CN105837558A - Reagent and method for fluorescence detection of hypochlorous acid - Google Patents
Reagent and method for fluorescence detection of hypochlorous acid Download PDFInfo
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Abstract
The invention provides a reagent and method for fluorescence detection of a hypochlorous acid. The reagent is 2,2'-((1E,1'E)-((phenylurea nimoto)-bi(4,1-phenylene)-bi(ethylene 2,1-substituent)-bi(1,3,3-trimethyl-3H-indole-1-iodonium) iodine compound, namely PPEI for short. The detection method is quantitative detection of the content of the hypochlorous acid in an HEPES solution of which the pH is 7.0. The detection method has high sensitivity and selectivity on the hypochlorous acid; the detection process is simple, convenient, sensitive and fast; the detection result is accurate.
Description
Technical field
The present invention relates to hypochlorous acid detection technique, be specifically related to a kind of reagent and synthetic method thereof, and this reagent is in detection time
Application in chloric acid.
Background technology
As a kind of active oxygen most important in organism, the hypochlorous acid under hypochlorite and protonated form thereof, it is common that in mistake
Hydrogen oxide and chloride ion react generate, whole during need peroxidase that reaction is catalyzed.Hypochlorite and we
Life closely bound up, such as in life, common bleaching water, the main component of disinfectant solution are exactly sodium hypochlorite.Hypochlorite is joined
With numerous physiology, pathological process, play an important role in organism.Because hypochlorous acid can multiple with organism
Biomolecule is reacted, and such as fatty acid, cholesterol, and multiple proteins, especially its sterilizing power directly influence life
The health status of object.Currently, with respect to hypochlorous analysis method mainly have iodometric titration method (APHA, AWWA, WPCF,
Métodos Normalizados para el Análisis de Aguas Pota-blesy Residuals,Díaz de Santos,Madrid,
1992, pp.55 61), electrochemical methods (Duan Chunxia, Tian Lei, Wu Yingga, Wang Chengjun, Haiquan. potentiometric determination
Sodium hypochlorite and the content [J] of hydrogen peroxide in de-hypochlorous acid electrolyte. China's chlor-alkali, 2011,12:38-39), chromatography is (high
Spring is beautiful, Zu Rusong. Drinking Water by Ion Chromatography is smelt acid group hypochlorite chlorate anions [J]. and China Health engineering, 2004,
3 (2): 109-110).
In the present invention, synthesize a kind of compound based on 1,8-naphthalimide, by hypochlorous acid and compound before the reaction
The change of rear fluorescence, it is achieved hypochlorous detection.
Summary of the invention:
It is an object of the invention to provide the detection by quantitative time chlorine that a kind of selectivity is good, highly sensitive, response time fast, detection limit is low
The reagent of acid, and the application that this reagent is in hypochlorous acid detects.
The present invention provides a kind of hypochlorous reagent of fluoroscopic examination, and it is
2,2'-((1E,1'E)-((phenylazanediyl)bis(4,1-phenylene))bis(ethene-2,1-diyl))bis(1,3,3-trimethyl-3H-ind
Ol-1-ium) iodide, is called for short: PPEI, Chinese: 2,2'-((1E, 1'E)-((phenylurea diyl) two (4,1-phenylene) two (second
Alkene 2,1-substituent group) two (1,3,3-trimethyl-3H-indole-1-) iodide, its structural formula:
The synthetic method of PPEI, step is:
By bromo-for 4-1,8-naphthalic anhydride and n-propylamine 1 1.1 reflux in molar ratio in ethanol, and decompression is distilled off solvent, ice second
Acid is recrystallized to give white solid N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride；
At CuSO4·5H2Under O catalysis, by N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride and Feldalat NM 1:1.1 in molar ratio is in methanol
Backflow 8h, adds 1mol/L hydrochloric acid after having reacted, sucking filtration, washing and drying, filter cake dichloromethane is crossed post, obtained white
Solid N-n-pro-pyl-4-methoxyl group-1,8-naphthalic anhydride；
By white solid N-n-pro-pyl-4-methoxyl group-1,8-naphthalic anhydride refluxes 10h in 55%HI, and reactant liquor pours distilled water into
In, sucking filtration, washing, it is dried, obtains faint yellow solid N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride；
Faint yellow solid N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride and hexamethylenamine 1:4 in molar ratio are joined trifluoroacetic acid
In, reflux at 120 DEG C 10h, adds appropriate chloroform and hydrochloric acid, is stirred overnight, and separatory, organic facies is spin-dried for, and ethanol is heavily tied
Crystalline substance obtains yellow solid N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-naphthalic anhydride；
By yellow solid N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-naphthalic anhydride and 1,2,3,3-tetramethyl-3H-indole iodide
The ratio of 1:1.1 refluxes in ethanol 10h under piperidines is catalyzed in molar ratio, sucking filtration after cooling, and filter cake washing with alcohol is dried
To red brown solid PPEI.
