CN109239039A - A kind of acetaldehyde detection method and its application based on fluorescence probe - Google Patents
A kind of acetaldehyde detection method and its application based on fluorescence probe Download PDFInfo
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Abstract
The present invention provides a kind of acetaldehyde detection method and its application based on fluorescence probe are the methods of the first detection acetaldehyde based on fluorescence probe.Specific detection method is: using probe P1 as fluorescent reagent, in the solution system of DMSO-Tris (pH=7.4,6:4, v/v), double condensation reaction realization occurs to the specific detection of acetaldehyde using the reactivity and probe P1 of acetaldehyde.The detection method shows higher single-minded selectivity and sensitivity to acetaldehyde, detection process simplicity, strong antijamming capability, quick, sensitive, and testing result is accurate.
Description
Technical field
The present invention relates to acetaldehyde detection technique, particularly relates to a kind of acetaldehyde detection method based on fluorescence probe and its answer
With.
Background technique
Acetaldehyde be have greater activity two carbon saturation aldehyde, it is colourless, inflammable, volatile, be not easy in lipid it is biological
Concentration.Acetaldehyde is industrially widely used, be mainly used as production acetic acid raw material, be also used for adjoining suck, adjoin suck bases, peracetic acid,
The synthesis of the chemical reagent such as chloral and ethylene glycol；Mirror is silver-plated, leather kneading, papermaking, synthetic rubber and production aniline dyes,
Acetaldehyde is all used in the technical process such as cosmetics, plastic products；In addition, acetaldehyde also acts as the curing agent of gelatin fiber, fish
The preservative and food flavor of product.Acetaldehyde is widely present in daily life, so far, it has been found that in 150 kinds of foods
Contain acetaldehyde.Acetaldehyde is widely present in alcoholic beverage, is confirmed as I class carcinogenic substance by international cancer research institution (IARC).
The acetaldehyde of human body intake low concentration causes eye, nose and upper respiratory tract irritation and bronchitis.The acetaldehyde for taking in high concentration will
Lead to anesthetic effect, clinical manifestation has headache, drowsiness, clouded in mind and bronchitis, pulmonary edema, diarrhea, albuminuria liver and the heart
Flesh Steatosis, serious person can lead to death.Therefore, the method for quick, sensitive, single-minded detection acetaldehyde is developed in beverage wine, life
The fields such as object science, agricultural product quality and safety have important research significance.
Fluorescence probe have many advantages, such as the good, high sensitivity of selectivity, it is easy to operate quickly, it is few to detectable substance damage wide
The general metal cation being applied in detection environmental and biological materials system, anion, active small molecular etc. in organism.Fluorescence
Probe is a kind of intermolecular interaction to be converted to optical signal transfer easy to identify to extraneous tool.Fluorescence probe with
After particular target analytes are had an effect, significant change can occur for fluorescence signal to reach testing goal.This application provides
Acetaldehyde detection method of the first based on fluorescence probe realizes the specific recognition detection to acetaldehyde.
Summary of the invention
The present invention proposes a kind of acetaldehyde detection method based on fluorescence probe, solves the inspection of acetaldehyde in beverage wine and agricultural product
Survey technical problem difficult, that detection sensitivity is low.
