CN106632188B - The fluorescence probe of one kind detection formaldehyde and its preparation and application - Google Patents
The fluorescence probe of one kind detection formaldehyde and its preparation and application Download PDFInfo
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Abstract
The present invention provides the fluorescence probe of a kind of detection formaldehyde, with structure shown in Formulas I-IV, by the way that by the corresponding cumarin replaced of phenyl ring, first in toluene with lawesson reagent back flow reaction, products therefrom continues obtained with hydrazine hydrate back flow reaction in ethanol.Fluorescence probe provided by the invention unstressed configuration, but fast reaction that can be specific with formaldehyde generation in aqueous solution itself, generates the product with hyperfluorescence, to realize the detection of special sensitivity and quantitative analysis of formaldehyde.Stability is good, being capable of long-term preservation use；Detection signal-to-noise ratio is high, and sensitivity is good；With outstanding selectivity, formaldehyde can be specifically detected in complex biological sample；With good biological membrane permeability, thus the detection of formaldehyde in living cells can be used for；Detection rapid reaction can provide testing result to the formaldehyde in aqueous solution in 1 minute；It will not influence Formaldehyde in Environment concentration while detecting formaldehyde.The general structure of probe of the present invention:
Description
Technical field
The invention belongs to Environmental Analytical Chemistry and field of biological detection, are related to fluorescence probe, its preparation of a kind of detection formaldehyde
Method and the application in detection environment and in biological sample in content of formaldehyde.
Background technique
Formaldehyde is a kind of colourless gas, there is special penetrating odor, to the irritating effect such as human eye, nose.It is highly concentrated in environment
The formaldehyde of degree has sensitization, teratogenesis and the toxicity such as carcinogenic to human body, and formaldehyde was thus confirmed as 1 class carcinogenic substance in 2006.Therefore,
Detect in environment, especially furniture, new fitting space, new garment material, the content of formaldehyde even in food be one it is important and
The work being of practical significance.
The toxic effect of environment middle and high concentration formaldehyde is at home and abroad furtherd investigate.However in contrast, in recent years
Come in the nearly all cell of people finder's body the presence of endogenous formaldehyde！By taking cerebral tissue as an example, the study found that cerebral tissue
In physiology endogenous formaldehyde be in higher level, wherein concentration of formaldehyde is 0.2mmol/L or so, hippocampal tissue in cortical tissue
For 0.4mmol/L or so, prompt it that may participate in the normal physiological activity of brain；And endogenous formaldehyde in brain cell
Abnormal aggregation can aldehyde ketone stress, the various inducements such as oxidative stress under the action of, cause nerve cell dysfunction, denaturation
Death leads to study, memory dysfunction.Currently, since shortage formaldehyde is accurate in biological in-situ environment, simplicity quantitative analysis
Detection method, the physiological and pathological Effect study of formaldehyde is extremely restricted.How easily testing and evaluation
The concentration level and tissue distribution of endogenous formaldehyde have emphatically for predicting and assessing the progress and degree of related disease
The clinical meaning wanted.However, conventional detection method such as spectrophotometry, red, orange, green, blue, yellow (ROGBY) etc. is in medicine and life science
Application there are many restrictions, as detection sensitivity is poor, it is difficult to realize the real-time online of formaldehyde in living cells or living tissue
Detection etc., this is restricted physiology and pathological effect research of the formaldehyde in living body biological sample.Therefore, exploitation is suitable for
Life of the good formaldehyde rapid analysis and test method of high sensitivity, the selectivity of complicated living body biological sample to Study on Endogenous formaldehyde
Reason pathological effect has great importance.
Small-molecule fluorescent probe is one of the efficient tool for detecting intracellular molecules event.Small-molecule fluorescent probe detection method
With high sensitivity, good selective, furthermore Small-molecule probe usually has good biological membrane permeability, and can pass through
Its Absorption And Metabolism property in vivo of structure optimization is adjusted, therefore is more suitable for micro metabolism point in living cells/living tissue
The detection of son.Only a small amount of fluorescence probe for formaldehyde examination is reported at present, and there is detection reaction is slow, sensitive for majority
Property difference problem, and part formaldehyde can be consumed while detecting formaldehyde, to disturb the dense of endogenous formaldehyde in biological sample
Degree.Therefore, develop high sensitivity and the novel fluorescence probe of endogenous formaldehyde concentration will not be disturbed, be current probe research neck
The forward position in domain and hot spot.
