CN111239053A - A method for detecting critical polymerization concentration of compounds by dynamic mass reset method - Google Patents

A method for detecting critical polymerization concentration of compounds by dynamic mass reset method Download PDF

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CN111239053A
CN111239053A CN201811432594.8A CN201811432594A CN111239053A CN 111239053 A CN111239053 A CN 111239053A CN 201811432594 A CN201811432594 A CN 201811432594A CN 111239053 A CN111239053 A CN 111239053A
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dynamic mass
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梁鑫淼
王荣
刘艳芳
张秀莉
王纪霞
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Dalian Institute of Chemical Physics of CAS
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Abstract

The invention discloses a method for determining critical polymerization concentration of a compound based on a dynamic mass reset signal. The device used is a resonant waveguide grating and the signal detected is the dynamic mass change of the substance near the sensor surface. When the solution reaches a more stable state, the non-polymerized molecules do not undergo dynamic mass rearrangement, whereas the polymerized molecules are capable of causing dynamic mass rearrangement. The critical micelle concentration can be deduced by detecting a series of dynamic mass reset signals of different concentrations of the compound. The method has the advantages of small sample dosage, high flux, wide application range and the like, and can provide a new way for the polymerization determination of the compound.

Description

一种动态质量重置法检测化合物临界聚合浓度的方法A method for detecting critical polymerization concentration of compounds by dynamic mass reset method

技术领域technical field

本发明涉及光学传感器的应用领域,具体来讲,本发明创建了一种利用共振波导光栅传感器检测化合物的动态质量重置信号,以判断化合物是否产生聚合的方法。The present invention relates to the application field of optical sensors, in particular, the present invention creates a method for detecting a dynamic mass reset signal of a compound by using a resonant waveguide grating sensor to judge whether the compound produces polymerization.

背景技术Background technique

化合物聚合是一种常见的物理现象。当溶液中的化合物浓度达到一定值,即临界胶束浓度(critical aggregation concentrations,CACs)时,化合物就会聚集形成胶束,同时,各种性质就会发生变化。因此,CAC的测定在实际应用中具有非常重要的意义。在药物测定领域,化合物聚合形成胶束后,会对酶或受体产生非特异性吸附,造成生化实验或细胞实验的假阳性结果。目前,检测化合物聚合的主要物理方法是扫描电镜法,动态光散射法、核磁共振氢谱法,这些手法存在通量低、成本高等问题,对实验条件、设备要求高。通过动态质量重置法测定样品CAC值,具有简单、省时、高效率等优点,因此可以作为一种检测化合物聚合的有效方法。Compound polymerization is a common physical phenomenon. When the concentration of compounds in the solution reaches a certain value, that is, critical aggregation concentrations (CACs), the compounds will aggregate to form micelles, and at the same time, various properties will change. Therefore, the determination of CAC is of great significance in practical applications. In the field of drug determination, after the compound polymerizes to form micelles, it will produce non-specific adsorption to enzymes or receptors, resulting in false positive results in biochemical experiments or cell experiments. At present, the main physical methods for detecting compound polymerization are scanning electron microscopy, dynamic light scattering, and hydrogen nuclear magnetic resonance spectroscopy. These methods have problems of low throughput, high cost, and high requirements for experimental conditions and equipment. Determination of sample CAC value by dynamic mass reset method has the advantages of simplicity, time saving and high efficiency, so it can be used as an effective method to detect compound polymerization.

