CN115825019A - Method for detecting heparin sodium based on water-soluble cationic AIE fluorescent molecules and application - Google Patents
Method for detecting heparin sodium based on water-soluble cationic AIE fluorescent molecules and application Download PDFInfo
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- CN115825019A CN115825019A CN202210967689.XA CN202210967689A CN115825019A CN 115825019 A CN115825019 A CN 115825019A CN 202210967689 A CN202210967689 A CN 202210967689A CN 115825019 A CN115825019 A CN 115825019A
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- 229920000669 heparin Polymers 0.000 title claims abstract description 71
- ZFGMDIBRIDKWMY-PASTXAENSA-N heparin Chemical compound CC(O)=N[C@@H]1[C@@H](O)[C@H](O)[C@@H](COS(O)(=O)=O)O[C@@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O[C@H]2[C@@H]([C@@H](OS(O)(=O)=O)[C@@H](O[C@@H]3[C@@H](OC(O)[C@H](OS(O)(=O)=O)[C@H]3O)C(O)=O)O[C@@H]2O)CS(O)(=O)=O)[C@H](O)[C@H]1O ZFGMDIBRIDKWMY-PASTXAENSA-N 0.000 title claims abstract description 38
- 229960001008 heparin sodium Drugs 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title description 5
- 125000002091 cationic group Chemical group 0.000 title description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims abstract description 33
- 229960002897 heparin Drugs 0.000 claims abstract description 33
- 238000001514 detection method Methods 0.000 claims abstract description 29
- 239000007850 fluorescent dye Substances 0.000 claims abstract description 15
- 230000002776 aggregation Effects 0.000 claims abstract description 11
- 238000004220 aggregation Methods 0.000 claims abstract description 11
- 230000000694 effects Effects 0.000 claims abstract description 11
- 239000000523 sample Substances 0.000 claims abstract description 11
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- 238000006862 quantum yield reaction Methods 0.000 claims abstract description 8
- 230000004044 response Effects 0.000 claims abstract description 7
- 238000010791 quenching Methods 0.000 claims abstract description 4
- 230000000171 quenching effect Effects 0.000 claims abstract description 4
- 230000007547 defect Effects 0.000 claims abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 230000005284 excitation Effects 0.000 claims description 5
- 238000002189 fluorescence spectrum Methods 0.000 claims description 2
- 230000002708 enhancing effect Effects 0.000 claims 1
- 230000001939 inductive effect Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000012085 test solution Substances 0.000 claims 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 abstract description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical class C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 3
- 238000005259 measurement Methods 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000005611 electricity Effects 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000012490 blank solution Substances 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000600 disaccharide group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000011155 quantitative monitoring Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
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- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
The invention discloses an application of a water-soluble and positively-charged fluorescent probe TPA-3Py in heparin sodium detection. TPA-3Py is obtained by covalently linking three methylated vinylpyridines to each of the three arms of a triphenylamine molecule. The heparin can induce the fluorescent molecules to generate aggregation-induced emission effect, the fluorescence intensity is obviously enhanced along with the increase of the content of the heparin, the good fluorescence turn-on response is realized, and the defect that quenching is caused by aggregation when the fluorescent probe detects the heparin in the prior art is overcome. When 10 mu M TPA-3Py aqueous solution is used for heparin detection, stable fluorescence intensity is achieved within 5min, and the linear range is 0-6.14mg/L (R) 2 = 0.9938), the lowest detection limit was 49.53ng/mL, and the quantum yield was 4.85%. For the detection of heparin sodium, the TPA-3Py probe adopted by the invention overcomes the quenching phenomenon caused by aggregation and shows obvious AIE effect. The fluorescent probe TPA-3Py for detecting the heparin sodium has the advantages of high sensitivity, high fluorescence intensity, quick response and stable signal. The TPA-3Py fluorescent molecule has simple structure and can be detectedThe detection method is simple and easy to implement, and is worth popularizing and applying in the aspect of heparin sodium content detection.
Description
Technical Field
The invention belongs to the technical field of medicines, particularly relates to the field of heparin sodium detection, and particularly discloses a phenomenon that a water-soluble TPA-3Py molecule with positive charge can be combined with heparin sodium with negative charge to be aggregated and the fluorescence is remarkably enhanced.
