CN108587606A - A kind of quick high-selectivity analyzes the purposes of hypochlorous fluorescence probe - Google Patents
A kind of quick high-selectivity analyzes the purposes of hypochlorous fluorescence probe Download PDFInfo
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- CN108587606A CN108587606A CN201810428269.8A CN201810428269A CN108587606A CN 108587606 A CN108587606 A CN 108587606A CN 201810428269 A CN201810428269 A CN 201810428269A CN 108587606 A CN108587606 A CN 108587606A
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- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- G01N21/6402—Atomic fluorescence; Laser induced fluorescence
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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Abstract
The present invention relates to the purposes that a kind of quick high-selectivity analyzes hypochlorous fluorescence probe.Specifically, probe of the invention is a kind of p-aminophenyl phenols compound, can be used as hypochlorous acid fluorescence probe for hypochlorous detection.This kind of probe can realize following at least one of technique effect：Hypochlorous acid is identified with high selectivity；Quickly hypochlorous acid can be realized and be responded；It may be implemented to hypochlorous High Sensitive Analysis；Property is stablized, and can be used with long-term preservation.
Description
Technical field
Purposes the present invention relates to p-aminophenyl phenols compound as hypochlorous acid fluorescence probe, can be rapidly to secondary chlorine
The highly selective sensitive identification of acid or its can hypochlorous concentration in determination sample.
Background technology
Hypochlorous acid is a kind of powerful oxidant as the reactive oxygen species in life entity, it is by hydrogen peroxide and chlorine
What ion generated under peroxide enzyme effect.In immune system, hypochlorous acid to cell differentiation, migration, conduction all play to
Important role is closed, while hypochlorous acid can also prevent bacterium, fungi, poisoning intrusion human body.Although hypochlorous acid has health
Protective effect, but may to destroy host with the reactions such as DNA, RNA, aliphatic acid, cholesterol, protein thin for excessive hypochlorous acid
Born of the same parents lead to many diseases.For example, artery sclerosis, injury of lungs, hepatic ischemia, neuronal degeneration, even cancer.In daily life,
Hypochlorous to use widely, hypochlorous acid is usually used in bleaching agent and sanitizer, such as drinking water and swimming-pool water
Deng.Remaining hypochlorous acid can cause water pollution in water, and to health, there are potential hazards.Due to hypochlorous high reaction
Property and non-specificity lead to the secondary chlorine in life entity once the higher water body of hypochlorous acid content is drunk or contacted to life entity
Acid content, which cannot maintain, will just cause a series of disease within the scope of normal physiological level.
In short, a kind of effectively detection of development especially can detect hypochlorous analysis method under the conditions of physiological level is
It is very necessary.Nowadays the hypochlorous analysis method of detection reported include iodometric titration method, spectrophotometric Colo,
High performance liquid chromatography, chemiluminometry, fluorescence probe analytic approach etc..The fluorescence probe in these numerous detection methods
Become researcher's concern since it has the unique advantages such as highly sensitive, highly selective, easy to operate and real-time analysis
Focus.However, there are still some defects for the hypochlorous acid fluorescence probe reported at present, including selectivity is not good enough, sensitivity is inadequate
Height, poorly water-soluble, synthesis are complicated.In consideration of it, development is quick, highly selective, highly sensitive, the simple hypochlorous acid fluorescence of synthesis is visited
Needle is that those skilled in the art are badly in need of the Important Problems solved.
Invention content
This field is badly in need of preparing a kind of simple quick high-selectivity hypochlorous acid fluorescence probe, secondary so as to effectively detect
Chloric acid.For this purpose, the present invention has synthesized a kind of novel hypochlorous acid fluorescence probe, synthesis is simple, selectivity is good, high sensitivity,
Hypochlorous acid can be identified at once.It is p-aminophenyl phenols specifically, the present invention provides a kind of hypochlorous acid fluorescence probe
Object is closed, structure is as follows：
Preferably, fluorescence probe of the invention is：
It is the probe by the way that the present invention will be corresponded to the present invention also provides the preparation method of hypochlorous acid fluorescence probe
Corresponding p-aminophenyl phenols compound flows back 4 hours in acetonitrile solution with 1,8 naphthalimide of nitrogen butyl -4- chlorine and synthesizes system
.
The present invention also provides the detection preparations for detecting hypochlorous acid concentration in sample, and it includes the probes of the present invention.
