The water-soluble zwitterionic and cationic tetra-substituted zinc(II) phthalocyanines: Synthesis, photophysical, photochemical and protein binding properties

The synthesis and characterization of tetra-{2-[N-((3-dimethylamino)propyl)carbamate]oxyethyl} substituted zinc(II) phthalocyanine (ZnPc) and its sulfobetaine (S-ZnPc), betaine (B-ZnPc), N-Oxide (N-ZnPc) and cationic (Q-ZnPc) derivatives were described in this study. All novel phthalocyanines were characterized by UV–Vis, FT-IR, 1H NMR, mass spectroscopic techniques and elemental analysis as well. The solubility of these phthalocyanines was enhanced in polar solvents and aquatic media by the conversion of amidoamine groups on the substituents to the zwitterionic sulfobetaine, betaine, N-Oxide, and quaternary ammonium counterparts which make them promising candidates for treatment of cancer via photodynamic therapy (PDT) method. Although the photophysical and photochemical properties of newly synthesized tetra-{2-[N-((3-dimethylamino)propyl)carbamate]oxyethyl} substituted zinc(II) phthalocyanine (ZnPc) was investigated in DMSO, its zwitterionic and cationic derivatives were examined in both DMSO and aqueous solutions. The binding behavior of zwitterionic and cationic zinc(II) phthalocyanines were investigated by bovine serum albumin (BSA) protein in aqueous solutions for determination of transportation abilities of these phthalocyanines in the blood.

The novel tetra-{2-[N-((3-dimethylamino)propyl)carbamate]oxyethyl} substituted zinc(II) phthalocyanine (ZnPc) and its sulfobetaine (S-ZnPc), betaine (B-ZnPc), N-Oxide (N-ZnPc) and quaternized (Q-ZnPc) derivatives were synthesized for the first time. All the synthesized zwitterionic (S-ZnPc, B-ZnPc and N-ZnPc) and cationic (Q-ZnPc) phthalocyanines showed excellent solubility in water. These phthalocyanines are promising as photosensitizers for cancer treatment by photodynamic therapy due to their high singlet oxygen generation properties.Figure optionsDownload as PowerPoint slide