A kind of hypochlorous method of fluoroscopic examination that the present invention provides, is to determine in the HEPES solution that pH is 7.0 based on PPEI
Amount ground detects hypochlorous content.This detection method, shows high sensitivity and selectivity to hypochlorous acid, detection process is easy,
Sensitive, quick, testing result is accurate.Concretely comprise the following steps:
(1), preparation pH=7.0, concentration be the HEPES buffer solution of 10mmol/L, the first of the PPEI of preparation 2mmol/L
Alcoholic solution；
(2), 200:1 by volume, by HEPES-CH3The methanol solution of OH (1:1, pH 7.0) solution and PPEI is added to do
In clean fluorescence cuvette, detecting on Fluorescence spectrophotometer, along with treating the addition of test sample, the fluorescence intensity of 620nm is gradually
Weakening, the fluorescence intensity of 515nm gradually strengthens；
(3), the HEPES-CH of 2000 μ L3OH (1:1, pH 7.0) solution, the methanol solution of PPEI of 10 μ L are added to separately
In one fluorescence cuvette, add respectively the volume of liquor natrii hypochloritis be 10,20,30,40,50,60,70,80,
90, during 100,110,120,130,140,150 μ L, Fluorescence spectrophotometer measures 620nm with 515nm corresponding
Fluorescence intensity, calculates the fluorescence intensity ratio (I at 620nm and 515nm620/I515) be respectively 0.1559,0.3012,0.3759,
0.4525、0.5571、0.6921、0.7967、0.9389、1.0286、1.1056、1.1923、1.3005、1.4373、1.6096、
1.7265, with sodium hypochlorite concentration as abscissa, with I620/I515Drawing figure for vertical coordinate, the work obtaining sodium hypochlorite concentration is bent
Line；Equation of linear regression is: I515/I620The unit of=0.01076c+0.05415, c is μm ol/L；
(4), by HEPES-CH3OH (1:1, pH 7.0) solution 2000 μ L and PPEI methanol solution 10 μ L is added to clean glimmering
In light cuvette, draw V μ l testing sample solution with microsyringe, join in this clean fluorescence cuvette, divide at fluorescence
Detect on light photometer, the fluorescence intensity recorded is substituted into the equation of linear regression of step (3), obtains concentration c, testing sample CTreat test sample=2000 μ L × c × 10-6/ V μ L, can try to achieve hypochlorous concentration.
Compared with prior art, the invention have the advantages that and effect: 1, detection system is with low cost；2, the inspection of the present invention
Survey method, shows high susceptiveness and selectivity to hypochlorous acid；3, detection means is simple, it is only necessary to by fluorescence spectrophotometry
Instrument can realize.
