CN109897080A - High selection hypersensitive liver cancer-specific peroxynitrite probe and its application - Google Patents
High selection hypersensitive liver cancer-specific peroxynitrite probe and its application Download PDFInfo
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- CN109897080A CN109897080A CN201910193876.5A CN201910193876A CN109897080A CN 109897080 A CN109897080 A CN 109897080A CN 201910193876 A CN201910193876 A CN 201910193876A CN 109897080 A CN109897080 A CN 109897080A
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- peroxynitrite
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Abstract
The present invention relates to a kind of high selection hypersensitive liver cancer cell specificity peroxynitrite fluorescence probes.Specifically, probe of the invention is a kind of naphthoyl imide compounds, can be used as detection of the peroxynitrite fluorescence probe for peroxynitrite in liver cancer cells.This kind of probe can realize following at least one of technical effect: identify peroxynitrite with high selectivity；Quickly peroxynitrite can be realized and be responded；The hypersensitive analysis to peroxynitrite may be implemented；The quantitative analysis to peroxynitrite may be implemented；The peroxynitrite in specific detection liver cancer cells may be implemented；Property is stablized, and can be used with long-term preservation.
Description
Technical field
The present invention relates to naphthoyl imide compounds as peroxynitrite fluorescence probe, can be to peroxidating nitrous
The analysis of hydrochlorate high selection hypersensitive or its concentration that can measure peroxynitrite in sample, and selectively targeted liver
Cancer cell.
Background technique
Active oxygen and reactive nitrogen species participate in various physiological processes in life system, including signal transduction, inflammation and antioxygen
Change damage.Peroxynitrite as one of active oxygen and active nitrogen oxidizing species, it be by nitric oxide and
Superoxide radical reaction generates, and has high a reactivity and unstability, signal transduction in life system and antibacterial
It plays an important role in effect.However since it damages the nitrification of protein, nucleic acid, lipid etc., peroxynitrite
Be considered as it is harmful, the abnormal accumulation of peroxynitrite will lead to many diseases in cell, including ischemia-reperfusion damage
Wound, diseases associated with inflammation, neurodegenerative disease, even cancer.The concentration of peroxynitrite in cancer cell is general
It is higher than the concentration of normal cell, but different cancer cells is distinguished without reliable method, and detect physiology due to lacking
The robust techniques of horizontal peroxynitrite, mechanism of action of the peroxynitrite in cancer cell are complete not yet
Illustrate.Therefore, seek a kind of specific peroxynitrite in Sensitive Detection life entity, and can be selectively targeted
The technology of liver cancer cells is vital.
In recent years, the method for the detection peroxynitrite in registration road has spectrophotometric Colo, high-efficient liquid phase color
Spectrometry, chemiluminometry, fluorescence probe analytic approach etc., wherein fluorescence probe because its high selection, hypersensitive, synthesis it is simple etc.
Unique advantage and become researcher's focus of attention.There are still certain to lack for fluorescence probe analysis method reported at present
It falls into, such as sensitivity is low, poor selectivity, poorly water-soluble, synthesis complexity etc..Other active oxygens and active nitrogen and peroxide in life entity
It is similar to change nitrite property, it can constitute potential interference, and the mistake in physiological environment to the detection of peroxynitrite
Nitrite oxidation content is lower.General detection method is unable to the peroxynitrite in specific detection liver cell, because
This, developing highly selective highly sensitive fluorescence probe becomes project urgently to be solved.In short, development it is highly selective, highly sensitive,
The peroxynitrite fluorescence probe of simple, good water solubility, the selectively targeted liver cell of synthesis is those skilled in the art
Member's urgent problem
Summary of the invention
This field urgent need prepares a kind of simple high selection hypersensitive specificity liver cancer cells peroxynitrite fluorescence
Probe, so as to effectively detect the peroxynitrite in liver cancer cells.For this purpose, the present invention has synthesized a kind of novel mistake
Nitrite oxidation fluorescence probe, synthesis is simple, selectivity is good, high sensitivity, can be in specific recognition liver cancer cells
Peroxynitrite.Specifically, being naphthalimide the present invention provides a kind of peroxynitrite fluorescence probe
Compound, structure are as follows:
Preferably, fluorescence probe of the invention is:
It is by the way that the present invention will be corresponded to the present invention also provides the preparation method of peroxynitrite fluorescence probe
Probe corresponding naphthoyl imide compounds and gala saccharide compound in the mixed solution of distilled water and methylene chloride
It flows back 6 hours and synthesizes and be made.
The present invention also provides the detection preparations for detecting peroxynitrite concentration in sample, and it includes the present invention
Probe.Preferably, detection preparation of the invention also includes the operation instructions of product.It is further preferred that detection system of the invention
Agent also includes the buffer for measuring the peroxynitrite concentration in sample.
