Cationic porphycenes as potential photosensitizers for antimicrobial photodynamic therapy

J Med Chem. 2010 Nov 11;53(21):7796-803. doi: 10.1021/jm1009555.


Structures of typical photosensitizers used in antimicrobial photodynamic therapy are based on porphyrins, phthalocyanines, and phenothiazinium salts, with cationic charges at physiological pH values. However, derivatives of the porphycene macrocycle (a structural isomer of porphyrin) have barely been investigated as antimicrobial agents. Therefore, we report the synthesis of the first tricationic water-soluble porphycene and its basic photochemical properties. We successfully tested it for in vitro photoinactivation of different Gram-positive and Gram-negative bacteria, as well as a fungal species (Candida) in a drug-dose and light-dose dependent manner. We also used the cationic porphycene in vivo to treat an infection model comprising mouse third degree burns infected with a bioluminescent methicillin-resistant Staphylococcus aureus strain. There was a 2.6-log(10) reduction (p < 0.001) of the bacterial bioluminescence for the PDT-treated group after irradiation with 180 J·cm(-2) of red light.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bacterial Infections / drug therapy*
  • Burns / drug therapy
  • Burns / microbiology
  • Candida / drug effects
  • Cations
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Male
  • Methicillin-Resistant Staphylococcus aureus
  • Mice
  • Mice, Inbred BALB C
  • Photochemotherapy*
  • Photosensitizing Agents / chemical synthesis*
  • Photosensitizing Agents / chemistry
  • Photosensitizing Agents / pharmacology
  • Porphyrins / chemical synthesis*
  • Porphyrins / chemistry
  • Porphyrins / pharmacology
  • Solubility
  • Staphylococcal Infections / drug therapy
  • Staphylococcal Infections / microbiology
  • Structure-Activity Relationship


  • Cations
  • Photosensitizing Agents
  • Porphyrins
  • porphycene