Assessing amphiphilic ABAB Zn(II) phthalocyanines with enhanced photosensitization abilities in in vitro photodynamic therapy studies against cancer

Autors/es

Revuelta-Maza, Miguel Á.; Mascaraque, Marta; González-Jiménez, Patricia; González-Camuñas, Arturo; Nonell, Santi; Juarranz, Ángeles; de la Torre, Gema; Torres, Tomás

Abstract

We have previously demonstrated that singlet oxygen photosensitization abilities of Zn(II) phthalocyanines (Zn(II)Pcs) are enhanced through α-functionalization with bulky fluorinated substituents (i.e., bis(trifluoromethyl)phenyl units) at facing positions of ABAB Zn(II)Pcs, where A and B refer to differently functionalized isoindoles. In this work, we have prepared the Zn(II)Pc ABAB 1 endowed with hydrophilic triethylene glycol monomethyl ether (i.e., at the A isoindoles) to provide solubility in aqueous media, together with its A₃B and A₄ counterparts, and compared their ability to behave as photosensitizers for photodynamic therapy. All photophysical data, aggregation studies and preliminary in vitro biological assays in cell cultures of SCC-13 (squamous cell carcinoma) and HeLa (cervical cancer cells), have proved ABAB 1 as the best photosensitizer of the series.