CN105837458B - A kind of fluorescence probe and preparation method thereof and the application in detection peroxy acid - Google Patents
A kind of fluorescence probe and preparation method thereof and the application in detection peroxy acid Download PDFInfo
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- CN105837458B CN105837458B CN201610213856.6A CN201610213856A CN105837458B CN 105837458 B CN105837458 B CN 105837458B CN 201610213856 A CN201610213856 A CN 201610213856A CN 105837458 B CN105837458 B CN 105837458B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/24—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings
- C07C225/26—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings
- C07C225/32—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones the carbon skeleton containing carbon atoms of quinone rings having amino groups bound to carbon atoms of quinone rings or of condensed ring systems containing quinone rings of condensed quinone ring systems formed by at least three rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
Abstract
Application the present invention relates to a kind of fluorescence probe and preparation method thereof and in detection peroxy acid.Described fluorescence probe is 5 dimethylamine acenaphthenequinones, with the structure as shown in (I).Preparation method, comprises the following steps：In N2Under protection, by 5 bromine acenaphthenequinones, dimethylamine hydrochloride, cuprous iodide and potassium hydroxide and N, N dimethylformamide are mixed, and the 7h of heating response 2 is filtered, and is dried, and separation obtains target product.Fluorescence strengthens after the fluorescence probe of the present invention, itself unstressed configuration, with peroxy acid effect, and fluorescence intensity is proportional to the concentration of peroxy acid, so as to indicate the presence of peroxy acid or quantitative determine the concentration of peroxy acid.
Description
Technical field
The present invention relates to fluorescence probe field, it is specifically related to a kind of fluorescence available for selective enumeration method peroxy acid and visits
Pin.
Background technology
The epoxy of alkene turns to the main application of peroxy acid.For example, being used as bleaching agent in textile and paper industry.Due to
Strong antibacterial action, Peracetic acid and peroxide citric acid are widely used as disinfectant.Its biggest advantage is only remaining after sterilization
Nontoxic water and acid, it is more environmentally-friendly compared with other chlorine-containing compounds.So, be widely used in food and drink, hospital and
Agriculturally.But Peracetic acid has strong and stimulating for skin, respiratory tract and eyes.Also therefore, how peroxide is accurately detected
Acetic acid is just particularly important.There is document report to point out to be found that the presence of porphyryl peroxy acid in the urine of patient CEP, therefore
The possibility that activity in vivo oxygen oxidation macromolecular carboxylic acid is changed into peroxy acid is present.If method can be in human body accurately
Detection peroxy acid, this for further investigation peroxy acid in vivo physiology and the kinetics mechanism of pathologic process have it is important
Meaning.
At present, the method for detection peroxy acid is very few, and detects that the method for Peracetic acid is not within minority, but due to Peracetic acid
Often coexisted with hydrogen peroxide, the interference of hydrogen peroxide causes accuracy in detection not high；Some methods have limitation, it is impossible to detect gas phase
Peracetic acid；Also method must be detected immediately after collecting sample, and condition is harsh.Therefore, a kind of selectivity is studied good, using model
Enclose wide, the method for convenient and reliable detection Peracetic acid even peroxy acid is significant.
The content of the invention
There is provided a kind of fluorescence probe that can be used for selective enumeration method peroxy acid aiming above mentioned problem by the present invention.
Fluorescence strengthens after such fluorescence probe, itself unstressed configuration, with peroxy acid effect, and fluorescence intensity is proportional to peroxy acid
Concentration, so as to indicate the presence of peroxy acid or quantitative determine the concentration of peroxy acid.
The present invention is adopted the following technical scheme that：A kind of fluorescence probe, described fluorescence probe is 5- dimethylamine-acenaphthenequinone, tool
Just like the structure shown in (I)：
The preparation method of above-mentioned fluorescence probe, comprises the following steps：In N2Under protection, by the bromo- acenaphthenequinones of 5-, dimethylamine salt
Hydrochlorate, cuprous iodide and potassium hydroxide are mixed with DMF, heating response 2-7h, are filtered, and are dried, and separation is obtained
Target product.
Above-mentioned preparation method, the mol ratio of the bromo- acenaphthenequinones of 5- and dimethylamine hydrochloride, cuprous iodide, potassium hydroxide is 1:
1:0.1:2。
Above-mentioned preparation method, reaction temperature is 50-100 DEG C.
Application of the above-mentioned fluorescence probe in qualitatively or quantitatively detection peroxy acid.Its mechanism of action is：With non-blooming
5- dimethylamine-acenaphthenequinone is fluorescence probe, after peroxy acid effect, 4- dimethylamine -1,8- naphthalene anhydrides of hyperfluorescence is generated, so as to pass through
The difference of fluorescence intensity before and after reaction, reaches the presence for indicating peroxy acid or quantitative determines the purpose of the concentration of peroxy acid.
