罗丹明及香豆素衍生物新功能荧光染料的研究
摘要
生命活动是由许多的生物活性物质参与的各种化学反应的结果,包括很多活性的金属离子及生物小分子等。近些年来,荧光检测技术已经被广泛地应用于生物成像,生物监测,免疫分析和环境保护等方面。荧光增强型分子探针可以有效地避免生物体的自身干扰,而基于能量转移的荧光比率型探针更是备受关注。在众多优秀的荧光团中,罗丹明和香豆素类的染料由于其良好的光稳定性和易于修饰的特点,越来越多地应用于生物实验中。
本论文设计并合成了一例罗丹明B衍生物D2。作为专一识别Cu2+的探针,在水溶液中,可以很好的选择性识别Cu2+,而对其它常见金属离子都没有响应。紫外吸收光谱显示D2对较低浓度Cu2+的检测仍呈良好的线性关系,最低检出限为1.29×10-7mol/L。对于1×10-6mol/L的Cu2+仍可以实现裸眼可见的颜色变化,且识别过程可逆。制成试纸可以检测含Cu2+ppm级别水样。
利用PET机理,设计合成了一例罗莎明类荧光增强型Ag+探针,以冠醚[15]aneNO2S2为配体,在纯水相测试体系中对Ag+检出限可达9.3×10-8mol/L,且响应快速。第一次真正意义上实现了可以细胞内成像的Ag+荧光探针,具有重要生理意义。同时利用理论计算证实了的在水相中对Ag+的荧光响应要远远大于对于Cu2+和Hg2+的响应,很好的解释了实验现象。
设计合成了一例新型的香豆素衍生物荧光分子T1,基于ICT机理可以作为Cys和Hcy的新型反应型探针。被测物的加入,可以有效地引起吸收波长发生70nm的蓝移,并伴随着荧光强度的明显增强,并可在细胞中以及人血浆样品中检测Cys/Hcy。
基于FRET机理,设计了两例比率检测Cu2+的荧光分子探针T1RB-1和T1RB-2。以香豆素衍生物作为能量供体,罗丹明作为能量受体。特别对于探针T1RB-2,由于将C=N双键还原为C-N,在络合Cu2+的同时,对于Cu+也有响应,这与探针T1RB-1不同,分析其原因可能是由于电子分布及空间构型造成的。T1RB-2能够穿透过细胞膜对不同的活细胞进行荧光呈像,且可以荧光比率检测细胞内的Cu2+并定位在溶酶体中。
将罗丹明与香豆素/萘酰亚胺利用炔苯基连接,使能量供体和受体之间有一定的空间转角,实现了经空间转移与经键能量转移(TBET)的同时发生。可增加赝斯托克斯位移至200nm。
The activity of life is an effect of different chemical reactions by lots of biological active substances, including metal ions and small active molecules. In recent years, fluorescent technology has been widely used in bioimaging, biosensing, medical diagnosis and environmental detection. The fluorescence-enhanced signal can avoid the interference well, and the fluorometric methods based on energy transfer have attracted more attentions. Among these talent fluorophores, because of the good photostability and easy to modify, rhodamine and coumarin derivative have been more and more used in the biological experiments.
Designed and synthesized a new type of Rodamine B derivative D2. As a specific probe for Cu2+in aqueous solution, the detection process was not effect by other ions. The color change reduced by1×10-6mol/L Cu2+still can be seen by naked eyes. The binding process of the probe and the Cu2+is reversible. D2has potential application for detection Cu2+in the actual environment for rapid real-time analysis.
Rosamine derivative RC-1, bearing macrocyclic ligand [15]aneNO2S2as receptor, was synthesized as an enhanced fluorescent chemosensor for Ag+in absolute aqueous solution. The detection limit was9.3×10-8mol/L. The fluorescence images in living cells show the potential application of RC-1. The difference of fluorescence enhancement process after binding with Ag+/Hg2+in acetonitrile/water solution was first clarified by theoretical calculations.
A novel molecule T1with efficient intramolecular charge transfer was designed as a fluorescent chemodosimeter for cysteine (Cys) and homocysteine (Hcy). Upon addition of Cys/Hcy, T1exhibited greatly enhanced fluorescence intensity as well as a large absorption peak shift (70nm), and can be used for bioimaging of Cys/Hcy in living cells and detection in human plasma by visual color change. The detection mechanism was clarified by'H NMR, mass spectrometry analysis and Gaussian calculations.
A couple of fluorescent tools bearing rhodamine B and aza-coumarin groups have been synthesized as selective and quantitative probes for Cu2+. Based on FRET mechanism, compounds T1RB-1and T1RB-2exhibited selective changes in the absorption and emission spectra towards Cu2+ion over miscellaneous cations. Interesting, the different electron density and structure geometry make chemosensor T1RB-2, which has C-N in the structure could bind with Cu2+, simultaneously with Cu+, that was not like probe T1RB-1with C=N. T1RB-2 could penetrate the membrane and detect Cu2+by ratiometry imaging in living cells. The probe T1RB-2also exhibits subcellular localized fluorescence staining of lysosome.
