瓜环与荧光染料的自组装及其应用研究
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摘要
瓜环(cucurbit[n]uril,CB[n],n=5-10),又称葫芦脲,因其异于已有的超分子大环主体如冠醚、环糊精及杯芳烃等的结构特征受到超分子化学领域学者的广泛关注。瓜环参与的超分子化学体系广泛应用于环境化学、催化、材料化学、生命科学及纳米科学等领域。荧光染料与瓜环形成的络合物在检测、成像、激光及其他方面有着广泛的应用。
苯乙烯类半菁染料DSMI被CB[6]内包后呈现出高达270倍的荧光增强。通过紫外、荧光、核磁及质谱等方法确定DSMI-CB[6]络合物的化学计量比为1：1。大幅荧光增强是由CB[6]变形的空腔阻止DSMI的扭转分子内电荷转移及CB[6]与DSMI之间的离子-偶极相互作用产生的。而其主要原因是CB[6]变形的空腔,这可以通过计算结果确认。然后利用染料和CB[6]在不同pH下的荧光组建了一个可逆的分子逻辑门,这为利用超分子作用模式设计荧光分子逻辑门打下了坚实的基础。
DSMI与CB[7]及DNA都能络合,研究发现DSMI与CB[7]络合物的化学计量比为1：2,而且DSMI-CB[7]络合物比DSMI-DNA络合物拥有更强的络合亲和力,因此,CB[7]对染料与DNA之间的络合有一定的抑制作用。本论文在DSMI的基础上设计合成了D2并研究了其与CB[7]及DNA之间的超分子络合作用,D2分子的叉状结构使得D2、CB[7]与DNA之间可能形成三元络合物,可以在一定程度上消除CB[7]对染料与DNA络合作用的抑制效果。
同时本论文设计合成了一例近红外荧光染料Hsd,该染料以半菁染料形式吸收而以Cy7的形式发射,因此产生了高达224nm的Stokes位移。量子化学计算结果显示染料大Stokes位移是由分子内电荷转移及内转换共同产生的结果。而且,该染料在溶液及固定细胞中都能对RNA选择性响应,是一例很好的近红外RNA探针。染料本身不能进入活细胞,但是在CB[7]的辅助下可以进入活细胞对细胞内RNA进行选择性染色。CB[7]的引入为扩大一些无细胞通透性荧光染料的应用范围提供了一种新的超分子化学方法。
最后,本论文设计合成了一例可与CB[8]自组装的分子信标MB。该分子信标荧光基团及淬灭基团末端分别带有一个萘甲醚基团及甲基紫菁基团,可以与CB[8]形成三元络合物。三元络合物的形成会拉近荧光基团与淬灭基团之间的距离,增加其FRET效率,有望提高分子信标的信噪比。这种设计原理为改进分子信标性能提供了一个新的方法。
Cucurbit[n]urils, because of their different structures from the existed supramolecular microcyclar hosts such as crownether, cyclodextrin, and calixarene, were intensively studied by supramolecular chemists. The cucurbit[n]uril supramolecular systems were widely used in the fields of environmental chemistry, catalysis, material chemistry, life science and nanotechnology. Meanwhile, the complexes of fluorescent dyes and cucurbit[n]urils have been widely used in detection, imaging, laser and other aspects.
About270-fold fluorescence enhancement was observed when the hemicyanine dye, trans-4-[4-(dimethylamino)styryl]-l-methylpyridinium iodide (DSMI), was included by cucurbit[6]uril (CB[6]). The1:1stoichiometry of DSMI-CB[6] complex was determined through optical spectra analysis and1H NMR measurement. The large fluorescence enhancement was achieved by prohibiting the twisted intramolecular charge transfer (TICT) process of DSMI inside the distorted cavity of CB[6], together with the ion-dipole interaction between DSMI and CB[6]. The distortion of the CB[6] cavity, being as the major reason for the huge fluorescence enhancement, was further confirmed by the calculation results. And then a resettable and reconfigurable logic gate was constructed with DSMI and CB[6] under different pH situations. This study lays a solid foundation for the design of molecular logic gates via supramolecular interaction mode.
DSMI could bind with both CB[7] and DNA and DSMI could be included by CB[7] with1:2stoichiometry to form DSMI-CB[7] complex, which has a larger binding affinity than the DSMI-DNA complex. Therefore, CB[7] would inhibit the binding interaction between DSMI and DNA. Then we synthesised a novel hemicyanine derivation D2and investigated its supramolecular interaction between CB[7] and DNA. The branched structure of D2could induce the formation of DNA-D2-CB[7] ternary complex, which could decrease the inhibition of CB[7] to the binding affinity of dyes and DNA.
A near-infrared fluorescent dye Hsd was designed and synthesized, which absorbed as hemicyane and emitted as Cy7and therefore produced a Stokes shift as large as224nm. Quantum chemistry calculations demonstrate that the large Stokes shift is produced by the combination of intramolecular charge transfer (ICT) and internal conversion. Significantly, Hsd showed selectively response to RNA in aqueous solution and fixed cells. Moreover, Hsd could be uptaken into the cells under the assistance of cucurbit[7]uril and selectively stain RNA in living cells. The introducing of CB[7] provides a novel platform to amplify the application of some cell-impermeant fluorescent stains through the supramolecular chemistry methods.
