CN101892046A - Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof - Google Patents
Colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof Download PDFInfo
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- CN101892046A CN101892046A CN2010102094433A CN201010209443A CN101892046A CN 101892046 A CN101892046 A CN 101892046A CN 2010102094433 A CN2010102094433 A CN 2010102094433A CN 201010209443 A CN201010209443 A CN 201010209443A CN 101892046 A CN101892046 A CN 101892046A
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Abstract
The invention relates to a colorimetric fluorescence probe for high selectivity multiple biological thiol and a preparation method thereof, particularly to the colorimetric fluorescence probe which uses selenazole ring as an identification receptor, takes an anthraquinone derivant as an information report functional group, can high selectively distinguish and identify cysteine, homocysteine and glutathione and the preparation method thereof, belonging to the technical field of life science. The colorimetric fluorescence probe has the following structure formula as shown in the specification. The colorimetric fluorescence probe is prepared by grinding and reacting a diamine compound corresponding to the colorimetric fluorescence probe for the high selectivity multiple biological thiol and selenium dioxide in an agate mortar for 15-90 min at the grinding temperature of 10-35 DEG C, the mole ratio of the corresponding diamine compound to the selenium dioxide is 1:1-5, and the reaction formula is shown in the specification. The invention can directly distinguish and identify the cysteine, the homocysteine and the glutathione by eyes, and carry out imaging analysis on biological thiol in living cells. The invention has the advantages of simple method, environmental protection and industrial production.
Description
Technical field
The present invention relates to colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof, being specifically related to a class is identification receptor, is the report information functional group with the anthraquinone derivative with the selenazoles ring, and can distinguish colorimetric fluorescence probe of identification halfcystine, homocysteine and gsh and preparation method thereof by highly selective, belong to the life science technical field.
Background technology
Mercaptan is the very important material of a class in life system and the chemical science.Small molecules mercaptan extensively is distributed in cell, blood plasma and the tissue, plays an important role in the redox equilibrium with keeping in the organism at the important physiological activity of participation.Gsh (glutathione, GSH) be the abundantest small molecules sulfur alcohol compound (1～10mM) that exists in the cell, can combine with the toxic compounds that enters body, heavy metal ion or carcinogenic substance etc., short its excretes, in therefore playing and detoxification.In addition; gsh is a kind of antioxidant of protective enzyme and other proteinic sulfydryls; it is the chief component of non-albumen sulfydryl in the cell; participate in intracellular redox reaction; reduced form (GSH) plays keying action with the ratio of Sleep-promoting factor B (GSSG) content in keeping vivo oxidation reduction balance, the ANOMALOUS VARIATIONS of this ratio will cause the generation of diseases such as heart trouble, tumour and multiple abalienation.Halfcystine (cysteine, Cys) and homocysteine (be also referred to as homocysteine, homocysteine Hcy) also is two important sulfur alcohol compounds that exist in the organism.The reduction regular meeting of cysteine content cause grow slowly, hair fades, oedema, listless, hepatic diseases, skin injury and disease such as thin and weak.The rising of homocysteine concentration in blood plasma will be accompanied by diseases such as myocardial infarction, exhausting, venous thromboembolism.The content of homocysteine is higher than normal value also may cause senile dementia (Alzheimer ' s disease), nervous center defective, conceived complication, enteritis and osteoporosis diseases.In addition, the isocyatic rising of oxidation state Cys and Hcy in the blood sample, perhaps the reduction of reduced form GSH concentration all is the distinctive characteristic index of oxidative stress.Since contain mercaptan amino acid can well reflect cellular oxidation stress degree, so the amino acid whose change in concentration of thio-alcohol has begun to serve as diagnosis and has detected the clinical indices of various metabolic disturbance diseases in the blood sample.
