Obtenção e caracterização de ftalocianinas com substituintes quirais com potencial aplicação em terapia fotodinâmica / Synthesis and characterization ofphthalocyanines with chiralsubstituints with potencialfor use in Photodynamic Therapy

AUTOR(ES)
FONTE

IBICT - Instituto Brasileiro de Informação em Ciência e Tecnologia

DATA DE PUBLICAÇÃO

29/02/2012

RESUMO

The main objective of this project is the synthesis and characterization of new phthalocyanines with chiral substituents to improve their photophysical and photochemical properties for use as photosensitizers in Photodynamic Therapy. Three new phthalocyanines were synthesized and characterized, one with the racemic mixture of 1-(4-bromophenyl)- ethanol, and the other two with the pure enantiomers, (R) - 1 - ( 4-bromophenyl)-ethanol and (S)-1-(4-bromophenyl)-ethanol. The compounds were characterized by 1H NMR spectroscopy and mass spectrometry. The photophysical and photochemical characteristics were determined by analysis of UV-Vis absorption, excitation and emission spectra, and the determination of the aggregation constant values. The quantum yield of generation of reactive species was determined by the indirect method, using the diphenylisobenzofuran (DPBF) as suppressor. The results showed three different values of aggregation constant for phthalocyanines sinthesized, with the macrocycle modify with enantiomeric (R) alcohol with the lowest one. The results also showed that this same phthalocyanines has a bigger quantum yield of generation of reactive oxygen species than the others. These two results are consistent with the fact that a lower aggregation results in a higher quantum yield in the generation of reactive oxygen species, and that the geometry of the substituents studied is directly related to the behavior of phthalocyanines. With respect to biological results, established by analysis of fluorescence microscopy, the three phthalocyanines interact with the cell line studied, MCF7 (breast epithelial tissue). However, through the images, was not possible to define the exact content of each compound that interact with the cell.

ASSUNTO(S)

quimica ftalocianianinas terapia fotodinâmica fotossensibilizador fotoquímica síntese phthalocyanine photodynamic therapy photosensitizer photochemistry synthesis

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