CN108610289A - A kind of quick high-selectivity hypersensitive hypobromous acid fluorescence probe - Google Patents
A kind of quick high-selectivity hypersensitive hypobromous acid fluorescence probe Download PDFInfo
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- 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"
- G01N2021/6439—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" with indicators, stains, dyes, tags, labels, marks
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Abstract
The present invention relates to a kind of quick high-selectivity hypersensitive hypobromous acid fluorescence probes.Specifically, probe of the invention is a kind of 1,8 naphthalimide compound of 4 amino, can be used as detection of the hypobromous acid fluorescence probe for hypobromous acid.This probe can realize following at least one of technique effect：Hypobromous acid is identified with high selectivity；Quickly hypobromous acid can be realized and be responded；The High Sensitive Analysis to hypobromous acid may be implemented；The analysis to hypobromous acid may be implemented；Property is stablized, and can be used with long-term preservation；And there is stronger anti-interference ability.
Description
Technical field
The present invention relates to 4- amino -1,8- naphthoyl imide compounds as hypobromous acid fluorescence probe, can be rapidly to secondary
Bromic acid carries out the concentration of hypobromous acid in hypersensitive Selective recognition and determination sample.
Background technology
Hypobromous acid is considered as the bromine substance (RBS) in reactive endogenous reaction species.During it is considered thermophilic always
The key components of the host system of defense of property granulocyte.Macrophage and eosinophil can utilize acidophil granules thin
Born of the same parents' peroxidase (EPO), hydrogen peroxide (H2O2) and bromide ion (Br-) reaction release HOBr.HOBr is to immune response to pass
It is important, host tissue damage and arthritis, angiocardiopathy, cancer, asthma, neurodegenerative disease, kidney can be caused
Disease, cystic fibrosis and inflammatory bowel disease.But detection HOBr faces many challenges in vivo, because HOBr is only in solution
Middle generation, the pK at 25 DEG CaIt is 8.8.In addition, hypobromous acid is effective bleaching oxidant, chemical and physical features and hypochlorous acid
It is closely similar, it is difficult to be differentiated with conventional method.Compared with other detection techniques, fluorescence probe has high sensitivity, examines in real time
The features such as survey and non-intrusion measurement, is as the indispensable tool of biomolecule in monitoring cell.Even if in studying physiological and disease
Reason process has developed multiple types active specy.But the small molecule fluorescent of the HOBr in up to the present report detection cell
Probe is still seldom.In addition, because of the continuous function in cell, linear probe should be more suitable for visualization status redox
Journey.
Therefore, the method for development detection hypobromous acid has great importance.In recent years, based on the design of fluorescence probe with this
It is of much attention to detect hypobromous acid.Therefore, highly sensitive and highly selective detection hypobromous acid is very for us
Important.
In consideration of it, development can effectively detect the analysis method that can especially detect hypobromous acid under the conditions of physiological level
It is of crucial importance and significant.Nowadays the analysis method for the detection hypobromous acid reported includes volumetric analysis, optics point
Analysis method, the chromatography of ions (ICP), hypobromous acid select the methods of electrode method and on-line analysis method.In these numerous detection methods
Middle fluorescence probe is researcher's focus of attention since its peculiar advantage forms.However, report at present and fluorescence probe
There are still some problems, including selectivity is not good enough, sensitivity is not high enough, response speed is not fast enough, synthesis is complicated.In short, hair
It is that those skilled in the art are badly in need of solution to open up quick, highly selective, highly sensitive, the simple hypobromous acid fluorescence binary channels probe of synthesis
Certainly.
