大斯托克斯位移荧光染料的合成、性能及应用

发布时间：2018-03-31 16:04

本文选题：罗丹荧类和萘酰亚胺类荧光染料　切入点：斯托克斯位移　出处：《燕山大学》2016年硕士论文

【摘要】：有机荧光染料具有合成简单及生物相容好等优点,已成为活细胞荧光成像的主要工具。而斯托克斯位移作为荧光的重要物理常数,对染料的设计有着导向作用。本文设计合成了系列新型大斯托克斯位移的罗丹荧类和萘酰亚胺类荧光染料,并研究了其结构、性能及生物应用。本文首先从罗丹明和荧光素共同具有的氧杂蒽母体出发,用四氢喹喔啉基团加以修饰,设计合成出罗丹荧荧光染料(RD)。通过对RD进行修饰,得到罗丹荧甲酯化、甲醇化和溴苯衍生物(RD-JZ、RS-JC和RD-XB)。光谱性能检测结果表明,此类罗丹荧荧光染料不但可在近红外区域发射,还具有较大的斯托克斯位移(在水溶液中斯托克斯位移值最大,分别为RD:178 nm,RD-JZ:130 nm,RD-JC:130 nm,RD-XB:150 nm);衍生物RD-XB可在谷胱甘肽硫转移酶(GST)的酶催化作用下选择性识别谷胱甘肽(GSH)。活细胞荧光成像检测结果表明,三个罗丹荧衍生物都可以进行活细胞荧光成像;并且在GST蛋白存在的情况下,衍生物RD-XB可专一性识别活细胞中的GSH,发出红色荧光。这种新型罗丹荧类荧光染料的开发与应用,为细胞多色检测提供了更广阔的发展前景。从4-溴-1,8-萘酐出发,设计合成出可对溶酶体中NO进行靶向定位识别的荧光探针Lyso NO-Naph,探针较大的共轭面使得其具有较大的斯托克斯位移。光谱测试结果表明,Lyso NO-Naph在乙腈中斯托克斯位移值最大为143 nm。探针可与NO发生选择性的缩合反应,生成一种蓝色荧光物质,表现为对NO的选择性识别。Lyso NO-Naph具有较低的NO检测限(7.769?M),并且在pH 4-12范围内光谱稳定。基于吗啉官能团的溶酶体定位能力,Lyso NO-Naph能够对酸性细胞器溶酶体(pH 4-6)中的NO识别并活细胞荧光成像。此萘酰亚胺荧光探针的合成与应用,为后续活细胞溶酶体NO检测奠定了基础。
[Abstract]:Organic fluorescent dyes have the advantages of simple synthesis and good biocompatibility, and have become the main tool for fluorescence imaging of living cells. Stokes shift is regarded as an important physical constant of fluorescence. In this paper, a series of novel large Stokes shift Rhodanophores and naphthalimide fluorescent dyes have been designed and synthesized, and their structures have been studied. Properties and biological applications. Firstly, based on the oxygen heterotracene matrix of Rhodamine and fluorescein, the rhodamine fluorescent dye RDN was designed and synthesized with tetrahydroquinoxaline group. Through the modification of Rd, the methyl ester of Rhodamine fluorophore was obtained. The spectral properties of RD-JZO RS-JC and RD-XB0.Results show that this kind of rosin fluorescent dye not only emits in near infrared region, but also has a large Stokes shift (maximum Stokes shift value in aqueous solution). The derivative RD-XB can selectively recognize glutathione glutathione (GSH) under the catalysis of glutathione S-transferase (GST). The results of living cell fluorescence imaging showed that all of the three derivatives could be used for living cell fluorescence imaging. In the presence of GST protein, the derivative RD-XB can specifically recognize GSHs in living cells and emit red fluorescence. It provides a broad development prospect for cell polychromatic detection. Starting from 4- bromo-1 and 8-naphthalic anhydride, A fluorescent probe, Lyso no Naphs, was designed and synthesized, which can be targeted for the identification of no in lysosomes. The larger conjugate surface of the probe makes it have a large Stokes shift. The spectral test results show that the NO-Naph has a Stokes shift in acetonitrile. The maximum value is 143 nm. The probe can react selectively with no. A blue fluorescent substance is produced, which is characterized by selective recognition of no. Lyso NO-Naph has a lower no detection limit of 7.769? Based on the lysosomal localization ability of morpholine functional group, Lyso NO-Naph can recognize no in the acidic organelle lysosome (pH 4-6) and image it in living cells. The synthesis and application of this naphthyl imide fluorescence probe were studied. It lays a foundation for the detection of lysosomal no in living cells.
【学位授予单位】：燕山大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O657.3

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