吲哚类方酸菁染料、半菁染料的合成与应用研究
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摘要
菁染料具有摩尔消光系数大、易于合成和纯化、适当的荧光量子产率等优点,已经被广泛应用于许多领域,如：太阳能电池、pH探针、离子探针等。由于菁染料能与很多生物分子,如蛋白、核酸相互作用,并引起光谱的移动、强度的变化,因而这类染料在生物领域应用极为广泛。本文主要针对吲哚类菁染料进行合成与相关性能的研究。
基于方酸菁染料光稳定性不好、水溶性差等缺点,设计并合成了三个含有酰胺基团的方酸菁染料。相关实验结果表明,酰胺基团的引入,可以明显改善染料的光稳定性、降低染料在水中的聚集,提高染料在水中的摩尔消光系数和荧光量子产率。并且与牛血清白蛋白(BSA)的作用发现,含有两个酰胺基团的对称方酸菁染料Ⅱb(2,4-二(1-(N,N-二乙氨基羰甲基))-3,3-二甲基吲哚-2-甲烯基)-3-氧-1-环丁烯-1-醇)的荧光强度和BSA浓度之间有很好的线性关系,可在0.2-3μmol-1范围内对BSA进行定量检测。
选择光稳定性好的苯乙烯类菁染料作为研究对象,合成了六个由不同连接基团连接的两种波长范围的双半菁染料。使染料在水中的自身荧光降低,提高染料与生物分子作用的灵敏度。测试结果发现,染料Ⅲc(1,1’-(1,6-己二基)-双(2-(4-二甲胺基苯乙烯基)-3,3-二甲基吲哚))对脱氧核糖核酸(DNA)响应很好,作用后荧光最大增强可达90倍,比相应的单染料增强倍数大15倍,而且可对0.02-30μmol-1的DNA进行定量检测。而染料Ⅲh(1,1’-(对二苄基)-双(2-(4-二甲胺基苯丁烯基)-3,3-二甲基吲哚))则对BSA响应较好,最大增强可达19倍,是相应单染料增强倍数的13倍,可对0.02-8.5μmol-1的BSA定量检测。而且有四个双染料可以进入活细胞,为这类染料在细胞器可视化方面的应用研究建立基础。
设计合成了一系列具有固态荧光的苯乙烯类菁染料,通过单晶衍射发现,这类染料在固态分子间不存在π-π堆积作用,是这类染料具有固态荧光的主要原因。而且染料的阴离子由于可与染料主体的不同位置的H原子具有氢键作用,在晶体形成方面起重要作用。
合成了六个pH敏感的苯乙烯类菁染料,溶液中的pH滴定结果显示,它们的光谱随pH的改变变化明显,并伴有波长的移动。其中四个染料的pKa适于活细胞酸性细胞器成像,细胞通透性实验显示这些染料都具有很好的细胞膜通透性。其中,染料Vd(1,3,3-三甲基-2-(4-羟基苯乙烯基)-5-硝基吲哚)具有双发射性质,可以双色细胞成像。
Cyanine dyes possess many good characteristics such as high extinction coefficient, simple routs of syntheses and steps of purification, proper fluorescence quantum yield, etc. These make them be used as organic solar cells, pH probes and ion sensors, and so on. Cyanine dyes can also be applied in biological yields since they can associate with many bio-molecules such as protein or nucleic acid with changes of spectra in wavelength and intensity. In this thesis, cyanine dyes based on 2,3,3,-trimethyl-3H-indolium are synthesized and their corresponding properties are studied.
Three squarylium dyes have been designed and synthesized for improving their limited photo-stability and low water-solubility. The results show the introduction of carbamoylmethyl group can improve photostability of the dyes, decrease the aggregates and increase molar extinction coefficient and fluorescence quantum yield in water. The results of the dyes association with BSA present a better linear relationship between the fluorescence intensity of the dyeⅡb and BSA concentration can be obtained, which indicate the dye can detect BSA quantitatively in the range of 0.02-3μmol/L.
Six bis-hemicyanine dyes with different linking groups based on styrene cyanine dyes have been synthesized in order to decrease the self-fluorescence of the dye in water and increase the sensitivity in association with biomolecules. The results show the fluorescence intensity of dye IIIc enhance 90 times after association with DNA, and the number is 15 times of that of corresponding mono-cyanine dyeⅢa. On the other hand, after interaction with BSA, the fluorescence intensity of the dyeⅢh increase about 19 times, which is 13 times of corresponding mono-cyanine dyeⅢe. Moreover, four bis(hemicyanine) dyes are membrane-permeable in live cells, which indicate they have potential to visualize the organelle in live cells.
A series of styrene cyanine dyes with solid-state emission have been developed. The X-ray diffraction data show there are no obvious n-πstacking interaction between adjacent dye molecules, which lead to their intensive emission in solid-state. The anion of the dye plays an important role in the formation of the crystals because it can form H-bond with atom H in different position of the dye.