Given this, developed the detection that various analysis is used for biological thiol, especially colorimetric and fluorescent spectrometry have obtained abundant development and have obtained bigger progress, but only are confined to: improve the sensitivity of probe and selectivity, shortening time of response with can realize detecting in real time and the broadening useful range to satisfy requirement in the practical application etc.Recently, people such as de Silva have elaborated the superiority of multivariate analysis probe on Nature, and wherein more topmost is that it can overcome and analyzes the plurality of target thing and need inject the deficiency that multiple probe brings simultaneously.Though polynary probe has certain development, almost all be used to analyze hydrogen ion and metallic cation, still do not appear in the newspapers and can distinguish the probe of discerning these biological thiols effectively.Therefore, the synthetic class of design can be distinguished the polynary probe of discerning multiple biological thiol becomes the major objective that the present invention will solve.
Summary of the invention
The objective of the invention is to distinguish identification halfcystine, homocysteine and gsh problem, propose colorimetric fluorescence probe for high selectivity multiple biological thiol and preparation method thereof at the active somatic cell intensive amount in order to solve prior art.
The objective of the invention is to be achieved through the following technical solutions.
Colorimetric fluorescence probe for high selectivity multiple biological thiol of the present invention, a class with the selenazoles ring be identification receptor, with the multiple biological thiol colorimetric fluorescence probe of anthraquinone derivative as the report information functional group, its structural formula is as follows:
In the formula: R
1, R
2, R
3, R
4, R
5, R
6A kind of in hydrogen atom, alkyl, alkoxyl group, sulfonic group or the ester group; R
1, R
2, R
3, R
4, R
5, R
6Can be identical or different.
The preparation method of colorimetric fluorescence probe for high selectivity multiple biological thiol of the present invention is: carry out griding reaction with corresponding diamino compounds of colorimetric fluorescence probe for high selectivity multiple biological thiol and tin anhydride in agate mortar and make, grinding temperature is 10～35 ℃, milling time is 15～90min, and the mol ratio of corresponding diamino compounds and tin anhydride is 1: 1～5; Its reaction structure formula is:
The colorimetric fluorescence probe for high selectivity multiple biological thiol that aforesaid method obtains can produce different absorption spectrum simultaneous distinct colors with halfcystine, homocysteine and gsh effect respectively to be changed and fluorescence emission spectrum, thereby realizes the selectivity identification to halfcystine, homocysteine and gsh; And all can not cause the obvious change of absorption spectrum and fluorescence emission spectrum with other non-mercaptan amino acid effects, and these occurrences of amino acid do not disturb to the quantitative assay of biological thiol; But hatch behind 10～60min just transfered cell with cell, thereby realize biological thiol Determination on content in the pair cell.
Mentality of designing: anthraquinone and its derivative Chang Zuowei chromophoric group and fluorophore are widely used in the design of negatively charged ion and metal ion probe, and these probes often are accompanied by the variation of solution colour and fluorescence spectrum in the process of recognition objective thing.In addition, the result of study that the conclusion of having reported and we obtain shows that the selenazoles ring can be used as the acceptor of highly selective identification mercaptan.On this basis, we design and have synthesized with two amido anthraquinone derivatives as report information functional group and the organic selenazoles ring mercaptan probe as acceptor.We guess that in a single day the diamines in the two amido anthraquinone derivatives forms the selenazoles loop type, and absorption spectrum has blue shift largely.When add biological thiol in probe solution after, the dismemberent of selenazoles will cause the red shift of absorption spectrum.Importantly, the effect of multi-form or degree may take place with carbonyl in the anthraquinone in other functional groups in the biological thiol (as amino, carboxyl etc.), thus cause in various degree the red shift absorption spectrum and the appearance of fluorescence spectrum, and then they are distinguished.
Beneficial effect
The present invention can directly distinguish identification halfcystine, homocysteine and gsh by enough eyes, and can carry out imaging analysis to biological thiol in viable cell, and this preparation method is simple, environmental protection, and cost is low, but suitability for industrialized production.