动态质量重置法(dynamic mass redistribution,DMR)的原理,主要是利用共振波导光栅生物传感器将传感器表面的折射率的变化以通过共振角(或波长)变化检测出。具体来说,共振波导光栅(resonant waveguide grating,RWG)生物传感器利用衍射光栅的方式将光共振偶联进入波导,导致在溶液-表面界面发生全内反射,进而在界面产生消逝波,消逝波从传感器表面指数衰减,它衰减到初始值的1/e的距离被称为贯穿深度。当采用恒定角度的复合偏振光照射波导时,只有特定的波长的光才会沿着波导传播,波长与贯穿深度内的折射率有关;当贯穿深度内的物质的质量发生重置,折射率发生变化,沿波导传播的波长的变化就可以被记录下来。当采用单色光照射传感器时,记录的信息为光的共振偶联角度(或波长)的变化。理论上,贯穿深度内任何质量密度的变化,均可以引起动态质量重置。利用这种原理,动态质量重置法已经被广泛用来检测细胞中的物质的变化。The principle of dynamic mass redistribution (DMR) is mainly to use the resonant waveguide grating biosensor to detect the change of the refractive index of the sensor surface through the change of the resonance angle (or wavelength). Specifically, the resonant waveguide grating (RWG) biosensor utilizes diffraction gratings to resonantly couple light into the waveguide, resulting in total internal reflection at the solution-surface interface, which in turn generates an evanescent wave at the interface. The sensor surface decays exponentially, and the distance at which it decays to 1/e of the initial value is called the penetration depth. When the waveguide is irradiated with compound polarized light at a constant angle, only light of a specific wavelength will propagate along the waveguide, and the wavelength is related to the refractive index in the penetration depth; when the mass of the material in the penetration depth is reset, the refractive index occurs Changes in wavelengths propagating along the waveguide can be recorded. When the sensor is illuminated with monochromatic light, the information recorded is the change in the resonant coupling angle (or wavelength) of the light. Theoretically, any change in mass density throughout the depth can cause dynamic mass reset. Using this principle, dynamic mass reset methods have been widely used to detect changes in substances in cells.

这种原理同样可以被用来检测化合物本身的聚合。当达到一个较稳定的状态时(即化合物完成自身在溶液中的扩散后,聚合与解聚速率达到接近,聚合物的浓度不再发生变化,表面静止的平衡状态),非聚合状态的分子在溶液中为均匀分布的状态,均匀分布的分子的质量密度不会随时间发生明显变化,因而不会产生动态质量重置信号;而聚合状态的分子在溶液中分布不均匀,随着时间的变化,其质量密度会发生较大改变,因而会引起动态质量重置。通过测定化合物不同浓度时的动态质量响应信号,可以推算出临界胶束浓度。This principle can also be used to detect the polymerization of the compound itself. When a relatively stable state is reached (that is, after the compound completes its own diffusion in the solution, the polymerization and depolymerization rates are close to each other, the concentration of the polymer does not change, and the surface is in a static equilibrium state), the molecules in the non-polymerized state are in the equilibrium state. The solution is in a state of uniform distribution, and the mass density of the uniformly distributed molecules will not change significantly with time, so no dynamic mass reset signal will be generated; while the molecules in the aggregated state are not uniformly distributed in the solution, and change with time. , its mass density will change greatly, thus causing dynamic mass reset. By measuring the dynamic mass response signal at different concentrations of the compound, the critical micelle concentration can be deduced.

发明内容SUMMARY OF THE INVENTION

本发明公开了利用共振波导光栅传感器的动态质量重置法检测化合物聚合的方法。The invention discloses a method for detecting compound polymerization using a dynamic mass reset method of a resonant waveguide grating sensor.

所述的共振波导光栅传感器,可包括基材、包埋了光栅或周期性结构的波导薄层。The resonant waveguide grating sensor may include a substrate, a thin waveguide layer embedded with gratings or periodic structures.

