CN108558702A - Bisulfite fluorescence probe and its preparation based on naphthoquinones and application - Google Patents
Bisulfite fluorescence probe and its preparation based on naphthoquinones and application Download PDFInfo
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Abstract
The present invention provide a kind of bisulfite based on naphthoquinones fluorescence probe and its preparation and application, chemical structural formula it is as shown in the figurePreparation method is prepared as raw material using acenaphthenequinone and itrile group ethyl acetate.The type probe has preferable selectivity and stronger anti-interference ability.The fluorescence probe that the present invention designs can be used for detecting the bisulfite in aqueous solution and table sugar, and the probe synthesis in the present invention is simple, can quickly detect the bisulfite in aqueous solution, and selective good, high sensitivity, probe lowest detection are limited to 26nM.
Description
Technical field
The invention belongs to bisulfite fluorescence probe preparation fields, and in particular to a kind of bisulfite based on naphthoquinones
Fluorescence probe and its preparation and application.
Background technology
Bisulfites is widely used as preservative, antioxidant, antiseptic and bleaching agent in the food industry, can
Food Oxidation is prevented, inhibits enzymatic browning and non-enzymatic browning, and the stabilization of food can be promoted with microbial reaction, to food
Product achieve the effect that fresh-keeping.Therefore it is widely used in the food processings such as grape, dry fruit, potato, fruit juice and grape wine.
In medicine, medicinal material usually is processed with the method for sulfur fumigation, purpose is conducive to the drying of some ratio of rhizome medicinal material, contributes to
Insect prevention, bleaching that is mould proof and being usually used in Chinese medicine in Chinese medicine storage is hyperchromic, but will produce HSO in process3 -, when
HSO3 -When residual quantity is more, it is likely to result in the change of Chinese medicine active ingredient itself, influences the quality and curative effect of Chinese medicine.It is long
Phase takes HSO3 -The excessively high Chinese medicine of residual quantity can generate serious harm to human body.Therefore about HSO3 -In food and drug
Content it is many country all by stringent control, for example, in China, the content of grape wine and beer bisulfite is not
Must be more than 0.05mg/kg, the bisulfite salt content in sugar must not exceed 0.10g/kg.
Adjacent naphthoquinones is a kind of fluorescent dye reported in 2005, because containing strong electron-withdrawing groups groups such as ketone, itrile groups, it is this kind of
With substances such as mercaptan, amine quick necleophilic reaction can occur for dyestuff in organic solvent.It can be used for fluorescence identifying in PBS solution
Sensing of biological activity mercaptan Cys, Hcy and H2S.Due to active too high, a variety of nucleophilics such as mercaptan and hydrogen sulfide of such compound
Performance enough reacts, and selectivity is poor.Relative to mercaptan and hydrogen sulfide, sodium hydrogensulfite has higher nucleophilic addition
Reactivity, therefore this patent reduces its necleophilic reaction activity, to realize to SO by the way that itrile group is become ester group2Spy
Opposite sex identification sensing.New thinking is provided to design the novel highly selective fluorescence probe based on nucleophilic addition.
Invention content
The present invention propose it is a kind of in the bisulfite fluorescence probe of naphthoquinones and its preparation and application, using naphthoquinones as fluorescence
Group, double bond is reaction site, constructs fluorescence probe (I).With bisulfite Michael addition adducts occur for probe, to real
The detection to bisulfite is showed.
Realize the technical scheme is that：A kind of bisulfite fluorescence probe based on naphthoquinones, structural formula such as (I) institute
Show：
The preparation method of the bisulfite fluorescence probe based on naphthoquinones, steps are as follows：
(1) acenaphthenequinone is dissolved in toluene, itrile group ethyl acetate, ammonium acetate and acetic acid is added thereto, in reflux temperature
Lower reaction 6-10h is cooled to room temperature after reaction, and toluene is removed with Rotary Evaporators, and sodium bicarbonate aqueous solution is added and carries out
It after dilution, is extracted with dichloromethane and water, merging is concentrated to give yellow-gray solid, is tied again with chloroform and n-hexane
Crystalline substance obtains the mixture of compound 1-a and 1-b；
(2) mixture that step (1) obtains is dissolved in acetonitrile, potassium carbonate is added, reacts 4-8h at a reflux temperature,
After reaction, it isolates and purifies to obtain the fluorescence probe that structural formula is (I).