Summary of the invention
It is an object of the present invention to provide the fluorescence probes of a kind of detection formaldehyde, are a kind of novel specific small molecules
Fluorescence probe has structure shown in Formulas I, II, III or IV:
Wherein:
R1For hydrogen, C1-C4Alkyl etc.；
R2For hydrogen, C1-C4Alkyl etc.；
N is natural number 1 or 2.
A further object of the present invention is to provide the preparation method of compound shown in Formulas I, II, III and IV, passes through following system
Preparation Method is realized:
For the compound shown in the Formulas I, 7 N-R1, R2Substituted cumarin and lawesson reagent is in dry reflux in toluene
Reaction 6 hours, cooled and filtered, filtrate are spin-dried for rear resulting product and are dissolved in ethyl alcohol, and it is small that 80% hydrazine hydrate back flow reaction 3 is added
When, end of reaction obtains compound shown in Formulas I through extraction, concentration and column chromatographic purifying.Compound shown in Formula II, III and IV is adopted
With similar synthetic method, it is made using the corresponding cumarin replaced of phenyl ring as starting material.
Wherein R1、R2Definition is the same as above with n.
It is also another object of the present invention to provide compounds shown in Formulas I, II, III and IV to detect Formaldehyde in Environment in preparation
Application in the detection agent of content.It can be realized by following steps: (1) compound shown in preparation formula I, II, III or IV first
Aqueous solution；(2) above-mentioned solution divides several pieces, is respectively placed in closed environment, and is filled with known different amounts of formaldehyde in the environment,
Its fluorescence intensity is surveyed after 10 hours；(3) with the mapping of fluorescence intensity PARA FORMALDEHYDE PRILLS(91,95) concentration, working curve is obtained；(4) it will be prepared in the first step
Compound solution be placed in environment to be detected overnight, survey its fluorescence intensity；(5) working curve and obtained using third step
Fluorescence intensity measured by four steps calculates the content of formaldehyde in environment.
A further object of the present invention is to provide compound shown in Formulas I, II, III and IV in preparation detection biological sample
Application in the detection agent of content of formaldehyde.The present invention can be realized by taking the application in living cells as an example by following steps: cell training
It supports and compound shown in Formulas I, II, III or IV is added in base, make to be incubated for 30 minutes at its final concentration of 5 μM, 37 DEG C, observe and record
Cell fluorescence intensity, fluorescence probe provided by the invention are characterized in that itself only has faint fluorescence in physiological environment,
But the product with hyperfluorescence can be generated with formaldehyde specificity fast reaction, and existed between fluorescence intensity and concentration of formaldehyde linear
Correlation, to realize the specific detection and quantitative analysis of PARA FORMALDEHYDE PRILLS(91,95).
Fluorescence probe of the present invention has the advantages that (1) stability is good, being capable of long-term preservation use；(2)
Due to probe unstressed configuration itself, only just there is fluorescence after reacting with formaldehyde, therefore, detection signal-to-noise ratio is high, and sensitivity is good；(3)
With outstanding selectivity, formaldehyde can be specifically detected in complex biological sample；(4) have good biomembrane penetrating
Property, thus the detection of formaldehyde in living cells can be used for；(5) detection rapid reaction can give the formaldehyde in aqueous solution in 1 minute
Testing result out；(6) it will not influence Formaldehyde in Environment concentration while detecting formaldehyde.
Detailed description of the invention
Fig. 1 is the change in fluorescence that fluorescent probe molecule I-1 reacts front and back with formaldehyde.
Fig. 2 is the change in fluorescence of fluorescent probe molecule I-1 PARA FORMALDEHYDE PRILLS(91,95) reaction front and back.
Fig. 3 is the selectivity of fluorescent probe molecule I-1 PARA FORMALDEHYDE PRILLS(91,95).
Fig. 4 is fluorescent probe molecule I-1 PARA FORMALDEHYDE PRILLS(91,95) concentration dependent fluorescence enhancement.
