Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction

5-Aminolevulinic acid-based photodynamic therapy (ALA-PDT) is gaining increasing acceptance in medicine as an effective technique for the treatment of a variety of neoplastic lesions. Unfortunately, the efficacy of ALA-PDT is limited by the hydrophilic nature of the molecule, leading to poor penetra...

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Autores principales: Gola, G.F., Di Venosa, G.M., Sáenz, D.A., Calvo, G.H., Cabrera, G.M., Casas, A.G., Ramírez, J.A.
Formato: JOUR
Materias:
Esters
5-aminolevulinic acid
ALA derivatives
Alkyl esters
In-vitro evaluation
Malignant tissues
Multicomponents
Neoplastic lesions
Three component
Photodynamic therapy
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_20462069_v6_n92_p89492_Gola
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_20462069_v6_n92_p89492_Gola
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spelling todo:paper_20462069_v6_n92_p89492_Gola2023-10-03T16:38:39Z Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction Gola, G.F. Di Venosa, G.M. Sáenz, D.A. Calvo, G.H. Cabrera, G.M. Casas, A.G. Ramírez, J.A. Esters 5-aminolevulinic acid ALA derivatives Alkyl esters In-vitro evaluation Malignant tissues Multicomponents Neoplastic lesions Three component Photodynamic therapy 5-Aminolevulinic acid-based photodynamic therapy (ALA-PDT) is gaining increasing acceptance in medicine as an effective technique for the treatment of a variety of neoplastic lesions. Unfortunately, the efficacy of ALA-PDT is limited by the hydrophilic nature of the molecule, leading to poor penetration through malignant tissues. This fact prompted the development of more lipophilic ALA derivatives, such as alkyl esters, although this strategy has potential drawbacks, mainly associated with the instability of ALA in solution. In this paper we describe a more versatile methodology for obtaining ALA esters based on the three-component Passerini reaction, which involves mild conditions and a straightforward procedure, allowing efficient generation of chemically diverse libraries of ALA conjugates. The preliminary in vitro evaluation of the new designed compounds allowed us to find a new promising conjugate with enhanced photodynamic properties compared to ALA. © 2016 The Royal Society of Chemistry. Fil:Di Venosa, G.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sáenz, D.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Cabrera, G.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Casas, A.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_20462069_v6_n92_p89492_Gola
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Esters
5-aminolevulinic acid
ALA derivatives
Alkyl esters
In-vitro evaluation
Malignant tissues
Multicomponents
Neoplastic lesions
Three component
Photodynamic therapy
spellingShingle Esters
5-aminolevulinic acid
ALA derivatives
Alkyl esters
In-vitro evaluation
Malignant tissues
Multicomponents
Neoplastic lesions
Three component
Photodynamic therapy
Gola, G.F.
Di Venosa, G.M.
Sáenz, D.A.
Calvo, G.H.
Cabrera, G.M.
Casas, A.G.
Ramírez, J.A.
Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
topic_facet Esters
5-aminolevulinic acid
ALA derivatives
Alkyl esters
In-vitro evaluation
Malignant tissues
Multicomponents
Neoplastic lesions
Three component
Photodynamic therapy
description 5-Aminolevulinic acid-based photodynamic therapy (ALA-PDT) is gaining increasing acceptance in medicine as an effective technique for the treatment of a variety of neoplastic lesions. Unfortunately, the efficacy of ALA-PDT is limited by the hydrophilic nature of the molecule, leading to poor penetration through malignant tissues. This fact prompted the development of more lipophilic ALA derivatives, such as alkyl esters, although this strategy has potential drawbacks, mainly associated with the instability of ALA in solution. In this paper we describe a more versatile methodology for obtaining ALA esters based on the three-component Passerini reaction, which involves mild conditions and a straightforward procedure, allowing efficient generation of chemically diverse libraries of ALA conjugates. The preliminary in vitro evaluation of the new designed compounds allowed us to find a new promising conjugate with enhanced photodynamic properties compared to ALA. © 2016 The Royal Society of Chemistry.
format JOUR
author Gola, G.F.
Di Venosa, G.M.
Sáenz, D.A.
Calvo, G.H.
Cabrera, G.M.
Casas, A.G.
Ramírez, J.A.
author_facet Gola, G.F.
Di Venosa, G.M.
Sáenz, D.A.
Calvo, G.H.
Cabrera, G.M.
Casas, A.G.
Ramírez, J.A.
author_sort Gola, G.F.
title Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
title_short Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
title_full Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
title_fullStr Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
title_full_unstemmed Synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent Passerini reaction
title_sort synthesis of chemically diverse esters of 5-aminolevulinic acid for photodynamic therapy via the multicomponent passerini reaction
url http://hdl.handle.net/20.500.12110/paper_20462069_v6_n92_p89492_Gola
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