Background
Heparin sodium is widely used as an anticoagulant in clinical application, is used for preventing diseases such as thrombosis in operation and treatment, has side effects such as bleeding in the clinical application process, and is very necessary for quantitative monitoring of heparin sodium. Heparin sodium is the most negatively charged class of linear glycosaminoglycans, the negative charge of which is derived from three sulfonic acid groups and one carboxylic acid group on the main disaccharide unit. The fluorescent probe for detecting heparin sodium electrostatically adsorbs negatively charged heparin sodium molecules through the positive charge of the fluorescent probe, so that the fluorescent signal is enhanced due to the aggregation of the probe. The conventional fluorescent probe is combined with heparin sodium, and the ACQ phenomenon is caused by aggregation, so that the detection capability is reduced. The AIE molecules are almost non-fluorescent in a solution state, but become intense to emit light when an analyte induces aggregation, so that the ACQ problem is fundamentally solved, and the AIE molecules are a powerful tool for analysis and detection research at present. Triphenylamine is a commonly used AIE parent nucleus structure, three methylated vinylpyridines are respectively covalently connected to three arms of a triphenylamine molecule to obtain a TPA-3Py molecule, and the molecule has strong water solubility and positive charge. The invention discovers that the long-chain heparin sodium with negative electricity can be combined with TPA-3Py, and the long-chain heparin sodium with negative electricity can be aggregated and can limit the intramolecular movement of the long-chain heparin sodium, so that the long-chain heparin sodium with negative electricity can turn on the fluorescence response. The invention utilizes the phenomenon to develop the application of TPA-3Py molecules to heparin sodium detection.
According to relevant documents, no report about a method for detecting the content of the heparin sodium by utilizing TPA-3Py molecules is found at present.
Disclosure of Invention
The invention aims to provide a fluorescent probe which can overcome the defect of quenching (ACQ) caused by aggregation in the detection performance of heparin in the prior art, and the fluorescent probe is developed to be applied to heparin sodium detection by adopting an aggregation-induced emission fluorescent probe.
Based on the above purpose, the technical scheme of the invention is as follows:
1) Selecting an AIE fluorescent molecule: the TPA-3Py fluorescent molecule is selected, is obtained by respectively covalently connecting three methylated vinylpyridines on three arms of a triphenylamine molecule, has water solubility and positive charge, and has the following specific structural formula:
2) Examining the AIE properties of TPA-3 Py: the molecule has weak fluorescence in aqueous solution, but the fluorescence intensity is gradually increased along with the gradual increase of the ethanol content in the solution, thereby proving the AIE effect of TPA-3 Py.
3) The development of the application of TPA-3Py in heparin detection: as the concentration of heparin increases, the fluorescent signal of TPA-3Py is obviously enhanced, and the sodium heparin has good fluorescent 'on' response to the TPA-3Py probe. Specifically, TPA-3Py aqueous solution with the concentration of 10 mu M is adopted to detect heparin sodium, the concentration of heparin is 7 different concentrations of 0-12mg/L, the maximum fluorescence emission intensity is measured at the 462nm excitation wavelength after the heparin is placed for 15min, and the linear relation between the heparin sodium and the fluorescence intensity under the maximum emission wavelength is obtained. The linear relation is good, the linear equation is y =0.807x +0.780 2 =0.9938, linear range 0-6.14mg/L. The lowest detection limit is 49.53ng/mL, and the quantum yield reaches 4.85%.
The invention has the following advantages:
for detection of heparin sodium, the TPA-3Py probe showed a wider linear range, a lower minimum detection limit, and a higher quantum yield. The fluorescent probe of the invention has rapid response, high fluorescence intensity, stable signal, high sensitivity, simple structure of fluorescent molecules, simple and easy detection method and easy popularization.