The ratio between amount of substance of 1-a and 1-b is 1 in step (1) mixture：1.
The structure of 1-a (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate in the step (1)
Formula isThe structural formula of 1-b (E) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) is
The ratio between amount of substance of acenaphthenequinone, itrile group ethyl acetate, ammonium acetate and acetic acid is 1 in the step (1)：(1-3)：
(0.2-0.5)：(0.5-1.5).
The reflux temperature is 100-120 DEG C.
The ratio between amount of substance of mixture and potassium carbonate is 12 in the step (2)：(1-1.2).
The application of bisulfite of the fluorescence probe in detection environmental water sample, sugar.
The variation of uv-vis spectra and fluorescence spectrum before and after bisulfite is added in test probe storing liquid respectively, glimmering
The excitation wavelength of light is 365nm；Detect the detection of aqueous solution sulfite hydrogen radical.
The variation of fluorescence spectrum is：When being excited with 365nm light, the fluorescence at 430nm enhances rapidly, and about 35min reaches
Peak.
The beneficial effects of the invention are as follows：(1) this patent is related to a kind of novel fluorescence probe；(2) even if in a mM grade
Bisulfite in the presence of, probe (I) can also react well with bisulfite；(3) the probe synthesis in the present invention
Simply, the bisulfite in aqueous solution can be quickly detected, selective good, high sensitivity, probe (I) lowest detection are limited to
26nM。
Description of the drawings
In order to more clearly explain the embodiment of the invention or the technical proposal in the existing technology, to embodiment or will show below
There is attached drawing needed in technology description to be briefly described, it should be apparent that, the accompanying drawings in the following description is only this
Some embodiments of invention for those of ordinary skill in the art without creative efforts, can be with
Obtain other attached drawings according to these attached drawings.
Fig. 1 is 1,2,3 compound 1-a and 1-b of embodiment1H NMR spectras.
Fig. 2 is 1,2,3 probe (I) of embodiment1H NMR spectras.
Fig. 3 is 1,2,3 probe (I) of embodiment13C NMR spectras.
Fig. 4 be PBS buffer (10mM, pH=7.4) system in, when 10 μM of probes (I) are reacted with 50 μM of bisulfites,
Fluorescence spectrum changes with time figure.
Fig. 5 is 10 μM of probes (I) and various concentration bisulfite (0- in PBS buffers (10mM, pH=7.4) system
50 μM) reaction fluorescence spectra.
Fig. 6 is 10 μM of probes (I) and Asia of the concentration range at 0-50 μM in PBS buffers (10mM, pH=7.4) system
When bisulfate ion reacts, the linear relationship chart of fluorescence intensity and bisulfite concentration at 430nm.
Fig. 7 be in PBS buffers (10mM, pH=7.4) system, 10 μM of probes (I) and its be added different anion and
Fluorescence emission spectrogram of compound when (50 μM) reaction 35min of small molecule at 430nm.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical scheme 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,
The every other embodiment that those of ordinary skill in the art are obtained under the premise of not making the creative labor, belongs to this hair
The range of bright protection.
Embodiment 1
Compound (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate (1-a) and (E) -2- cyanogen
The synthesis of base -2- (- 1 (2H)-subunit of 2- oxos naphthylene) (1-b)
Acenaphthenequinone 1.00g (5.49mmol) is weighed, is dissolved in 20mL toluene, itrile group ethyl acetate 0.62g is added thereto
(5.56mmol), ammonium acetate 0.1g (1.30mmol), acetic acid 0.3g (5.00mmol).6h is reacted at 100 DEG C, reaction terminates
Afterwards, it is cooled to room temperature, can remove toluene after addition sodium bicarbonate aqueous solution is diluted with Rotary Evaporators uses dichloromethane
Alkane and water are extracted, and magnesium sulfate is used in combination to dry organic phase, and merging is concentrated to give yellow-gray solid, is carried out with chloroform and n-hexane
Recrystallization, obtains the mixture of compound 1-a and 1-b, and wherein 1-b is relatively soluble in n-hexane, is identified in mixture through nuclear-magnetism
The content of 1-a and 1-b is about 1：1.