The technical scheme of the present invention is realized as follows:
A kind of acetaldehyde detection method based on fluorescence probe, steps are as follows:
(1) pH=7.4 are prepared, concentration is the Tris buffer solution of 10 mM, after being mixed in proportion with dimethyl sulfoxide (DMSO)
Mixed solution A；Using DMSO as probe P1 solution that solvent compound concentration is 1 mM；
(2) mixed solution A, is added to clean fluorescence cuvette by the acetaldehyde solution that 100 μm of ol/L concentration is prepared with distilled water
In, and probe P1 solution is added, acetaldehyde solution is then sequentially added, the volume of addition is successively are as follows: 0 μ L, 3 μ L, 6 μ L, 9 μ
L, 12 μ L, 15 μ L, 18 μ L, 21 μ L, while using 440 nm as excitation wavelength, it is measured in Fluorescence Spectrometer at 544 nm
Fluorescent emission intensity, using the fluorescence intensity at 544 nm as ordinate, obtains dense based on acetaldehyde using the concentration of acetaldehyde as abscissa
The working curve of degree, equation of linear regression are as follows: F585 nmThe unit of=2215.496C+827.705, C are μm ol/L；
(3) mixed solution A and probe P1 solution are added in clean fluorescence cuvette, draw V μ L with microsyringe and waits for
Sample solution is added in the fluorescence cuvette containing mixed solution A and probe P1 solution, tests in Fluorescence Spectrometer,
Fluorescent emission intensity at 544 nm measured is substituted into the equation of linear regression of step (2), obtains concentration C, sample to be tested
Concentration CTo test sample=3000*C/V, CTo test sampleUnit be μm ol/L.
The volume ratio that Tris buffer solution is mixed with DMSO in the step (1) is 4:6.
Fluorescence probe reference literature (RSC Adv., 2015,5, the 7083-7089) synthesis for acetaldehyde detection,
The synthetic route of probe are as follows:
。
The concentration range of linearity of a kind of acetaldehyde detection method based on fluorescence probe, the method for the detection acetaldehyde is 0-
0.7 μM, minimum detectability is 4.9 × 10-8 mol/L。
The application of acetaldehyde of the acetaldehyde detection method based on fluorescence probe in detection beverage wine, agricultural product.
It is that technical solution of the present invention can generate the utility model has the advantages that
(1) acetaldehyde detection method of the invention is to be used for acetaldehyde detection method based on fluorescence probe for the first time.It is provided by the invention
Fluorescence enhancement type probe has preferable single-minded selection, anti-interference and higher sensitivity relative to fluorescent quenching type probe；
Fluorescence enhancement type probe for acetaldehyde detection is limited to 4.9 × 10 to the lowest detection of acetaldehyde-8Mol/L, detection process simplicity,
Strong antijamming capability, quick, sensitive, testing result is accurate, has stronger practical application value.
(2) mechanism of fluorescence probe P1 of the invention identification acetaldehyde: being added acetaldehyde in the identification system containing probe P1,
Double condensation reaction occurs for the amino in aldehyde radical and probe molecule structure in acetaldehyde molecular structure, and generating, there is the imines of fluorescence to produce
Object P1-CH3CHO releases fluorescence signal.By high resolution mass spectrum (HR-MS) to product P1-CH3The structure of CHO has carried out really
It demonstrate,proves (attached drawing 7).The experimental results showed that P1-CH3CHO calculated value [M+H]+[M+Na]+Respectively 295.1195 Hes
317.1014, HR-MS results correspond to 295.1189 and 317.1006, which confirms the mechanism of action shown in attached drawing 6.
Detailed description of the invention
Fig. 1 is fluorescence probe P1 fluorescence selectivity figure of the invention, 440 nm of excitation wavelength；
Fig. 2 is the anti-interference figure that fluorescence probe P1 of the invention identifies acetaldehyde, 440 nm of excitation wavelength, launch wavelength 544
nm；
Fig. 3 is the pH scope of application figure that fluorescence probe P1 of the invention identifies acetaldehyde, 440 nm of excitation wavelength, launch wavelength 544
nm；
Fig. 4 is the fluorescence titration figure that fluorescence probe P1 of the invention identifies acetaldehyde, 440 nm of excitation wavelength；
Fig. 5 is the minimum detection limit figure that fluorescence probe P1 of the invention identifies acetaldehyde, 440 nm of excitation wavelength, launch wavelength 544
nm；
Fig. 6 is the mechanism figure that fluorescence probe P1 of the invention identifies acetaldehyde；
Fig. 7 is the Mechanism Validation high resolution mass spectrum figure that fluorescence probe P1 of the invention identifies acetaldehyde.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Those of ordinary skill in the art's every other embodiment obtained under that premise of not paying creative labor, belongs to this hair
The range of bright protection.