Description of drawings
Fig. 1 is the influences of different analytes to target compound (10 μ M) absorption spectrum;
Fig. 2 is the influences of different analytes to target compound (10 μ M) fluorescence spectrum;
Fig. 3 is that different analytes exist the variation of target compound solution colour down;
Fig. 4 is the influence of the GSH of different concns (0～900 μ M) to target compound (10 μ M) absorption spectrum;
Fig. 5 is the influence of the GSH of different concns (0～900 μ M) to target compound (10 μ M) absorption spectrum;
Fig. 6 is the influence of the GSH of different concns (20～120 μ M) to target compound (10 μ M) absorption spectrum;
Fig. 7 is the influence of the GSH of different concns (0～900 μ M) to target compound (10 μ M) fluorescence spectrum;
Fig. 8 is the influence of the GSH of different concns (0～900 μ M) to target compound (10 μ M) fluorescence spectrum;
Fig. 9 is the influence of the GSH of different concns (0～100 μ M) to target compound (10 μ M) fluorescence spectrum;
Figure 10 is the influences of different analytes to target compound (10 μ M) absorption spectrum quantitative analysis GSH (300 μ M) result;
Figure 11 is the influences of different analytes to target compound (10 μ M) fluorescence spectrum quantitative analysis GSH (300 μ M) result;
Figure 12 is the co-focusing imaging figure of target compound mark live body HeLa cell;
The co-focusing imaging figure of Figure 13 live body HeLa cell that to be the target compound mark handled through NEM.
Embodiment
The present invention will be further described below in conjunction with embodiment.
Embodiment
With 238.2mg (1mmol) 1,2-two amido anthraquinones and 221.9mg (2mmol) tin anhydride be porphyrize in agate mortar respectively, then with two kinds of compound behind the porphyrize, continue to grind 1h, mixture after will grinding then is dissolved in the trichloromethane, filters, and boils off solvent under the decompression, resistates separates through column chromatography, trichloromethane is done eluent, then leacheate is removed the trichloromethane eluent, gets the pure product 261.8mg of target compound, yield 84%, reaction formula is as follows:
The nucleus magnetic hydrogen spectrum of the target compound that obtains and high resolution mass spectrum characterization data are as follows:
1H-NMR?(400MHz，DMSO-d
6)δ(*10
-6)：7.95(t，J＝7.0Hz，2H)，8.20(d，J＝7.6Hz，2H)，8.34(d，J＝2.8Hz，2H)；
HRMS(ESI?positive)：[M+H]
+calcd?for?C
14H
7N
2O
2Se?314.96676，found314.96644。
The target compound that obtains is carried out discriminance analysis to assay, assay is halfcystine Cys, homocysteine Hcy, gsh GSH, arginine Arg, L-Ala Ala, tyrosine Tyr, Methionin Lys, Histidine His, aspartic acid Asp, Xie Ansuan Val, leucine Leu, tryptophane Try, methionine(Met) Met, proline(Pro) Pro, phenylalanine Phep, Serine Ser, Threonine Thr, L-glutamic acid Glu and glycine Gly, the concentration of assay is 300 μ M, and its concrete discriminance analysis step is:
Under 25 ℃, target compound and the assay of 10 μ M is dissolved in phosphate buffer soln and the alcoholic acid mixed system, mix behind the 1h test UV spectrum and fluorescence spectrum and observe its colour-change simultaneously; The phosphate buffer soln that is added is 20mM, and its pH is 7.4, and the volume ratio of ethanol and water is 1: 1; Used excitation wavelength is 490nm, exciting and launching slit width all is 5nm, the UV spectrum spectrogram that test obtains as shown in Figure 1, the fluorescence spectrum spectrogram that obtains of test as shown in Figure 2, its colour-change as shown in Figure 3,1 represents target compound and Cys among its figure, 2 represent target compound and Hcy, 3 represent target compound and GSH, and 4 represent target compound, and 5 represent target compound and other amino acid whose naturally mixtures;
The target compound that obtains is carried out quantitative analysis to GSH, and its concrete steps are:
