GLUT1-positive cells, while cytotoxicity assays demonstrated negligible dark toxicity and potent light-induced phototoxic effectsThis work has been supported by the Spanish MICIU/AEI/10.130 39/501100011033/FEDER, UE (PID2023-149483NB-C21, PID2023- 151167NB-I00), the Comunidad de Madrid and the Spanish State through the Recovery, Transformation and Resilience Plan [“Materiales Disruptivos Bidimensionales (2D)” (MAD2D-CM) (UAM1)-MRR Materiales Avanzados], and the European Union through the Next Generation EU funds. IMDEA Nanociencia acknowledges support from the “Severo Ochoa” Programme for Centres of Excellence in R&D (MINECO, CEX2020-001039-S). This work was also financially supported by the Research Grants Council of the Hong Kong Special Administration Region, China, through the Collaborative Research Fund (Ref. No. C4057-24GF)ElsevierDepartamento de Química OrgánicaFacultad de CienciasGobierno de España20252025-12-18research articlehttp://purl.org/coar/resource_type/c_2df8fbb1VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10486/743320https://dx.doi.org/10.1016/j.bioorg.2025.109376reponame:Biblos-e Archivo. Repositorio Institucional de la UAMinstname:Universidad Autónoma de MadridInglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial 4.0 Internationalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:repositorio.uam.es:10486/7433202026-06-23T12:46:27Z
dc.title.none.fl_str_mv Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
title Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
spellingShingle Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
Paramio Calvo, Irene
Photodynamic therapy
Phthalocyanines
Amphiphiles
Self-assembly
Nanoparticles
Glucose transporters
Química
title_short Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
title_full Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
title_fullStr Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
title_full_unstemmed Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
title_sort Self-assembled nanoparticles of glycosylated AABB-type phthalocyanines for selective photodynamic therapy
dc.creator.none.fl_str_mv Paramio Calvo, Irene
Dai, Gaole
Torres Cebada, Tomás
Ng, Dennis K.P.
Torre Ponce, Gema de la
author Paramio Calvo, Irene
author_facet Paramio Calvo, Irene
Dai, Gaole
Torres Cebada, Tomás
Ng, Dennis K.P.
Torre Ponce, Gema de la
author_role author
author2 Dai, Gaole
Torres Cebada, Tomás
Ng, Dennis K.P.
Torre Ponce, Gema de la
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Departamento de Química Orgánica
Facultad de Ciencias
Gobierno de España
dc.subject.none.fl_str_mv Photodynamic therapy
Phthalocyanines
Amphiphiles
Self-assembly
Nanoparticles
Glucose transporters
Química
topic Photodynamic therapy
Phthalocyanines
Amphiphiles
Self-assembly
Nanoparticles
Glucose transporters
Química
description Photodynamic therapy (PDT) is still hindered by limitations such as poor bioavailability and insufficient selectivity towards tumor cells. To overcome these drawbacks, nanostructured delivery systems have emerged as promising platforms due to their ability to enhance bioavailability and achieve efficient tumor targeting. In this context, nanoparticles (NPs) formed by the self-assembly of highly amphiphilic photosensitizers (PS) in aqueous media are particularly attractive. Among the various PS available, phthalocyanines (Pcs) are especially suitable for constructing nanoassemblies for PDT owing to their outstanding optical and photophysical properties, as well as their ability to form stable nanoaggregates in water through a combination of ππ stacking and hydrophobic interactions. In this work, we describe the design, synthesis, and evaluation of two amphiphilic, glucose- functionalized zinc(II) phthalocyanines (Zn(II)Pcs) as self-assembled PS for PDT. These derivatives are obtained from binaphthyloxy-linked AABB-type Zn(II)Pc synthons previously reported by our group, which are functionalized at the binaphthol ring with glucose units via Sonogashira coupling or copper-catalyzed click reaction. The resulting amphiphiles, GluPc-1 and GluPc-2, spontaneously self-assemble into stable NPs (15–30 nm) that undergo partial disassembly inside cells, which restores the photophysical properties required for efficient PDT. Notably, the glucose moieties exposed on the NP surface enhance selective uptake by tumor cells overexpressing glucose transporters (GLUT-1). Biological studies in cancerous (A549 and HT29) and non- cancerous (HEK293) cell lines confirmed preferential uptake in GLUT1-positive cells, while cytotoxicity assays demonstrated negligible dark toxicity and potent light-induced phototoxic effects
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-12-18
dc.type.none.fl_str_mv research article
http://purl.org/coar/resource_type/c_2df8fbb1
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://hdl.handle.net/10486/743320
https://dx.doi.org/10.1016/j.bioorg.2025.109376
url https://hdl.handle.net/10486/743320
https://dx.doi.org/10.1016/j.bioorg.2025.109376
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial 4.0 International
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Biblos-e Archivo. Repositorio Institucional de la UAM
instname:Universidad Autónoma de Madrid
instname_str Universidad Autónoma de Madrid
reponame_str Biblos-e Archivo. Repositorio Institucional de la UAM
collection Biblos-e Archivo. Repositorio Institucional de la UAM
repository.name.fl_str_mv
repository.mail.fl_str_mv
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