基于衍生化的生物分子选择性检测方法探索
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摘要
生物样品组成的复杂多样性、极宽的动态丰度等使得对其的分析难度增加,通常要求所采用的分析方法不仅要具有足够的灵敏度,同时还要具备良好的选择性。对目标分析物进行衍生化不仅可以改善检测灵敏度,也可以改变分析的选择性,因此在生物样品分析检测中得到广泛应用。新型衍生化试剂的设计、合成,衍生化方法的发展一直是生命科学、分析化学等领域的研究热点。
本文以衍生化技术为手段,选用两种不同的衍生化试剂对硫醇、蛋白质、多肽等生物分子的衍生化方法开展研究。以4-硝基-1,8-萘酐(NNA)作为探针,对硫醇类物质进行光谱检测。在实验条件下,NNA与半胱氨酸(Cys)反应所得4-巯基取代产物可以通过分子内亲核取代过程进一步转化为4-氨基取代产物,由于Cys的巯基与羧基之间可以通过六元环形成分子内氢键作用从而加速了巯基的离去,促进了巯基取代产物的转化,溶液最大吸收和最大发射波长分别位于435nm和530nm,在荧光灯照射下发射出明亮的黄绿色荧光；而其他小分子硫醇与NNA反应所得巯基取代产物不发生分子内亲核取代反应或转化为氨基取代产物的速率较慢,溶液的最大吸收和最大发射波长分别位于390nm和490nm,在荧光灯的照射下发射出蓝色荧光。所发展的方法可用于对Cys进行选择性荧光、比色和裸眼识别。
以4-氟-7-硝基-2,1,3-苯并氧杂恶二唑(NBD-F)作为探针,研究其在不同反应介质中对巯基和氨基化合物的光谱响应。在酸性、中性及添加阴离子或阳离子表面活性剂的中性水溶液中,巯基均表现出了良好的反应活性,其中,NBD-F与Cys、高半胱氨酸(Hcy)及巯基乙胺(MEA)反应所得巯基取代产物会通过分子内亲核取代反应过程进一步转变为对应的氨基取代产物,而且转化速率以及产物的稳定性也会因反应介质的不同发生改变；在特定的反应介质中(如在添加阳离子表面活性剂CTAB的中性水溶液中),NBD-F与巯基丙酸(MPA)和N-乙酰半胱氨酸(NAC)反应所得巯基取代产物会进一步转变为吸收波长更长的非荧光产物。利用这种光谱响应特性建立了在水溶液中对包括Cys、Hcy、MEA等在内7种小分子硫醇进行差异化识别的方法。
研究NBD-F与牛血清白蛋白(BSA)和卵清蛋白(OVA)反应的光谱特征。在酸性、中性水溶液中,由于BSA和OVA结构差异,致使两者与NBD-F的反应活性存在明显不同；向反应溶液中添加阴离子或阳离子表面活性剂可以改变蛋白质与NBD-F的反应性能。进一步以NBD-F作为衍生化试剂,在不同pH值条件下对鼠肝肿瘤组织蛋白提取液及其酶解产物进行柱前衍生,并通过HPLC-LIF进行分离分析,实验结果表明调整反应介质的pH值可以改变NBD-F与样品各组分之间的反应活性,从而起到改变检测选择性的作用。
为了实现生物样品的色谱分离-在线衍生-荧光检测,设计了一种基于中空纤维膜、可用于毛细管电泳-激光诱导荧光检测(CE-LIF)平台的蛋白质在线衍生反应器。小分子荧光衍生化试剂可以通过自由扩散进入反应器中,与分子量大于纤维膜截留分子量的样品发生反应,衍生化产物迁移至检测窗口处被检测。所构建的装置具有接口死体积小、制作和使用成本低廉等优点,适用于生物大分子的在线荧光衍生。
The components in biological samples are complicated and their dynamic abundances are extremely broad. It requires more sensitively and selectively analytic methods to determine the components in real samples. Derivatization is such a method that can not only enhance the sensitivity but also improve the selectivity of detection. It has aroused much attention in the design and synthesis of new derivatization reagents and the development of derivatization technique in the areas of life science, analytical chemistry and some other research areas.
