CN108003869A - A kind of fluorescence probe of highly sensitive detection hypochlorite and its synthetic method and application - Google Patents
A kind of fluorescence probe of highly sensitive detection hypochlorite and its synthetic method and application Download PDFInfo
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Abstract
Fluorescence probe and its synthetic method and application the invention discloses a kind of highly sensitive detection hypochlorite, belong to chemical analysis detection technique field.Probe of the present invention is obtained by aldehyde radical benzothiazole fluorogen with azanol by dehydrating condensation, has following general structure：The fluorogen of this probe is benzothiazole skeleton structure, and the response group to hypochlorite is azanol unit.The single ultraviolet absorption peak of probe in the solution is located at ~ 350 nm, without notable fluorescent emission.After being reacted with hypochlorite, its ultraviolet absorption peak red shift to ~ 410 nm；Fluorescent emission significantly increases at ~ 540 nm, and yellow fluorescence is sent under ultraviolet lamp.The probe molecule has hypochlorite high selectivity and sensitivity, and detection range is 0.5-18 μm of olL‑1, detect and be limited to 0.08 μm of olL‑1.The probe can be used for the image checking of hypochlorite in living cells.
Description
Technical field
The invention belongs to chemical analysis detection technique field, and in particular to a kind of molecule of Fluorometric assay hypochlorite is visited
Pin and preparation method thereof and the application in terms of hypochlorite is detected.
Background technology
Hypochlorite (ClO-) or hypochlorous acid (HClO) be a kind of common disinfectant and oxidant.And in vivo
It is a kind of extremely important active oxygen, plays an important role in many physiology courses and disease.Such as, occur in human body inflammation
During, by Myeloperoxidase catalyzing hydrogen peroxide and the ClO of chlorion generation-With powerful sterilizing function.It is another
Aspect ClO-The abnormal metabolism of energy can cause the oxidation of amino-oxide group acid, protein, cholesterol and nucleic acid in human body, so that
The function of obtaining these important biomolecule molecules gets muddled.Therefore, highly sensitive, high selection detection hypochlorite method is developed to people
The accurate measurements of body health status are very important.
The method of traditional detection hypochlorite has titration, electrochemical method etc..But these method general operations are cumbersome,
And it is difficult to realize the in situ detection of bioactivity sample.And molecular probe Fluorometric assay hypochlorite is utilized to have at sample
Reason is succinct, measuring speed is fast, can realize the advantages that detection in real time in situ, is developed and utilizes in recent years.But exploitation at present
The probe molecule for being used to detect hypochlorite there is some defects, as sensitivity is low, synthesis is cumbersome, and manufacturing cost is high, reacts
Complicated mechanism is difficult to accurate reproduction etc., and (document Jin X.L.Sens.Actuators are B.2016,232,300；Fan
J.L.Analyst.2015,140,4594；Liao,Y-X.RSC Adv.,2015,5,18275；Li
X.H.Sens.Actuators B.2017.247.609.).Deposited it would therefore be highly desirable to which the hypochlorite probe for developing function admirable overcomes
The above problem.
The content of the invention
For the above situation, it is an object of the present invention to provide the highly sensitive detection time that a kind of new easily prepared, performance are stablized
The fluorescence probe of chlorate anions, and the synthetic method of the probe is provided, also go out in this foundational development and high selection is carried out to hypochlorite
Property and highly sensitive detection method.
To realize the object of the invention, one aspect of the present invention has stronger special oxidisability using hypochlorite, can aoxidize
The organic group of special electron rich, design certain structure hydroxyamine groups selectivity aoxidized by hypochlorite；On the other hand
The benzothiazole of aldehyde radical has an excellent spectral characteristic, its aldehyde radical with after azanol condensation reaction, fluorescence can be effectively quenched, and
After hypochlorite aoxidizes azanol, and the transmitting of its hyperfluorescence can be recovered.Based on this, a kind of azanol is devised as response group, aldehyde
The fluorescent molecular probe that is used to detect hypochlorite of the benzothiazole of base as illuminophore.
The fluorescent molecular probe of the detection hypochlorite, it is characterised in that general structure is as follows：
Wherein, R1For S, O or NH；R2For SH, OH or NH2；N is 1 to 18 integer；
It is preferred that：R1For S or O；R2For SH or OH；N is 1 to 6 integer,
More preferably：R1For S；R2For OH.N is 1 to 4 integer.
More preferably：
Its synthetic method is specific as follows：
Aldehyde radical benzothiazole is dissolved in organic solvent with azanol, adds organic base, back flow reaction, obtains after isolating and purifying
To probe molecule.
