基于苯并吡喃腈和氮杂香豆素的近红外荧光探针的合成及性能研究

发布时间：2018-05-14 21:37

本文选题：荧光探针 + 近红外　；参考：《华中师范大学》2017年硕士论文

【摘要】：近年来,荧光探针由于具有成本低、合成简单、选择性好、灵敏度高、生物相容性好以及能够在生物体环境内进行实时在线检测等优点,被广泛运用于生物、环境、化学等领域。较之于发射光谱在可见光区的荧光探针,近红外(650-900 nm)荧光探针不仅具有更强的组织穿透能力以及对生物体的危害较小,而且荧光背景干扰很小,有利于其在细胞成像方面的应用。因此,发展近红外荧光探针具有重要的生物意义。在本论文中,我们发展了两种近红外荧光探针,并且对它们的光学性能以及实际应用进行了研究。1.我们合成了一种以苯并吡喃腈衍生物为荧光基团的近红外硒代半胱氨酸(Sec)荧光探针Probe 1,该探针以2,4-二硝基苯醚为反应位点,并且运用~1HNMR、~(13)CNMR、MS以及HR-MS对其结构进行了表征。实验表明Probe 1在温和条件下能够快速地选择性识别Sec,同时,伴随着明显的近红外荧光信号的增强以及颜色的变化。而且,该探针还能够检测活细胞外源性以及内源性的Sec,在生物领域具有潜在的应用价值。2.我们以氮杂香豆素为荧光基团设计合成了一种比色型以及比率型识别HSO_3~-/SO32-的近红外荧光探针Probe2,运用~1HNMR、~(13)CNMR、MS以及HR-MS对其结构进行了确认。实验表明Probe2能在温和条件下快速地(30s)选择性识别HSO_3~-/SO_3~(2-),与此同时伴随着明显的颜色变化以及比率型荧光光谱的变化。另外,Probe2不仅能够检测食品中HSO_3~-的含量,而且,还能够用于检测活细胞外源性以及内源性的HSO_3~-,表明该探针具有良好的应用前景。
[Abstract]:In recent years, fluorescent probes have been widely used in biology and environment because of their advantages of low cost, simple synthesis, good selectivity, high sensitivity, good biocompatibility and real-time on-line detection in biological environment. Chemistry, etc. Compared with fluorescence probes with emission spectra in the visible region, the near infrared fluorescence probes not only have stronger tissue penetration and less harm to organisms, but also have little interference with fluorescence background. It is beneficial to its application in cell imaging. Therefore, the development of near infrared fluorescence probe has important biological significance. In this thesis, we have developed two near infrared fluorescence probes and studied their optical properties and practical applications. A near infrared selenocysteine (Sec1) fluorescence probe with benzopyranonitrile derivatives as the fluorescent group was synthesized. The probe was characterized by 1H NMRMMS and HR-MS. The probe was composed of 2H 4- dinitrophenyl ether as the reaction site. The experimental results show that Probe 1 can recognize Secs quickly and selectively under mild conditions, at the same time, the enhancement of NIR fluorescence signal and the change of color are accompanied by the enhancement of NIR fluorescence signal. Moreover, the probe can detect exogenous and endogenous Secs in living cells, which has potential application value in biological field. We have designed and synthesized a colorimetric and ratio based near infrared fluorescence probe Probe2 which recognizes HSO3 and / SO32- by using azacoumarin as the fluorescence group. The structure of Probe2 has been confirmed by 1HNMR-13CNMRMS and HR-MS. The experimental results show that Probe2 can be used to selectively identify HSOs 3s / s at mild conditions, accompanied by obvious changes in color and ratio fluorescence spectra. In addition, Probe2 can not only detect the content of HSO3- in food, but also can be used to detect exogenous and endogenous HSO3- in living cells, which indicates that the probe has a good application prospect.
【学位授予单位】：华中师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O657.3

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