临界胶束浓度的检测方法如下:The detection method of critical micelle concentration is as follows:

1)向检测平台底部嵌有共振波导光栅传感器的微孔板中加入空白溶液,平衡基线至平稳;1) Add a blank solution to the microplate with the resonant waveguide grating sensor embedded in the bottom of the detection platform, and balance the baseline to be stable;

2)重新平衡基线,加入系列浓度样品,测定一定时间;2) Rebalance the baseline, add a series of concentration samples, and measure for a certain period of time;

3)选取测定时间中某个时间点,读取该时间点下各浓度样品对应的信号值;3) Select a certain time point in the measurement time, and read the signal value corresponding to each concentration sample under this time point;

4)以样品浓度的对数为横坐标,动态质量重置的变化相关为纵坐标,分别以水平线和斜线拟合各坐标,水平线与斜线之间的交点为临界胶束浓度。4) Taking the logarithm of the sample concentration as the abscissa, and the change correlation of dynamic mass reset as the ordinate, fitting each coordinate with a horizontal line and an oblique line, and the intersection between the horizontal line and the oblique line is the critical micelle concentration.

共振波导光栅传感器包括基材、包埋了光栅或周期性结构的波导薄层。A resonant waveguide grating sensor includes a substrate, a thin layer of waveguides with embedded gratings or periodic structures.

样品包括单一化合物或组合物。A sample includes a single compound or composition.

单一化合物为有机小分子或大分子采用空白溶液进行溶解,浓度为未产生沉淀的任意浓度;所述组合物为两种或两种以上的小分子或大分子的组合,采用空白溶液进行溶解,浓度为未产生沉淀的任意浓度。The single compound is an organic small molecule or macromolecule and is dissolved in a blank solution, and the concentration is any concentration that does not produce precipitation; the composition is a combination of two or more small molecules or macromolecules, and is dissolved in a blank solution, The concentration is any concentration at which precipitation does not occur.

空白溶液,包括单一溶剂、混合溶剂、盐溶液。Blank solution, including single solvent, mixed solvent, salt solution.

单一溶剂为水,甲醇,乙醇等传感器和孔板能够耐受的溶剂;所述混合溶剂为两种或两种以上单一溶剂组成的传感器和孔板能够耐受的溶剂,溶剂间的比例为可以相互溶解的任意比例;所述盐溶液为含有一种或多种无机盐的单一溶剂或混合溶剂,无机盐浓度为不发生析出的任意浓度。The single solvent is water, methanol, ethanol and other solvents that the sensor and the orifice plate can tolerate; the mixed solvent is the solvent that the sensor and the orifice plate composed of two or more single solvents can withstand, and the ratio between the solvents is acceptable. Any ratio of mutual dissolution; the salt solution is a single solvent or mixed solvent containing one or more inorganic salts, and the inorganic salt concentration is any concentration that does not precipitate.

一定时间是指溶液达到稳定的时间,具体为在加入溶液后的5-10分钟,10-20分钟,20-50分钟,50-120分钟的时域。A certain time refers to the time for the solution to reach stability, specifically, the time domain of 5-10 minutes, 10-20 minutes, 20-50 minutes, and 50-120 minutes after adding the solution.

某个时间,是指溶液达到稳定状态的时间内的任意一个时间点。A certain time refers to any time point within the time when the solution reaches a steady state.

检测平台为康宁第三代Epic成像仪。The detection platform is Corning's third-generation Epic imager.

本方法适用于化合物,组合物,溶剂可为单一溶剂,混合溶剂,盐溶液。This method is applicable to compounds, compositions, and the solvent can be single solvent, mixed solvent, or salt solution.

发明的有益效果:可在微量条件下进行,采用自动化操作系统,具有样品用量少、通量高的优点;适用范围广,可对各种溶剂中的样品进行测定;扩大了动态质量重置实验的应用范围,可以模拟细胞测定环境,测定的临界胶束浓度可以为细胞水平动态质量实验提供假阳性判断的参考,无需购置其他装置。Beneficial effects of the invention: it can be carried out under micro conditions, adopts an automated operating system, and has the advantages of less sample consumption and high throughput; wide application range, can measure samples in various solvents; enlarged dynamic mass reset The application range of the experiment can simulate the cell measurement environment, and the measured critical micelle concentration can provide a reference for false-positive judgments for cell-level dynamic quality experiments, without the need to purchase other devices.