Preferably, detection preparation of the invention also includes the buffer for measuring the hypochlorous acid concentration in sample.
The present invention also provides the methods of hypochlorous 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 the probes of the present invention to prepare for detecting the use in sample in the preparation of hypochlorous acid concentration
On the way.
The hypochlorous acid fluorescence probe of the present invention can be acted on hypochlorous acid, the variation of fluorescence spectrum be generated, to realize
To hypochlorous quantitative detection.
Specifically, the present invention hypochlorous acid fluorescence probe respectively with potassium ion, calcium ion, sodium ion, magnesium ion, zinc from
Son, copper ion, ferrous ion, ferric iron, nitrate ion, nitrite ion, chlorion, sulfate ion, peroxidating
Hydrogen, other substances such as potassium superoxide, which are acted on, cannot lead to substantially changeing for fluorescence spectrum, to realize to hypochlorous
Selective recognition, and then can be optionally used for excluding these potassium ions, calcium ion, sodium ion, magnesium ion, zinc ion, copper ion,
Ferrous ion, ferric iron, nitrate ion, nitrite ion, chlorion, sulfate ion, hydrogen peroxide, potassium superoxide
Interference of the presence of other ions to hypochlorous quantitative determination in equal substances and human body.
The colorimetric fluorescence probe of the present invention reacts very sensitive with hypochlorous acid, to be conducive to hypochlorous rapid inspection
It surveys.
Selectively, the stability of hypochlorous acid fluorescence probe of the invention is good, and then being capable of long-term preservation use.
Further, hypochlorous acid fluorescence probe of the invention is the glimmering color probe of quick high-selectivity hypochlorous acid, and synthesizes letter
It is single, be conducive to commercialized popularization and application.
Description of the drawings
Fig. 1 a are (5 μM) fluorescence spectrums being added before and after hypochlorous acid (0-5 μM) of probe
Fig. 1 b various concentrations hypochlorous acid (0-1 μM) meets good linear relationship to probe (5 μM).
Fig. 2 is (5 μM) response times being added after hypochlorous acid (5 μM) of probe；
Fig. 3 is the influence of substance common in human body to the fluorescence intensity of probe (5 μM).Wherein number 1-28 is respectively sky
In vain, potassium ion, calcium ion, sodium ion, magnesium ion, zinc ion, copper ion, ferrous ion, ferric ion, nitrate anion from
Son, nitrite ion, chlorion, sulfite ion, sulfurous acid hydrogen radical ion, sulfate ion, vulcanized sodium, cysteine
(500 μM), homocysteine (500 μM), glutathione (5mM), hydrogen peroxide, tertbutanol peroxide, potassium superoxide, hydroxyl
Free radical, tertbutanol peroxide free radical, peroxy radical, nitric oxide, peroxynitrite (5 μM), sodium hypochlorite (5 μ
M) (in addition to special indicate, other analyte concentrations are 100 μM).What block diagram represented is that probe exists in the presence of different analytes
Fluorescence intensity level at 557nm.
Specific implementation mode：
The present invention provides synthetic route, method and its spectrum of above-mentioned quick high-selectivity hypochlorous acid fluorescence probe
Energy.
The hypochlorous acid fluorescence probe of the present invention is a kind of p-aminophenyl phenols compound, has following structure general formula
In above formula：R1, R2, R3, R4, R5, R6, R7, R8, R9, it is hydrogen atom, linear or branched alkyl group, linear chain or branched chain alcoxyl
Base, sulfonic group, ester group, carboxyl；R1, R2, R3, R4, R5, R6, R7, R8And R9, can be identical or different.
The synthetic route and method of such hypochlorous acid fluorescent needle are as follows：
Specifically, fluorescence probe of the invention can be prepared via a method which, by certain mol proportion (such as 1:1-1:6)
The chloro- 1,8- naphthalimides of nitrogen butyl -4- and p-aminophenyl phenols compound (such as 1:1-1:6) it is dissolved in acetonitrile, the two
Molar ratio is (1:3) and then it is added cesium carbonate (such as 1:1~1:6) it, is heated to reflux a period of time (such as 4h), then utilizes height
Press pump is filtered, and filtrate is obtained, and filtrate becomes our crude product.If obtaining purer product, filtrate can be used
Dichloromethane and methanol mixed system (such as v/v, 100:1) it carries out pillar layer separation and obtains sterling.