Wherein, R1, R2N is same as above.
The organic solvent is dichloromethane, in ethanol, tetrahydrofuran, dimethylformamide, 1-methyl-2-pyrrolidinone
It is one or more of.
Organic base is triethylamine, piperidines, the one or more in pyridine.
Reaction temperature is solvent reflux temperature in the above method.
The reaction time is 0.5-24h in the above method.
It is preferred that its preparation method is as follows：
Azanol and triethylamine, back flow reaction 2-8h are added after aldehyde radical benzothiazole is dissolved in ethanol, vacuum distillation removes
Isolate and purify to obtain probe molecule compound after solvent.
1 synthetic method of compound is as follows：
Azanol and triethylamine, back flow reaction 2h are added after aldehyde radical benzothiazole is dissolved in ethanol, vacuum distillation removes
Isolate and purify to obtain probe molecule compound 1 after solvent.Reaction process is as follows：
Qualitative and quantitative determination is carried out to hypochlorite using the molecular probe, for hypochlorous acid in water body or biosystem
The detection of root.
Hypochlorite is detected using fluorescence method, the molecular probe is dissolved in the mixing of water and dimethyl sulfoxide (DMSO)
In buffer system, the solution of hypochlorite containing various concentrations is added, its fluorescence intensity at 540nm is tested, is then existed with solution
Fluorescence intensity makees standard drawing to the concentration of hypochlorite at 540nm, according to standard drawing, quantitatively detects hypochlorite solution to be measured and contains
Amount.
During using Fluorometric assay, the fluorescent molecular probe is 0.5-1 μm of olL to the detectable concentration of hypochlorite-1,
Detection is limited to 0.08 μm of olL-1。
Another application mode of the molecular probe of detection hypochlorite of the present invention is by by cell biological sample
Cultivated with the molecular probe, the hypochlorite in cell biological sample is carried out using the method for fluorescence imaging to pick up survey.
The molecular probe of Fluorometric assay hypochlorite of the present invention, it is preferred to use aldehyde radical benzothiazole passes through with azanol
Condensation reaction synthesizes to obtain, and aldehyde radical benzothiazole is fluorophor；Azanol is the response group of hypochlorite.
Synthesis and the detection method of the probe are illustrated in greater detail in the embodiment of this specification.By fluorescence of the present invention
Molecular probe is dissolved in the mixing buffer solution of water and dimethyl sulfoxide (DMSO) (DMSO), after hypochlorite is added, hypochlorite
Hydroxyamine groups can be aoxidized, so as to suppress the torsion quenching effect of-C=N- keys, significantly increase probe solution fluorescent emission, room temperature
Under hypochlorite can be tested.
The molecular probe specific features of Fluorometric assay hypochlorite of the present invention are as follows：
The fluorescent probe molecule is with good stability and optical property, before reaction maximum absorption wave it is a length of~350nm,
Without notable fluorescent emission；With the addition of hypochlorite, probe molecule occurs one small in uv atlas at~410nm
Absworption peak, and present at~540nm and strong fluorescent emission, the yellow fluorescence observed.
Advantage of the present invention：The probe molecule raw material is easy to get, and synthetic yield is higher, up to more than 65%.Optical property is steady
Fixed (probe solution can stablize storage more than three months indoors, its spectral quality remains unchanged), sensitivity is higher, to hypochlorous acid
Root recognition capability is strong, and selectivity is good, and response speed is very fast, and response range is 0.5-18 μm of olL-1, low (0.08 μ of test limit
M, the method for the 3 times of blank sample standard deviations provided based on International Union of Pure and Applied Chemistry), therefore, the type probe
Detection available for hypochlorite in water body and biosystem.
Brief description of the drawings
Fig. 1 is the nuclear magnetic resonance spectroscopy for the molecular probe that the present invention synthesizes.
Fig. 2 is 10 μm of olL of the present invention-1Molecular probe UV absorption spectrogram after various concentrations hypochlorite is added, from a
To m, hypochlorite concentration is respectively 0,0.5,1,2,4,6,8,10,12,14,16,18,20 μm of olL-1, solution system is water
With the mixing buffer solution (H of dimethyl sulfoxide (DMSO)2O/DMSO=9/1, v/v, 10mM HEPES, pH 7.4), abscissa is wavelength,
Ordinate is absorbance.
Fig. 3 is 10 μm of olL of the present invention-1Molecular probe fluorescence emission spectrogram of compound after various concentrations hypochlorite is added,
From a to m, hypochlorite concentration is respectively 0,0.5,1,2,4,6,8,10,12,14,16,18,20 μm of olL-1, abscissa is ripple
Long, ordinate is fluorescence intensity.