附图说明Description of drawings

图1动态质量重置法测定化合物聚合的原理,(A)-非聚合状态,(B)-聚合状态。Fig. 1 The principle of determination of compound polymerization by dynamic mass reset method, (A)-non-polymerized state, (B)-polymerized state.

图2(A)-丹酚酸C的动态质量重置信号,(B)-原花青素的动态质量重置信号,(C)-烟酸的动态质量重置信号,(D)红景天提取物的的动态质量重置信号。Figure 2 (A)-Dynamic mass reset signal of salvianolic acid C, (B)-Dynamic mass reset signal of procyanidin, (C)-Dynamic mass reset signal of niacin, (D) Rhodiola rosea extract The dynamic quality of the reset signal.

图3(A)-丹酚酸C的临界聚合浓度的测定,(B)-原花青素的临界聚合浓度的测定,(C)-烟酸的临界聚合浓度的测定,(D)-红景天提取物的临界聚合浓度的测定。Figure 3 (A) - Determination of critical polymerization concentration of salvianolic acid C, (B) - Determination of critical polymerization concentration of procyanidins, (C) - Determination of critical polymerization concentration of nicotinic acid, (D) - Extraction of Rhodiola rosea Determination of the critical polymerization concentration of the material.

具体实施方式Detailed ways

下面结合附图对本发明的实施例作详细说明:实施例在以本发明技术方案为前提下进行实施,给出了详细的实施方式和具体的操作过程,但本发明的保护范围不限于下述的实施例。Below in conjunction with the accompanying drawings, the embodiments of the present invention are described in detail: the embodiments are implemented on the premise of the technical solutions of the present invention, and provide detailed embodiments and specific operation processes, but the protection scope of the present invention is not limited to the following example.

实施例1:丹酚酸C、原花青素和烟酸的临界聚合浓度的测定Example 1: Determination of the critical polymerization concentration of salvianolic acid C, procyanidins and niacin

检测平台为康宁第三代Epic成像仪,测试在康宁Epic微孔板中进行,微孔板底部包含有共振波导光栅的。检测的信号为动态质量重置引起的波长位移变化。The detection platform is Corning's third-generation Epic imager. The test is carried out in Corning Epic microplates. The bottom of the microplate contains resonant waveguide gratings. The detected signal is the wavelength shift change caused by dynamic mass reset.

首先是样品配置,准确称取丹酚酸C粉末1mg,用HBSS(1×汉克斯平衡盐溶液,添加20mM Hepes,pH 7.2)进行溶解,获得400μg/mL的溶液。接着,取100μL的400μg/mL的溶液,进行梯度稀释,最终获得400μg/mL,200μg/mL,100μg/mL,50μg/mL,25μg/mL,12.5μg/mL,6.25μg/mL,3.125μg/mL,1.5625μg/mL,0.7813μg/mL,0.3907μg/mL,0.1953μg/mL,0.0977μg/mL,0.0488μg/mL,0.0244μg/mL,0.0122μg/mL的系列溶液。原花青素和烟酸采用同样的配置方法。The first is sample configuration. Accurately weigh 1 mg of salvianolic acid C powder, dissolve with HBSS (1×Hanks balanced salt solution, add 20 mM Hepes, pH 7.2) to obtain a solution of 400 μg/mL. Next, take 100 μL of the 400 μg/mL solution for gradient dilution, and finally obtain 400 μg/mL, 200 μg/mL, 100 μg/mL, 50 μg/mL, 25 μg/mL, 12.5 μg/mL, 6.25 μg/mL, 3.125 μg/mL mL, 1.5625μg/mL, 0.7813μg/mL, 0.3907μg/mL, 0.1953μg/mL, 0.0977μg/mL, 0.0488μg/mL, 0.0244μg/mL, 0.0122μg/mL series of solutions. Proanthocyanidins and niacin are formulated in the same way.