The present invention also provides the methods of peroxynitrite concentration in detection sample comprising by probe of the invention
The step of being contacted with sample to be tested.
The present invention also provides probes of the invention to prepare the system for detecting peroxynitrite concentration in sample
Purposes in agent.
Peroxynitrite fluorescence probe of the invention can be acted on peroxynitrite, generate fluorescence spectrum
Variation, to realize to the quantitative detection of peroxynitrite.
Specifically, peroxynitrite fluorescence probe of the invention respectively with potassium ion, potassium ion, sodium ion, calcium
Ion, magnesium ion, copper ion, nitrate anion, nitrite anions, hydrogen peroxide, potassium superoxide etc. are to realize to peroxinitrites
The Selective recognition of salt.
Peroxynitrite fluorescence probe of the invention reacts very sensitive with peroxynitrite, to be conducive to
Detection to peroxynitrite.
Selectively, the stability of peroxynitrite fluorescence probe of the invention is good, so can long-term preservation make
With.
Further, peroxynitrite fluorescence probe of the invention is highly selective hypersensitive peroxynitrite
Fluorescence probe, and synthesize simply, be conducive to commercialized popularization and application.
Detailed description of the invention
Fig. 1 a is (5 μM) of the probe fluorescence spectrums being added before and after peroxynitrite (0-50 μM)；
Fig. 1 b is the working curve of probe (5 μM) quantitative analysis various concentration peroxynitrite (0-15 μM).
Fig. 2 is that spectrum changes with time situation (5 μM) addition peroxynitrites (10 μM) of probe afterwards.
Fig. 3 is influence of the substance common in human body to probe (5 μM) fluorescence intensity.Wherein number 1-25 is respectively sky
White, potassium ion, sodium ion, calcium ion, magnesium ion, copper ion, fluorine ion, chloride ion, bromide ion, sulfate radical, carbonate, nitric acid
Root, nitrite anions, nitric oxide, tertbutanol peroxide, hydrogen peroxide, tertbutanol peroxide free radical, hydroxyl radical free radical, super oxygen
Change potassium, singlet oxygen, cysteine (500 μM), homocysteine (500 μM), glutathione (5mM), hypochlorous acid, peroxidating
Nitrite (50 μM) (in addition to special indicate, other analyte concentrations are 100 μM).What histogram represented is different analytes
In the presence of probe fluorescence intensity at 550nm ratio.
Fig. 4 is probe (20 μM) to liver cancer cells Targeting Performance proof diagram, wherein HepG2, MGC803, A549, SHSY5Y
Respectively represent liver cancer cells, stomach cancer cell, lung carcinoma cell, neuroblastoma cell.It is thin that Cal-NHP, NHP respectively represent liver cancer
Born of the same parents' specificity peroxynitrite probe, without liver cancer cell specificity peroxynitrite probe.
Specific embodiment:
The present invention provides above-mentioned highly selective highly sensitive liver cancer cell specificity peroxynitrite fluorescence probes
Synthetic route, method and its spectrum property.
Liver cancer cell specificity peroxynitrite fluorescence probe of the invention is a kind of naphthoyl imide compounds,
Have following structure general formula
In above formula: R1, R2, R3, R4, R5, R6, R7, R8, R9For 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 R9It can be identical or different.
The synthetic route and method of such liver cancer cell specificity peroxynitrite fluorescence probe are as follows:
Specifically, liver cancer cell specificity fluorescence probe of the invention can be prepared via a method which, by certain mole
Naphthoyl imide compounds and gala saccharide compound than (such as 1:1-1:20) are dissolved in distilled water and methylene chloride, the two
Molar ratio be (1:1), be then refluxed for a period of time (such as 12h), extraction, reduced pressure backspin solvent evaporated.Then it will produce
Object and triethylamine (5ml) are dissolved in the mixed system of 9ml first alcohol and water (such as 8:1), stirring at normal temperature for a period of time, reduced pressure
Under be spin-dried for solvent, can be by the mixed system of crude product methylene chloride and methanol (such as v/ if to obtain purer product
V, 10:1) carry out pillar layer separation obtain sterling.
Therefore, the present invention also provides galactolipins is used for liver cancer targeting cell detection peroxynitrite fluorescence in preparation
Purposes in probe.
The present invention also provides naphthoyl imide compounds to prepare the fluorescence probe for detecting peroxynitrite
In purposes.
Peroxynitrite fluorescence probe of the invention is noteworthy characterized by being capable of high selection hypersensitive specific recognition
Peroxynitrite and can be accurately to peroxinitrites in the presence of other intracorporal ions of people in liver cancer cells
Salt carries out quantitative analysis.
