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Artículo

Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties

Vignoni, MarianaIcon ; Walalawela, Niluksha; Bonesi, Sergio MauricioIcon ; Greer, Alexander; Thomas, Andrés HéctorIcon
Fecha de publicación: 03/2018
Editorial: American Chemical Society
Revista: Molecular Pharmaceutics
ISSN: 1543-8384
Idioma: Inglés
Tipo de recurso: Artículo publicado
Clasificación temática:
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Resumen

A new series of decyl chain [-(CH2)9CH3] pterin conjugates have been investigated by photochemical and photophysical methods, and with theoretical solubility calculations. To synthesize the pterins, a nucleophilic substitution (SN2) reaction was used for the regioselective coupling of the alkyl chain to the O site over the N3 site. However, the O-alkylated pterin converts to N3-alkylated pterin under basic conditions, pointing to a kinetic product in the former and a thermodynamic product in the latter. Two additional adducts were also obtained from an N-amine condensation of DMF solvent molecule as byproducts. In comparison to the natural product pterin, the alkyl chain pterins possess reduced fluorescence quantum yields (F) and increased singlet oxygen quantum yields (-). It is shown that the DMF-condensed pterins were more photostable compared to the N3- and O-alkylated pterins bearing a free amine group. The alkyl chain pterins efficiently intercalate in large unilamellar vesicles, which is a good indicator of their potential use as photosensitizers in biomembranes. Our study serves as a starting point where the synthesis can be expanded to produce a wider series of lipophilic, photooxidatively active pterins.
Palabras clave: Fluorescence , Lipophilic Pterins , Luvs , Singlet Oxygen , Synthesis
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info:eu-repo/semantics/openAccess Excepto donde se diga explícitamente, este item se publica bajo la siguiente descripción: Creative Commons Attribution-NonCommercial-ShareAlike 2.5 Unported (CC BY-NC-SA 2.5)
Identificadores
URI: http://hdl.handle.net/11336/58752
DOI: https://dx.doi.org/10.1021/acs.molpharmaceut.7b00136
URL: https://pubs.acs.org/doi/10.1021/acs.molpharmaceut.7b00136
Colecciones
Articulos(CIHIDECAR)
Articulos de CENTRO DE INVESTIGACIONES EN HIDRATOS DE CARBONO
Citación
Vignoni, Mariana; Walalawela, Niluksha; Bonesi, Sergio Mauricio; Greer, Alexander; Thomas, Andrés Héctor; Lipophilic Decyl Chain-Pterin Conjugates with Sensitizer Properties; American Chemical Society; Molecular Pharmaceutics; 15; 3; 3-2018; 798-807
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