巯嘌呤核苷的选择性合成和巯嘌呤核苷卟啉合成的初步探讨
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摘要
以恶性肿瘤(癌症)、心血管疾病以及糖尿病等为代表的非传染性疾病,正在成为人类致命的“杀手”,其中癌症威胁居首。白血病是严重危害人类健康的血液系统恶性肿瘤,目前化疗是临床治疗白血病最常用的方法,但疗效并不令人满意；使用抗癌药物是治疗白血病的有效途径之一。探索合成并开发定位作用强、抗癌活性大、毒副作用小的治疗白血病的新型抗癌药物具有非常重要的意义。根据药物类似设计原理和拼合原理,设计并初步探讨了β-巯嘌呤核苷卟啉的合成方法,对实验条件进行了探讨,没有得到相应的巯嘌呤核苷卟啉,对实验结果分析,结构表征确定了所得化合物结构,设计实验验证所得的结果,并对所得化合物的抗癌活性进行初步的探讨。
本论文包括以下几个方面的内容：
(1)综述了卟啉类化合物的应用、核苷卟啉类化合物的合成应用和嘌呤核苷类化合物的应用及合成进展。
(2)设计并成功选择性合成了9-β-D-巯嘌呤核苷,通过正交实验探究了其最优的条件。
(3)合成并讨论了5-[4-(2-溴乙氧基)]苯基-10,15,20-三苯基卟啉的合成条件,合成并简捷分离得到较纯的5-(4-溴甲氧基)苯基-10,15,20-三苯基卟啉。
(4)根据药物设计的拼合原理和类似物设计原理,探索了3类β-巯嘌呤核苷卟啉化合物合成条件,没有得到相应的核苷卟啉,获得了新的化合物,且用1 HNMR, UV, IR, MS等对获得的化合物进行了结构表征,确定了所得化合物的结构,并对实验结果进行分析,设计了验证实验,证实了上面的实验结论。
(5)测试所得到的化合物的紫外和荧光光谱；采用MTT比色法,对所得到的化合物对宫颈癌细胞(HELA)和肝癌细胞(BEL-7402)的体外抗癌活性进行了初步的探讨。实验结果表明对两种癌细胞有一定的抑制作用。
The non-communicable diseases, such as malignant tumor (cancer), cardiovascular disease, and diabetes are becoming the most deadly "killer" for human. Cancer was the biggest threat among them. Leukemia is a serious body immune system cancer. At present, chemotherapy is widely applied for clinical leukemia treatment. Antineoplastic antibiotic drug is one of the effective treatments for leukemia. However, antineoplastic antibiotic drugs used by now mostly have the disadvantage that they can not be directionally transported to the cancer cells and they have strong poison and side effect for human. Therefore, it is very important to explore and develop new anticancer drugs which are more active and specific in killing the cancer cell. In this thesis, according to the theories and methods of designing analg drugs and combination principles, theβ-mercaptopurine ribonucleoside-porphyrins were designed and studied. In despite of improving and discussing the experiment conditions, they were not obtained. We analysed and discussed the results, characterized the compounds we obtained. The results were testified by a series of experiments and their anticancer biological activities were preliminarily studied. The main contents were summarized as following:
(1) Recent research in application of porphyrin was reviewed. The synthesis and applicationsin of nucleoside-porphyrin and purine nucleoside were summarized here.
(2) 9-β-D-mercaptopurine nucleoside were designed and synthesized selectively and their optimal conditions were obtained from the orthogonal experiments.
(3) The excellent synthetic condition, simple sepration method of 5-(4-bromoethoxy)phenyl-10,15,20-triphenylporphyrin were obtained.
(4) According to the theories and methods of drug design (analog design and combination principles), three kinds ofβ-mercaptopurine ribonucleoside-porphyrins were designed and studied. We failed to get the target molecule but a new compound whose structure was characterized by MS, IR, and1H NMR spectra. The unexpected results were analysed and discussed and testified by a series of experiments.
(5) The ultraviolet-visible absorption spectra and fluorescence spectra were measured for above compounds. Investigation of their biological activities with two kinds of tumor cells including cell cycle(HELA) and liver cancer(BEL-7402) were preliminarily cultivated for the new porphyrins using MTT method. The result showed that these compounds can inhibit these cancer cells in some way.
本论文包括以下几个方面的内容：
(1)综述了卟啉类化合物的应用、核苷卟啉类化合物的合成应用和嘌呤核苷类化合物的应用及合成进展。
(2)设计并成功选择性合成了9-β-D-巯嘌呤核苷,通过正交实验探究了其最优的条件。
(3)合成并讨论了5-[4-(2-溴乙氧基)]苯基-10,15,20-三苯基卟啉的合成条件,合成并简捷分离得到较纯的5-(4-溴甲氧基)苯基-10,15,20-三苯基卟啉。
(4)根据药物设计的拼合原理和类似物设计原理,探索了3类β-巯嘌呤核苷卟啉化合物合成条件,没有得到相应的核苷卟啉,获得了新的化合物,且用1 HNMR, UV, IR, MS等对获得的化合物进行了结构表征,确定了所得化合物的结构,并对实验结果进行分析,设计了验证实验,证实了上面的实验结论。
(5)测试所得到的化合物的紫外和荧光光谱；采用MTT比色法,对所得到的化合物对宫颈癌细胞(HELA)和肝癌细胞(BEL-7402)的体外抗癌活性进行了初步的探讨。实验结果表明对两种癌细胞有一定的抑制作用。
The non-communicable diseases, such as malignant tumor (cancer), cardiovascular disease, and diabetes are becoming the most deadly "killer" for human. Cancer was the biggest threat among them. Leukemia is a serious body immune system cancer. At present, chemotherapy is widely applied for clinical leukemia treatment. Antineoplastic antibiotic drug is one of the effective treatments for leukemia. However, antineoplastic antibiotic drugs used by now mostly have the disadvantage that they can not be directionally transported to the cancer cells and they have strong poison and side effect for human. Therefore, it is very important to explore and develop new anticancer drugs which are more active and specific in killing the cancer cell. In this thesis, according to the theories and methods of designing analg drugs and combination principles, theβ-mercaptopurine ribonucleoside-porphyrins were designed and studied. In despite of improving and discussing the experiment conditions, they were not obtained. We analysed and discussed the results, characterized the compounds we obtained. The results were testified by a series of experiments and their anticancer biological activities were preliminarily studied. The main contents were summarized as following:
(1) Recent research in application of porphyrin was reviewed. The synthesis and applicationsin of nucleoside-porphyrin and purine nucleoside were summarized here.
(2) 9-β-D-mercaptopurine nucleoside were designed and synthesized selectively and their optimal conditions were obtained from the orthogonal experiments.
(3) The excellent synthetic condition, simple sepration method of 5-(4-bromoethoxy)phenyl-10,15,20-triphenylporphyrin were obtained.
(4) According to the theories and methods of drug design (analog design and combination principles), three kinds ofβ-mercaptopurine ribonucleoside-porphyrins were designed and studied. We failed to get the target molecule but a new compound whose structure was characterized by MS, IR, and1H NMR spectra. The unexpected results were analysed and discussed and testified by a series of experiments.
(5) The ultraviolet-visible absorption spectra and fluorescence spectra were measured for above compounds. Investigation of their biological activities with two kinds of tumor cells including cell cycle(HELA) and liver cancer(BEL-7402) were preliminarily cultivated for the new porphyrins using MTT method. The result showed that these compounds can inhibit these cancer cells in some way.
引文
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