靛玉紅衍生物的合成及應(yīng)用
發(fā)布時(shí)間:2018-04-26 05:12
本文選題:靛玉紅 + 靛玉紅肟。 參考:《天津理工大學(xué)》2014年碩士論文
【摘要】:靛玉紅,也被稱為炮彈樹堿,是我國(guó)首創(chuàng)的抗白血病藥。它是由兩個(gè)吲哚環(huán)縮合而成的一個(gè)V字型分子,與靛藍(lán)分子內(nèi)的兩個(gè)氫鍵不同,其分子內(nèi)只有一個(gè)氫鍵,使得另一個(gè)吲哚環(huán)上的羰基氧原子由于沒有形成氫鍵暴露在外,從而提供了與癌細(xì)胞DNA的結(jié)合位點(diǎn)。又因它的結(jié)構(gòu)與鳥嘌呤相近,因而可以與鳥嘌呤相互作用而發(fā)生π-π絡(luò)合,形成分子絡(luò)合物。由此阻斷了腫瘤細(xì)胞DNA的合成而發(fā)揮了抗癌作用。但由于靛玉紅的高熔點(diǎn),較差的脂溶性及水溶性,因此對(duì)靛玉紅衍生物的研究成為科研工作者的研究熱點(diǎn)。 本論文主要工作如下: (1)對(duì)40%的粗品靛玉紅進(jìn)行柱層析分離提純,,以氯仿和乙酸乙酯為洗脫劑,經(jīng)過二次洗脫,干燥得紫紅色結(jié)晶。利用IR,1HNMR,HRMS對(duì)其進(jìn)行了結(jié)構(gòu)表征,表明提取物成分單一,純度高。 (2)以提取后的靛玉紅為原料,與鹽酸羥胺,氫氧化鉀反應(yīng)得到靛玉紅肟;在溶劑存在下與乙酰氯反應(yīng)制得N-乙;逵窦t。利用IR,1HNMR,HR-MS對(duì)靛玉紅肟及N-乙;逵窦t進(jìn)行了結(jié)構(gòu)表征。UV性能、熒光性能進(jìn)行了測(cè)定,發(fā)現(xiàn)靛玉紅乙酰化后,由于羰基的引入,使得N-乙;逵窦t具有良好的熒光性能,是一種新型的熒光探針化合物。 (3)以N-乙;逵窦t為熒光探針,對(duì)陽(yáng)離子表面活性劑D1821,陰離子表面活性劑SDS,兩性離子表面活性劑BS-12的CMC分別進(jìn)行了測(cè)定,測(cè)定結(jié)果與文獻(xiàn)報(bào)道值一致。 (4)以N-乙;逵窦t為熒光探針,通過對(duì)其與DNA相互作用的研究,發(fā)現(xiàn)N-乙;逵窦t與DNA的作用方式為靜態(tài)猝滅,且有較高的靈敏度。
[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.
【學(xué)位授予單位】:天津理工大學(xué)
【學(xué)位級(jí)別】:碩士
【學(xué)位授予年份】:2014
【分類號(hào)】:R914
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