A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties

Journal of the Brazilian Chemical Society

Universidade de Aveiro, Aveiro, Portugal¹  Universidade de São Paulo, Ribeirão Preto, Brazil¹  Serra, Osvaldo A.¹  Vinhado, Fábio S.¹  Neri, Cláudio R.¹  Iamamoto, Yassuko¹  Martins, Patrícia R.¹  Tedesco, Antonio Cláudio¹  Cavaleiro, José A. S.¹  Silva, Ana Margarida G.¹  Tomé, Augusto C.¹  Ribeiro, Anderson O.¹  Neves, Maria G. P. M. S.¹  Maestrin, Ana Paula J.¹ 

关键词: photosensitizer;    photodynamic activity;    chlorins;    photobleaching;   

DOI  :  10.1590/S0103-50532004000600021

学科分类：化学（综合）

来源: SciELO

【 摘 要 】

Photodynamic therapy (PDT) is based on the accumulation of a photosensitizer, such as a porphyrin or a chlorin, in a malignant tissue after its administration. Chlorins exhibit photophysical properties similar to those of the porphyrin macrocycles, but with intensified and red-shifted Q bands, making chlorin-containing systems even better candidates for PDT. In this contribution, we report the synthesis of 5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)porphyrin, (2) and its transformation to the novel chlorin derivatives 4, (5,10,20-tris(pentafluorophenyl)-15-(4-pyridyl)-tetrahydro-1H- N-methyl-pyrrolo [3,4-b]porphyrin and 5, (5,10,15-tris(pentafluorophenyl)-20-(4-pyridyl)-tetrahydro-1H- N-methyl-pyrrolo[3,4-b]porphyrin) by 1,3-dipolar cycloaddition with an azomethine ylide. The new products have been characterized by UV-Vis, 1H NMR and FAB-MS. The photophysics, photochemical and photobleaching properties of chlorin 4 have been evaluated. Its quantum yield of photobleaching (fPb, mol Einstein-1) was 0.047±0.014. In order to demonstrate the production of 1O2 when 4 is used as a photosensitizer, uric acid tests have been carried out. The results indicate that chlorin 4 can be considered a promising photosensitizer in PDT.

【 授权许可】

Unknown