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

Tarhouni M., Durand D., Onal E., Aggad D., Isci Ü., Ekineker G., ...Daha Fazla

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, cilt.22, sa.7, ss.552-561, 2018 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 22 Sayı: 7
  • Basım Tarihi: 2018
  • Doi Numarası: 10.1142/s1088424618500554
  • Dergi Adı: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.552-561
  • Anahtar Kelimeler: phthalocyanine, photodynamic therapy, mitochondrion targeting, triphenylphosphonium, PHOTOCHEMICAL PROPERTIES, THERAPY, MECHANISMS, GENERATION
  • Marmara Üniversitesi Adresli: Hayır

Özet

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.