Fig. 5 is that fluorescent probe molecule I-1 detects content of formaldehyde in new cabinet.
Fig. 6 is the endogenous formaldehyde in fluorescent probe molecule I-1 detection National People's Congress's brain microvessel endothelial cells in vitro.
Fig. 7 is the endogenous of fluorescent probe molecule I-1 detection Senlie dementia model APP mouse brain slices living tissue hippocampus
Formaldehyde.
Specific embodiment
The present invention will be further described with reference to the accompanying drawings and examples, and embodiment below does not limit model of the invention
It encloses.
Embodiment 1: the preparation of fluorescent probe molecule I-1
7- diethyl amino coumarin (500 milligrams) and lawesson reagent (1.86 grams) are in dry reflux in toluene reaction 6
Hour.After reaction, cold filtration, filtrate is spin-dried for being dissolved in ethyl alcohol after solvent, is added 80% hydrazine hydrate, and back flow reaction 3 hours.Reaction
It finishing, is spin-dried for solvent, water is added, three times with the extraction of dichloro formaldehyde, merge organic phase, anhydrous sodium sulfate is dry, column chromatographic purifying,
It obtains I-1 (yield 65%).LC-MS:m/z 232.3010 [M+H]+。
Embodiment 2: the preparation of fluorescent probe molecule II-1
Ayapanin (500 milligrams) and lawesson reagent (1.86 grams) react 6 hours in dry reflux in toluene.
After reaction, cold filtration, filtrate is spin-dried for being dissolved in ethyl alcohol after solvent, is added 80% hydrazine hydrate, and back flow reaction 3 hours.End of reaction,
It is spin-dried for solvent, water is added, three times with the extraction of dichloro formaldehyde, merges organic phase, anhydrous sodium sulfate is dry, and column chromatographic purifying obtains II-
1 (yield 70%).LC-MS:m/z 191.2066 [M+H]+。
Embodiment 3: fluorescent probe molecule I-1 reacts the change in fluorescence of front and back with formaldehyde
Probe molecule is dissolved with a small amount of DMSO, the PBS solution of PBS buffer solution or formaldehyde is separately added into, makes probe molecule
Final concentration of 10 μM, final concentration of 500 μM of formaldehyde.It is excited, is recorded with 450nm using fluorescence spectrophotometer photometry after reaction 10min
Fluorescence intensity of the solution at maximum emission wavelength (about 500nm), so determine probe molecule reacted with formaldehyde after fluorescence intensity
Enhancing, as shown in Figure 1.
Embodiment 4: fluorescent probe molecule II-1 reacts the change in fluorescence of front and back with formaldehyde
Probe molecule is dissolved with a small amount of DMSO, the PBS solution of PBS buffer solution or formaldehyde is separately added into, makes probe molecule
Final concentration of 10 μM, final concentration of 500 μM of formaldehyde.It is excited, is recorded with 450nm using fluorescence spectrophotometer photometry after reaction 10min
Fluorescence intensity of the solution at maximum emission wavelength (about 500nm), so determine probe molecule reacted with formaldehyde after fluorescence intensity
Enhancing, as shown in Figure 2.
Embodiment 5: the selectivity of fluorescent probe molecule I-1 PARA FORMALDEHYDE PRILLS(91,95)
Probe molecule is dissolved with a small amount of DMSO, PBS buffer solution is added and is configured to solution, be separately added into PBS buffer solution
All kinds of samples to be tested that may interfere with formaldehyde analysis of dissolution, make final concentration of 10 μM of probe molecule, each sample to be tested is dense eventually
Degree is 300 μM.Excited with 450nm after reaction 30min using fluorescence spectrophotometer photometry, recording solution maximum emission wavelength (about
Fluorescence intensity under 500nm), and then determine the selectivity of probe molecule PARA FORMALDEHYDE PRILLS(91,95), as shown in Figure 3.
