meso-5,10,15,20-四[4-(N-吡咯烷基)苯基]卟啉的合成及对牛血清白蛋白的作用

基于卟啉对癌细胞的特殊亲和作用和吡咯烷化合物的抗肿瘤及抗癌活性,设计并合成了具有吡咯烷结构的新型卟啉化合物——meso-5,10,15,20-四4-(N-吡咯烷基)苯基]卟啉(TBPPH2),利用荧光光度法和紫外-可见分光光度法研究了TBPPH2与牛血清白蛋白(BSA)的相互作用.实验发现,TBPPH2利用疏水作用力进入BSA的疏水性腔,与BSA形成配合物并引起BSA的静态荧光猝灭.在TBPPH2与BSA的相互作用过程中,TBPPH2与BSA以摩尔比1∶1牢固结合,TBPPH2与BSA分子中色氨酸间的最近距离r=2.4nm.反应平衡常数KA=2.51×104L/mol,反应熵变ΔS=84.18J/(mol·K),TBPPH2与BSA的结合常数KB=5.13×105L/mol.研究结果表明,吡咯烷基卟啉可能成为一类新型的抗肿瘤及抗病毒药物.

Synthesis of meso-5,10,15,20-Tetra[4-(N-pyrrolidinyl)phenyl] Porphyrin and Its Interaction with Bovine Serum Albumin

A novel pyrrolidino-porphyrin, meso-5,10,15,20-tetra4-(N-pyrrolidinyl)phenyl] porphyrin(TBPPH2), was synthesized based on the porphyrin′s special affinity for cancer cells and the antitumor activity of pyrrolidine compounds. Its structure was characterized by UV-Vis spectra, elemental analysis and 1HNMR. In order to study the possible anticancer activity of TBPPH2, the interaction model based on TBPPH2 and bovine serum albumin(BSA) was built, and the binding mechanism was studied with UV-Vis spectra and fluorescence spectra. The research results indicate that BSA strongly bind to TBPPH2 with the molar ratio of 1∶1, the hydrophobic force was the main binding force, the shortest binding distance r was 2.4 nm, the equilibrium constant KA was 2.51×104 L/mol, the reaction entropy ΔS was 84.18 J/(mol·K), the binding constant KB was 5.13×105 L/mol. The research results show that it is possible for the porphyrins with pyrrolidinyl groups to become a new type of the antitumor drugs.