Finally, a molecular beacon MB which could be assembled with CB[8] was designed and synthesized. The fluorescence and quencher groups on the molecular beacon possessed a naphthalene ether group and methylviologen group respectively, which could form a ternary complex with CB[8] and bring the fluorophore closer to the quencher. The formation of the ternary complex would increase the efficiency of FRET and is expected to improve the signal-to-noise ratio of molecular beacon. This idea provides a new method for improving the performance of molecular beacon.
苯乙烯类半菁染料DSMI被CB[6]内包后呈现出高达270倍的荧光增强。通过紫外、荧光、核磁及质谱等方法确定DSMI-CB[6]络合物的化学计量比为1：1。大幅荧光增强是由CB[6]变形的空腔阻止DSMI的扭转分子内电荷转移及CB[6]与DSMI之间的离子-偶极相互作用产生的。而其主要原因是CB[6]变形的空腔,这可以通过计算结果确认。然后利用染料和CB[6]在不同pH下的荧光组建了一个可逆的分子逻辑门,这为利用超分子作用模式设计荧光分子逻辑门打下了坚实的基础。
DSMI与CB[7]及DNA都能络合,研究发现DSMI与CB[7]络合物的化学计量比为1：2,而且DSMI-CB[7]络合物比DSMI-DNA络合物拥有更强的络合亲和力,因此,CB[7]对染料与DNA之间的络合有一定的抑制作用。本论文在DSMI的基础上设计合成了D2并研究了其与CB[7]及DNA之间的超分子络合作用,D2分子的叉状结构使得D2、CB[7]与DNA之间可能形成三元络合物,可以在一定程度上消除CB[7]对染料与DNA络合作用的抑制效果。
同时本论文设计合成了一例近红外荧光染料Hsd,该染料以半菁染料形式吸收而以Cy7的形式发射,因此产生了高达224nm的Stokes位移。量子化学计算结果显示染料大Stokes位移是由分子内电荷转移及内转换共同产生的结果。而且,该染料在溶液及固定细胞中都能对RNA选择性响应,是一例很好的近红外RNA探针。染料本身不能进入活细胞,但是在CB[7]的辅助下可以进入活细胞对细胞内RNA进行选择性染色。CB[7]的引入为扩大一些无细胞通透性荧光染料的应用范围提供了一种新的超分子化学方法。
最后,本论文设计合成了一例可与CB[8]自组装的分子信标MB。该分子信标荧光基团及淬灭基团末端分别带有一个萘甲醚基团及甲基紫菁基团,可以与CB[8]形成三元络合物。三元络合物的形成会拉近荧光基团与淬灭基团之间的距离,增加其FRET效率,有望提高分子信标的信噪比。这种设计原理为改进分子信标性能提供了一个新的方法。
Cucurbit[n]urils, because of their different structures from the existed supramolecular microcyclar hosts such as crownether, cyclodextrin, and calixarene, were intensively studied by supramolecular chemists. The cucurbit[n]uril supramolecular systems were widely used in the fields of environmental chemistry, catalysis, material chemistry, life science and nanotechnology. Meanwhile, the complexes of fluorescent dyes and cucurbit[n]urils have been widely used in detection, imaging, laser and other aspects.
About270-fold fluorescence enhancement was observed when the hemicyanine dye, trans-4-[4-(dimethylamino)styryl]-l-methylpyridinium iodide (DSMI), was included by cucurbit[6]uril (CB[6]). The1:1stoichiometry of DSMI-CB[6] complex was determined through optical spectra analysis and1H NMR measurement. The large fluorescence enhancement was achieved by prohibiting the twisted intramolecular charge transfer (TICT) process of DSMI inside the distorted cavity of CB[6], together with the ion-dipole interaction between DSMI and CB[6]. The distortion of the CB[6] cavity, being as the major reason for the huge fluorescence enhancement, was further confirmed by the calculation results. And then a resettable and reconfigurable logic gate was constructed with DSMI and CB[6] under different pH situations. This study lays a solid foundation for the design of molecular logic gates via supramolecular interaction mode.
DSMI could bind with both CB[7] and DNA and DSMI could be included by CB[7] with1:2stoichiometry to form DSMI-CB[7] complex, which has a larger binding affinity than the DSMI-DNA complex. Therefore, CB[7] would inhibit the binding interaction between DSMI and DNA. Then we synthesised a novel hemicyanine derivation D2and investigated its supramolecular interaction between CB[7] and DNA. The branched structure of D2could induce the formation of DNA-D2-CB[7] ternary complex, which could decrease the inhibition of CB[7] to the binding affinity of dyes and DNA.
A near-infrared fluorescent dye Hsd was designed and synthesized, which absorbed as hemicyane and emitted as Cy7and therefore produced a Stokes shift as large as224nm. Quantum chemistry calculations demonstrate that the large Stokes shift is produced by the combination of intramolecular charge transfer (ICT) and internal conversion. Significantly, Hsd showed selectively response to RNA in aqueous solution and fixed cells. Moreover, Hsd could be uptaken into the cells under the assistance of cucurbit[7]uril and selectively stain RNA in living cells. The introducing of CB[7] provides a novel platform to amplify the application of some cell-impermeant fluorescent stains through the supramolecular chemistry methods.
Finally, a molecular beacon MB which could be assembled with CB[8] was designed and synthesized. The fluorescence and quencher groups on the molecular beacon possessed a naphthalene ether group and methylviologen group respectively, which could form a ternary complex with CB[8] and bring the fluorophore closer to the quencher. The formation of the ternary complex would increase the efficiency of FRET and is expected to improve the signal-to-noise ratio of molecular beacon. This idea provides a new method for improving the performance of molecular beacon.
引文
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