Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes

Bioorg Med Chem Lett. 2017 Jan 15;27(2):156-161. doi: 10.1016/j.bmcl.2016.11.094. Epub 2016 Dec 2.

Abstract

Sixteen porphyrins, including neutral, anionic and cationic meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins were herein evaluated in terms of their photosensitizing properties against HaCaT keratinocytes. After an initial screening, the cationic porphyrins were studied in more details, by both determining their log POW and performing PDT assays in lower porphyrin concentrations. Porphyrins presenting two or more adjacent positively charged groups, directly linked to the macrocycle meso positions, appeared to be the most effective photosensitizers. The present study also included the dicationic 5,10-diphenyl-15,20-di(1-methylpyridinium-4-yl)porphyrin (14b), which has previously shown promising results on a psoriasis-like in vivo model. Overall results indicated that the beneficial effect related to porphyrins on psoriasis can be related to the decreasing of keratinocyte viability. Furthermore, some of the cationic porphyrins studied appeared as candidates to be utilized as photosensitizers for psoriasis treatment.

Keywords: HaCaT keratinocytes; Photodynamic therapy (PDT); Photosensitizer; Porphyrins; Psoriasis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Humans
  • Keratinocytes / cytology
  • Keratinocytes / drug effects*
  • Light
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / pharmacology*
  • Porphyrins / chemical synthesis
  • Porphyrins / pharmacology*
  • Psoriasis / drug therapy
  • Pyridinium Compounds / chemical synthesis
  • Pyridinium Compounds / pharmacology*

Substances

  • 5,10-diphenyl-15,20-di(1-methylpyridinium-4-yl)porphyrin
  • Photosensitizing Agents
  • Porphyrins
  • Pyridinium Compounds