Invention content
This field urgent need is a kind of to prepare the simple quickly overdelicate hypobromous acid fluorescence probe of high selection, so as to effective
Detect hypobromous acid.For this purpose, the present invention has synthesized a kind of novel hypobromous acid fluorescence probe, synthesis is simple, selectivity is good, sensitive
Degree is high, can quickly identify hypobromous acid.It is amino -1 4- specifically, the present invention provides a kind of hypobromous acid fluorescence probe,
8- naphthoyl imide compounds,
Its structure is as follows：
Preferably, fluorescence probe of the invention is：
It is molten in ethyl alcohol by chloro- 1, the 8- naphthalene anhydrides of 4- the present invention also provides the preparation method of hypobromous acid fluorescence probe
It is reacted with 2- aminoethyl morpholines in liquid and fluorophore compounds is made, and will be corresponding to the corresponding fluorophore compounds of probe of the present invention
It reacts and is made with monoethanolamine in ethylene glycol monomethyl ether solution.
The present invention also provides the detection preparations for detecting hypobromous acid concentration in sample, and it includes the probes of the present invention.
The present invention also provides the methods of hypobromous acid concentration in detection sample comprising by the probe of the present invention and waits for test sample
The step of this contact.
The present invention also provides preparing for detecting the purposes in sample in the preparation of hypobromous acid concentration.
The hypobromous acid fluorescence probe of the present invention can be acted on hypobromous acid, the variation of fluorescence spectrum be generated, to realize
Quantitative detection to hypobromous acid.
Specifically, the present invention hypobromous acid fluorescence probe respectively with potassium ion, calcium ion, magnesium ion, sodium ion, zinc from
Son, nitrate ion, nitrite ion, nitric oxide, hydroxyl radical free radical, tert-butyl peroxide, tertbutanol peroxide, single line
State oxygen, potassium superoxide etc. cannot lead to substantially changeing for fluorescence probe spectrum, to realize the Selective recognition to hypobromous acid,
And then can be optionally used for excluding potassium ion, sodium ion, zinc ion, nitrate ion, in nitrite ion and human body its
The interference that the presence of his Common materials quantitative determines hypobromous acid.
The hypobromous acid fluorescence probe of the present invention is swift in response with hypobromous acid, to be conducive to the instant detection to hypobromous acid.
Selectively, the stability of hypobromous acid fluorescence probe of the invention is good, and then being capable of long-term preservation use.
Further, hypobromous acid fluorescence probe of the invention is fast high-sensitive hypobromous acid fluorescence probe, and synthesizes letter
It is single, be conducive to commercialized popularization and application.
Description of the drawings
Fig. 1 is that the fluorescence spectrum after hypobromous acid (0-10 μM) and linear relationship is added in (5 μM) of probe；
Fig. 2 is that (5 μM) of probe is added hypobromous acid (5 μM) fluorescence spectrum changes with time figure afterwards.
Fig. 3 is influence of the different ions (10 μM) to probe (5 μM) fluorescence intensity, respectively blank, potassium ion, calcium from
Son, magnesium ion, sodium ion, zinc ion, nitrate ion, nitrite ion, nitric oxide, hydroxyl radical free radical, peroxidating uncle
What the block diagrams such as butyl, tertbutanol peroxide, singlet oxygen, potassium superoxide, sodium hypochlorite, hypobromous acid represented is different analytes
In the presence of probe 550nm fluorescence intensity.
Specific implementation mode：
The present invention provides synthetic route, method and its light of above-mentioned quick high-selectivity hypersensitive hypobromous acid fluorescence probe
Spectrality energy.
The hypobromous acid fluorescence probe of the present invention is a kind of 4- amino -1,8- naphthalimide compound, is had following structure
General formula
In above formula：R1、R2、R3、R4、R5For hydrogen atom, linear or branched alkyl group, straight or branched alkoxyl, sulfonic group, ester
Base, carboxyl；R1、R2、R3、R4、R5It can be identical or different.
The synthetic route and method of such hypobromous acid fluorescence probe are as follows：
Specifically, fluorescence probe of the invention can be prepared via a method which, by certain mol proportion (such as 1: 1~1:
5) chloro- 1, the 8- naphthalene anhydrides of 4- are dissolved in ethyl alcohol, and a certain proportion of 2- aminoethyl morpholines (such as 1: 1~1: 5) are added and then are closing
A period of time (such as 6h), reduced pressure backspin solvent evaporated are stirred to react at suitable temperature (such as 85 DEG C).If obtained
The mixed system (such as 75: 1, v/v) of solid dichloromethane and methanol can be carried out pillar layer separation and obtained by purer product
To sterling, i.e., corresponding fluorophore compounds.