1H NMR(CDCl3,400MHz,ppm):8.74 (d, J=7.40Hz, 1H), 8.44 (dd, J=7.20Hz, 1H),
8.20 (d, J=1.28Hz, 1H), 8.18 (d, J=1.28Hz, 1H), 8.12 (d, J=8.28Hz, 2H), 8.09 (d, J=
12.48Hz, 1H), 7.82 (d, J=8.08Hz, 2H), 7.78 (d, J=9.20Hz, 2H), 4.54 (m, J=7.16Hz, 4H),
1.49 (m, J=7.08Hz, 6H).
The synthesis of probe (I)：
Weigh mixture (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate and (E) -2- cyano -
For 2- (- 1 (2H)-subunit of 2- oxos naphthylene) (332mg, 1.2mmol) in the round-bottomed flask of 50mL, 8mL acetonitriles, which are added, makes it
Dissolving is added potassium carbonate (13.8mg, 0.10mmoL), reacts 4h at a temperature of 100 DEG C, after reaction, be cooled to room temperature, and uses
Rotary Evaporators remove solvent, are extracted later with dichloromethane, merge organic phase, are dried with anhydrous sodium sulfate, remove dichloromethane
Alkane, by silica gel column chromatography separation, (eluant, eluent is petroleum ether to crude product：Ethyl acetate=10:1, v/v) yellow probe (I), is obtained.
1H NMR(CDCl3,400MHz,ppm):8.68 (d, J=7.40Hz, 1H), 8.34 (t, J=7.31Hz, 2H),
8.23 (d, J=8.24Hz, 1H), 7.89 (t, J=7.72Hz, 1H), 7.78 (t, J=7.84Hz, 1H), 4.52-4.57 (m, J
=7.12Hz, 2H)；
13C NMR(CDCl3,100MHz,ppm):179.50,163.39,139.12,136.76,135.01,132.43,
132.28,132.09,128.65,128.27,127.20,126.67,122.90,122.73,113.39,62.88。
Embodiment 2
Compound (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate (1-a) and (E) -2- cyanogen
The synthesis of base -2- (- 1 (2H)-subunit of 2- oxos naphthylene) (1-b)
Acenaphthenequinone 1.00g (5.49mmol) is weighed, is dissolved in 20mL toluene, itrile group ethyl acetate 1.22g is added thereto
(10.98mmol), ammonium acetate 0.17g (2.2mmol), acetic acid 0.16g (2.74mmol).8h is reacted under 110 DEG C of reflux temperatures,
After reaction, it is cooled to room temperature, toluene can be removed with Rotary Evaporators, after addition sodium bicarbonate aqueous solution is diluted,
It is extracted with dichloromethane and water, is used in combination magnesium sulfate to dry organic phase, merging is concentrated to give yellow-gray solid, with chloroform and just
Hexane is recrystallized, and the mixture of compound 1-a and 1-b is obtained, and wherein 1-b is relatively soluble in n-hexane, is identified through nuclear-magnetism
The content of 1-a and 1-b is about 1 in mixture：1.
The synthesis of probe (I)：
Weigh mixture (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate and (E) -2- cyano -
For 2- (- 1 (2H)-subunit of 2- oxos naphthylene) (332mg, 1.2mmol) in the round-bottomed flask of 50mL, 8mL acetonitriles, which are added, makes it
Dissolving is added potassium carbonate (15.2mg, 0.11mmoL), 6h is reacted under 110 DEG C of reflux temperatures, after reaction, is cooled to room
Temperature removes solvent with Rotary Evaporators, is extracted later with dichloromethane, merge organic phase, dried with anhydrous sodium sulfate, removes two
Chloromethanes, by silica gel column chromatography separation, (eluant, eluent is petroleum ether to crude product：Ethyl acetate=10:1, v/v) yellow probe, is obtained
(Ⅰ)。
Embodiment 3
Compound (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate (1-a) and (E) -2- cyanogen
The synthesis of base -2- (- 1 (2H)-subunit of 2- oxos naphthylene) (1-b)
Acenaphthenequinone 1.00g (5.49mmol) is weighed, is dissolved in 20mL toluene, itrile group ethyl acetate 1.86g is added thereto
(16.47mmol), ammonium acetate 0.21g (2.74mmol), acetic acid 0.49g (8.24mmol).10h is reacted at 120 DEG C, reaction terminates
Afterwards, it is cooled to room temperature, can remove toluene after addition sodium bicarbonate aqueous solution is diluted with Rotary Evaporators uses dichloromethane
Alkane and water are extracted, and magnesium sulfate is used in combination to dry organic phase, and merging is concentrated to give yellow-gray solid, is carried out with chloroform and n-hexane
Recrystallization, obtains the mixture of compound 1-a and 1-b, and wherein 1-b is relatively soluble in n-hexane, is identified in mixture through nuclear-magnetism
The content of 1-a and 1-b is about 1：1.