Fig. 4 be hypochlorite concentration standard curve figure, i.e. 10 μm of olL-1Molecular probe of the present invention, reaction it is front and rear
Fluorescent emission intensity and the linear relationship of hypochlorite concentration at 540nm；Abscissa is the concentration of hypochlorite, and ordinate is glimmering
Light emitting intensity level.
Fig. 5 is molecular probe of the present invention to hypochlorite selectivity；That is 10 μM of molecular probes of the present invention, add 20 μm of ol
L-1Active oxide material (tBuOOH、Fe3+、H2O2、NO、1O2、·OH、·O2 –, TBHP) after, the fluorescent emission intensity at 540nm
Value；Abscissa is the material of test, and coordinate is fluorescent emission intensity value.
Fig. 6 is the imaging picture that molecular probe of the present invention detects the intracellular hypochlorites of Hela.(A, B) is the present invention respectively
Fluorescence probe (10 μm of olL-1) culture HeLa light field picture and fluorescence picture；(C, D) is fluorescence probe of the present invention respectively
(10μmol·L-1) and hypochlorite (20 μm of olL-1) culture Hela cells light field picture and fluorescence picture.Scale：50
μm。
Embodiment
Following embodiments are used to illustrate the present invention, but are not limited to the scope of the present invention.
Embodiment 1：The synthesis of fluorescent molecular probe of the present invention
Carboxyl benzothiazole (0.135g, 0.5mmol) and azanol (0.033g, 1.0mmol) are dissolved in ethanol (10mL), added
Enter triethylamine (0.101g, 1.0mmol) heating reflux reaction 2h afterwards.After question response, vacuum distillation removes solvent, column chromatography
Firmly separation (eluant, eluent is the mixed solution of methylene chloride/methanol=2/3) obtains product as white solid 0.183g (yields：
65%).Product structure formula is as follows:
1H NMR(400MHz,DMSO):δ 11.63 (s, 1H), 8.45 (s, 1H), 8.18 (d, J=7.6Hz, 1H), 8.09
(d, J=7.7Hz, 1H), 7.99 (s, 1H), 7.56 (d, J=7.8Hz, 2H), 7.49 (d, J=7.6Hz, 1H), 2.36 (s,
3H).(see Figure S1).MS[ESI]:m/z,calcd for[M+H]+258.06；found 285.01..
Embodiment 2：Fluoroscopic examination of the probe to hypochlorite
Above-mentioned obtained molecular probe is dissolved in the mixing buffer solution (H of water and dimethyl sulfoxide (DMSO)2O/DMSO=9/1, v/
V, 10mM HEPES, pH 7.4)), it is configured to 10 μm of olL-1Probe solution.Add what 2mL was prepared in the cuvette of 3mL
10μmol·L-1Probe solution of the present invention, uniformly mixes after being then respectively adding the hypochlorite of various concentrations, it is ultraviolet to test its
With fluorescence spectrum, as a result such as Fig. 2, shown in 3.With solution, fluorescent emission intensity value maps the concentration of hypochlorite at 540nm,
Hypochlorite concentration is in 0.5-18 μm of olL-1In the range of when, good linear relationship (Fig. 4) is presented between the two.And this is visited
Pin from some other Typical reactive oxidation material influence, such as：tBuOOH、Fe3+、H2O2、NO、1O2、·OH、·O2 –、TBHP。
Under the conditions of existing for above-mentioned interfering ion, probe containing hypochlorite to still having good selectivity and sensitivity (Fig. 5).
By cell with containing after probe nutrient solution culture of the present invention, then with the hydroponics containing hypochlorite.Cell fluorescence into
As can observe red fluorescence (Fig. 6).
As can be seen that the present invention can realize qualitative and quantitative analysis to hypochlorite, high sensitivity, test limit is up to 0.08 μ
mol·L-1, and it is anti-interference strong, and can realize the detection of intracellular hypochlorite.
Claims (9)
1. a kind of fluorescent molecular probe for detecting hypochlorite, it is characterised in that general structure is as follows：
Wherein R1For S, O or NH；R2For SH, OH or NH2；N is 1 to 18 integer.
2. the fluorescent molecular probe of detection hypochlorite as claimed in claim 1, it is characterised in that
R1For S or O；R2For SH or OH；N is 1 to 6 integer.
3. the fluorescent molecular probe of detection hypochlorite as claimed in claim 2, it is characterised in that
R1For S；R2For OH；N is 1 to 4 integer.