Five pH probes based on styrene cyanine dyes have been synthesized. Their properties as pH probe are tested in water-ethanol mixed solvents. The results show their spectra change obviously with the shift of the wavelength when the pH of the solution is changed. The data indicate the pKa of four probes is fit to sense the acid organelle in live cells. The four probes are membrane-permeable in live cells and can be used to fluorescence image in live cells. Moreover, probe Vd behave dual-emission and can dual-color fluorescence image in live cells.
基于方酸菁染料光稳定性不好、水溶性差等缺点,设计并合成了三个含有酰胺基团的方酸菁染料。相关实验结果表明,酰胺基团的引入,可以明显改善染料的光稳定性、降低染料在水中的聚集,提高染料在水中的摩尔消光系数和荧光量子产率。并且与牛血清白蛋白(BSA)的作用发现,含有两个酰胺基团的对称方酸菁染料Ⅱb(2,4-二(1-(N,N-二乙氨基羰甲基))-3,3-二甲基吲哚-2-甲烯基)-3-氧-1-环丁烯-1-醇)的荧光强度和BSA浓度之间有很好的线性关系,可在0.2-3μmol-1范围内对BSA进行定量检测。
选择光稳定性好的苯乙烯类菁染料作为研究对象,合成了六个由不同连接基团连接的两种波长范围的双半菁染料。使染料在水中的自身荧光降低,提高染料与生物分子作用的灵敏度。测试结果发现,染料Ⅲc(1,1’-(1,6-己二基)-双(2-(4-二甲胺基苯乙烯基)-3,3-二甲基吲哚))对脱氧核糖核酸(DNA)响应很好,作用后荧光最大增强可达90倍,比相应的单染料增强倍数大15倍,而且可对0.02-30μmol-1的DNA进行定量检测。而染料Ⅲh(1,1’-(对二苄基)-双(2-(4-二甲胺基苯丁烯基)-3,3-二甲基吲哚))则对BSA响应较好,最大增强可达19倍,是相应单染料增强倍数的13倍,可对0.02-8.5μmol-1的BSA定量检测。而且有四个双染料可以进入活细胞,为这类染料在细胞器可视化方面的应用研究建立基础。
设计合成了一系列具有固态荧光的苯乙烯类菁染料,通过单晶衍射发现,这类染料在固态分子间不存在π-π堆积作用,是这类染料具有固态荧光的主要原因。而且染料的阴离子由于可与染料主体的不同位置的H原子具有氢键作用,在晶体形成方面起重要作用。
合成了六个pH敏感的苯乙烯类菁染料,溶液中的pH滴定结果显示,它们的光谱随pH的改变变化明显,并伴有波长的移动。其中四个染料的pKa适于活细胞酸性细胞器成像,细胞通透性实验显示这些染料都具有很好的细胞膜通透性。其中,染料Vd(1,3,3-三甲基-2-(4-羟基苯乙烯基)-5-硝基吲哚)具有双发射性质,可以双色细胞成像。
Cyanine dyes possess many good characteristics such as high extinction coefficient, simple routs of syntheses and steps of purification, proper fluorescence quantum yield, etc. These make them be used as organic solar cells, pH probes and ion sensors, and so on. Cyanine dyes can also be applied in biological yields since they can associate with many bio-molecules such as protein or nucleic acid with changes of spectra in wavelength and intensity. In this thesis, cyanine dyes based on 2,3,3,-trimethyl-3H-indolium are synthesized and their corresponding properties are studied.
Three squarylium dyes have been designed and synthesized for improving their limited photo-stability and low water-solubility. The results show the introduction of carbamoylmethyl group can improve photostability of the dyes, decrease the aggregates and increase molar extinction coefficient and fluorescence quantum yield in water. The results of the dyes association with BSA present a better linear relationship between the fluorescence intensity of the dyeⅡb and BSA concentration can be obtained, which indicate the dye can detect BSA quantitatively in the range of 0.02-3μmol/L.
Six bis-hemicyanine dyes with different linking groups based on styrene cyanine dyes have been synthesized in order to decrease the self-fluorescence of the dye in water and increase the sensitivity in association with biomolecules. The results show the fluorescence intensity of dye IIIc enhance 90 times after association with DNA, and the number is 15 times of that of corresponding mono-cyanine dyeⅢa. On the other hand, after interaction with BSA, the fluorescence intensity of the dyeⅢh increase about 19 times, which is 13 times of corresponding mono-cyanine dyeⅢe. Moreover, four bis(hemicyanine) dyes are membrane-permeable in live cells, which indicate they have potential to visualize the organelle in live cells.
A series of styrene cyanine dyes with solid-state emission have been developed. The X-ray diffraction data show there are no obvious n-πstacking interaction between adjacent dye molecules, which lead to their intensive emission in solid-state. The anion of the dye plays an important role in the formation of the crystals because it can form H-bond with atom H in different position of the dye.
Five pH probes based on styrene cyanine dyes have been synthesized. Their properties as pH probe are tested in water-ethanol mixed solvents. The results show their spectra change obviously with the shift of the wavelength when the pH of the solution is changed. The data indicate the pKa of four probes is fit to sense the acid organelle in live cells. The four probes are membrane-permeable in live cells and can be used to fluorescence image in live cells. Moreover, probe Vd behave dual-emission and can dual-color fluorescence image in live cells.
引文
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