靛玉红衍生物的合成及应用

发布时间：2018-04-26 05:12

本文选题：靛玉红 + 靛玉红肟　；参考：《天津理工大学》2014年硕士论文

【摘要】：靛玉红，也被称为炮弹树碱，是我国首创的抗白血病药。它是由两个吲哚环缩合而成的一个V字型分子，与靛蓝分子内的两个氢键不同，其分子内只有一个氢键，使得另一个吲哚环上的羰基氧原子由于没有形成氢键暴露在外，从而提供了与癌细胞DNA的结合位点。又因它的结构与鸟嘌呤相近，因而可以与鸟嘌呤相互作用而发生π-π络合，形成分子络合物。由此阻断了肿瘤细胞DNA的合成而发挥了抗癌作用。但由于靛玉红的高熔点,较差的脂溶性及水溶性，因此对靛玉红衍生物的研究成为科研工作者的研究热点。本论文主要工作如下：（1）对40%的粗品靛玉红进行柱层析分离提纯，，以氯仿和乙酸乙酯为洗脱剂，经过二次洗脱，干燥得紫红色结晶。利用IR，1HNMR，HRMS对其进行了结构表征，表明提取物成分单一，纯度高。（2）以提取后的靛玉红为原料，与盐酸羟胺，氢氧化钾反应得到靛玉红肟；在溶剂存在下与乙酰氯反应制得N-乙酰基靛玉红。利用IR，1HNMR，HR-MS对靛玉红肟及N-乙酰基靛玉红进行了结构表征。UV性能、荧光性能进行了测定，发现靛玉红乙酰化后，由于羰基的引入，使得N-乙酰基靛玉红具有良好的荧光性能，是一种新型的荧光探针化合物。（3）以N-乙酰基靛玉红为荧光探针，对阳离子表面活性剂D1821，阴离子表面活性剂SDS，两性离子表面活性剂BS-12的CMC分别进行了测定，测定结果与文献报道值一致。（4）以N-乙酰基靛玉红为荧光探针，通过对其与DNA相互作用的研究，发现N-乙酰基靛玉红与DNA的作用方式为静态猝灭，且有较高的灵敏度。
[Abstract]:Indirubin, also known as cannonine, is the first anti-leukemia drug in China. It is a V-shaped molecule formed by condensation of two indole rings, which is different from the two hydrogen bonds in indigo. There is only one hydrogen bond in the molecule, so that the carbonyl oxygen atom in the other indole ring is exposed because it does not form a hydrogen bond. This provides a binding site to cancer cell DNA. Because its structure is similar to that of guanine, it can interact with guanine to form 蟺-蟺 complex and form molecular complex. This blocked the synthesis of tumor cell DNA and played an anti-cancer role. However, due to the high melting point, poor fat solubility and water solubility of indirubin, the research of indirubin derivatives has become a research hotspot. The main work of this thesis is as follows: (1) 40% crude indirubin was separated by column chromatography, chloroform and ethyl acetate were used as eluent, after secondary elution, purplish red crystal was obtained by drying. The structure of the extract was characterized by IR 1H N MRMS. The results showed that the extract was single in composition and high in purity. (2) Indirubin was prepared by reaction with hydroxylamine hydrochloride, potassium hydroxide and acetyl chloride in the presence of solvent. The structure and fluorescence properties of indirubin oxime and N-acetylindirubin were characterized by IR 1HNMR-HR-MS. It was found that after acetylation of indirubin, N- acetyl indirubin had good fluorescence properties due to the introduction of carbonyl group. It is a novel fluorescent probe compound. The CMC of cationic surfactants D1821, anionic surfactants and amphoteric surfactants BS-12 were determined using N-acetylindirubin as fluorescence probe. The results were in agreement with the reported values. Using N- acetyl indirubin as fluorescence probe, the interaction between N- acetyl indirubin and DNA was studied. It was found that the interaction between N- acetyl indirubin and DNA was static quenching and high sensitivity.
【学位授予单位】：天津理工大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914

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