Synthesis, photophysical studies and anticancer activity of a new halogenated water-soluble porphyrin

Photochem Photobiol. Jul-Aug 2007;83(4):897-903. doi: 10.1111/j.1751-1097.2007.00073.x.


A water-soluble halogenated porphyrin, namely 5,10,15,20-tetrakis(2-chloro-3-sulfophenyl)porphyrin (TCPPSO(3)H), was prepared and evaluated as sensitizer for photodynamic therapy (PDT). Photophysical properties of TCPPSO(3)H, such as high photostability, long triplet lifetime and high singlet oxygen quantum yield suggest high effectiveness of this class of halogenated porphyrins in PDT. TCPPSO(3)H is non-toxic in the dark and causes a significant photodynamic effect examined against MCF7 (human breast carcinoma), SKMEL 188 (human melanoma) and S91(mouse melanoma) cell lines upon red light irradiation (cutoff < 600 nm) at low light doses. Time-dependent cellular uptake of TCPPSO(3)H reached plateau at 120 min and was the highest for S91, 20% lower for MCF7 and 70% lower for SKMEL 188. Our results show that this halogenated water-soluble porphyrin is an efficient photosensitizer and reveal the potential of this class of compounds as PDT agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Drug Screening Assays, Antitumor
  • Halogens / chemistry
  • Humans
  • Photochemistry*
  • Porphyrins / chemical synthesis*
  • Porphyrins / pharmacology*
  • Solubility
  • Tumor Cells, Cultured
  • Water / chemistry*


  • Antineoplastic Agents
  • Halogens
  • Porphyrins
  • Water