Used chemical reagent, solvent, metal ion etc. during fluorescence probe P1 is prepared in the present invention to be purchased from
Aladdin Reagent Company.It is total using Bruker company DTX-400 type nuclear-magnetism in the confirmation and performance test process of fluorescence probe P1
Shake spectrometer, and solvent is deuterated chloroform, records nuclear magnetic resonance spectroscopy as internal standard using TMS and carbon is composed；Using the Q- of Thermo company
Exactive HR-MS mass spectrograph records high resolution mass spectrum data.It is divided using Agilent company of the U.S. Cary100 UV, visible light
Photometer records absorption spectrum.
One, the preparation of fluorescence probe P1
Bromo- 1, the 8- naphthalic anhydride of 2.76 g (10 mM) 4- and the anhydrous second of 300 mL are added in 500 mL round-bottomed flasks
Alcohol.It is heated to reflux, bromo- 1, the 8- naphthalic anhydride of 4- is made to suspend in ethanol, stir the lower hydrazine hydrate solution that 5 mL 80% are added dropwise,
1 h is added.Continue 12 h that flow back.It is cooled to room temperature, filtering, obtained solid are with ethanol washing 3 times, column chromatography for separation (eluant, eluent
Volume ratio is CH3OH:CH2Cl2=1:10), available 2.05 g of brick-red solid after vacuum drying.85 % of yield.
Nuclear magnetic resonance hydrogen spectruming determining:1H NMR (400 MHz, DMSO, ppm) δ: 4.73 (s, 2 H), 5.75
(s, 2 H), 7.27 (d, 1 H, J = 8.0 Hz), 7.67 (t, 1 H, J = 6.0 Hz), 8.32 (d, 1 H,
J = 8.0 Hz), 8.45 (d, 1 H, J = 4.0 Hz), 8.66 (d, 1 H, J = 8.0 Hz), 9.24 (s, 1
H)；
Carbon-13 nmr spectra measurement:13C NMR (100 MHz, DMSO, ppm) δ: 160.66, 160.55, 154.03,
134.87, 131.00, 128.77, 128.32, 124.64, 121.73, 118.99, 107.11, 104.63;
High resolution mass spectrum measurement: HR-MS m/z:Calcd for C12H11N4O2 + ([M+H+]+) 243.0882, found
243.0873 [M+H+]+。
Two, the method for fluorescence enhancement detection acetaldehyde
Embodiment 1
A kind of acetaldehyde detection method based on fluorescence probe, steps are as follows:
Prepare pH be 7.4, the Tris buffer solution that concentration is 10 mM, matched with above-mentioned buffer solution and dimethyl sulfoxide (DMSO)
Set the mixed solution A that volume ratio is 4:6, and the probe P1 solution for being 1 mM with DMSO compound concentration.It is investigated with Fluorescence Spectrometer
Selectivity of the probe P1 to acetaldehyde in mixed solution A.As shown in Figure 1, under shooting condition at 440 nm, individual probe
P1 (10 μM) has faint fluorescent emission intensity in mixed solution A at 544 nm, after acetaldehyde (10 eq.) is added,
Fluorescent emission intensity at 544nm is remarkably reinforced, but when addition other materials (100 μM), the fluorescence hair of solution system
Penetrate intensity no significant change compared with the fluorescent emission intensity of independent probe system.
The experimental results showed that, probe P1 has the single-minded selectivity of preferable fluorescence to acetaldehyde in mixed solution A above.