Accompanying drawing illustrates:
The nucleus magnetic hydrogen spectrum figure of the PPEI of Fig. 1 a embodiment 1 preparation
The nuclear-magnetism carbon spectrogram of the PPEI of Fig. 1 b embodiment 1 preparation
The mass spectrum of the PPEI of Fig. 1 c embodiment 1 preparation
Fig. 2 embodiment 2PPEI and the fluorescent emission figure of sodium hypochlorite effect
Fig. 3 embodiment 3PPEI and the fluorescence block diagram of various analytes
Fig. 4 embodiment 4 measures the working curve of sodium hypochlorite
Fig. 5 embodiment 5 measures the fluorescent emission figure of sample
Detailed description of the invention:
Embodiment 1
In 60mL ethanol, add 4-bromo-1,8-naphthalic anhydride 8.312g (30mmol) and n-propylamine 3.218mL (33mmol),
Backflow 5h, after reaction terminates, decompression is distilled off solvent, crude product distilled water wash, vacuum drying, more heavily ties with glacial acetic acid
Crystalline substance obtains white solid N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride 8.496g, productivity 89.3%；
In 60mL methanol, add N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride 7.925g (25mmol), Feldalat NM 1.485g (27.5
And the CuSO of catalytic amount mmol)4·5H2O, reflux 8h, is concentrated by reactant liquor after having reacted, and adds the 1mol/L salt of 30mL
Acid, sucking filtration, filter cake distilled water wash is also vacuum dried, and dichloromethane does eluant and crosses post, obtains white solid N-n-pro-pyl
-4-methoxyl group-1,8-naphthalic anhydride 5.974g, productivity 88.8%；
N-n-pro-pyl-4-methoxyl group-1,8-naphthalic anhydride 5.382g (20mmol) joins in the HI solution of 20mL55%, returns
Stream 10h, during reactant liquor pours distilled water into afterwards, sucking filtration, filter cake distilled water wash, vacuum drying, obtain faint yellow solid
N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride 4.821g, productivity 94.5%；
N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride 3.827g (15mmol) and hexamethylenamine 8.411g (60mmol) adds
In 20mL trifluoroacetic acid, reflux at 120 DEG C 10h, and reactant liquor is poured into after having reacted the 1M of 100mL chloroform and 100mL
In hydrochloric acid mixed solution, overnight, separatory obtains organic facies to stirring at normal temperature, and aqueous phase, with chloroform (30mL*3), merges organic facies,
It is dried with anhydrous sodium sulfate, after being spin-dried for organic facies, obtains yellow solid N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-with ethyl alcohol recrystallization
Naphthalic anhydride 3.170g, productivity 74.7%；
N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-naphthalic anhydride 0.566g (2mmol) and 1,2,3,3-tetramethyl-3H-indole
Iodide 0.662g (2.2mmol), is dissolved in 20mL ethanol, refluxes 10 hours under 100 μ L piperidines catalysis, cold
But sucking filtration after, filter cake, with washing with alcohol (5mL*3), is vacuum dried and obtains red brown solid, be target compound PPEI,
1.030g, productivity 91.0%.
1H NMR(DMSO-d6): δ 8.71 (s, 1H), 8.54 (d, 2H, J=14.1), 8.36 (d, 1H, J=7.4), 8.07 (s, 1H),
7.72 (d, 1H, J=7.2), 7.60 (m, 2H), 7.50 (t, 1H, J=7.5), 7.40 (s, 1H), 4.00 (t, 2H, J=6.8), 3.85 (s,
3H), 1.77 (s, 6H), 1.63 (m, 2H, J=14.4,7.0), 0.92 (t, 3H, J=7.3) (Fig. 1 a)；13C NMR(DMSO-d6,
150MHz):δ(ppm):11.97,21.51,27.21,32.97,41.18,50.50,113.51,119.52,122.28,122.99,
125.53,127.02,128.99,132.00,132.53,142.50,163.02,164.05,180.22 (Fig. 1 b)；Elementary analysis
(calcd.%) for C28H27IN2O3: C, 59.37, H, 4.80, N, 4.95, find: C, 59.34, H, 4.82, N, 4.98；ESI–MS
m/z:[PPEI-I]+(439.2017. Fig. 1 c)
Embodiment 2
Preparation pH=7.0, concentration are the HEPES buffer solution of 10mmol/L, and prepare the PPEI of 2mmol/L with methanol
Solution；HEPES-CH 2000 μ L3The PPEI methanol solution of OH (1:1, pH 7.0) solution and 10 μ L is added to totally
Fluorescence cuvette in, take the solution of sodium hypochlorite, be gradually added in this cuvette with microsyringe, sample-adding limit, limit is at fluorescence
Detecting on spectrophotometer, along with the addition of sodium hypochlorite, the fluorescence intensity of 620nm gradually weakens, the fluorescence intensity of 515nm
Gradually strengthen.Fluorescent emission figure is shown in Fig. 2.
