The new water soluble zinc(II) phthalocyanines substituted with morpholine groups- synthesis and optical properties

Khezami K., Harmandar K., BAĞDA E., BAĞDA E., Sahin G., Karakodak N., ...More

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, vol.401, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 401
  • Publication Date: 2020
  • Doi Number: 10.1016/j.jphotochem.2020.112736
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Agricultural & Environmental Science Database, BIOSIS, Chemical Abstracts Core, Chimica, INSPEC
  • Keywords: Zinc phthalocyanine, Water soluble, Photophysical, Photochemical, DNA binding, BSA binding, PHOTODYNAMIC THERAPY, DNA PHOTOCLEAVAGE, DNA/BSA BINDING, PHOTOSENSITIZERS, DERIVATIVES, COBALT(II)
  • Sivas Cumhuriyet University Affiliated: Yes


Two new tetra- or octa-substituted zinc(II) phthalocyanines (1 and 2) bearing 3-(morpholinomethyl)phenyl groups were synthesized via Suzuki-Miyaura coupling method. These phthalocyanines (1 and 2) were converted to their water-soluble derivatives (1Q and 2Q) by quaternization of nitrogen atoms on the morpholine groups. The photochemical and photophysical properties of the non-ionic zinc(II) phthalocyanines (1 and 2) were explored in DMSO. On the other hand, these properties of the quaternized cationic derivatives (1Q and 2Q) were studied in both DMSO and aqueous solutions for determination of their photosensitizing capabilities in photodynamic therapy. The ct-DNA interaction of synthesized 1Q and 2Q were investigated and binding constants were found as 6.3 x 10(4) and 1.5 x 10(5) M, respectively. The binding constant values were found at similar levels of ethidium bromide (EB), which is a well-known intercalator. The spontaneous and exothermic nature of binding mechanisms were proved according to the calculated thermodynamic constants. Strong interactions of 1Q and 2Q with ct-DNA were also found with EB displacement assay and gel electrophoresis. Additionally, the bovine serum albumin (BSA) binding behavior of the new compounds (1Q and 2Q) were determined in water solution to verify the transporting capability of these phthalocyanines in the circulatory system and these values were found as 7.0 x 10(5) and 1.6 x 10(7) M-1 for 1Q and 2Q, respectively.