Therefore, the present invention also provides para-aminophenol to prepare for detecting the purposes in hypochlorous fluorescence probe.
The present invention also provides p-aminophenyl phenols compounds to prepare for detecting the use in hypochlorous fluorescence probe
On the way.
The highly sensitive identification hypochlorous acid fluorescence probe of quick high-selectivity of the present invention is noteworthy characterized by being capable of quick Gao Xuan
Can quantitative analysis accurately be carried out to hypochlorous acid in the presence of selecting the quick identification hypochlorous 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- naphthalimides of (scheme 1) 290mg (1mmol) nitrogen butyl -4- are dissolved in 15mL acetonitriles, add 110mg
Then (1mmol) para-aminophenol is added cesium carbonate 326mg (1mmol) reflux 2h, is then filtered, obtained using high-pressure pump
To filtrate, filtrate becomes our crude product.It, can be by filtrate dichloromethane and methanol if obtaining purer product
Mixed system (such as v/v, 100:1) the isolated sterling of chromatographic column is carried out, obtains yellow pure product 200mg, yield is
50%.
Chloro- 1, the 8- naphthalimides of 290mg (1mmol) nitrogen butyl -4- are dissolved in 15mL acetonitriles by (scheme 2), are added
Then 220mg (2mmol) para-aminophenol is added cesium carbonate 652mg (2mmol) reflux 4h, is then taken out using high-pressure pump
Filter, obtains filtrate, and filtrate becomes our crude product.If obtaining purer product, can by filtrate dichloromethane and
Methanol mixed system (such as v/v, 100:1) it carries out chromatographic column to purify to obtain sterling, obtains yellow pure product 260mg, produce
Rate is 65%.
Chloro- 1, the 8- naphthalimides of 290mg (1mmol) nitrogen butyl -4- are dissolved in 15mL acetonitriles by (scheme 3), are added
Then 330mg (3mmol) para-aminophenol is added cesium carbonate 978mg (3mmol) reflux 4h, is then taken out using high-pressure pump
Filter, obtains filtrate, and filtrate becomes our crude product.If obtaining purer product, can by filtrate dichloromethane and
Methanol mixed system (such as v/v, 100:1) the isolated sterling of chromatographic column is carried out, yellow pure product 300mg is obtained, is produced
Rate is 75%.
Chloro- 1, the 8- naphthalimides of 290mg (1mmol) nitrogen butyl -4- are dissolved in 15mL acetonitriles by (scheme 4), are added
Then 330mg (3mmol) para-aminophenol is added cesium carbonate 1956mg (6mmol) reflux 2h, is then taken out using high-pressure pump
Filter, obtains filtrate, and filtrate becomes our crude product.If obtaining purer product, can by filtrate dichloromethane and
Methanol mixed system (such as v/v, 100:1) the isolated sterling of chromatographic column is carried out.Yellow pure product 330mg is obtained, is produced
Rate is 82%.
Chloro- 1, the 8- naphthalimides of 290mg (1mmol) nitrogen butyl -4- are dissolved in 15mL acetonitriles by (scheme 5), are added
Then 330mg (3mmol) para-aminophenol is added cesium carbonate 1956mg (6mmol) reflux 4h, is then taken out using high-pressure pump
Filter, obtains filtrate, and filtrate becomes our crude product.If obtaining purer product, can by filtrate dichloromethane and
Methanol mixed system (such as v/v, 100:1) the isolated sterling of chromatographic column is carried out.Yellow pure product 360mg is obtained, is produced
Rate is 90%.
Embodiment 2
Fig. 1 a are (5 μM) fluorescence spectrum variation diagrams that hypochlorous acid (0-5 μM) is added of hypochlorous acid fluorescence probe.Fig. 1 b are different
Linear relationship chart of the concentration hypochlorous acid (0-1 μM) to probe (5 μM).
The parallel sample that multiple concentration and probe concentrations are 5 μM is configured in 10mL colorimetric cylinders, then by the hypochlorous acid of various concentration
It is added in test system, 2 minutes is stood after rocking uniformly.Said determination is carried out in pure water (5mM PBS, pH 7.4)
, used probe is probe prepared in embodiment 1, and all spectrum tests all measure at 25 DEG C.