Embodiment 2
A kind of acetaldehyde detection method based on fluorescence probe, steps are as follows:
Prepare pH be 7.4, the Tris buffer solution that concentration is 10 mM, with above-mentioned buffer solution and DMSO configuration volume ratio be 4:6
Mixed solution A, and with DMSO compound concentration be 1 mM probe P1 solution.In 19 clean fluorescence cuvettes, respectively
The DMSO solution of the mixed solution A of 3000 μ L and the probe P1 of 30 μ L is added, then is separately added into the acetaldehyde of 10 molar equivalents
With other analytes (all kinds of aldehydes, amino acids, peroxide etc.) of 10 molar equivalents, detected in Fluorescence Spectrometer,
The histogram for drawing the corresponding 544 nm fluorescence intensity of different analytes, obtains fluorescent emission histogram (attached drawing 2).
The experiment proved that probe P1 to identification of the acetaldehyde in mixed solution A not by the interference of other above-mentioned analytes, tool
There is preferable anti-interference.
Embodiment 3
A kind of acetaldehyde detection method based on fluorescence probe, steps are as follows:
Preparing pH is respectively 4.3,5.3,6.3,7.4,8.2,9.4, and concentration is the Tris buffer solution of 10 mM, with above-mentioned buffering
Solution and DMSO configuration volume ratio are mixed solution A 1, A2, A3, A4, A5, the A6 of 4:6, and are with DMSO compound concentration
The probe P1 solution of 1 mM.Independent probe P1 (10 μM) and probe P1 (10 μM) and acetaldehyde (10 have been investigated with Fluorescence Spectrometer
Eq.) the fluorescent emission intensity in mixed solution A 1-A6.As shown in figure 3, under shooting condition at 440 nm, individual probe
P1 (10 μM) has at 544 nm faint in the mixed solution A that pH value is respectively 4.3,5.3,6.3,7.4,8.2,9.4
Fluorescent emission intensity, and fluorescent emission intensity variation less, when above-mentioned solution system be added acetaldehyde (10 eq.) after, body
The fluorescent emission intensity tied up at 544 nm is remarkably reinforced.
The experimental results showed that, probe P1 can complete the identification of acetaldehyde within the scope of more wide in range pH above, have
The preferable scope of application.
Embodiment 4
A kind of acetaldehyde detection method based on fluorescence probe, steps are as follows:
Prepare pH be 7.4, the Tris buffer solution that concentration is 10 mM, with above-mentioned buffer solution and DMSO configuration volume ratio be 4:6
Mixed solution A, and with DMSO compound concentration be 1 mM probe P1 solution.The second of 100 μm of ol/L concentration is configured with distilled water
Aldehyde solution is added to the DMSO solution of the probe P1 of the mixed solution A and 30 μ L of 3 mL in clean fluorescence cuvette, gradually
The volume that acetaldehyde solution is added is respectively 0 μ L, 3 μ L, 6 μ L, 9 μ L, 12 μ L, 15 μ L, 18 μ L, 21 μ L, while with 440
Nm is excitation wavelength, and the fluorescent emission intensity at 544 nm is measured in Fluorescence Spectrometer, using the concentration of acetaldehyde as abscissa, with
Fluorescence intensity at 544 nm is ordinate, obtains the working curve of acetaldehyde concentration, equation of linear regression are as follows: F544 nm =
The unit of 2215.496C+827.705, C are μm ol/L(attached drawing 4 and Fig. 5).