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
500mg (1.46mmol) naphthoyl imide compounds are dissolved in 10mL water and methylene chloride (1:1) by (scheme 1),
450mg (1.21mmol) gala saccharide compound reflux 12h is added, reduced pressure backspin solvent evaporated is extracted.By product and
Triethylamine (5ml) is dissolved in the mixed system of 9ml first alcohol and water (8:1), stirring at normal temperature 12h, is spin-dried for solvent under reduced pressure, such as
Fruit will obtain purer product, the mixed system (such as v/v, 10:1) of crude product methylene chloride and methanol can be carried out column
Chromatographic isolation obtains sterling, obtains yellow pure product 430mg, yield 54%.
500mg (1.46mmol) naphthoyl imide compounds are dissolved in 10mL water and methylene chloride (1:1) by (scheme 2),
708mg (1.9mmol) gala saccharide compound reflux 12h is added, reduced pressure backspin solvent evaporated is extracted.By product and three
Ethamine (5ml) is dissolved in the mixed system of 9ml first alcohol and water (8:1), stirring at normal temperature 12h, is spin-dried for solvent under reduced pressure, if
Purer product is obtained, the mixed system (such as v/v, 10:1) of crude product methylene chloride and methanol can be subjected to column color
Isolated sterling is composed, yellow pure product 511mg, yield 64% are obtained.
500mg (1.46mmol) naphthoyl imide compounds are dissolved in 10mL water and methylene chloride (1:1) by (scheme 3),
1417mg (3.8mmol) gala saccharide compound reflux 12h is added, reduced pressure backspin solvent evaporated is extracted.By product and
Triethylamine (5ml) is dissolved in the mixed system of 9ml first alcohol and water (8:1), stirring at normal temperature 12h, is spin-dried for solvent under reduced pressure, such as
Fruit will obtain purer product, the mixed system (such as v/v, 10:1) of crude product methylene chloride and methanol can be carried out column
Chromatographic isolation obtains sterling, obtains yellow pure product 551mg, yield 69%.
500mg (1.46mmol) naphthoyl imide compounds are dissolved in 10mL water and methylene chloride (1:1) by (scheme 4),
2834mg (7.6mmol) gala saccharide compound reflux 12h is added, reduced pressure backspin solvent evaporated is extracted.By product and
Triethylamine (5ml) is dissolved in the mixed system of 9ml first alcohol and water (8:1), stirring at normal temperature 12h, is spin-dried for solvent under reduced pressure, such as
Fruit will obtain purer product, the mixed system (such as v/v, 10:1) of crude product methylene chloride and methanol can be carried out column
Chromatographic isolation obtains sterling, obtains yellow pure product 710mg, yield 89%.
500mg (1.46mmol) naphthoyl imide compounds are dissolved in 10mL water and methylene chloride (1:1) by (scheme 5),
3730mg (10mmol) gala saccharide compound reflux 6h is added, reduced pressure backspin solvent evaporated is extracted.By product and three
Ethamine (5ml) is dissolved in the mixed system of 9ml first alcohol and water (8:1), stirring at normal temperature 6h, is spin-dried for solvent under reduced pressure, if
Purer product is obtained, the mixed system (such as v/v, 10:1) of crude product methylene chloride and methanol can be subjected to column color
Isolated sterling is composed, yellow pure product 415mg, yield 52% are obtained.
Embodiment 2
Fig. 1 a is (5 μM) of the probe fluorescence spectrums being added before and after peroxynitrite (0-50 μM).Fig. 1 b is different dense
Nitrite oxidation (0-15 μM) is spent to the linear relationship chart of probe (5 μM).
The parallel sample that multiple concentration and probe concentrations are 5 μM is configured in 10mL colorimetric cylinder, then by the peroxidating of various concentration
Nitrite is added in test system, is stood after rocking uniformly.Said determination is in pure water (20mM PBS, pH 7.4) system
Middle progress, used probe is probe prepared in embodiment 1, and all spectrum tests are measured at 25 DEG C
's.
Its fluorescence intensity change is tested with Fluorescence Spectrometer, can clearly be found out from Fig. 1 a, with peroxinitrites
The increase of salinity, the fluorescence intensity at 550nm gradually increase.Also, it can be seen that fluorescence probe (5 μM) was added by Fig. 1 b
After nitrite oxidation (0-15 μM), presented between the value of fluorescence intensity and the concentration of peroxynitrite at wavelength
Good linear relationship, this proves that quantitative analysis can be carried out to peroxynitrite by means of the fluorescence probe.
Embodiment 3
Fig. 2 is (5 μM) of the probe response times being added after peroxynitrite (10 μM).50 are taken out from probe mother liquor
μ L is placed in the test system of 10mL, and then 10 μM of peroxynitrite is added in test system, vertical after rocking uniformly
Its fluorescence intensity change is tested with Fluorescence Spectrometer.Said determination is carried out in pure water (20mM PBS, pH 7.4) system
, used probe is probe prepared in embodiment 1, and all spectrum tests are measured at 25 DEG C.