4. the fluorescent molecular probe of detection hypochlorite as claimed in claim 3, it is characterised in that fluorescent molecular probe is specific
Structure is：
。
5. the method for the fluorescent molecular probe of synthesis detection hypochlorite as claimed in claim 1, it is characterised in that by such as
Lower method is realized：
I
It will be dissolved in organic solvent with azanol with the aldehyde radical benzothiazole shown in general formula I, addition organic base, back flow reaction,
Probe molecule is obtained after isolating and purifying；
Wherein：R1For S, O or NH；R2For SH, OH or NH2；N is 1 to 18 integer；
The organic solvent is dichloromethane, one kind in ethanol, tetrahydrofuran, dimethylformamide, 1-methyl-2-pyrrolidinone
It is or several；Organic base is triethylamine, piperidines, the one or more in pyridine.
6. the synthetic method of the fluorescent molecular probe of detection hypochlorite as claimed in claim 4, it is characterised in that by such as
Lower method is realized：
II
Azanol and triethylamine, back flow reaction, decompression are added after being dissolved in ethanol with the aldehyde radical benzothiazole shown in Formula II
Isolate and purify to obtain probe molecule compound after solvent is distilled off.
7. the application of the fluorescent molecular probe of the detection hypochlorite as described in one of claim 1-4, it is characterised in that
Hypochlorite in water body and biosystem is qualitatively or quantitatively determined using the molecular probe.
8. the application of the fluorescent molecular probe of detection hypochlorite as claimed in claim 7, it is characterised in that examined using fluorescence
During survey, molecular probe of the present invention is dissolved in the mixing buffer system of water and dimethyl sulfoxide (DMSO), added containing various concentrations time chlorine
Acid group solution, tests its fluorescence intensity at 540 nm, then with solution at 540 nm fluorescent emission intensity to hypochlorous acid
The concentration of root makees standard drawing, according to standard drawing, quantitatively detects content of the hypochlorite in solution to be measured.
9. the application of the fluorescent molecular probe of detection hypochlorite as claimed in claim 7, it is characterised in that by by cell
Biological sample is cultivated with molecular probe of the present invention, and the hypochlorite in cell biological sample is carried out using the method for fluorescence imaging
Pick up survey.
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| CN109406467A (en) * | 2018-10-16 | 2019-03-01 | 商丘师范学院 | Division aptamer sensor and its application for ATP detection |
| CN110372632A (en) * | 2019-07-26 | 2019-10-25 | 广东轻工职业技术学院 | A kind of fluorescent probe molecule and its preparation method and application of quick identification hypochlorite ion |
| CN110627756A (en) * | 2019-10-10 | 2019-12-31 | 中国科学院新疆理化技术研究所 | Colorimetric-fluorescent probe for detecting hypochlorite, preparation method and application thereof |
| CN111087362A (en) * | 2019-12-18 | 2020-05-01 | 商丘师范学院 | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof |
| CN113218922A (en) * | 2021-03-12 | 2021-08-06 | 天津理工大学 | Coumarin skeleton-based rapid hypochlorite ratio detection type fluorescent probe and application thereof |
| CN113563257A (en) * | 2021-07-30 | 2021-10-29 | 忻州师范学院 | Hypochlorite fluorescent probe, preparation method and application thereof, and hypochlorite detection method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109406467A (en) * | 2018-10-16 | 2019-03-01 | 商丘师范学院 | Division aptamer sensor and its application for ATP detection |
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| CN110372632A (en) * | 2019-07-26 | 2019-10-25 | 广东轻工职业技术学院 | A kind of fluorescent probe molecule and its preparation method and application of quick identification hypochlorite ion |
| CN110372632B (en) * | 2019-07-26 | 2021-04-06 | 广东轻工职业技术学院 | Fluorescent probe molecule for rapidly identifying hypochlorite ions and preparation method and application thereof |
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| CN111087362A (en) * | 2019-12-18 | 2020-05-01 | 商丘师范学院 | Fluorescent probe for detecting formaldehyde with high selectivity, and synthetic method and application thereof |
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| CN113563257A (en) * | 2021-07-30 | 2021-10-29 | 忻州师范学院 | Hypochlorite fluorescent probe, preparation method and application thereof, and hypochlorite detection method |
| CN113563257B (en) * | 2021-07-30 | 2022-03-29 | 忻州师范学院 | Hypochlorite fluorescent probe, preparation method and application thereof, and hypochlorite detection method |
| CN115161022A (en) * | 2022-07-12 | 2022-10-11 | 皖西学院 | Cationic fluorescent carbon dots sensitively responding to hypochlorous acid and preparation method thereof |
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