Its fluorescence intensity change is tested with Fluorescence Spectrometer, can clearly be found out from Fig. 1 a, hypochlorous acid is dense with being added
The increase of degree, the fluorescence intensity at 557nm gradually increase.Also, it can be seen from illustration 1b at 557nm, hypochlorous acid fluorescence
Fluorescence intensity presents good linear relationship after hypochlorous acid (0-1 μM) is added in (5 μM) of probe, this is proved by means of the fluorescence
Probe can carry out quantitative analysis to hypochlorous acid.
Embodiment 3
Fig. 2 is (5 μM) response times being added after hypochlorous acid (5 μm) of probe.50 μ L are taken out from probe mother liquor to be placed in
Then 5 μM of hypochlorous acid is added in test system by the test system of 10mL, surveyed immediately with Fluorescence Spectrometer after rocking uniformly
Try its fluorescence intensity change.Said determination is carried out in pure water (5mM PBS, pH 7.4), and used probe is to implement
Prepared probe in example 1, and all spectrum tests all measure at 25 DEG C.
By scheming it will be clear that after hypochlorous acid is added, 2min or so fluorescence intensities reach maximum value simultaneously after testing
It remains unchanged, this illustrates that the probe is swift in response with hypochlorous acid, can provide quick analysis method for hypochlorous measurement.
Embodiment 4
Fluorescence intensity of Fig. 3 different ions analyte to probe (5 μM).Analyte be respectively blank, potassium ion, calcium from
Son, sodium ion, magnesium ion, zinc ion, copper ion, ferrous ion, ferric ion, nitrate ion, nitrite ion,
Chlorion, sulfite ion, sulfurous acid hydrogen radical ion, sulfate ion, vulcanized sodium, cysteine (500 μM), half Guang of homotype
Propylhomoserin (500 μM), glutathione (5mM), hydrogen peroxide, tertbutanol peroxide, potassium superoxide, hydroxyl radical free radical, peroxidating uncle
Butanol free radical, peroxy radical, nitric oxide, peroxynitrite (5 μM), sodium hypochlorite (5 μM) (are indicated except special
Outside, other analyte concentrations are 100 μM).Fluorescence of the probe at 557nm in the presence of being different analytes that block diagram represents
Intensity value.Said determination is carried out in pure water (5mM PBS, pH 7.4), and used probe is prepared in embodiment 1
Probe, and all spectrum tests all measure at 25 DEG C.Specifically, the Duplicate Samples that multiple concentration and probe concentrations are 5 μM are configured
Then product are added a certain amount of analyte, shake up in 10mL colorimetric cylinders, measured after 2 minutes.
From figure 3, it can be seen that will not to significantly interfere with probe strong to hypochlorous fluorescence for existing common ion in organism
Degree, therefore probe has good selectivity.
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 (8)
1. following compound is being prepared for detecting the purposes in sample in hypochlorous kit, wherein the compound has
With lower structure
Wherein：R1, R2, R3, R4, R5, R6, R7, R8, R9For independently selected from by hydrogen atom, linear or branched alkyl group, straight chain or branch
The group of chain alkoxy, sulfonic group, ester group and hydroxyl composition；And R therein1, R2, R3, R4, R5, R6, R7, R8And R9Can it is identical or
It is different.
2. purposes according to claim 1, wherein the compound is the compound such as lower structure：
3. purposes according to claim 1, wherein the sample is water or blood.
4. purposes according to claim 1, wherein the detection is qualitative detection or quantitative detection.
5. purposes according to claim 1, wherein the detection carries out under buffer system.
6. purposes according to claim 5, wherein the pH of the buffer system is 7.4.
7. purposes according to claim 1, wherein institute's kit also contains buffer.
8. purposes according to claim 1, wherein institute's kit also contains operation instructions.
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| CN201810428269.8A CN108587606A (en) | 2018-05-07 | 2018-05-07 | A kind of quick high-selectivity analyzes the purposes of hypochlorous fluorescence probe |
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| CN201810428269.8A CN108587606A (en) | 2018-05-07 | 2018-05-07 | A kind of quick high-selectivity analyzes the purposes of hypochlorous fluorescence probe |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354618A (en) * | 2021-06-02 | 2021-09-07 | 济南大学 | Hypochlorous acid fluorescent probe capable of targeting cell lysosome, preparation method and application |
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2018
- 2018-05-07 CN CN201810428269.8A patent/CN108587606A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354618A (en) * | 2021-06-02 | 2021-09-07 | 济南大学 | Hypochlorous acid fluorescent probe capable of targeting cell lysosome, preparation method and application |
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Application publication date: 20180928 |