Non-aggregated axially disubstituted silicon phthalocyanines: Synthesis, DNA cleavage and in vitro cytotoxic/phototoxic anticancer activities against SH-SY5Y cell line

Barut B., Biyikhoglu Z., YALÇIN C. Ö., Abudayyak M.

DYES AND PIGMENTS, cilt.172, 2020 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 172
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.dyepig.2019.107794
  • Dergi Adı: DYES AND PIGMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aerospace Database, Chimica, Communication Abstracts, Compendex, INSPEC, Metadex, Civil Engineering Abstracts
  • Anahtar Kelimeler: Non-aggregated, Silicon phthalocyanine, DNA damage, Neuroblastoma, Phototoxicity, PHOTODYNAMIC THERAPY, PHOTOCHEMICAL PROPERTIES, SOLUBLE PHTHALOCYANINES, ZN(II) PHTHALOCYANINE, DNA/BSA BINDING, TOPOISOMERASE-I, PHOTOCLEAVAGE, BODIPY, MECHANISMS
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

In this paper, axially {6-[3-(dimethylamino)phenoxy]hexyl}oxy and {6-[3-(diethylamino)phenoxy]hexyl}oxy groups substituted silicon phthalocyanines were synthesized by reaction of SiPcCl2 with 6-[3-(dimethylamino) phenoxy]hexan-1-ol and 6-[3-(diethylamino)phenoxy]hexan-1-ol in the presence of NaH in toluene. The identity of silicon phthalocyanines was confirmed by H-1 NMR, C-13 NMR, FT-IR, UV-Vis and mass spectrometry. The aggregation behaviors of the compounds were examined in different solvents and concentrations in DMSO. In all studied solvents and concentrations, the compounds were non-aggregated. These compounds have been screened for DNA cleavage using agarose gel electrophoresis and cytotoxic/phototoxic effects against human neuroblastoma cell line (SH-SY5Y) using MTT assay. The results showed that the compounds (1a and 2a) cleaved significantly supercoiled plasmid DNA in a concentration-dependent fashion with irradiation. The compounds (1a and 2a) exhibited low dark toxicity but excellent phototoxicity with IC50 values 0.56 and 4.46 mu M, respectively toward SH-SY5Y cell line. The finding highlights that these compounds presented great potential for photodynamic therapy.