Application examples
Minimum detectability experiment:
Good detection limit is to examine whether a probe molecule has one of standard of application value.Preparing pH is 7.4, concentration
For the Tris buffer solution of 10 mM, the mixed solution A that volume ratio is 4:6 is configured with above-mentioned buffer solution and DMSO, and uses DMSO
Compound concentration is the probe P1 solution of 1 mM.Fixed probe P1 concentration is 10 μM, measures its response to the acetaldehyde of various concentration
Intensity, with the increase of acetaldehyde concentration, system fluorescent emission intensity constantly enhancing at 544 nm, research finds that solution fluorescence is sent out
It is 0-0.7 μM of (R that intensity, which is penetrated, in the acetaldehyde concentration range of linearity2=0.993), being computed (3 σ/k) obtains the probe molecule to second
The detection of aldehyde is limited to 4.9 × 10-8 mol/L。
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (5)
1. a kind of acetaldehyde detection method based on fluorescence probe, it is characterised in that the following steps are included:
(1) pH=7.4 are prepared, concentration is the Tris buffer solution of 10 mM, must be mixed after mixing in proportion with dimethyl sulfoxide molten
Liquid A；Using dimethyl sulfoxide as probe P1 solution that solvent compound concentration is 1 mM；
(2) mixed solution A, is added to clean fluorescence cuvette by the acetaldehyde solution that 100 μm of ol/L concentration is prepared with distilled water
In, and probe P1 solution is added, acetaldehyde solution is then sequentially added, the volume of addition is successively are as follows: 0 μ L, 3 μ L, 6 μ L, 9 μ
L, 12 μ L, 15 μ L, 18 μ L, 21 μ L, while using 440 nm as excitation wavelength, it is measured in Fluorescence Spectrometer at 544 nm
Fluorescent emission intensity, using the fluorescence intensity at 544 nm as ordinate, obtains dense based on acetaldehyde using the concentration of acetaldehyde as abscissa
The working curve of degree, equation of linear regression are as follows: F585 nmThe unit of=2215.496C+827.705, C are μm ol/L；
(3) mixed solution A and probe P1 solution are added in clean fluorescence cuvette, draw V μ L with microsyringe and waits for
Sample solution is added in the fluorescence cuvette containing mixed solution A and probe P1 solution, tests in Fluorescence Spectrometer,
Fluorescent emission intensity at 544 nm measured is substituted into the equation of linear regression of step (2), obtains concentration C, sample to be tested
Concentration CTo test sample=3000 * C/V, CTo test sampleUnit be μm ol/L.
2. the acetaldehyde detection method according to claim 1 based on fluorescence probe, it is characterised in that: in the step (1)
The volume ratio that Tris buffer solution is mixed with DMSO is 4:6.
3. the acetaldehyde detection method according to claim 1 based on fluorescence probe, which is characterized in that the knot of the probe P1
Structure are as follows:
。
4. the acetaldehyde detection method according to claim 1 based on fluorescence probe, it is characterised in that: the detection acetaldehyde
The concentration range of linearity of method is 0-0.7 μM, and minimum detectability is 4.9 × 10-8 mol/L。
5. the acetaldehyde detection method according to claim 1-4 based on fluorescence probe is in detection beverage wine, agricultural production
The application of acetaldehyde in product.
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| CN114235767A (en) * | 2021-12-16 | 2022-03-25 | 东莞理工学院 | Fluorescent fiber for detecting formaldehyde and preparation method thereof |
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| CN114736135A (en) * | 2022-04-22 | 2022-07-12 | 华南理工大学 | Difunctional small organic molecule DATH for detecting and degrading acetaldehyde as well as preparation method and application thereof |
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| CN114736135B (en) * | 2022-04-22 | 2023-06-20 | 华南理工大学 | Dual-functional organic micromolecule DATH for detecting and degrading acetaldehyde as well as preparation method and application thereof |
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Effective date of registration: 20210104 Address after: 463000 3rd floor, No.2 standard workshop, Southeast of the intersection of Xingye Avenue and Ruhe Avenue, Zhumadian City, Henan Province Patentee after: Henan LianJian pharmaceutical analysis Co.,Ltd. Address before: No.116 Huayuan Road, Jinshui District, Zhengzhou City, Henan Province 450003 Patentee before: INSTITUTE OF AGRICULTURAL QUALITY STANDARDS AND TESTING TECHNOLOGY, HENAN ACADEMY OF AGRICULTURAL SCIENCES |