The fluorophore compounds of certain mol proportion (such as 1: 3~1: 5) are dissolved in ethylene glycol monomethyl ether, are added a certain proportion of
Monoethanolamine (such as 1: 3~1: 5) then be stirred to react at suitable temperature (such as 140 DEG C) a period of time (such as 12h),
Reduced pressure backspin solvent evaporated.It, can be by the mixture of solid dichloromethane and methanol if obtaining purer product
System (such as 50: 1, v/v) carries out pillar layer separation and obtains sterling.
Therefore, the use the present invention also provides chloro- 1, the 8- naphthalene anhydrides of 4- in preparing the fluorescence probe for detecting hypobromous acid
On the way.
The quick high-selectivity hypersensitive identification hypobromous acid fluorescence probe of the present invention is noteworthy characterized by being capable of quick Gao Xuan
Can quantitative analysis accurately be carried out to hypobromous acid in the presence of selecting the quick identification hypobromous acid of personality and other ions in human body.
It below will be by the way that the present invention be described in more detail by following embodiment.Following embodiment is merely illustrative,
It should be understood that the present invention is not limited by following embodiments.
Embodiment 1
Chloro- 1, the 8- naphthalene anhydrides of 232mg (1mmol) 4- are dissolved in 15mL ethyl alcohol by (scheme 1), add 130mg (1mmol) 2-
Then aminoethyl morpholine is stirred to react 6h at 85 DEG C, rotates dry ethyl alcohol after reaction, that is, obtain crude product.It is final to use two
The mixed system (75: 1, v/v) of chloromethanes and methanol carries out pillar layer separation, obtains white pure product 235.3mg, yield is
65%.
344mg (1mmol) fluorophore compounds are dissolved in 15mL ethylene glycol monomethyl ethers, 183.24mg (3mmol) is added
Then monoethanolamine is stirred to react 12h at 140 DEG C, rotate dry glycol methyl ether after reaction, that is, obtain crude product.Finally
Pillar layer separation is carried out using the mixed system (50: 1, v/v) of dichloromethane and methanol, obtains yellow pure product 305.8mg,
Yield is 58%.
Chloro- 1, the 8- naphthalene anhydrides of 232mg (1mmol) 4- are dissolved in 15mL ethyl alcohol by (scheme 2), add 195mg (1.5mmol)
Then 2- aminoethyl morpholines are stirred to react 6h at 85 DEG C, rotate dry ethyl alcohol after reaction, that is, obtain crude product.It is final to use
The mixed system (75: 1, v/v) of dichloromethane and methanol carries out pillar layer separation, obtains white pure product 320.25mg, produces
Rate is 75%.
344mg (1mmol) fluorophore compounds are dissolved in 15mL ethylene glycol monomethyl ethers, 213.78mg is added
Then (3.5mmol) monoethanolamine is stirred to react 12h at 140 DEG C, rotate dry glycol methyl ether after reaction, that is, obtains thick
Product.It is final to carry out pillar layer separation using the mixed system (50: 1, v/v) of dichloromethane and methanol, obtain the pure production of yellow
Product 390.45mg, yield 70%.
Chloro- 1, the 8- naphthalene anhydrides of 232mg (1mmol) 4- are dissolved in 15mL ethyl alcohol by (scheme 3), add 260mg (2mmol) 2-
Then aminoethyl morpholine is stirred to react 6h at 85 DEG C, rotates dry ethyl alcohol after reaction, that is, obtain crude product.It is final to use two
The mixed system (75: 1, v/v) of chloromethanes and methanol carries out pillar layer separation, obtains white pure product 408.36mg, yield
It is 83%.