By figure it will be clear that after peroxynitrite is added, reach most through detection 3s or so fluorescence intensity
It is worth and remains unchanged greatly, this illustrates that the probe is swift in response with peroxynitrite, can be the survey of peroxynitrite
Quick analysis method is provided surely.
Embodiment 4
Fig. 3 is influence of the different analytes to probe (5 μM) fluorescence spectrum.
Analyte is respectively blank, potassium ion, sodium ion, calcium ion, magnesium ion, copper ion, fluorine ion, chloride ion, bromine
Ion, sulfate radical, carbonate, nitrate anion, nitrite anions, nitric oxide, tertbutanol peroxide, hydrogen peroxide, the tertiary fourth of peroxidating
Alcohol free radical, hydroxyl radical free radical, potassium superoxide, singlet oxygen, cysteine (500 μM), homocysteine (500 μM), paddy
(in addition to special indicate, other analyte concentrations are 100 μ for the sweet peptide of Guang (5mM), hypochlorous acid, peroxynitrite (50 μM)
M).Fluorescence intensity of the probe at 550nm in the presence of being different analytes that histogram represents.Said determination is in pure water
It is carried out in (20mM PBS, pH7.4) system, used probe is probe prepared in embodiment 1, and all spectrum are surveyed
Examination is measured at 25 DEG C.Specifically, the parallel sample that multiple concentration and probe concentrations are 5 μM is configured in 10mL colorimetric cylinder, so
After a certain amount of analyte is added, shake up, measured after 1 minute.Can clearly it be found out by Fig. 3, the probe is to peroxidating Asia
Nitrate has high selectivity.
Embodiment 4
Fig. 4 is probe (20 μM) to the proof diagram of liver cancer cells Targeting Performance, wherein HepG2, MGC803, A549,
SHSY5Y respectively represents liver cancer cells, stomach cancer cell, lung carcinoma cell, neuroblastoma cell.Probe of the present invention is denoted as Gal-
NHP (as prepared by embodiment 1), no sugar-modified NHP is as reference material:
Liver cancer cell specificity peroxynitrite probe can selectively targeted liver cancer cells, can be clear by Fig. 4
See that probe has good Targeting Performance.
Although with above embodiments describe the present invention, it should be appreciated that before without departing substantially from spirit of the 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 (10)
1. compound has following structure
Wherein: R1, R2, R3, R4, R5, R6, R7, R8And 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. compound according to claim 1 is the compound such as flowering structure:
3. the preparation for detecting peroxynitrite content in sample, it includes the compounds having following structure:
Wherein: R1, R2, R3, R4, R5, R6, R7, R8And 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.
4. preparation according to claim 3, wherein the compound is:
5. preparation according to claim 3, wherein the sample is water or blood.
6. the method for preparing the compound of claims 1 or 2 comprising following steps:
Naphthoyl imide compounds are reacted with gala saccharide compound, reaction product and triethylamine are then dissolved in first alcohol and water
Mixed system in react.
7. method according to claim 6 comprising following reaction step:
8. the method for according to claim 6 or 7, wherein the molar ratio of the naphthoyl imide compounds and gala saccharide compound
For 1:1-1:20.
9. the method for according to claim 6 or 7, wherein the molar ratio of the naphthoyl imide compounds and gala saccharide compound
For 1:5-1:6.
10. the method for according to claim 6 or 7, wherein being purified by chromatographic isolation to the crude product after reaction.
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Cited By (5)
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| CN111943887A (en) * | 2020-09-11 | 2020-11-17 | 济南大学 | Fluorescent probe for high-selectivity recognition of phosphate, preparation method and application |
| CN111995573A (en) * | 2020-09-04 | 2020-11-27 | 济南大学 | High-sensitivity nitrite colorimetric fluorescent probe, preparation method and application |
| CN115160391A (en) * | 2022-07-20 | 2022-10-11 | 湘潭大学 | Preparation and application of targeted nitroso peroxide fluorescent probe |
| CN115504935A (en) * | 2022-09-19 | 2022-12-23 | 南通大学 | Fluorescent probe for detecting nitrite, preparation method and application |
| CN115160391B (en) * | 2022-07-20 | 2024-04-26 | 湘潭大学 | Preparation and application of targeted nitrosoperoxide fluorescent probe |
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| CN115160391B (en) * | 2022-07-20 | 2024-04-26 | 湘潭大学 | Preparation and application of targeted nitrosoperoxide fluorescent probe |
| CN115504935A (en) * | 2022-09-19 | 2022-12-23 | 南通大学 | Fluorescent probe for detecting nitrite, preparation method and application |
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