CN118308091A - Stable luminous liquid and application thereof - Google Patents
Stable luminous liquid and application thereof Download PDFInfo
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- CN118308091A CN118308091A CN202410290823.6A CN202410290823A CN118308091A CN 118308091 A CN118308091 A CN 118308091A CN 202410290823 A CN202410290823 A CN 202410290823A CN 118308091 A CN118308091 A CN 118308091A
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- luminol
- buffer
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- luminescence
- solution
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- 239000007788 liquid Substances 0.000 title claims abstract description 35
- HWYHZTIRURJOHG-UHFFFAOYSA-N luminol Chemical compound O=C1NNC(=O)C2=C1C(N)=CC=C2 HWYHZTIRURJOHG-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000004020 luminiscence type Methods 0.000 claims abstract description 31
- 239000007800 oxidant agent Substances 0.000 claims abstract description 13
- 239000000872 buffer Substances 0.000 claims description 11
- -1 polyol compound Chemical class 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910001868 water Inorganic materials 0.000 claims description 8
- 239000003623 enhancer Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 6
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000006174 pH buffer Substances 0.000 claims description 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 4
- 229960001922 sodium perborate Drugs 0.000 claims description 4
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 3
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 239000008351 acetate buffer Substances 0.000 claims description 2
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 2
- 239000008363 phosphate buffer Substances 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229940045872 sodium percarbonate Drugs 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 claims 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 abstract description 12
- 230000001590 oxidative effect Effects 0.000 abstract description 8
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- WGLQHUKCXBXUDV-UHFFFAOYSA-N 3-aminophthalic acid Chemical compound NC1=CC=CC(C(O)=O)=C1C(O)=O WGLQHUKCXBXUDV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract description 2
- 238000003759 clinical diagnosis Methods 0.000 abstract description 2
- 238000001514 detection method Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 230000005281 excited state Effects 0.000 abstract description 2
- 230000005283 ground state Effects 0.000 abstract description 2
- 239000013076 target substance Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 4
- 235000019799 monosodium phosphate Nutrition 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- RVJVDCVIJCBUTH-UHFFFAOYSA-M sodium;5-amino-2h-phthalazin-3-ide-1,4-dione Chemical compound [Na+].O=C1N[N-]C(=O)C2=C1C(N)=CC=C2 RVJVDCVIJCBUTH-UHFFFAOYSA-M 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- ZOPIBCDDKMAEII-UHFFFAOYSA-N 4-(1,2,4-triazol-1-yl)phenol Chemical compound C1=CC(O)=CC=C1N1N=CN=C1 ZOPIBCDDKMAEII-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- WGYFACNYUJGZQO-UHFFFAOYSA-N aminomethanetriol Chemical compound NC(O)(O)O WGYFACNYUJGZQO-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000006179 pH buffering agent Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
Abstract
The luminol-containing chemiluminescent liquid is an important analytical reagent and is widely applied to a plurality of fields such as scientific research, clinical diagnosis, environment and food sample detection. The luminescence mechanism is that luminol reacts with oxidant in the presence of horseradish peroxidase or a catalyst with horseradish peroxidase activity to generate 3-aminophthalic acid in an excited state, and the luminol emits light with the wavelength of about 425nm when the luminol returns to a ground state. The target substance can be quantitatively detected by measuring the luminous intensity. The invention provides a stable luminous solution, in particular to a stable luminol solution.
Description
Technical field:
The invention relates to the field of biochemical reagents, in particular to a chemiluminescent solution prepared based on luminol.
The background technology is as follows:
The luminol-containing chemiluminescent liquid is an important analytical reagent and is widely applied to a plurality of fields such as scientific research, clinical diagnosis, environment and food sample detection. The luminescence mechanism is that luminol reacts with oxidant in the presence of horseradish peroxidase or a catalyst with horseradish peroxidase activity to generate 3-aminophthalic acid in an excited state, and the luminol emits light with the wavelength of about 425nm when the luminol returns to a ground state. The target substance can be quantitatively detected by measuring the luminous intensity.
Commercial chemiluminescent solutions are typically prepared and sold as AB solutions. Wherein, the solution A mainly contains luminol, a luminescence enhancer, a PH buffer and water, and the solution B mainly contains an oxidant, a PH buffer and water. Before use, the AB liquid is mixed according to a certain proportion and added into a system to be detected, so that chemiluminescence can be detected. However, although the luminol solid is relatively stable, its aqueous solution is very susceptible to degradation during storage. At present, the luminescence signals of the commercial luminescence liquid are obviously attenuated after being stored for 3 months at 4 ℃.
In view of this, the present invention provides a stable luminescent solution, especially a stable luminol solution. The luminol solution comprises the following components:
(1) Contains luminol with concentration of 0.2-30mmol/L;
(2) At least one stabilizer, the concentration of which is 0.01-1mmol/L;
(3) At least one luminescence enhancer at a concentration of 1-30mmol/L;
(4) At least one pH buffer is contained at a concentration of 20-300mmol/L.