Drawings
FIG. 1 is a spectrum of the fluorescence intensity of TPA-3Py (8. Mu.M) at different ethanol concentrations (a), a combination graph of the increase of the fluorescence intensity at the maximum excitation wavelength with the increase of the ethanol content (b) λ ex (TPA-3 Py) =476nm, slit 2.5/2.5nm
FIG. 2 is a graph showing the relationship between the fluorescence spectrum (a) and the linearity of TPA-3Py (10. Mu.M) binding to heparin at different concentrations, λ ex (TPA-3 Py) =462nm, slit 10/10nm
FIG. 3 Effect of TPA-3Py (10. Mu.M) reaction time with Hep (12 mg/mL) =462nm,. Lamda.ex (TPA-3 Py) =462nm, slit 10/10nm
The specific implementation mode is as follows:
examples of the implementation
1. Investigation of the AIE Properties of TPA-3Py
(1) Preparation of TPA-3Py mother liquor
Accurately weighing 0.0015g of TPA-3Py solid powder into a 25mL volumetric flask, dissolving the powder with a proper amount of deionized water, and then fixing the volume to a scale mark. The obtained AIE-3 solution had a concentration of 66.219. Mu.M
(2) Preparation of TPA-3Py detection solution
11 centrifuge tubes of 1.5mL were taken, 0.181mL of TPA-3Py mother liquor was added, followed by anhydrous ethanol of 0,0.139,0.278,0.417,0.555,0.694,0.833,0.972,1.110,1.250 and 1.319mL volumes to a volume of 1.5mL.
(3) Fluorescence intensity measurement
The prepared solution was taken, the excitation wavelength was 476nm, the slit was 2.5nm, and the fluorescence emission intensity was measured. TPA-3Py is a water-soluble molecule that fluoresces very weakly in aqueous solution, with increasing fluorescence intensity with increasing ethanol component in solution, as shown in FIG. 1. It was confirmed that polymerization occurred after the addition of ethanol and that the TPA-3Py probe showed AIE properties.
2. Detection capability of TPA-3Py on heparin
(1) Preparation of heparin sodium mother liquor
Accurately weighing 0.0075g of heparin sodium standard (Nicotai Dongcheng pharmaceutical group Co., ltd.) into a 100mL volumetric flask, adding deionized water, dissolving, and fixing the volume to a scale mark to obtain heparin sodium standard solution with the concentration of 75 mg/L.
(2) Preparation of heparin detection solution
Taking 7 centrifuge tubes with the volume of 1.5mL, adding 0.227mL of TPA-3Py mother liquor, then respectively adding heparin sodium mother liquor with the volume of 0,0.04,0.08,0.12,0.16,0.20 and 0.24mL, and finally using deionized water to fix the volume to 1.5mL.
(3) Fluorescence intensity measurement
And (3) taking the solution to be measured, reacting for 5 minutes in a dark place at room temperature, and measuring the fluorescence intensity at the excitation wavelength of 462nm by using a slit of 10nm.
As shown in FIG. 2, the fluorescence of TPA-3Py molecule in aqueous solution is very weak, and the maximum emission wavelength of TPA-3Py (10 μ M) is shifted from 610nm to 645nm after heparin is added, resulting in red shift and significant increase of fluorescence intensity. Fluorescence changes indicate that the electrostatic interaction between the negatively charged heparin and the positively charged TPA-3Py molecule forms a TPA-3Py + hep ligand. The steric hindrance is increased, and the intramolecular rotation of the fluorescent molecule is restricted, so that the fluorescence intensity is increased.
(4) Linear relationship detection
Relative fluorescence intensity at maximum emission wavelength (I/I) 0 ) Plotting with heparin concentration yields the linear equation y =0.807x +0.780, (R) 2 = 0.9938), and the results demonstrated a good linear relationship with 10 μm tpa-3Py in the heparin concentration range of 0-6.14mg/L (fig. 2 b).
3. Effect of reaction time on fluorescence intensity
The effect of reaction time was examined by measuring the fluorescence intensity of the complexes TPA-3Py (10. Mu.M) and Hep (12 mg/mL) at the maximum emission wavelength within 20min (FIG. 3). The fluorescence intensity of the molecule was stable at about 580 minutes without significant fluctuation within 20 minutes, and the reaction time for measuring AIE-3 was set to 5 minutes. The above results indicate that heparin rapidly binds to TPA-3Py in a more stable complex.
4. Determination of the Limit of detection (LOD) of heparin by TPA-3Py Probe
10 blank solutions of TPA-3Py (without heparin sodium) were prepared and the fluorescence intensity of the blanks was measured. The data were obtained using Excel to calculate standard deviation. A series of TPA-3Py solutions containing different concentrations of heparin were prepared and the fluorescence intensity was measured. Drawing the fluorescence intensity change diagram at the maximum emission wavelength under different heparin concentrations, and calculating the slope of the straight line and R by using the linear relation diagram of the TPA-3Py relative fluorescence intensity and the heparin concentration 2 . The data used were substituted into the detection limit calculation formula LOD =3 δ/S.