Method is as follows：In the solution containing peroxy acid, the pH of regulation solution is 2.5-10.5, adds above-mentioned fluorescence and visits
Pin, determines fluorescence intensity at 530nm.
The present invention, the structure such as (III) of described peroxy acid is shown：
Wherein, R be alkyl substituent, aryl substituent orDescribed R ' is hydrogen or alkyl substituent.
It is preferred that, described alkyl substituent is C1-C10Alkyl.
It is preferred that, described peroxy acid is Peracetic acid, peroxysuccinic acid, benzoyl hydroperoxide, metachloroperbenzoic acid, mistake
Oxygen amino acid, peroxide peptide or peroxide protein.
The present invention, when described fluorescence probe is applied to detection peroxy acid, it is compound of the generation with structure (II),
So as to cause change in fluorescence；
The beneficial effects of the invention are as follows：The fluorescence probe of the present invention, fluorescence is significantly increased in the presence of peroxy acid, can
For high selectivity, high sensitivity it is qualitative and quantitatively detect peroxy acid.Especially, the fluorescence probe can be used in biosystem
The detection of peroxy acid, this for further investigation peroxy acid in vivo physiology and the kinetics mechanism of pathologic process have it is important
Meaning.
Brief description of the drawings
Fig. 1 is the principle schematic that the fluorescence probe that the present invention is synthesized detects peroxy acid.
Fig. 2 is the fluorescence probe that the present invention is synthesized1H NMR spectras.
Fig. 3 is the mass spectrum for the fluorescence probe that the present invention is synthesized.
Fig. 4 a are fluorescence probe and the ultraviolet-visible absorption spectroscopy after Peracetic acid response in embodiment 2.
Fig. 4 b are fluorescence probe and the fluorescence emission spectrum after Peracetic acid response in embodiment 2.
Fig. 5 is selective schematic diagram of the fluorescence probe to Peracetic acid in embodiment 2.
Fig. 6 is detects schematic diagram of the fluorescence probe to excessive Peracetic acid in embodiment 2.
Fig. 7 is quantitative detection of the fluorescence probe to Peracetic acid in embodiment 2.
Fig. 8 is fluorescence intensity of the fluorescence probe under different pH conditions in embodiment 2.
Fig. 9 is fluorescence probe and Peracetic acid, peroxysuccinic acid, benzoyl hydroperoxide, metachloroperbenzoic acid in embodiment 2
Fluorescence emission spectrum after response.
Figure 10 is fluorescence probe and various peroxide amino acid, peroxide glutathione, peroxide bovine serum albumin sound in embodiment 2
Should rear fluorescence emission spectrum.
Embodiment
The synthesis of the 5- dimethylamine of embodiment 1-acenaphthenequinone fluorescence probe
(1) synthesis of 5- dimethylamine-acenaphthenequinone fluorescence probe
1st, the synthesis of the bromo- acenaphthenequinones of 5-：
Under nitrogen protection, 3g acenaphthenequinones (16.5mmol), 5mL bromine (180mmol) are taken, 50mL single port bottle is added to
In, under stirring, 60-70 DEG C is to slowly warm up to, 8h is reacted.Reaction solution is cooled to room temperature, saturation Na is added dropwise thereto2SO3It is molten
Liquid, untill red bromine all consumption, then filters, dries, and obtains crude product, and recrystallized 4-5 times with acetic acid.Obtain flaxen
The bromo- acenaphthenequinone sterling 3.9g of 5-, the yield of the compound is 90%.
2nd, 5- dimethylamine-acenaphthenequinone fluorescence probe synthesis：
Under nitrogen protection, the bromo- acenaphthenequinones of 208mg 5- (0.8mmol), 65.2mg dimethylamine hydrochlorides are taken respectively
(0.8mmol), 15.2mg cuprous iodides (0.08mmol), 89.8mg potassium hydroxide (1.6mmol), the DMF that 50mL is dried, 80
Spend in oil bath and stir.Reaction is tracked by TLC, and reaction is stopped afterwards completely to consumption of raw materials.Question response liquid is cooled down, filtering, filtrate
It is spin-dried for obtaining dark red solid.Separated that (solvent is dichloromethane using column chromatography：Methanol=1：200v/v), obtain dark red
The solid powder 45mg of color, yield is 25%.
(2) 5- dimethylamine-acenaphthenequinone fluorescence probe1H H NMR spectroscopies and mass spectrum
5- dimethylamine-acenaphthenequinone fluorescence probe of synthesis1H H NMR spectroscopies and mass spectrum are as shown in Figures 2 and 3.