The stabilizer is a water-soluble polyalcohol compound and is characterized by being one or more of 1, 2-glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, glycerol, 1,2, 4-butanetriol and 1,2, 6-hexanetriol.
The luminescence enhancer at least contains one organic amine compound, preferably pyridine and substituted pyridine compounds.
The PH buffer is one or more of phosphate buffer, trihydroxy aminomethane buffer, carbonate buffer and acetate buffer.
PH has a significant impact on the speed and intensity of chemiluminescence. The use of a pH buffer to control a relatively constant pH is critical throughout the process of producing chemiluminescence. And, in general, alkaline media are more conducive to chemiluminescent light generation. To facilitate the generation of rapid, stable chemiluminescence, the pH of the luminol solution is controlled between 7.5 and 10.5, preferably between 8 and 10, by a pH buffer.
The luminous liquid simultaneously comprises an oxidant, wherein the oxidant is one or more of hydrogen peroxide, hydrogen peroxide urea compound, peracetic acid, sodium perborate and sodium percarbonate.
The oxidant and the luminol are respectively prepared, stored respectively and mixed according to a certain proportion before use.
The medium used for dissolving the luminol, stabilizer, luminescence enhancer, PH buffer and oxidizing agent is water.
The luminescent liquid provided by the invention has the outstanding advantage that the storage stability is obviously improved compared with that of commercial luminescent liquid. According to experimental data of the inventor, the luminous liquid provided by the invention is stored for 2 years at 4 ℃, and the luminous intensity decay is less than 10%. The comparative experiment shows that the addition of the polyol does not affect the luminous intensity, but the stability of the luminous liquid is obviously improved.
Description of the drawings:
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below.
FIG. 1 shows luminescence kinetics of luminol solution and newly prepared luminescence solution in stability experiment, left graph shows background luminescence without horseradish peroxidase, and right graph shows chemiluminescence after enzyme addition.
FIG. 2 is a graph showing luminescence kinetics of luminol solution and luminescence liquid accelerated to age for 3 days in a 37-degree oven in a stability test, a left graph showing background luminescence without horseradish peroxidase, and a right graph showing chemiluminescence after enzyme addition.
FIG. 3 is a graph showing luminescence kinetics of luminol solution and luminescence liquid at 4℃for 2 years in stability experiments, left graph showing background luminescence without horseradish peroxidase, and right graph showing chemiluminescence after enzyme addition.
FIG. 4 shows luminescence kinetics of luminol solution without polyol and newly configured luminescence solution in stability experiment, left graph shows background luminescence without horseradish peroxidase, and right graph shows chemiluminescence after enzyme addition.
FIG. 5 is a graph showing luminescence kinetics of a luminol solution without polyol and luminescence after 1 month at 4℃in a stability test, a left graph showing background luminescence without horseradish peroxidase, and a right graph showing chemiluminescence after enzyme addition.
FIG. 6 is a graph showing luminescence kinetics of a luminol solution without polyol and luminescence after 3 months at 4℃in a stability test, the left graph shows background luminescence without horseradish peroxidase, and the right graph shows chemiluminescence after enzyme addition.
Specific examples:
Example 1 preparation of luminol solution:
Adding water, luminol, 1, 2-glycol, phenothiazine-10-propane sodium sulfonate, N, N-dimethyl pyridine and disodium hydrogen phosphate into a 100ml volumetric flask respectively, shaking for dissolving, adjusting the pH of the solution to 8.9 with hydrochloric acid and sodium hydroxide, fixing the volume, and shaking for later use. The final concentration of each component is as follows:
luminol, 1mmol/L1, 2-ethanediol, 0.05mmol/L
Phenolthiazine-10-propane sulfonic acid sodium salt, 1mmol/L
N, N-lutidine, 0.5mmol/L
Disodium hydrogen phosphate, 50mmol/L
Preparing an oxidant solution: adding water, sodium dihydrogen phosphate and hydrogen peroxide urea compound into a 100ml volumetric flask, adjusting pH7 with hydrochloric acid and sodium hydroxide, fixing volume, and shaking. The final concentration of each component is as follows:
hydrogen peroxide urea compound: 2mmol/L
Sodium dihydrogen phosphate: 20mmol/L
Example 2, luminol solution luminescence kinetics and stability experiments:
Taking newly prepared luminous liquid, mixing the luminous liquid which is subjected to accelerated aging for 3 days in a 37-DEG C oven and the luminous liquid which is placed for 2 years at 4 ℃ after preparation, placing the AB liquid in a cuvette according to the volume ratio of 1/1, respectively adding horseradish peroxidase with the final concentration of 25pg/ml, and measuring the curve of the change of the chemiluminescence intensity with time by using a dynamic mode of a fluorometer, wherein the curve is shown in figures 1,2 and 3.
