卟啉富勒烯二元复合物的合成及性质研究化学;有机化学专业论文.docxVIP

摘要摘要 摘要 摘要 卟啉类化合物由于具有优异的细胞内吞能力，和较好的癌细胞靶向性使其 较早被应用于光动力学治疗。富勒烯分子在受到光激发后，具有较高的三重激 发态效率，从而能够通过产生激发态氧而被用于光动力学治疗，但是由于其激 发波长处于紫外区，对于正常细胞同样具有较强的破坏作用，同时其在癌细胞 中靶向富集的能力不强，从而严重阻碍了其实际应用。如果将具有良好癌细胞 靶向性的卟啉化合物与富勒烯相结合，不仅能改善其靶向富集的能力，同时利 用卟啉化合物较宽的光吸收范围，也能避免在治疗过程中对正常细胞产生强的 光敏性毒性。 本文利用CuI催化的多组分反应，设计合成了一种新型脒键键连的卟啉一富 勒烯二元复合物l，并利用Y．环糊精将复合物1和氨基卟啉2、富勒烯的参比单 体进行包合，制成了具有一定水溶性的Y．环糊精包合物。我们利用小鼠腹部单核 巨噬细胞瘤(RAW 264．7)检测了以上三种包合物在5x10西mol／L、lxl0。6 mol／L、 2x10’7mol／L浓度下的光动力学治疗作用。实验表明，光照条件下三种光敏剂都 具有明显的细胞毒性，而卟啉．富勒烯体系在光照下的细胞毒性效果要明显优于 卟啉、富勒烯单体包合物。新型卟啉．富勒烯二元复合物的合成不仅为拓展不同 的给受体化合物的光动力学研究提供了新的思路，同时包合物的制备方法也能够 解决类似体系水溶性差的问题。 由于卟啉．富勒烯共价键连体系具有复杂的电子能量转移过程，所以本文还 设计了卟啉类衍生化的环糊精，试图研究非共价键连卟啉．富勒烯体系与共价键 连体系的光动力学治疗效果差异。 关键词：卟啉；富勒烯；包合物；光动力学治疗 Abstract Abstract Porphyrins have been widely applied in photodynamic therapy(PDT)due to 也eir excellent endocytic capacity and enrichment ability in cancel．Fullerene can also be used in PDT．When exposed under light，it call be excited to its triplet excited states with high efficiency,and subsequently transfer the energy to oxygen atom to produce excited state oxygen which has significant cytotoxicity．But the practical application of fullerene is limited because the excitation light used in fullerene system is in the ultraviolet region which can also damage the normal cells，and it Can not be enriched in CanCer eell． If we connect the porphyrins to fuUerene，we can improve the enrichment ability of photosensitizer in cancer cells，and Can avoid the cytotoxicity tO the normal cells by using a relatively wide absorption wavelength of the porphyrins in visible region． In this thesis，we designed and synthesized a novel amidine bond connected porphyrin—fullerene compound l via CuI catalyzed multi—component reaction．Then we prepared three water soluble inclusion complexes through enclosing compound 1， referene compound 2 and fullerene wim 7-cyclodextdn．RAW 264．7 tumor cells were used tO detect the photocytotoxicity of these 7-CD inclusion complexes at concentration of 5xlO。6 mol／L，l×10。6 mol／L a