344mg (1mmol) fluorophore compounds are dissolved in 15mL ethylene glycol monomethyl ethers, 244.32mg (4mmol) is added
Then monoethanolamine is stirred to react 12h at 140 DEG C, rotate dry glycol methyl ether after reaction, that is, obtain crude product.Finally
Pillar layer separation is carried out using the mixed system (50: 1, v/v) of dichloromethane and methanol, obtains yellow pure product
470.66mg yield 80%.
Chloro- 1, the 8- naphthalene anhydrides of 232mg (1mmol) 4- are dissolved in 15mL ethyl alcohol by (scheme 4), add 390mg (3mmol) 2-
Then aminoethyl morpholine is stirred to react 6h at 85 DEG C, rotates dry ethyl alcohol after reaction, that is, obtain crude product.It is final to use two
The mixed system (75: 1, v/v) of chloromethanes and methanol carries out pillar layer separation, obtains white pure product 559.8mg, yield is
90%.
344mg (1mmol) fluorophore compounds are dissolved in 15mL ethylene glycol monomethyl ethers, it is single to add 305.4mg (5mmol)
Then ethanol amine is stirred to react 12h at 140 DEG C, rotate dry glycol methyl ether after reaction, that is, obtain crude product.Finally make
Pillar layer separation is carried out with the mixed system (50: 1, v/v) of dichloromethane and methanol, obtains yellow pure product 565mg, yield
It is 87%.
1H-NMR (400MHz, CDCl3) δ (* 10-6)：1.21 (t, J=6Hz, 6H), 3.38-3.43 (m, 4H), 4.78
(d, J=4Hz, 2H), 5.36 (d, J=12Hz, 1H), 5.46 (d, J=20Hz, 1H), 5.98-6.08 (m, 1H), 6.43 (d, J
=8Hz, 1H), 6.65 (d, J=12Hz, 2H), 6.79 (d, J=8Hz, 1H), 7.16 (d, J=8Hz, 1H), 7.39 (d, J=
8Hz, 1H), 7.47 (d, J=8Hz, 1H), 7.60-7.67 (m, 3H), 8.05 (d, J=8Hz, 1H), 8.64 (d, J=12Hz,
1H).ESI-MS calcd for C32H28NO6[M+H]+522.1911 found 522.261.
Embodiment 2
Fig. 1 is (5 μM) fluorescence spectrum variation diagrams being added after hypobromous acid (0-10 μM) of hypobromous acid fluorescence probe.It can from figure
Clearly to find out, with the increase that hypobromous acid concentration is added, the fluorescence intensity at solution 550nm continuously decreases.Also, by inserting
As can be seen that the knots modification of fluorescence intensity and the hypobromous acid concentration of addition present good linear relationship at 550nm, this is demonstrate,proved figure
It is bright to carry out quantitative analysis to hypobromous acid by means of the fluorescence probe.
Embodiment 3
Fig. 2 is that (5 μM) of hypobromous acid fluorescence probe is added hypobromous acid (5 μM) fluorescence spectrum changes with time figure afterwards.By scheming
It will be clear that after hypobromous acid is added, fluorescence intensity moment quenching after testing reaches platform, this illustrate the probe with time
Bromic acid is swift in response, and can provide quick analysis method for the measurement of hypobromous acid.
Embodiment 4
As shown in Figure 3,1-18 is respectively blank probe, nitrate ion, nitrite ion, nitric oxide, mistake in figure
Nitrite oxidation, hydroxyl radical free radical, tert-butyl peroxide, hydrogen peroxide, tertbutanol peroxide, singlet oxygen, potassium superoxide,
Sodium hypochlorite, potassium ion, sodium ion, calcium ion, magnesium ion, zinc ion and hypobromous acid.Relative to nitrate ion, nitrite anions
Ion, nitric oxide, peroxynitrite, hydroxyl radical free radical, tert-butyl peroxide, hydrogen peroxide, tertbutanol peroxide, list
Line state oxygen, potassium superoxide, sodium hypochlorite etc. cannot cause the significant changes of probe solution fluorescence spectrum, and fluorescence intensity is higher and base
This is consistent.After hypobromous acid is added, fluorescence intensity quenches rapidly, has huge difference with above-mentioned related activity oxygen.In addition, fixed
It is not also interfered by metal ions such as potassium ion, sodium ion, calcium ion, magnesium ion, zinc ions when amount analysis hypobromous acid.To sum up table
Bright, which has higher selectivity to hypobromous acid.