Embodiment 6: fluorescent probe molecule I-1 PARA FORMALDEHYDE PRILLS(91,95) concentration dependent fluorescence enhancement
Probe molecule is dissolved with a small amount of DMSO, PBS buffer solution is added and is configured to solution, be separately added into various concentration
Formalin makes final concentration of 10 μM of probe molecule, is excited, is recorded with 450nm using fluorescence spectrophotometer photometry after reacting 10min
Fluorescence intensity of the solution at maximum emission wavelength (about 500nm), and then determine probe molecule PARA FORMALDEHYDE PRILLS(91,95) concentration dependent fluorescence
Enhancing, as shown in Figure 4.
Embodiment 7: fluorescent probe molecule I-1 detects content of formaldehyde in new cabinet
It is 10 μM of probe solution that concentration is added in 96 well culture plates, is protected from light, and uncaps and is respectively placed in ventilated environment and new
In cabinet.It is excited using multi-function microplate reader with 450nm, in 5min, 10min, 15min, 30min, 60min, 120min,
Fluorescence intensity of the 180min and 240min detection probe solution at maximum emission wavelength (about 500nm).As a result as shown in figure 5,
When probe solution is placed in 5min in new cabinet, fluorescence intensity is significantly risen, and is hereafter extended at any time and is constantly risen.And it is placed in
Control group in ventilated environment is significantly improved in the fluorescence intensity nothing of same time point.This prompt, fluorescent probe molecule I-1 energy
The formaldehyde in air environment is detected rapidly and sensitively.
Embodiment 8: fluorescent probe molecule I-1 detects the endogenous formaldehyde in National People's Congress's brain microvessel endothelial cells in vitro
Brain microvessel endothelial cell is inoculated on glass slide, CO2It cultivates in cell incubator to 80% or so fusion rate.
Experiment is divided into three groups, and endogenous formaldehyde removes 200 μM of NaHSO of control group3Preincubate 30min；Formaldehyde examination experimental group list adds
10 μM of Small-molecule probe is incubated for 15min；Detection group first uses 200 μM of NaHSO after endogenous formaldehyde is removed3Preincubate 30min,
Add 10 μM of probe preincubate 15min.After carrying out above-mentioned processing, confocal laser scanning microscope cell fluorescence intensity becomes
Change.As a result as shown in fig. 6, NaHSO3Control group unstressed configuration, probe groups show stronger fluorescence intensity, and NaHSO3Preincubate
After removing endogenous formaldehyde, intensity of cellular fluorescence is significantly reduced, it was demonstrated that this probe can identify the endogenous first in living cells
Aldehyde.
Embodiment 9: fluorescent probe molecule I-1 detects the interior of Senlie dementia model APP mouse brain slices living tissue hippocampus
Source property formaldehyde
C57BL/6 mouse or the quick sacrificed by decapitation of Senlie dementia model APP transgenic mice take out brain and are put into 4 DEG C
In artificial cerebrospinal fluid 1.1 ingredient of artificial cerebrospinal fluid is (mM): 75 sucrose, 87NaCl, 2.5KCl, 15NaH2PO4, 7MgCl2,
0.5CaCl2, 25NaHCO3With 25 glucose.Suitable 4 DEG C of artificial cerebrospinal fluids 1 are poured into vibratome platform, and brain is placed
In slice machine platform, the coronal section brain piece of 300 μ m thicks containing cerebral hippocampus region is cut, is transferred to and is passed through 95%O2
And 5%CO24 DEG C of artificial cerebrospinal fluids 2 in 30min it is spare.2 ingredient of artificial cerebrospinal fluid is (mM): 124NaCl, 3KCl,
1.25NaH2PO4, 1.0MgSO4, 2CaCl2And 26NaHCO3.Gained brain piece is divided into three groups, and first group is to be incubated in 20 μM of probes
The C57BL/6 mouse brain slices of 30min, second group of APP Transgenic Mice Brain piece to be incubated for 30min in 20 μM of probes, third group
It is APP Transgenic Mice Brain piece first in 200 μM of NaHSO330min is incubated for add 20 μM of probes after PBS cleans brain piece and incubate in advance
Educate 30min.It carries out above-mentioned processing hindbrain piece to be cleaned 3 times with PBS, confocal laser scanning microscope brain piece fluorescence intensity.As a result
It has been shown that, in cerebral hippocampus and cortical region, the fluorescence intensity of C57BL/6 mouse brain slices is in reduced levels, and APP transgenosis is small
The fluorescence intensity of mouse brain piece is significantly higher than C57BL/6 mouse brain slices, and 200 μM of NaHSO are added3It can make APP Transgenic Mice Brain piece
Fluorescence intensity significantly reduces.This prompt this small-molecule fluorescent probe can Visual retrieval go out the work group of senile dementia pathology model
The level for knitting endogenous formaldehyde in brain piece is significantly higher than normal mouse, and can reduce endogenous first by the intervention of formaldehyde scavenger
Aldehyde is horizontal.This result is that the Visual retrieval for being further used for endogenous formaldehyde in pathological model of probe has established experiment basis
(Fig. 7).