The coumarin/naphthalimide-rhodamine cassettes were constructed through a conjugated acetylene phenyl linker, which prevents the fluorophores from becoming planar, makes the energy transfer through space and through bond simultaneously. The pseudo-Stokes shifts could get to about200nm.
本论文设计并合成了一例罗丹明B衍生物D2。作为专一识别Cu2+的探针,在水溶液中,可以很好的选择性识别Cu2+,而对其它常见金属离子都没有响应。紫外吸收光谱显示D2对较低浓度Cu2+的检测仍呈良好的线性关系,最低检出限为1.29×10-7mol/L。对于1×10-6mol/L的Cu2+仍可以实现裸眼可见的颜色变化,且识别过程可逆。制成试纸可以检测含Cu2+ppm级别水样。
利用PET机理,设计合成了一例罗莎明类荧光增强型Ag+探针,以冠醚[15]aneNO2S2为配体,在纯水相测试体系中对Ag+检出限可达9.3×10-8mol/L,且响应快速。第一次真正意义上实现了可以细胞内成像的Ag+荧光探针,具有重要生理意义。同时利用理论计算证实了的在水相中对Ag+的荧光响应要远远大于对于Cu2+和Hg2+的响应,很好的解释了实验现象。
设计合成了一例新型的香豆素衍生物荧光分子T1,基于ICT机理可以作为Cys和Hcy的新型反应型探针。被测物的加入,可以有效地引起吸收波长发生70nm的蓝移,并伴随着荧光强度的明显增强,并可在细胞中以及人血浆样品中检测Cys/Hcy。
基于FRET机理,设计了两例比率检测Cu2+的荧光分子探针T1RB-1和T1RB-2。以香豆素衍生物作为能量供体,罗丹明作为能量受体。特别对于探针T1RB-2,由于将C=N双键还原为C-N,在络合Cu2+的同时,对于Cu+也有响应,这与探针T1RB-1不同,分析其原因可能是由于电子分布及空间构型造成的。T1RB-2能够穿透过细胞膜对不同的活细胞进行荧光呈像,且可以荧光比率检测细胞内的Cu2+并定位在溶酶体中。
将罗丹明与香豆素/萘酰亚胺利用炔苯基连接,使能量供体和受体之间有一定的空间转角,实现了经空间转移与经键能量转移(TBET)的同时发生。可增加赝斯托克斯位移至200nm。
The activity of life is an effect of different chemical reactions by lots of biological active substances, including metal ions and small active molecules. In recent years, fluorescent technology has been widely used in bioimaging, biosensing, medical diagnosis and environmental detection. The fluorescence-enhanced signal can avoid the interference well, and the fluorometric methods based on energy transfer have attracted more attentions. Among these talent fluorophores, because of the good photostability and easy to modify, rhodamine and coumarin derivative have been more and more used in the biological experiments.
Designed and synthesized a new type of Rodamine B derivative D2. As a specific probe for Cu2+in aqueous solution, the detection process was not effect by other ions. The color change reduced by1×10-6mol/L Cu2+still can be seen by naked eyes. The binding process of the probe and the Cu2+is reversible. D2has potential application for detection Cu2+in the actual environment for rapid real-time analysis.
Rosamine derivative RC-1, bearing macrocyclic ligand [15]aneNO2S2as receptor, was synthesized as an enhanced fluorescent chemosensor for Ag+in absolute aqueous solution. The detection limit was9.3×10-8mol/L. The fluorescence images in living cells show the potential application of RC-1. The difference of fluorescence enhancement process after binding with Ag+/Hg2+in acetonitrile/water solution was first clarified by theoretical calculations.
A novel molecule T1with efficient intramolecular charge transfer was designed as a fluorescent chemodosimeter for cysteine (Cys) and homocysteine (Hcy). Upon addition of Cys/Hcy, T1exhibited greatly enhanced fluorescence intensity as well as a large absorption peak shift (70nm), and can be used for bioimaging of Cys/Hcy in living cells and detection in human plasma by visual color change. The detection mechanism was clarified by'H NMR, mass spectrometry analysis and Gaussian calculations.
A couple of fluorescent tools bearing rhodamine B and aza-coumarin groups have been synthesized as selective and quantitative probes for Cu2+. Based on FRET mechanism, compounds T1RB-1and T1RB-2exhibited selective changes in the absorption and emission spectra towards Cu2+ion over miscellaneous cations. Interesting, the different electron density and structure geometry make chemosensor T1RB-2, which has C-N in the structure could bind with Cu2+, simultaneously with Cu+, that was not like probe T1RB-1with C=N. T1RB-2 could penetrate the membrane and detect Cu2+by ratiometry imaging in living cells. The probe T1RB-2also exhibits subcellular localized fluorescence staining of lysosome.
The coumarin/naphthalimide-rhodamine cassettes were constructed through a conjugated acetylene phenyl linker, which prevents the fluorophores from becoming planar, makes the energy transfer through space and through bond simultaneously. The pseudo-Stokes shifts could get to about200nm.
引文
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