A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties
A novel chlorin derivative of Meso-tris(pentafluorophenyl)-4-pyridylporphyrin: synthesis, photophysics and photochemical properties
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DOI：
10.1590/s0103-50532004000600021
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发表时间：
2004-12-01
影响因子：
1.4
通讯作者：
Cavaleiro, José A. S.
中科院分区：
文献类型：
--
作者：
Maestrin, Ana Paula J.;Ribeiro, Anderson O.;Cavaleiro, José A. S.
光动力疗法（PDT）基于光敏剂的积累。例如卟啉或二氢卟酚，在施用后存在于恶性组织中。二氢卟酚表现出与卟啉大环化合物类似的光物理性质，但具有增强和红移的 Q 带，使得含二氢卟酚的系统成为 PDT 的更好候选者。在这篇文章中，我们报告了 5,10,15-三(五氟苯基)-20-(4-吡啶基)卟啉的合成，(2) 及其转化为新型二氢卟酚衍生物 4。(5,10.20-三(五氟苯基)-15-(4-吡啶基)四氢-1H-N-甲基-吡咯 [3,4-b]卟啉和5,(5,10,15-三(五氟苯基)-20-(4吡啶基)-四氢-1H-N-甲基-吡咯并[3,4-b]卟啉)通过与甲亚胺叶立德进行1,3-偶极环加成反应。新产品已通过UV-Vis.H-1 NMR和 FAB-MS。对二氢卟酚 4 的光物理、光化学和光漂白特性进行了评估。其光漂白量子产率(phi(Pb)，mol Einstein(-1))为0.047+/-0.014。为了证明4作为光敏剂时O-1(2)的产生，进行了尿酸测试。结果表明二氢卟酚4可以考虑 一种在 PDT 中很有前途的光敏剂。
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.