Synthesis, spectroscopic characterization and biological evaluation of unsymmetrical aminosquarylium cyanine dyes

• Tipo: Artigo em Revista Científica Internacional
• Data: 2017

Autores

Friaes, S (Autor) Outra; Silva, AM (Autor) Outra; Boto, RE (Autor) Outra; Ferreira, D (Autor) Outra; Fernandes, JR (Autor) Outra; Souto, EB (Autor) Outra; Almeida, P (Autor) Outra; Vieira Ferreira, LFV (Autor) Outra; Reis, LV (Autor) Outra

Revista

Título: Bioorganic and Medicinal Chemistry

Vol. 25

Páginas: 3803-3814

ISSN: 0968-0896

Editora: Elsevier

Indexação

ISI Web of Knowledge - 24 Citações

Scopus - 25 Citações

Outras Informações

ID Authenticus: P-00M-VVE

DOI: 10.1016/j.bmc.2017.05.022

Abstract (EN): New unsymmetrical aminosquarylium cyanine dyes were synthesized and their potential as photosensitizers evaluated. New dyes, derived from benzothiazole and quinoline, were prepared by nucleophilic substitution of the corresponding O-methylated, the key intermediate that was obtained by methylation with CF3SO3CH3 of the related zwitterionic unsymmetrical dye, with ammonia and methylamine, respectively. All three news dyes herein described displayed intense and narrow bands in the Vis/NIR region (693-714 nm) and their singlet oxygen formation quantum yields ranged from 0.03 to 0.05. In vitro toxicity, in Caco-2 and HepG2 cells, indicated that dark toxicity was absent for concentrations up to 5 mu M (for the less active dye) or up to 1 mu M (for the two more active dyes). The three dyes present potential as photosensitizers, differing in irradiation conditions and period of incubation in the presence of irradiated dye. The less active dye needs a longer irradiation period to exhibit phototoxicity which is only evident after longer period of contact with cells (24 h). However, the remaining two more active dyes produce higher phototoxicity, even at shorter incubation periods (1 h), with shorter irradiation time (7 min). Although in different extents, these dyes show promising in vitro results as photosensitizers.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 12