Here we report the synthesis of eleven new BODIPYs (14–24) characterized by the presence of an aromatic ring on the 8 (meso) position and of iodine atoms on the pyrrolic 2,6 positions. These molecules, together with twelve BODIPYs already reported by us (1 − 12), represent a large panel of BODIPYs showing different atoms or groups as substituent of the aromatic moiety. Two physico-chemical features (1O2 generation rate and lipophilicity), which can play a fundamental role in the outcome as photosensitizers, have been studied. The in vitro photo-induced cell-killing efficacy of 23 PSs was studied on the SKOV3 cell line treating the cells for 24 h in the dark then irradiating for 2 h with a green LED device (fluence 25.2 J/cm2). The cell-killing efficacy was assessed with the MTT test and compared with that one of meso un-substituted compound (13). In order to understand the possible effect of the substituents, a predictive quantitative structure-activity relationship (QSAR) regression model, based on theoretical holistic molecular descriptors, was developed. The results clearly indicate that the presence of an aromatic ring is fundamental for an excellent photodynamic response, whereas the electronic effects and the position of the substituents on the aromatic ring do not influence the photodynamic efficacy.

Synthesis, photodynamic activity, and quantitative structure-activity relationship modelling of a series of BODIPYs

CARUSO, ENRICO;GARIBOLDI, MARZIA BRUNA;GRAMATICA, PAOLA;BANFI, STEFANO
2017-01-01

Abstract

Here we report the synthesis of eleven new BODIPYs (14–24) characterized by the presence of an aromatic ring on the 8 (meso) position and of iodine atoms on the pyrrolic 2,6 positions. These molecules, together with twelve BODIPYs already reported by us (1 − 12), represent a large panel of BODIPYs showing different atoms or groups as substituent of the aromatic moiety. Two physico-chemical features (1O2 generation rate and lipophilicity), which can play a fundamental role in the outcome as photosensitizers, have been studied. The in vitro photo-induced cell-killing efficacy of 23 PSs was studied on the SKOV3 cell line treating the cells for 24 h in the dark then irradiating for 2 h with a green LED device (fluence 25.2 J/cm2). The cell-killing efficacy was assessed with the MTT test and compared with that one of meso un-substituted compound (13). In order to understand the possible effect of the substituents, a predictive quantitative structure-activity relationship (QSAR) regression model, based on theoretical holistic molecular descriptors, was developed. The results clearly indicate that the presence of an aromatic ring is fundamental for an excellent photodynamic response, whereas the electronic effects and the position of the substituents on the aromatic ring do not influence the photodynamic efficacy.
2017
www.elsevier.com/locate/jphotobiol
BODIPY; Photodynamic therapy; QSAR; Singlet oxygen; Tumor cells; Apoptosis; Boron Compounds; Cell Line, Tumor; Chromatography, High Pressure Liquid; Humans; Quantitative Structure-Activity Relationship; Spectrometry, Mass, Electrospray Ionization; Spectrum Analysis; Photochemotherapy; Radiation; Radiological and Ultrasound Technology; Biophysics; Radiology, Nuclear Medicine and Imaging
Caruso, Enrico; Gariboldi, MARZIA BRUNA; Sangion, Alessandro; Gramatica, Paola; Banfi, Stefano
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11383/2061472
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