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

• Type: Article in International Scientific Journal
• Date: 2004

Authors

Maestrin, APJ (Author) Other; Ribeiro, AO (Author) Other; Tedesco, AC (Author) Other; Neri, CR (Author) Other; Vinhado, FS (Author) Other; Serra, OA (Author) Other; Martins, PR (Author) Other; Iamamoto, Y (Author) Other; Silva, AMG (Author) Other; Tome, AC (Author) Other; Neves, MGPMS (Author) Other; Cavaleiro, JAS (Author) Other

Journal

Title: Journal of the Brazilian Chemical Society

Vol. 15

Pages: 923-930

ISSN: 0103-5053

Publisher: Sociedade Brasileira de Quimica

Indexing

ISI Web of Knowledge - 30 Citations

Scopus - 32 Citations

Other information

Authenticus ID: P-000-7YX

DOI: 10.1590/s0103-50532004000600021

Abstract (EN): 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-(4pyridyl)-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.H-1 NMR and FAB-MS. The photophysics, photochemical and photobleaching properties of chlorin 4 have been evaluated. Its quantum yield of photobleaching (phi(Pb), mol Einstein(-1)) was 0.047+/-0.014. In order to demonstrate the production of O-1(2) 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 8