Water soluble {2-[3-(diethylamino)phenoxy]ethoxy} substituted zinc(II) phthalocyanine photosensitizers

Abstract

The new peripherally and non-peripherally tetra-(2-[3-(diethylamino)phenoxy] ethoxy) substituted zinc phthalocyanines (2a and 3a) were synthesized by cyclotetramerization of phthalonitrile derivatives (2 and 3). 2[3-(diethylamino)phenoxy] ethoxy group was chosen as substituent because the quaternization of the diethylamino functionality on the structure of this group produced water soluble zinc phthalocyanines (2b and 3b). The water solubility is very important for many different applications such as photosensitizers in the photodynamic therapy of cancer because the water soluble photosensitizers can be injected directly to the body and they can transport to cancer cells through blood stream. The new compounds were characterized by using elemental analysis, UV-vis, IR, H-1 NMR, C-13 NMR and mass spectroscopies. The photophysical and photochemical properties of these novel photosensitizer compounds were examined in DMSO (both non-ionic and ionic complexes) and in PBS (for ionic complexes) solutions. The investigation of these properties is very important for the usage of the compounds as photosensitizers for PDT because determination of these properties is the first stage of potential of the compounds as photosensitizers. The bovine serum albumin (BSA) and DNA binding behaviour of the studied water soluble zinc (II) phthalocyanines were also investigated in PBS solutions for the determination of biological activity of these compounds. (C) 2014 Elsevier B.V. All rights reserved.