The LOD of heparin was calculated to be 49.53ng/mL according to the formula.
5. Investigation of the fluorescent Quantum yield of TPA-3Py
The fluorescence quantum yield of TPA-3Py is measured by FS5 fluorescence spectrophotometer, and the instrument parts need to be replaced during measurement. Before measurement, an ultraviolet spectrophotometer is used for measuring the absorbance of the sample, and the measured absorbance of the sample is ensured to be less than 0.1. During measurement, the slit is adjusted to enable an emision signal value to reach the maximum, and meanwhile, the Ex slit is guaranteed to be 10 times of the Em slit.
The quantum yield of TPA-3Py was 2.61% in the absence of heparin, and the quantum yield of TPA-3Py increased to 4.85% after 12mg/L heparin was added.
For the detection of heparin sodium, the TPA-3Py probe adopted by the invention overcomes the ACQ phenomenon and shows obvious AIE effect. The fluorescent probe for heparin sodium detection has the advantages of rapid response, high sensitivity, high fluorescence intensity and stable signal. The TPA-3Py fluorescent molecule has simple structure, the detection method is simple and easy to implement, and the method is worth popularizing and applying in the aspect of measuring the content of the heparin sodium.
Claims (5)
1. A fluorescent probe is characterized in that the fluorescent probe can overcome the phenomenon of aggregation-induced quenching (ACQ) caused by aggregation in the prior art, and can reduce the defect of the detection capability of the fluorescent probe on heparin sodium, and the application of the fluorescent probe utilizing Aggregation Induced Emission (AIE) to the detection of the heparin sodium is developed.
2. Selecting an AIE fluorescent molecule according to claim 1. According to the nature that heparin is easily dissolved in water and is negatively charged, a water-soluble and positively charged molecule is selected, and the TPA-3Py fluorescent molecule has the following specific structural formula:
according to claim 1, characterized by the AIE properties of TPA-3 Py: TPA-3Py is a water-soluble molecule and has weak fluorescence in an aqueous solution, but the fluorescence intensity is remarkably increased along with the gradual increase of a poor solvent ethanol in the solution, so that the AIE effect of the TPA-3Py occurs.
3. According to claim 1, heparin is capable of inducing an AIE effect in TPA-3 Py: dissolving probe molecules in aqueous solution, adding heparin with different concentrations to obtain test solution, recording fluorescence emission spectrum by using a fluorescence instrument, and obviously enhancing the fluorescence intensity of TPA-3Py aqueous solution along with the addition of the heparin to generate AIE effect.
4. The use according to claim 1, wherein the TPA-3Py for detecting heparin is characterized in that:
as the concentration of heparin increases, the fluorescent signal of TPA-3Py is obviously enhanced, and the sodium heparin has good fluorescent 'opening' response to the TPA-3Py probe. Specifically, TPA-3Py aqueous solution with the concentration of 10 mu M is adopted to detect heparin sodium, the concentration of heparin is 7 different concentrations of 0-12mg/L, the maximum fluorescence emission intensity is measured at the 462nm excitation wavelength after the heparin is placed for 15min, and the linear relation between the heparin sodium and the fluorescence intensity under the maximum emission wavelength is obtained.
5. According to claim 4, the linear range of TPA-3Py aqueous solution with a concentration of 10 μ M for heparin is 0-6.14mg/L, the lowest detection limit is 49.53ng/mL, and the quantum yield is 4.85%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117106207A (en) * | 2023-10-19 | 2023-11-24 | 中国农业科学院农产品加工研究所 | Heparin sodium ratio type fluorescent hydrogel and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117106207A (en) * | 2023-10-19 | 2023-11-24 | 中国农业科学院农产品加工研究所 | Heparin sodium ratio type fluorescent hydrogel and preparation method and application thereof |
| CN117106207B (en) * | 2023-10-19 | 2024-02-23 | 中国农业科学院农产品加工研究所 | Heparin sodium ratio type fluorescent hydrogel and preparation method and application thereof |
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