We have studied the derivatization methods for biomolecules (including thiols, protiens, peptides and etc.) by using two different derivatization reagents. Firstly, we employed4-nitro-1,8-naphthalic anhydride (NNA) as a fluorescent probe for thiols. When reacted with Cys, the4-nitro in NNA was first replaced by mercapto group followed by the displacement of mercapto group with amino group to form4-amino substitute via intramolecular nucleophilic aromatic substitution. The hydrogen bond between the sulfur atom and the carboxylic acid group in Cys could help the leaving of alkylthio group, which therfore promoted the formation of4-amino substitute. The absorption and emission maxima of the4-amino substitute were at435nm and530nm, respectively, and the solution exhibited bright green-yellow fluorescence when irradiated with UV lamp. However, since the4-alkylthio substitutes of the other thiols reaced with NNA can not transfer to the4-amino substitutes during the experimental period, the reaction solutions had absorption and emission maxima at390nm and490nm, respectively, and presented blue fluorescence when irradiated with UV lamp. Thus Cys could be recognized selectively by fluorescent and UV methods and even by naked-eye.
Secondly, we used4-fluoro-7-nitrobenzo-2-oxa-l,3-diazole (NBD-F) as a probe to study its spectral responses towards thiol-containing and amino-containing compounds in different reaction meadia. Thiol group exhibited quite good reactivity in all the experimental conditions (in acidic, neutral and CTAB or SDS solutions). The thiol-substituent products of NBD-F reacted with Cys, Hcy and MEA would transfer to the corresponding amino-substituent products via intramolecular nucleophilic aromatic substitution. In addition, the rate of transfer and the stability of the products changed with the components of the media. In some specific media (such as in CTAB solution), the thiol-substituent products of NBD-F reacted with MPA and NAC would transfer to some long-wavelength but non-fluorescent products. Based on the individual sensing behavior of NBD-F towards different low-molecular-weight thiols, we could recognize these thiols (Cys, Hcy, MEA and etc.) to some extent.
Thirdly, we studied the time-dependent absorption and emission spectra of NBD-F reacted with bovine serum albumin (BSA) and ovalbumin (OVA). Due to the difference in structure of these two proteins, they presented quite different reactivities with NBD-F in acidic and neutral media. The addition of anionic or cationic surfactants would change the reactivities of the protiens with NBD-F. Real biological samples such as proteins extracted from rat liver tumor tissues and their enzymic hydrolysates were analyzed via high-performance liquid chromatography coupled with laser-induced fluorescence detector (HPLC-LIF) after been labeled with NBD-F. The results indicated that the selectivity of the detection would change with the reactivities of NBD-F and proteins which were definitely influenced by the pH value of the reaction media.
Finally, we designed a CE-LIF on-line protein derivatization reactor based on a hollow fiber membrane. Derivatization reagent with low molecular weight could permeate into the hollow fiber membrane to react with the active components whose molecular weights were larger than the molecular weight cutoffs (MWCO) of the membrane. The derivative products could be detected at the detection window. This device, with its merits such as small death volume of the interface, low cost and etc., has potential application in the analysis of biomacromolecules.
本文以衍生化技术为手段,选用两种不同的衍生化试剂对硫醇、蛋白质、多肽等生物分子的衍生化方法开展研究。以4-硝基-1,8-萘酐(NNA)作为探针,对硫醇类物质进行光谱检测。在实验条件下,NNA与半胱氨酸(Cys)反应所得4-巯基取代产物可以通过分子内亲核取代过程进一步转化为4-氨基取代产物,由于Cys的巯基与羧基之间可以通过六元环形成分子内氢键作用从而加速了巯基的离去,促进了巯基取代产物的转化,溶液最大吸收和最大发射波长分别位于435nm和530nm,在荧光灯照射下发射出明亮的黄绿色荧光；而其他小分子硫醇与NNA反应所得巯基取代产物不发生分子内亲核取代反应或转化为氨基取代产物的速率较慢,溶液的最大吸收和最大发射波长分别位于390nm和490nm,在荧光灯的照射下发射出蓝色荧光。所发展的方法可用于对Cys进行选择性荧光、比色和裸眼识别。
以4-氟-7-硝基-2,1,3-苯并氧杂恶二唑(NBD-F)作为探针,研究其在不同反应介质中对巯基和氨基化合物的光谱响应。在酸性、中性及添加阴离子或阳离子表面活性剂的中性水溶液中,巯基均表现出了良好的反应活性,其中,NBD-F与Cys、高半胱氨酸(Hcy)及巯基乙胺(MEA)反应所得巯基取代产物会通过分子内亲核取代反应过程进一步转变为对应的氨基取代产物,而且转化速率以及产物的稳定性也会因反应介质的不同发生改变；在特定的反应介质中(如在添加阳离子表面活性剂CTAB的中性水溶液中),NBD-F与巯基丙酸(MPA)和N-乙酰半胱氨酸(NAC)反应所得巯基取代产物会进一步转变为吸收波长更长的非荧光产物。利用这种光谱响应特性建立了在水溶液中对包括Cys、Hcy、MEA等在内7种小分子硫醇进行差异化识别的方法。
研究NBD-F与牛血清白蛋白(BSA)和卵清蛋白(OVA)反应的光谱特征。在酸性、中性水溶液中,由于BSA和OVA结构差异,致使两者与NBD-F的反应活性存在明显不同；向反应溶液中添加阴离子或阳离子表面活性剂可以改变蛋白质与NBD-F的反应性能。进一步以NBD-F作为衍生化试剂,在不同pH值条件下对鼠肝肿瘤组织蛋白提取液及其酶解产物进行柱前衍生,并通过HPLC-LIF进行分离分析,实验结果表明调整反应介质的pH值可以改变NBD-F与样品各组分之间的反应活性,从而起到改变检测选择性的作用。