The synthesis of probe (I)：
Weigh mixture (Z) -2- cyano -2- (- 1 (2H)-subunit of 2- oxos naphthylene) ethyl acetate and (E) -2- cyano -
For 2- (- 1 (2H)-subunit of 2- oxos naphthylene) (332mg, 1.2mmol) in the round-bottomed flask of 50mL, 8mL acetonitriles, which are added, makes it
Dissolving is added potassium carbonate (16.6mg, 0.12mmoL), 8h is reacted at 120 DEG C, after reaction, is cooled to room temperature, with rotation
Evaporimeter removes solvent, is extracted later with dichloromethane, merges organic phase, is dried with anhydrous sodium sulfate, removes dichloromethane, slightly
By silica gel column chromatography separation, (eluant, eluent is petroleum ether to product：Ethyl acetate=10:1, v/v) yellow probe (I), is obtained.
1. the fluorescence intensity that probe is reacted with bisulfite changes with time
Prepare PBS (10mM) buffer solution of pH=7.4；Probe (I) is weighed, is dissolved with DMSO, the accurate spy for preparing 2mM
Needle (I) storing liquid；Prepare the bisulfite of 20mM.The PBS buffer solutions of 2.0mL are added into cuvette, after mixing,
Probe (I) storing liquid of 10 a concentration of 2mM of μ L is added, adds 5 equivalent bisulfites, carries out fluorescence spectrum test.Such as Fig. 4
Shown, fluorescence intensity of the probe at 430nm gradually increases, and is reacted about in 35min and reaches balance.
2. the fluorescence intensity that probe is reacted with bisulfite is with the variation of bisulfite concentration
It is buffered in (10mM, pH=7.4) system to the PBS of 2mL, probe (I) storing liquid of 10 a concentration of 2mM of μ L is added,
Various concentration bisulfite (0-50 μM) is added, 35min is reacted, is excited with 365nm light, fluorescence spectrometry is carried out.With
The increase of bisulfite concentration, fluorescence intensity gradually increases.As shown in Figure 5 and Figure 6, to fluorescence intensity and bisulfite
Concentration carry out linear fit, it is found that when the concentration range of bisulfite is 0-50 μM, fluorescence intensity and concentration present fine
Linear relationship, detection is limited to 26nM, has very high sensitivity, far below sugared content (0.10g/kg) in aqueous solution,.3.
The influence of different anions and small molecule to probe
Prepare the different types of anion and small molecule storing solution of 20mM.(10mM, pH=7.4) is buffered to the PBS of 2mL
In system, probe (I) storing liquid of 10 a concentration of 2mM of μ L is added, then is separately added into the analyte of 20 equivalents：F-,Cl-,Br-,
I-,SO4 2-,NO3 -,NO2 -,CO3 2-,H2PO4 -,HPO4 2-,ACO-,SCN-,S2O3 2-,ClO-,HS-,HCO3 -,H2O2,Cys,Hcy,
GSH), after reacting 35min, fluorescence spectrometry is carried out.As shown in fig. 7, the experimental results showed that the anion of other types and small
Molecule does not react with probe, does not interfere specific recognition of the probe to bisulfite.