Embodiment 3
Preparation pH=7.0, concentration are the HEPES buffer solution of 10mmol/L, and prepare the PPEI of 2mmol/L with methanol
Solution；In 14 fluorescence cuvette, each HEPES-CH adding 2000 μ L3OH (1:1, pH 7.0) solution and 10 μ L
PPEI methanol solution, then be separately added into the sodium hypochlorite of 150 μ L, and the various analytes of 500 μ L: H2O2,ClO2 -,
ONOO-,F-,ClO3 -,CN-,NO2 -,S2-,SCN-,MnO4 -,ClO4 -,CO3 2-and P2O7 4-On Fluorescence spectrophotometer
Detection, draws the fluorescence intensity ratio (I at 620nm and 515nm that different analyte is corresponding620/I515) block diagram, (see figure
3).HOCl makes the I of PPEI620/I515Being changed to 1.7265 by 0.1030, other analyte does not the most cause PPEI's
I620/I515Change.
The experiment proved that, other analyte not interference system is to hypochlorous mensuration.
Embodiment 4
Preparation pH=7.0, concentration are the HEPES buffer solution of 10mmol/L, and prepare the PPEI solution of 2mmol/L with methanol,
Liquor natrii hypochloritis with distilled water preparation 2mmol/L；HEPES-CH 2000 μ L3OH (1:1, pH 7.0) solution and
The PPEI methanol solution of 10 μ L is added in fluorescence cuvette, add respectively the volume of liquor natrii hypochloritis be 10,20,30,40,
50, during 60,70,80,90,100,110,120,130,140,150 μ L, Fluorescence spectrophotometer measures 620nm
The fluorescence intensity corresponding with 515nm, calculates the fluorescence intensity ratio (I at 620nm and 515nm620/I515) respectively 0.1559,
0.3012、0.3759、0.4525、0.5571、0.6921、0.7967、0.9389、1.0286、1.1056、1.1923、1.3005、
1.4373,1.6096,1.7265, with sodium hypochlorite concentration as abscissa, with I620/I515Draw figure for vertical coordinate, obtain hypochlorous acid
The working curve of na concn；Equation of linear regression is: I515/I620The unit of=0.01076c+0.05415, c is μm ol/L；See figure
4。
Embodiment 5
Preparation pH=7.0 HEPES (10mmol/L) buffer solution, preparation 2mmol/L hypochloric acid water solution, and
PPEI solution with methanol preparation 2mmol/L；HEPES-CH 2000 μ L3OH (1:1, pH 7.0) solution and 10 μ L
PPEI methanol solution be added in clean fluorescence cuvette, take hypochlorous solution 85 μ L, with microsyringe be added to this ratio
In color ware, in fluorescence spectrophotometer, measure fluorescence intensity corresponding to 620nm with 515nm simultaneously, calculate 620nm and 515nm
Fluorescence intensity ratio (the I at place620/I515) it is 0.9722, by the equation of linear regression of embodiment 3, try to achieve c=85.32 × 10-6Mol/L,
Deviation is 0.38%；See Fig. 5.