Comparative example 1, luminol solution without polyol kinetics and stability experiments: adding water, luminol, phenothiazine-10-propane sodium sulfonate, N, N-dimethyl pyridine and disodium hydrogen phosphate into a 100ml volumetric flask respectively, oscillating for dissolving, adjusting the pH of the solution to 8.9 by using hydrochloric acid and sodium hydroxide, fixing the volume, and shaking for later use. The final concentration of each component is as follows:
luminol, 1mmol/L
Phenolthiazine-10-propane sulfonic acid sodium salt, 1mmol/L
N, N-lutidine, 0.5mmol/L
Disodium hydrogen phosphate, 50mmol/L
Preparing an oxidant solution: adding water, sodium dihydrogen phosphate and hydrogen peroxide urea compound into a 100ml volumetric flask, adjusting pH7 with hydrochloric acid and sodium hydroxide, fixing volume, and shaking. The final concentration of each component is as follows:
hydrogen peroxide urea compound: 2mmol/L
Sodium dihydrogen phosphate: 20mmol/L
The luminescence kinetics are shown in fig. 4, 5 and 6.
Comparative example 2, comparative experiment with a light-emitting liquid reported in the literature
1. According to document CN201110262359.2, a luminescent liquid is prepared as follows (noted as luminescent liquid CN):
and (3) solution A:
Luminol monosodium salt, 1mmol/L
P-iodophenol, 0.5mmol/L
4- (1, 2, 4-Triazol-1-yl) phenol, 1.5mmol/L
N, N-dimethylformamide, 1% (V/V)
Ethylene diamine tetraacetic acid disodium salt, 5mmol/L
Sodium benzoate, 0.1mmol/L
Sodium chloride, 3mmol/L
Tris-HCl buffer, 0.1mol/L
PH 8.4
And (2) liquid B:
hydrogen peroxide, 0.5mmol/L
Sodium perborate, 0.5mmol/L
Sodium benzoate, 0.1mmol/L
Ethylene diamine tetraacetic acid disodium salt, 5mmol/L
Tris-HCl buffer, 0.1mol/L pH 8.4
2. According to document US6432662, a luminescent liquid is formulated as follows (noted as luminescent liquid US):
Liquid A
Luminol sodium, 10mmol/L
Phenolthiazine-10-propane sulfonic acid sodium salt, 3mmol/L
Tris-HCl buffer, 0.4mol/L
PH 9.5
Liquid B
Sodium perborate, 8mmol/L
Sodium acetate, 0.1mol/L
PH 5.0
The formula of the luminous liquid is the same as that of example 1
The chemiluminescent signal-to-noise ratios in the presence of 25pg/ml horseradish peroxidase at 4℃for various times were as follows:
Day 0 | For 3 months | 6 Months of | For 12 months | 24 Months of | |
The luminous liquid of the invention | 1875 | 1872 | 1865 | 1823 | 1775 |
Luminous liquid CN | 561 | 525 | 372 | 326 | 5 |
Luminous liquid US | 277 | 253 | 188 | 159 | 10 |
Claims (7)
1. A luminous liquid capable of being stably stored comprises the following components:
(1) Contains luminol with concentration of 0.2-30mmol/L;
(2) At least one stabilizer, the concentration of which is 0.01-1mmol/L;
(3) At least one luminescence enhancer at a concentration of 1-30mmol/L;
(4) At least one pH buffer, the concentration of which is 20-300mmol/L;
(5) At least one oxidizing agent is contained, and the concentration of the oxidizing agent is 5-40mmol/L.
2. The luminescent liquid according to claim 1, wherein the stabilizer is a water-soluble polyol compound.
3. The polyalcohol compound of claim 2, wherein the polyalcohol compound is one or more of 1, 2-ethylene glycol, 1, 2-propylene glycol, 1, 3-propylene glycol, glycerol, 1,2, 4-butanetriol and 1,2, 6-hexanetriol.
4. The luminescent liquid according to claim 1, wherein the luminescence enhancer comprises at least one organic amine compound, preferably pyridine and substituted pyridine compounds.
5. The luminescent liquid according to claim 1, wherein the PH buffer is one or more of phosphate buffer, tris buffer, carbonate buffer and acetate buffer.
6. The luminescent liquid according to claim 1, wherein the oxidizing agent is one or more of hydrogen peroxide, hydrogen peroxide urea complex, peracetic acid, sodium perborate and sodium percarbonate.
7. The luminescent liquid according to claim 1, wherein the medium used for dissolving the luminol, the stabilizer, the luminescence enhancer, the PH buffer and the oxidizing agent is water.
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CN202410290823.6A CN118308091A (en) | 2024-03-14 | 2024-03-14 | Stable luminous liquid and application thereof |
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CN202410290823.6A CN118308091A (en) | 2024-03-14 | 2024-03-14 | Stable luminous liquid and application thereof |
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Family
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