4. application of the probe (I) in actual sample
In order to study application of the probe (I) in real life, we are the HSO in food by probe application3 -It is accurate
In detection.We test HSO in white granulated sugar3 -Content.The white granulated sugar for accurately weighing 500mg first is dissolved in 15ml's
In PBS (10mM, pH=7.4) buffer solution.Then the probe solution of final concentration of 10uM is added thereto, after reacting 30min
The fluorescence intensity at 430nm is measured, the content of sodium hydrogensulfite is then calculated according to the fluorescence standard curve of Fig. 6.We are practical
The content for measuring white granulated sugar sulfite hydrogen sodium is：14.0474mg/kg.And the content of national regulation sugar sulfite hydrogen sodium
100mg/kg is must not exceed, illustrates that the content of the sodium hydrogensulfite in the sugar that we are surveyed is not exceeded.Then pass through mark-on
5 μM of HSO is added in recycling normal direction sample3 -, shown in result table 1.By the experimental results showed that, probe (I) can be used for detect food
HSO in product3 -Content.
1 probe of table (I) detects the NaHSO in white granulated sugar3
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
With within principle, any modification, equivalent replacement, improvement and so on should all be included in the protection scope of the present invention god.
Claims (8)
1. a kind of bisulfite fluorescence probe based on naphthoquinones, it is characterised in that structural formula is such as shown in (I)：
2. the preparation method of the bisulfite fluorescence probe described in claim 1 based on naphthoquinones, it is characterised in that step is such as
Under：
(1) acenaphthenequinone is dissolved in toluene, itrile group ethyl acetate, ammonium acetate and acetic acid is added thereto, at a reflux temperature instead
It answers 6-10h, after reaction, be cooled to room temperature, toluene is removed with Rotary Evaporators, sodium bicarbonate aqueous solution is added and is diluted
Afterwards, it is extracted with dichloromethane and water, merging is concentrated to give yellow-gray solid, is recrystallized, is obtained with chloroform and n-hexane
To the mixture of compound 1-a and 1-b；
(2) mixture that step (1) obtains is dissolved in acetonitrile, potassium carbonate is added, reacts 4-8h at a reflux temperature, reacted
After, it isolates and purifies to obtain the fluorescence probe that structural formula is (I).
3. the preparation method of the bisulfite fluorescence probe according to claim 2 based on naphthoquinones, it is characterised in that：Institute
It is 1 to state the ratio between amount of substance of 1-a and 1-b in step (1) mixture：1.
4. the preparation method of the fluorescence probe of the bisulfite according to claim 2 based on naphthoquinones, it is characterised in that：
The structural formula of 1-a is in the step (1)The structural formula of 1-b is
5. the preparation method of the bisulfite fluorescence probe according to claim 2 based on naphthoquinones, it is characterised in that：Institute
It is 1 to state the ratio between amount of substance of acenaphthenequinone, itrile group ethyl acetate, ammonium acetate and acetic acid in step (1)：(1-3)：(0.2-0.5)：
(0.5-1.5)。
6. the preparation method of the bisulfite fluorescence probe according to claim 2 based on naphthoquinones, it is characterised in that：Institute
It is 100-120 DEG C to state reflux temperature.
7. the preparation method of the bisulfite fluorescence probe according to claim 2 based on naphthoquinones, it is characterised in that：Institute
It is 12 to state the ratio between amount of substance of mixture and potassium carbonate in step (2)：(1-1.2).
8. the application of bisulfite of the claim 1-7 any one of them fluorescence probe in detection environmental water sample, sugar.
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| ROMARIC LENK等: "1‑Oxo‑1H‑phenalene-2,3-dicarbonitrile Heteroaromatic Scaffold: Revised Structure and Mechanistic Studies", 《J. ORG. CHEM.》 * |
| 孙远强: "气体信使分子一氧化氮和二氧化硫衍生物荧光探针", 《山西大学博士学位论文》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111426662A (en) * | 2020-04-10 | 2020-07-17 | 江西理工大学 | Fluorescence detection method of sodium formaldehyde sulfoxylate (rongalite) |
| CN111426662B (en) * | 2020-04-10 | 2023-01-24 | 江西理工大学 | Fluorescence detection method of sodium formaldehyde sulfoxylate (rongalite) |
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| CN108558702B (en) | 2020-07-17 |
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