Claims (4)
1. a reagent PPEI, it is characterised in that structural formula is:
The synthetic method of a kind of reagent PPEI the most as claimed in claim 1, it is characterised in that step is:
By bromo-for 4-1,8-naphthalic anhydride and n-propylamine 1 1.1 reflux in molar ratio in ethanol, and decompression is distilled off solvent, ice second
Acid is recrystallized to give white solid N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride；
At CuSO4·5H2Under O catalysis, by N-n-pro-pyl-4-bromo-1,8-naphthalic anhydride and Feldalat NM 1:1.1 in molar ratio is in methanol
Backflow 8h, adds 1mol/L hydrochloric acid after having reacted, sucking filtration, washing and drying, filter cake dichloromethane is crossed post, obtained white
Solid N-n-pro-pyl-4-methoxyl group-1,8-naphthalic anhydride；
By white solid N-n-pro-pyl-4-methoxyl group-1,8-naphthalic anhydride refluxes 10h in 55%HI, and reactant liquor pours distilled water into
In, sucking filtration, washing, it is dried, obtains faint yellow solid N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride；
Faint yellow solid N-n-pro-pyl-4-hydroxyl-1,8-naphthalic anhydride and hexamethylenamine 1:4 in molar ratio are joined trifluoroacetic acid
In, reflux at 120 DEG C 10h, adds appropriate chloroform and hydrochloric acid, is stirred overnight, and separatory, organic facies is spin-dried for, and ethanol is heavily tied
Crystalline substance obtains yellow solid N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-naphthalic anhydride；
By yellow solid N-n-pro-pyl-3-formoxyl-4-hydroxyl-1,8-naphthalic anhydride and 1,2,3,3-tetramethyl-3H-indole iodide
The ratio of 1:1.1 refluxes in ethanol 10h under piperidines is catalyzed in molar ratio, sucking filtration after cooling, and filter cake washing with alcohol is dried
To red brown solid PPEI.
3. reagent PPEI application in detection hypochlorous acid as claimed in claim 1.
4. the hypochlorous method of fluoroscopic examination: it is characterized in that, step is:
(1), preparation pH=7.0, concentration be the HEPES buffer solution of 10mmol/L, the first of the PPEI of preparation 2mmol/L
Alcoholic solution；
(2), 200:1 by volume, by volume ratio 1:1, the HEPES-CH of pH 7.03OH solution and the methanol solution of PPEI
Being added in clean fluorescence cuvette, detect on Fluorescence spectrophotometer, along with treating the addition of test sample, the fluorescence of 620nm is strong
Degree gradually weakens, and the fluorescence intensity of 515nm gradually strengthens；
(3), volume ratio 1:1, the HEPES-CH of pH 7.0 of 2000 μ L3OH solution, the methanol solution of PPEI of 10 μ L add
In another fluorescence cuvette, add respectively the volume of liquor natrii hypochloritis be 10,20,30,40,50,60,70,
80, during 90,100,110,120,130,140,150 μ L, Fluorescence spectrophotometer measures 620nm and 515nm pair
The fluorescence intensity answered, calculates the fluorescence intensity ratio I at 620nm and 515nm620/I515Be respectively 0.1559,0.3012,0.3759,
0.4525、0.5571、0.6921、0.7967、0.9389、1.0286、1.1056、1.1923、1.3005、1.4373、1.6096、
1.7265, with sodium hypochlorite concentration as abscissa, with I620/I515Drawing figure for vertical coordinate, the work obtaining sodium hypochlorite concentration is bent
Line；Equation of linear regression is: I515/I620The unit of=0.01076c+0.05415, c is μm ol/L；
(4), by volume ratio 1:1, the HEPES-CH of pH 7.03OH solution 2000 μ L and PPEI methanol solution 10 μ L is added to totally
Fluorescence cuvette in, with microsyringe draw V μ l testing sample solution, join in this clean fluorescence cuvette, glimmering
Detect on light spectrophotometer, the fluorescence intensity recorded is substituted into the equation of linear regression of step (3), obtains concentration c, to be measured
Sample CTreat test sample=2000 μ L × c × 10-6/ V μ L, can try to achieve hypochlorous concentration.
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| CN106525805A (en) * | 2017-01-04 | 2017-03-22 | 山西大学 | Method for fluorescently detecting hypochlorous acid |
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