其次是实验测定,首先将每孔加入30μL HBSS(1×汉克斯平衡盐溶液,添加20mMHepes,pH 7.2),平衡基线10min。接着,重新平衡基线2min,将各梯度浓度的丹酚酸C溶液加入到微孔板中,每孔10μL,测定60分钟。每个浓度测定三次(由于预先向孔板中加入了30μLHBSS缓冲盐溶液,实际测定时的样品浓度为配置时浓度的四分之一)。选取10min时的DMR信号值,取平均值。以样品浓度的对数为横坐标,动态质量重置的变化为纵坐标,分别以水平线和斜线拟合各点,水平线与斜线之间的交点为临界胶束浓度。原花青素和烟酸采用同样的方法进行实验和数据分析。最终,实验获得的丹酚酸C、原花青素的临界聚合浓度分别为0.49μg/mL,1.65μg/mL,而烟酸在该体系下不发生聚合。The second is the experimental determination. First, 30 μL of HBSS (1×Hanks Balanced Salt Solution, 20 mM Hepes, pH 7.2) is added to each well, and the baseline is equilibrated for 10 min. Next, re-equilibrate the baseline for 2 min, add salvianolic acid C solutions of each gradient concentration into the microplate, 10 μL per well, and measure for 60 minutes. Each concentration was measured three times (because 30 μL of HBSS buffered saline solution was added to the well plate in advance, the sample concentration in the actual measurement was one-fourth of the concentration in the configuration). Select the DMR signal value at 10 min and take the average value. Taking the logarithm of the sample concentration as the abscissa, and the change of dynamic mass reset as the ordinate, each point was fitted with a horizontal line and an oblique line, and the intersection between the horizontal line and the oblique line was the critical micelle concentration. Proanthocyanidins and niacin were subjected to the same experiment and data analysis. Finally, the critical polymerization concentrations of salvianolic acid C and proanthocyanidin obtained in the experiment were 0.49 μg/mL and 1.65 μg/mL, respectively, while niacin did not polymerize in this system.

实施例2:红景天提取物临界聚合浓度的测定Example 2: Determination of the critical polymerization concentration of Rhodiola rosea extract

所使用的检测平台与实施例1相同。The detection platform used was the same as in Example 1.

首先是样品准备。红景天药材粉末10g,用100mL 70%乙醇超声提取1小时,旋转蒸发去除溶剂。准确称取药材浸膏1mg,用HBSS(1×汉克斯平衡盐溶液,添加20mM Hepes,pH7.2)溶解成400μg/mL的溶液。接着,取100μL的400μg/mL的溶液,进行梯度稀释,最终获得400μg/mL,200μg/mL,100μg/mL,50μg/mL,25μg/mL,12.5μg/mL,6.25μg/mL,3.125μg/mL,1.5625μg/mL,0.7813μg/mL,0.3907μg/mL,0.1953μg/mL,0.0977μg/mL,0.0488μg/mL,0.0244μg/mL,0.0122μg/mL的系列溶液。The first is sample preparation. 10 g of Rhodiola rosea powder was ultrasonically extracted with 100 mL of 70% ethanol for 1 hour, and the solvent was removed by rotary evaporation. Accurately weigh 1 mg of the medicinal material extract, and dissolve it into a 400 μg/mL solution with HBSS (1×Hanks balanced salt solution, adding 20 mM Hepes, pH 7.2). Next, take 100 μL of the 400 μg/mL solution for gradient dilution, and finally obtain 400 μg/mL, 200 μg/mL, 100 μg/mL, 50 μg/mL, 25 μg/mL, 12.5 μg/mL, 6.25 μg/mL, 3.125 μg/mL mL, 1.5625μg/mL, 0.7813μg/mL, 0.3907μg/mL, 0.1953μg/mL, 0.0977μg/mL, 0.0488μg/mL, 0.0244μg/mL, 0.0122μg/mL series of solutions.