Although with above embodiments describe the present invention, it should be appreciated that before the spirit without departing substantially from the present invention
It puts, the present invention further can be modified and be changed, and these modifications and variation all belong to the scope of protection of the present invention it
It is interior.
Claims (5)
1. compound has following structure
Wherein：R1、R2、R3、R4、R5For independently selected from by hydrogen atom, linear or branched alkyl group, straight or branched alkoxyl, sulphur
The group of acidic group, ester group and hydroxyl composition；And R therein1、R2、R3、R4、R5It can be identical or different.
2. compound according to claim 1, for the compound such as lower structure：
3. the preparation for detecting hypobromous acid content in sample, it includes the compounds having following structure：
Wherein：R1、R2、R3、R4、R5For independently selected from by hydrogen atom, linear or branched alkyl group, straight or branched alkoxyl, sulphur
The group of acidic group, ester group and hydroxyl composition：And R therein1、R2、R3、R4、R5It can be identical or different.
4. preparation according to claim 3, wherein the compound is：
5. preparation according to claim 3, wherein the sample is water or blood.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108774171A (en) * | 2018-07-24 | 2018-11-09 | 姜懿珊 | A kind of preparation and application of real-time Sensitive Detection hypochlorous acid fluorescence probe |
| CN110878085A (en) * | 2019-12-13 | 2020-03-13 | 山东省科学院生物研究所 | Rapid high-selectivity hypobromous acid fluorescent probe, preparation method and application |
| CN111333643A (en) * | 2018-12-18 | 2020-06-26 | 中国科学院大连化学物理研究所 | High-brightness, high-light stability and environmental insensitivity nuclear fluorescent probe |
| CN115141145A (en) * | 2022-07-09 | 2022-10-04 | 济南大学 | Fluorescence probe for detecting lysosome hypobromous acid, preparation method and application |
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| CN104910070A (en) * | 2015-04-20 | 2015-09-16 | 济南大学 | Rapid high-selectivity hypochloric acid fluorescence probe and application thereof |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104910070A (en) * | 2015-04-20 | 2015-09-16 | 济南大学 | Rapid high-selectivity hypochloric acid fluorescence probe and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| CHANG LIU ET AL.,: "A highly selective and sensitive fluorescent probe for hypochlorous acid and its lysosome-targetable biological applications", 《TALANTA》 * |
| XIAOJUN LIU ET AL.,: "High-Quantum-Yield Mitochondria-Targeting Near-Infrared Fluorescent Proble for Imaging Native Hypobromous acid in living cells and in vivo", 《ANALYTICAL. CHEMISTRY》 * |
| ZHANGRONG LOU ET AL.,: "Redox-responsive fluorescent probes with different design strategies", 《ACCOUNTS OF CHEMICAL RESEARCH》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108774171A (en) * | 2018-07-24 | 2018-11-09 | 姜懿珊 | A kind of preparation and application of real-time Sensitive Detection hypochlorous acid fluorescence probe |
| CN111333643A (en) * | 2018-12-18 | 2020-06-26 | 中国科学院大连化学物理研究所 | High-brightness, high-light stability and environmental insensitivity nuclear fluorescent probe |
| CN111333643B (en) * | 2018-12-18 | 2021-11-09 | 中国科学院大连化学物理研究所 | High-brightness, high-light stability and environmental insensitivity nuclear fluorescent probe |
| CN110878085A (en) * | 2019-12-13 | 2020-03-13 | 山东省科学院生物研究所 | Rapid high-selectivity hypobromous acid fluorescent probe, preparation method and application |
| CN115141145A (en) * | 2022-07-09 | 2022-10-04 | 济南大学 | Fluorescence probe for detecting lysosome hypobromous acid, preparation method and application |
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