Novel phthalocyanines containing resorcinol azo dyes; synthesis, determination of pKa values, antioxidant, antibacterial and anticancer activity

Abstract

There are many studies about effects on health of compounds having azo groups in literature. However, anticancer, antimicrobial and antioxidant properties of phthalocyanines containing azo dyes are unknown. Therefore, the new metallophthalocyanines (M: Mn, Co, Zn) substituted with resorcinol azo dyes were synthesized and anticancer, antimicrobial and antioxidant properties investigated. All phthalocyanines were synthesized by the microwave assisted method. The structures were characterized by elemental analysis, H-1 NMR, C-13 NMR, UV/vis, IR and Mass spectroscopy techniques. The antioxidant capacities were analyzed through radical scavenging of DPPH and chelating ability to ferrous cation. The highest DPPH activity was obtained from compounds (1c and 2c) and the best ferrous ion chelating activity was determined from compound 2. The antibiotic activities were evaluated by disc diffusion method. Compound 2 exhibited antibacterial activity against studied bacteria, but the other compounds had no significant antibacterial effect. Cytotoxicity, apoptotic and necrotic effects were examined on cancer cells MCF-7 and healthy fibroblast cells. Compounds 1, 1a and 2a seem to be proper for the future cancer therapy researches. pKa values were determined by potentiometrically according to the half-neutralization method in N,N-dimethyl formamide. The effect of pH on the electronic absorption spectra of compounds (1, 2, 1c and 2c) was reported. The newly synthesized compounds show positive solvatochromism behavior. (C) 2015 Elsevier B.V. All rights reserved.