Triphenylphosphonium-substituted phthalocyanine: Design, synthetic strategy, photoproperties and photodynamic activity


Tarhouni M., Durand D., Onal E., Aggad D., Isci U., Ekineker G., ...More

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.22, no.7, pp.552-561, 2018 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 22 Issue: 7
  • Publication Date: 2018
  • Doi Number: 10.1142/s1088424618500554
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded
  • Page Numbers: pp.552-561
  • Keywords: phthalocyanine, photodynamic therapy, mitochondrion targeting, triphenylphosphonium, PHOTOCHEMICAL PROPERTIES, THERAPY, MECHANISMS, GENERATION

Abstract

In line with current efforts to direct PDT photosensitizers to specific organelles such as mitochondria, a triphenylphosphonium-tetrasubstituted Zn phthalocyanine was designed, taking into account synthetic constraints. Triphenylphosphonium moieties were successfully introduced on alkyl bromide substituents on a pre-formed phthalocyanine. Photophysical and photochemical measurements showed that the photoproperties of the Zn phthalocyanine core were not affected by the triphenylphosphonium groups. Biological investigations demonstrated the dark innocuousness of the phthalocyanine up to 1 mu M, a concentration that exhibited a powerful phototoxicity. Cell death was confirmed to be photodynamically induced thanks to reactive oxygen species detection experiments. Nonetheless, the triphenylphosphonium moieties did not promote the accumulation of the phthalocyanine in mitochondria as significantly as expected.