为了实现生物样品的色谱分离-在线衍生-荧光检测,设计了一种基于中空纤维膜、可用于毛细管电泳-激光诱导荧光检测(CE-LIF)平台的蛋白质在线衍生反应器。小分子荧光衍生化试剂可以通过自由扩散进入反应器中,与分子量大于纤维膜截留分子量的样品发生反应,衍生化产物迁移至检测窗口处被检测。所构建的装置具有接口死体积小、制作和使用成本低廉等优点,适用于生物大分子的在线荧光衍生。
The components in biological samples are complicated and their dynamic abundances are extremely broad. It requires more sensitively and selectively analytic methods to determine the components in real samples. Derivatization is such a method that can not only enhance the sensitivity but also improve the selectivity of detection. It has aroused much attention in the design and synthesis of new derivatization reagents and the development of derivatization technique in the areas of life science, analytical chemistry and some other research areas.
We have studied the derivatization methods for biomolecules (including thiols, protiens, peptides and etc.) by using two different derivatization reagents. Firstly, we employed4-nitro-1,8-naphthalic anhydride (NNA) as a fluorescent probe for thiols. When reacted with Cys, the4-nitro in NNA was first replaced by mercapto group followed by the displacement of mercapto group with amino group to form4-amino substitute via intramolecular nucleophilic aromatic substitution. The hydrogen bond between the sulfur atom and the carboxylic acid group in Cys could help the leaving of alkylthio group, which therfore promoted the formation of4-amino substitute. The absorption and emission maxima of the4-amino substitute were at435nm and530nm, respectively, and the solution exhibited bright green-yellow fluorescence when irradiated with UV lamp. However, since the4-alkylthio substitutes of the other thiols reaced with NNA can not transfer to the4-amino substitutes during the experimental period, the reaction solutions had absorption and emission maxima at390nm and490nm, respectively, and presented blue fluorescence when irradiated with UV lamp. Thus Cys could be recognized selectively by fluorescent and UV methods and even by naked-eye.
Secondly, we used4-fluoro-7-nitrobenzo-2-oxa-l,3-diazole (NBD-F) as a probe to study its spectral responses towards thiol-containing and amino-containing compounds in different reaction meadia. Thiol group exhibited quite good reactivity in all the experimental conditions (in acidic, neutral and CTAB or SDS solutions). The thiol-substituent products of NBD-F reacted with Cys, Hcy and MEA would transfer to the corresponding amino-substituent products via intramolecular nucleophilic aromatic substitution. In addition, the rate of transfer and the stability of the products changed with the components of the media. In some specific media (such as in CTAB solution), the thiol-substituent products of NBD-F reacted with MPA and NAC would transfer to some long-wavelength but non-fluorescent products. Based on the individual sensing behavior of NBD-F towards different low-molecular-weight thiols, we could recognize these thiols (Cys, Hcy, MEA and etc.) to some extent.
Thirdly, we studied the time-dependent absorption and emission spectra of NBD-F reacted with bovine serum albumin (BSA) and ovalbumin (OVA). Due to the difference in structure of these two proteins, they presented quite different reactivities with NBD-F in acidic and neutral media. The addition of anionic or cationic surfactants would change the reactivities of the protiens with NBD-F. Real biological samples such as proteins extracted from rat liver tumor tissues and their enzymic hydrolysates were analyzed via high-performance liquid chromatography coupled with laser-induced fluorescence detector (HPLC-LIF) after been labeled with NBD-F. The results indicated that the selectivity of the detection would change with the reactivities of NBD-F and proteins which were definitely influenced by the pH value of the reaction media.
Finally, we designed a CE-LIF on-line protein derivatization reactor based on a hollow fiber membrane. Derivatization reagent with low molecular weight could permeate into the hollow fiber membrane to react with the active components whose molecular weights were larger than the molecular weight cutoffs (MWCO) of the membrane. The derivative products could be detected at the detection window. This device, with its merits such as small death volume of the interface, low cost and etc., has potential application in the analysis of biomacromolecules.
引文
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