Claims (6)
1. the fluorescence probe of one kind detection formaldehyde, which is characterized in that the fluorescence probe has structure shown in Formulas I:
Wherein: R1And R2Respectively C1-C4Alkyl.
2. the preparation method of the fluorescence probe of a kind of detection formaldehyde described in claim 1, which is characterized in that pass through following preparation
Method is realized:
7 N-R1, R2Substituted cumarin reacts 6 hours with lawesson reagent in dry reflux in toluene, cooled and filtered, filter
Liquid is spin-dried for rear resulting product and is dissolved in ethyl alcohol, is added 80% hydrazine hydrate back flow reaction 3 hours, end of reaction, through extraction, concentration and
Column chromatographic purifying obtains compound shown in Formulas I
Wherein R1、R2Definition with claim 1.
3. the fluorescence probe of a kind of detection formaldehyde according to claim 1 is in the detection of preparation detection Formaldehyde in Environment content
Application in agent.
4. application according to claim 3, which is characterized in that realized by following steps: (1) first shown in preparation formula I
The aqueous solution of compound；(2) above-mentioned aqueous solution point several pieces are taken, are respectively placed in closed environment, and are filled in the environment known
Different amounts of formaldehyde surveys its fluorescence intensity after 10 hours；(3) with the mapping of fluorescence intensity PARA FORMALDEHYDE PRILLS(91,95) concentration, working curve is obtained；(4)
The compound solution prepared in the first step is placed in environment to be detected overnight, its fluorescence intensity is surveyed；(5) it is obtained using third step
Working curve and the 4th step measured by fluorescence intensity, calculate environment in content of formaldehyde.
5. the fluorescence probe of a kind of detection formaldehyde according to claim 1 content of formaldehyde in preparation detection biological sample
Application in detection agent.
6. application according to claim 5, which is characterized in that realized by following steps: Formulas I being added in cell culture medium
Shown compound makes to be incubated for 30 minutes at its final concentration of 5 μM, 37 DEG C, observes and records cell fluorescence intensity, and fluorescence intensity
There is linear correlation between concentration of formaldehyde, to realize the specific detection and quantitative analysis of PARA FORMALDEHYDE PRILLS(91,95).
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| KR102012075B1 (en) * | 2017-07-12 | 2019-08-19 | 고려대학교 산학협력단 | Probe compound for detection of formaldehyde and Sensor for detection of formaldehyde comprising the same |
| CN109942533B (en) * | 2017-12-20 | 2021-04-27 | 浙江大学 | Coumarin hydrazone compounds, and preparation method and application thereof |
| CN108084134A (en) * | 2018-01-31 | 2018-05-29 | 长沙理工大学 | The synthesis of cumarin methyl hydrazone and its application as formaldehyde fluorescence probe |
| CN108676012A (en) * | 2018-08-01 | 2018-10-19 | 华侨大学 | A kind of preparation method of imines coumarin kind compound |
| CN109535147B (en) * | 2018-12-21 | 2021-07-20 | 大连理工大学 | Formaldehyde fluorescent probe with rapid response and preparation method and application thereof |
| CN109574971A (en) * | 2019-01-03 | 2019-04-05 | 济南大学 | A kind of two-photon formaldehyde fluorescence probe and its preparation method and application |
| CN110669504B (en) * | 2019-11-15 | 2022-01-04 | 北京建筑大学 | Fluorescent probe for detecting aldehyde characteristic odor substances in drinking water |
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