Exocyclically metallated tetrapyridinoporphyrazine as a potential photosensitizer for photodynamic therapy

Photochem Photobiol Sci. 2019 Nov 1;18(11):2792-2803. doi: 10.1039/c9pp00336c. Epub 2019 Oct 18.

Abstract

We report the first exocyclically metallated tetrapyridinoporphyrazine, [tetrakis-(trans-Pt(NH3)2Cl)-tetra(3,4-pyrido)porphyrazine-zinc(ii)](NO3)4 (4), synthesized in a multistep synthesis starting from 3,4-pyridinedicarbonitrile (1). The synthetic procedure involved a platination reaction of the intermediate tetra(3,4-pyrido)porphyrazine-zinc(ii) (2), whereby the zinc(ii) enhanced the solubility of the intermediate enabling the platination reaction. A similar approach to synthesize [tetrakis-(trans-Pt(NH3)2Cl)-tetra(3,4-pyrido)porphyrazine](NO3)4 (5) failed due to the unsuitable solubility properties of the intermediate tetra(3,4-pyrido)porphyrazine (3). The final product 4 and the intermediates were characterized, the photochemical and photophysical properties were determined and the photocytotoxicities were investigated. We demonstrate that the platinated tetra-pyridinoporphyrazine 4 is a potential photosensitizer for photodynamic therapy (PDT).

MeSH terms

  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Humans
  • Light
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Photochemotherapy
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology
  • Porphyrins / chemical synthesis
  • Porphyrins / chemistry*
  • Porphyrins / pharmacology
  • Reactive Oxygen Species / metabolism
  • Spectrometry, Fluorescence
  • Stereoisomerism
  • Zinc / chemistry*

Substances

  • Photosensitizing Agents
  • Porphyrins
  • Reactive Oxygen Species
  • Zinc