1HNMR(400MHz,CDCl3)δ(ppm):8.27(d,1H),7.98(d,1H),7.89(d,1H),7.59(dd,
1H),6.98(d,1H),3.19(s,6H)。
HRMS m/z C14H11NO2Calcd for 225.0791, C14H12NO2Calcd for 226.0791, found
[C14H12NO2]+226.0874。
The 5- dimethylamine of embodiment 2-acenaphthenequinone fluorescence probe is in the qualitative and quantitatively application in detection peroxy acid
(1) absorption of 5- dimethylamine-acenaphthenequinone fluorescence probe and transmitting spectrogram
0.5mL phosphate buffer solution (0.1M pH=7.40) and 10 μ L 5mM fluorescence probe storing solution is taken to be added to
In different centrifuge tubes, then by peracetic acid soln and 50mM volume that 5mM volume is 0,1,2.5,5,10 μ L it is successively
1.5th, 2,2.5,3,4,5,7,9,15,25 μ L peracetic acid soln is added in corresponding centrifuge tube, is eventually adding 4.5mL's
1,4- dioxane.Solution is added sequentially in cuvette, its ultraviolet absorptivity is surveyed, the width for setting grating is 5nm, is collected
350-550nm absorption spectrum information, then 430nm deexcitations are used, collect 440-700nm change in fluorescence situation.Measurement is ultraviolet
Visible absorption spectra (Fig. 4 a) and emission spectrum (Fig. 4 b).It is as shown in Figs. 4a and 4b, with the increase of peroxyacetic acid concentration, absorb
Red shift occurs for the position of wavelength；Fluorescent emission intensity gradually rises, and shows that probe has response to Peracetic acid.As a result fluorescence is shown
Maximum excitation wavelength after probe response is that 430nm, maximum emission wavelength are 530nm.
(2) selectivity of the 5- dimethylamine-acenaphthenequinone fluorescence probe to Peracetic acid
0.5mL phosphate buffer solution (0.1M pH=7.40) and the storing solution of 10 μ L 5mM fluorescence probes is taken to be added to
In different centrifuge tubes, then take successively 20 μM of Peracetic acid, 250 μM of hypochlorous acid, 250 μM of hydrogen peroxide, 250 μM of creating singlet oxygen,
250 μM of hypobromous acid, 250 μM of hydroxyl radical free radicals, 250 μM of peroxidating nitrosyl are added in corresponding centrifuge tube, are eventually adding
4.5mL 1,4- dioxane.Solution is added sequentially in cuvette, its fluorescence intensity is surveyed, setting is excited, transmite slit is
5nm, uses 430nm deexcitations, collects 440-700nm change in fluorescence situation.As a result as shown in figure 5, Fig. 5 shows fluorescence probe pair
Peracetic acid has good selectivity, and system fluorescence is significantly increased.Under condition determination, compared to Peracetic acid, other materials
Caused Fluorescence Increasing can be ignored.
(3) 5- dimethylamine-detection of the acenaphthenequinone fluorescence probe to excessive Peracetic acid
0.5mL phosphate buffer solution (0.1M pH=7.40) and 10 μ L 5mM fluorescence probe storing solution is taken to be added to
In different centrifuge tubes, then by peracetic acid soln and 50mM volume that 5mM volume is 0,1,2.5,5,10 μ L it is successively
1.5th, 2,2.5,3,4,5,7,9,15,25 μ L peracetic acid soln is added in corresponding centrifuge tube, is eventually adding 4.5mL's
1,4- dioxane.Solution is added sequentially to use 430nm deexcitations in cuvette, 440-700nm change in fluorescence feelings are collected
Condition.As a result as shown in fig. 6, as seen from Figure 6, with the growth of peroxyacetic acid concentration, fluorescence intensity gradually increases.
(4) quantitative detection of the 5- dimethylamine-acenaphthenequinone fluorescence probe to Peracetic acid
0.5mL phosphate buffer solution (0.1M pH=7.40) and 10 μ L 5mM fluorescence probe storing solution is taken to be added to
In different centrifuge tubes, then by peracetic acid soln and 50mM volume that 5mM volume is 0,1,2.5,5,10 μ L it is successively
1.5th, 2,2.5,3,4,5 μ L peracetic acid soln is added in corresponding centrifuge tube, is eventually adding 4.5mL Isosorbide-5-Nitrae-dioxy six
Ring.Solution is added sequentially to use 430nm deexcitations in cuvette, 440-700nm change in fluorescence situation is collected.As a result as schemed
Shown in 7, as seen from Figure 7, when the final test concentration of Peracetic acid is in below 50uM, fluorescence intensity and the peroxide second of fluorescence probe
Linear positive correlation well is presented in the concentration of acid.Corresponding equation of linear regression is F530nm=0.1809 × C (peroxide second
Acid)+6.4306, its linearly dependent coefficient is R=0.93961.
