罗萨明类荧光探针合成与性能研究

发布时间：2018-03-09 17:06

本文选题：罗萨明　切入点：荧光探针　出处：《郑州大学》2016年硕士论文　论文类型：学位论文

【摘要】：罗萨明荧光团属于罗丹明类荧光染料,是利用含不同取代基的芳香醛与3-氨基苯酚反应后制成,产物单一,避免了罗丹明B染料在非质子溶剂中内酯结构形成而导致的荧光淬灭。这类荧光染料的紫外最大吸收在550nm左右,最大荧光发射在570-590nm范围移动。本文设计合成八种罗萨明类化合物,即RosN_3,RosCHO,RosBQ,RosBrNO_2,RosCH_3-NO_2,RospH,RosPG和RosGSH,它们的结构经~1H NMR、~(13)C NMR、IR、HR-MS表征和确证,对其光谱性质进行探究,并将性能良好的荧光探针应用于细胞成像。合成的目标化合物中,RosN_3在DMF/PB(6:4 v/v,10 mM,pH=7.4)中对H_2S能够专一性识别。探针识别机理被证明为:芳香叠氮基团还原为芳香氨基后,发生光诱导电子转移(PET),荧光淬灭。该探针有较强的抗干扰能力,成功应用于MGC-803细胞中H2S的检测;RosCHO探针在Tris-HCl(10 mM)中加入NaHSO_3后,芳香醛与HSO_3-发生亲核加成反应,荧光增强,该探针能够在生物活细胞中检测HSO_3-;RosBQ探针在10%CH_3CH_2OH的PB缓冲液中对ClO-有识别功能,并成功应用于细胞实验;RospH探针在CH_3CH_2OH/Tris-HCl体系中对pH敏感;RosGSH探针对生物硫醇有响应。
[Abstract]:Rhodamine fluorescent group is a kind of Rhodamine fluorescent dye, which is prepared by the reaction of aromatic aldehydes containing different substituents with 3-aminophenol. The fluorescence quenching caused by the formation of lactone structure of Rhodamine B dye in non-proton solvent is avoided. The UV maximum absorption of this kind of dye is about 550 nm. The maximum fluorescence emission shifts in the range of 570-590nm. In this paper, eight rosamine compounds, RosN3N RosCHOO RosBQO RosBQO RosBrNO2N NORNO2S RosCH3-NO2S RosPG and RosGSH, have been designed and synthesized. Their structures have been characterized and confirmed by 1H NMR13C NMRIRHR-MS, and their spectral properties have been investigated, and the spectral properties of RosPG and RosGSH have been investigated. The fluorescence probe with good performance was applied to cell imaging. RosN _ 3 in the synthesized target compound was able to identify H2S specifically in DMF/PB(6:4 v / v ~ (10 m ~ (-1)) pH = 7.4). The mechanism of the probe identification was as follows: the aromatic azido group was reduced to aromatic amino group, and the molecular mechanism was proved to be that the aromatic azido group was reduced to aromatic amino group. Photoinduced electron transfer and fluorescence quenching were observed. The probe was successfully used to detect H2S in MGC-803 cells. When NaHSO_3 was added to the probe, aromatic aldehydes reacted with HSO3- and the fluorescence was enhanced. The probe can be used in living cells to detect that the HSO3-PQ probe has the ability to recognize ClO- in the PB buffer of Ch _ 3CHS _ 2O _ H at 10 and Ch _ 3CHS _ 2OH, and has been successfully used in the cell experiment to detect the pH sensitivity of the CH_3CH_2OH/Tris-HCl probe to biofilm in the presence of biologic mercaptan.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2016
【分类号】：O657.3

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