Synthesis of axially disubstituted silicon phthalocyanines and investigation of photodynamic effects on HCT-116 colorectal cancer cell line

Photodiagnosis Photodyn Ther. 2018 Sep:23:83-88. doi: 10.1016/j.pdpdt.2018.05.009. Epub 2018 Jun 16.

Abstract

Photodynamic therapy is one of the hot topics in cancer studies. Photosensitizing chemical substrates are stimulated by light having a specific wavelength to cause fatal effect on different kinds of targets. In this study, axially 4-{[(1E)-2-furylmethylene]amino}phenol, 4-{[(1E)-2-thienylmethylene]amino}phenol and 4-{[(1E)-(4-nitro-2-thienyl)methylene]amino}phenol disubstituted silicon phthalocyanines were synthesized as Photosensitizers for photodynamic therapy in cancer treatment. The structural characterizations of these novel compounds were performed by a combination of FT-IR, 1H-NMR, UV-vis and mass. All these newly prepared compounds did not show aggregation at the concentration range of 2 × 10-6-12 × 10-6 M in tetrahydrofurane and also did not show aggregation in different organic solvents at 2 × 10-6 M concentration. Phthalocyanines synthesized in this study were tested on HCT-116 colorectal cancer cells and stimulated by light has wavelength of 680 nm. The toxic effects on cancer cells which are caused by different concentrations of photosensitizing molecules have been examined and compared with the toxic effects on cancer cells that were kept in the dark. It is confirmed that these molecules caused toxic effects on colorectal cancer cells when they were stimulated by light but there was no toxic effect in the dark.

Keywords: Colorectal cancer; HCT-116; Photodynamic therapy; Silicon phthalocyanine; Synthesis.

MeSH terms

  • Colorectal Neoplasms / drug therapy*
  • HCT116 Cells
  • Humans
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Organosilicon Compounds / chemistry
  • Organosilicon Compounds / pharmacology*
  • Photochemotherapy / methods*
  • Photosensitizing Agents / pharmacology*
  • Spectroscopy, Fourier Transform Infrared

Substances

  • Indoles
  • Organosilicon Compounds
  • Photosensitizing Agents
  • silicon phthalocyanine