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Modulating the phototoxicity and selectivity of a porphyrazine towards epidermal tumor cells by coordination with metal ions.
Pinheiro, Pedro A; Pereira, Gabriel F M; Cunha, Leandro O; Leal, Julia P S C; Alvarenga, Meiry E; Martins, Felipe T; Silva, Heveline; Milani, Jorge L S; Tasso, Thiago T.
Afiliación
  • Pinheiro PA; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, 31270-901, Brazil.
  • Pereira GFM; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, 31270-901, Brazil.
  • Cunha LO; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, 31270-901, Brazil.
  • Leal JPSC; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Juiz de Fora, Juiz de Fora, Minas Gerais, 36036-900, Brazil.
  • Alvarenga ME; Institute of Chemistry, Universidade Federal de Goiás, Goiânia, Goiás, 74001-970, Brazil.
  • Martins FT; Institute of Chemistry, Universidade Federal de Goiás, Goiânia, Goiás, 74001-970, Brazil.
  • Silva H; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, 31270-901, Brazil.
  • Milani JLS; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Juiz de Fora, Juiz de Fora, Minas Gerais, 36036-900, Brazil.
  • Tasso TT; Chemistry Department, Institute of Exact Sciences, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, 31270-901, Brazil. thiago@qui.ufmg.br.
Photochem Photobiol Sci ; 23(9): 1757-1769, 2024 Sep.
Article en En | MEDLINE | ID: mdl-39242437
ABSTRACT
Porphyrazines (Pzs) are porphyrin derivatives that show potential application as photosensitizers for photodynamic therapy (PDT), but are still far less explored in the literature. In this work, we evaluate how the photophysics and phototoxicity of the octakis(trifluoromethylphenyl)porphyrazine (H2Pz) against tumor cells can be modulated by coordination with Mg(II), Zn(II), Cu(II) and Co(II) ions. Fluorescence and singlet oxygen quantum yields for the Pzs were measured in organic solvents and in soy phosphatidylcholine (PC) liposomes suspended in water. While H2Pz and the respective complexes with Cu(II) and Co(II) showed very low efficiency to fluoresce and to produce 1O2, the Mg(II) and Zn(II) complexes showed significantly higher quantum yields in organic solvents. The fluorescence of these two Pzs in the liposomes was sensitive to the fluidity of the membrane, showing potential use as viscosity markers. The cytotoxicity of the compounds was tested in HaCaT (normal) and A431 (tumor) cells using soy PC liposomes as drug carriers. Despite the low 1O2 quantum yields in water, the Mg(II) and Zn(II) complexes showed IC50 values against A431 cells in the nanomolar range when activated with low doses of red LED light. Their phototoxicity was ca. three times higher for the tumor cells compared to the normal ones, showing promising application as photosensitizers for PDT protocols. Considering that H2Pz and the respective Co(II) and Cu(II) complexes were practically non-phototoxic to the cells, we demonstrate the importance of the central metal ion in the modulation of the photodynamic activity of porphyrazines.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Porfirinas / Fármacos Fotosensibilizantes / Liposomas Límite: Humans Idioma: En Revista: Photochem Photobiol Sci Asunto de la revista: BIOLOGIA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Porfirinas / Fármacos Fotosensibilizantes / Liposomas Límite: Humans Idioma: En Revista: Photochem Photobiol Sci Asunto de la revista: BIOLOGIA / QUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Brasil Pais de publicación: Reino Unido