(5) influences of the different PH to 5- dimethylamine-acenaphthenequinone fluorescence probe fluorescence intensity
The storing solution of 10 μ L5mM fluorescence probes is taken to be added in different centrifuge tubes, then successively by 20 μ L 5mM peroxide second
Sour storing solution is added in corresponding centrifuge tube, be eventually adding 5mLpH be respectively 2.5,3.5,4.5,5.5,6.5,7.5,8.5,
9.5th, 10.5,11.5,12.5 1,4- dioxane and mixed liquor (the 1,4- dioxane of phosphate buffer solution:Phosphate
Cushioning liquid=9:In 1v/v).Solution is added sequentially in cuvette, its fluorescence intensity is surveyed, setting is excited, transmite slit is
5nm, uses 430nm deexcitations, and change in fluorescence situation is collected to the reaction solution under 11 condition of different pH.As a result as depicted in figure 8,
As seen from Figure 8, under the conditions of pH is 2.5 to 10.5 pH, the fluorescence of fluorescence probe can significantly increase under Peracetic acid effect
By force, pH has an impact to the fluorescence probe, and fluorescence intensity is stronger under PH=7.4 or so physiology PH.Also illustrate that the fluorescence is visited
Pin is relatively suitably applied in organism to carry out biological detection.
(6) emission spectrum of 5- dimethylamine-acenaphthenequinone fluorescence probe and peroxy acid
0.5mL phosphate buffer solution (0.1M pH=7.40) and 10 μ L 5mM fluorescence probe storing solution is taken to be added to
In different centrifuge tubes, then successively by 5 μM of Peracetic acid, peroxysuccinic acid, benzoyl hydroperoxide, metachloroperbenzoic acid solution adds
Enter into corresponding centrifuge tube, be eventually adding 4.5mL Isosorbide-5-Nitrae-dioxane.Solution is added sequentially to use in cuvette
430nm deexcitations, collect 440-700nm change in fluorescence situation.As a result as shown in figure 9, as seen from Figure 9, fluorescence probe is to this
Class peroxy acid has fine response, and system fluorescence is significantly increased.Illustrate that fluorescence probe is equally applicable to other carbochain peroxy acids.
(7) emission spectrum of 5- dimethylamine-acenaphthenequinone fluorescence probe and peroxy acid
0.5mL phosphate buffer solution (0.1M pH=7.40) and 10 μ L 5mM fluorescence probe storing solution is taken to be added to
In different centrifuge tubes, then successively by 5 μM of peroxide arginine, peroxide leucine, peroxide tyrosine, peroxide tryptophan, peroxide benzene
Alanine, peroxide cysteine, peroxide methionine, peroxide alanine, peroxide isoleucine, peroxide bovine serum albumin, peroxide paddy
The sweet peptide solution of Guang is added in corresponding centrifuge tube, is eventually adding 4.5mL Isosorbide-5-Nitrae-dioxane.Solution is added sequentially to ratio
430nm deexcitations are used in color ware, 440-700nm change in fluorescence situation is collected.As a result such as Figure 10, as seen from Figure 10, fluorescence is visited
For such peroxide amino acid, peroxide peptide, peroxide protein has fine response, and system fluorescence is significantly increased.Illustrate probe pair
Peroxy acid in organism is equally applicable.
Claims (8)
1. a kind of preparation method of fluorescence probe, it is characterised in that：Comprise the following steps：In N2Under protection, by the bromo- acenaphthenequinones of 5-, two
Methylamine hydrochloride, cuprous iodide and potassium hydroxide are mixed with DMF, heating response 2-7h, are filtered, and are dried, point
From obtaining target product；Described fluorescence probe is 5- dimethylamine-acenaphthenequinone, with the structure as shown in (I)：
2. preparation method according to claim 1, it is characterised in that：The bromo- acenaphthenequinones of 5- and dimethylamine hydrochloride, iodate are sub-
Copper, the mol ratio of potassium hydroxide are 1:1:0.1:2.
3. preparation method according to claim 1, it is characterised in that：Reaction temperature is 50-100 DEG C.
4. application of the fluorescence probe prepared in accordance with the method for claim 1 in qualitatively or quantitatively detection peroxy acid.
5. application according to claim 4, it is characterised in that method is as follows：In the solution containing peroxy acid, adjust molten
The pH of liquid is 2.5-10.5, adds the fluorescence probe described in claim 1, and fluorescence intensity is determined at 530nm.
6. the application according to claim 4 or 5, it is characterised in that the structure of described peroxy acid is such as shown in (III)：
Wherein, R be alkyl substituent, aryl substituent orDescribed R ' is hydrogen or alkyl substituent.
7. application according to claim 6, it is characterised in that：Described alkyl substituent is C1-C10Alkyl.
8. application according to claim 6, it is characterised in that：Described peroxy acid is Peracetic acid, peroxysuccinic acid, mistake
Oxybenzoic acid, metachloroperbenzoic acid, peroxide amino acid, peroxide peptide or peroxide protein.
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