其次是实验测定,首先向每孔加入30μL HBSS(1×汉克斯平衡盐溶液,添加20mMHepes,pH 7.2),平衡基线10min。接着,重新平衡基线2min,将各梯度浓度的丹酚酸C溶液加入微孔板中,每孔10μL,测定60分钟。每个浓度测定三次(由于预先向孔板中加入了30μLHBSS缓冲盐溶液,实际测定时的样品浓度为配置时浓度的四分之一)。选取10min时的DMR信号值,取平均值。以样品浓度的对数为横坐标,动态质量重置的变化为纵坐标,分别以水平线和斜线拟合各点,水平线与斜线之间的交点为临界胶束浓度。实验测得的红景天提取物的临界胶束浓度为3.55μg/mL。Followed by the experimental determination, firstly, 30 μL of HBSS (1×Hanks Balanced Salt Solution, supplemented with 20 mM Hepes, pH 7.2) was added to each well, and the baseline was equilibrated for 10 min. Next, re-equilibrate the baseline for 2 minutes, add salvianolic acid C solutions of each gradient concentration into the microplate, 10 μL per well, and measure for 60 minutes. Each concentration was measured three times (because 30 μL of HBSS buffered saline solution was added to the well plate in advance, the sample concentration in the actual measurement was a quarter of the concentration in the configuration). Select the DMR signal value at 10 min and take the average value. Taking the logarithm of the sample concentration as the abscissa, and the change of dynamic mass reset as the ordinate, each point was fitted with a horizontal line and an oblique line, and the intersection between the horizontal line and the oblique line was the critical micelle concentration. The experimentally measured critical micelle concentration of Rhodiola rosea extract was 3.55 μg/mL.

Claims (9)

1. A method for detecting critical polymerization concentration of a compound by a dynamic mass resetting method is characterized by comprising the following steps:
1) adding a blank solution into a microporous plate with a resonant waveguide grating sensor embedded at the bottom of the detection platform, and balancing a base line to be stable;
2) rebalancing the baseline, adding a series of concentration samples, and measuring for a certain time;
3) selecting a certain time point, and reading signal values corresponding to the concentration samples at the time point;
4) and taking the logarithm of the concentration of the sample as an abscissa, taking the change correlation of the dynamic mass resetting as an ordinate, fitting each coordinate by a horizontal line and an oblique line respectively, and taking the intersection point between the horizontal line and the oblique line as the critical micelle concentration.
2. The method of claim 1, wherein: the resonant waveguide grating sensor comprises a substrate, a waveguide thin layer embedded with a grating or a periodic structure.
3. The method of claim 1, wherein: the sample comprises a single compound or composition.
4. The method of claim 3, wherein: the single compound is organic micromolecule or macromolecule and is dissolved by adopting blank solution, and the concentration is any concentration which does not generate precipitate; the composition is a combination of two or more than two small molecules or macromolecules, and is dissolved by adopting a blank solution, wherein the concentration is any concentration which does not generate precipitates.
5. The method of claim 1, wherein: the blank solution comprises a single solvent, a mixed solvent and a salt solution.
6. The method of claim 5, wherein: the single solvent is a solvent which can be endured by sensors and pore plates such as water, methanol and ethanol; the mixed solvent is a solvent which can be endured by a sensor and a pore plate consisting of two or more single solvents, and the proportion of the solvents is any proportion which can be mutually dissolved; the salt solution is a single solvent or a mixed solvent containing one or more inorganic salts, and the concentration of the inorganic salts is any concentration at which precipitation does not occur.
7. The method of claim 1, wherein: the certain time refers to the time for the solution to reach stability, and specifically refers to the time domain of 5-10 minutes, 10-20 minutes, 20-50 minutes and 50-120 minutes after the solution is added.
8. The method of claim 1, wherein: the certain time refers to any time point within the time when the solution reaches a steady state.
9. The method of claim 1, wherein: the detection platform is a Corning third generation Epic imager.
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