Synthesis, spectroscopic studies and biological evaluation of acridine derivatives: The role of aggregation on the photodynamic efficiency


Por: Felip-León C, Martínez-Arroyo O, Díaz-Oltra S, Miravet JF, Apostolova N and Galindo F

Publicada: 1 mar 2018
Resumen:
Two new photoactive compounds (1 and 2) derived from the 9-amidoacridine chromophore have been synthesized and fully characterized. Their abilities to produce singlet oxygen upon irradiation have been compared. The synthesized compounds show very different self-aggregating properties since only 1 present a strong tendency to aggregate in water. Biological assays were conducted with two cell types: hepatoma cells (Hep3B) and human umbilical vein endothelial cells (HUVEC). Photodynamic therapy (PDT) studies carried out with Hep3B cells showed that non-aggregating compound 2 showed photoxicity, ascribed to the production of singlet oxygen, being aggregating compound 1 photochemically inactive. On the other hand suspensions of 1, characterized as nano-sized aggregates, have notable antiproliferative activity towards this cell line in the dark. (C) 2018 Elsevier Ltd. All rights reserved.

Filiaciones:
Felip-León C:
 Universitat Jaume I, Departamento de Química Inorgánica y Orgánica, Avda. Sos Baynat s/n, 12071 Castellón, Spain

Martínez-Arroyo O:
 Universitat Jaume I, Departamento de Química Inorgánica y Orgánica, Avda. Sos Baynat s/n, 12071 Castellón, Spain

 Universitat de València, Departamento de Farmacología, Avda. Blasco Ibañez n.15-17, 46010 Valencia, Spain

Díaz-Oltra S:
 Universitat Jaume I, Departamento de Química Inorgánica y Orgánica, Avda. Sos Baynat s/n, 12071 Castellón, Spain

 Universitat Jaume I, Departamento de Educación, Avda. Sos Baynat s/n, 12071 Castellón, Spain

Miravet JF:
 Universitat Jaume I, Departamento de Química Inorgánica y Orgánica, Avda. Sos Baynat s/n, 12071 Castellón, Spain

:
 Universitat de València, Departamento de Farmacología, Avda. Blasco Ibañez n.15-17, 46010 Valencia, Spain

Galindo F:
 Universitat Jaume I, Departamento de Química Inorgánica y Orgánica, Avda. Sos Baynat s/n, 12071 Castellón, Spain
ISSN: 0960894X





BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Editorial
Elsevier Ltd., THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND, Reino Unido
Tipo de documento: Article
Volumen: 28 Número: 5
Páginas: 869-874
WOS Id: 000426598500007
ID de PubMed: 29456110
imagen Green Published

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