Modulation of singlet oxygen generation and amphiphilic properties of trihydroxylated monohalogenated porphyrins

TOPKAYA TAŞKIRAN D., Arnoux P., DUMOULIN F.

JOURNAL OF PORPHYRINS AND PHTHALOCYANINES, vol.19, no.10, pp.1081-1087, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 19 Issue: 10
  • Publication Date: 2015
  • Doi Number: 10.1142/s1088424615500893
  • Journal Name: JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1081-1087
  • Keywords: porphyrin, heavy atom effect, fluorescence, singlet oxygen generation, triplet state, amphiphilicity, photosensitizer, PHOTODYNAMIC THERAPY, PHOTOSENSITIZERS, PHTHALOCYANINE, CANCER, FLUORESCENCE, THERANOSTICS, PLATINUM(II), AGENTS, YIELDS
  • Dokuz Eylül University Affiliated: Yes

Abstract

Two of the properties important for photodynamic therapy applications are systematically investigated on a trihydroxylated monohalogenated porphyrin core. Singlet oxygen generation can be increased thanks to the heavy atom effect, frequently provided by the introduction of halogen atoms on the photosensitizer. We compare the effect of the presence of the four halogen atoms with the analogous halogen-free porphyrin. Cell uptake is crucial as well for successful photodynamic outcome and is directly related to the amphiphilicity of the molecule. The five derivatives bearing H, F, Cl, Br or I atoms are compared in this regard. The presence of iodine atom induces a sharp difference in singlet oxygen generation compared to all the other derivatives investigated, but increases its lipophilicity, still in the limits suitable for biomedical applications.