Under 25 ℃, the GSH that the target compound of 10 μ M and target compound and concentration is respectively 10 μ M, 20 μ M, 30 μ M, 40 μ M, 50 μ M, 60 μ M, 70 μ M, 80 μ M, 90 μ M, 100 μ M, 120 μ M, 140 μ M, 160 μ M, 200 μ M, 300 μ M, 400 μ M, 500 μ M, 600 μ M, 700 μ M, 800 μ M, 900 μ M is dissolved in phosphate buffer soln and the alcoholic acid mixed system, mixes test UV spectrum and fluorescence spectrum behind the 1h; The phosphate buffer soln that is added is 20mM, and its pH is 7.4, and the volume ratio of ethanol and water is 1: 1; Used excitation wavelength is 490nm, and exciting and launching slit width all is 5nm, the UV spectrum spectrogram that obtains of test as shown in Figure 4 and Figure 5, the absorbancy at target compound 490nm place and the linear relationship of GSH concentration are as shown in Figure 6; The fluorescence spectrum spectrogram that obtains of test as shown in Figure 7 and Figure 8, the fluorescence intensity at target compound 594nm place and the linear relationship of GSH concentration are as shown in Figure 9;
Different chaff interferences are to the influence of target compound quantitative test GSH, and its concrete steps are:
Under 25 ℃, 10 μ M target compounds, 300 μ MGSH and 300 μ M chaff interferences are dissolved in phosphate buffer soln and the alcoholic acid mixed system test UV spectrum and fluorescence spectrum behind the mixing 1h; The phosphate buffer soln that is added is 20mM, and its pH is 7.4, and the volume ratio of ethanol and water is 1: 1; Used excitation wavelength is 490nm, and exciting and launching slit width all is 5nm; Chaff interference is respectively Arg, Ala, Tyr, Lys, His, Asp, Val, Leu, Try, Met, Pro, Phe, Ser, Thr, Glu and Gly, the UV spectrum spectrogram that obtains of test as shown in figure 10, histogram is the absorbancy at the 490nm place among the figure; The fluorescence spectrum spectrogram that obtains of test as shown in figure 11, histogram is the fluorescence intensity at the 594nm place among the figure; Histogram is represented target compound (1) respectively among Figure 10 and Figure 11, target compound+GSH+Arg (2), target compound+GSH+Ala (3), target compound+GSH+Tyr (4), target compound+GSH+Lys (5), target compound+GSH+His (6), target compound+GSH+Asp (7), target compound+GSH+Val (8), target compound+GSH+Leu (9), target compound+GSH+Try (10), target compound+GSH+Met (11), target compound+GSH+Pro (12), target compound+GSH+Phe (13), target compound+GSH+Ser (14), target compound+GSH+Thr (15), target compound+GSH+Glu (16), target compound+GSH+Gly (17) and target compound+GSH (18).
The cell imaging experiment:
Measure the ability of biological thiol in the active somatic cell in order to investigate target compound, we are applied to target compound the imaging analysis experiment of live body HeLa cell; After target compound (10 μ M) is hatched 30min, present strong red fluorescence as shown in figure 12 in the tenuigenin of HeLa cell, this result shows that target compound can permeates cell membranes and can target ground mark tenuigenin; In addition, we carry out the concentration of pre-treatment with biological thiol in the reduction cell with 50 μ M NEM pair cells earlier, and then hatch 30min with target compound (10 μ M), and the result shows that red fluorescence obviously reduces as shown in figure 13; These results show being caused by the change of biological thiol content in the cell really of change in fluorescence of target compound, and concrete steps are:
It is 10 that HeLa cell (Beijing consonance medical university cell centre) is adjusted cell density with DMEM/F12 nutrient solution (containing 10% foetal calf serum, 50U/mL penicillin, 50 μ g/mL Streptomycin sulphates)
-6Individual cell/mL places aseptic culture dish, cultivates in 37 ℃ of 5% CO2gas incubator; DMEM with serum-free cleans 3 times earlier, removes not adherent cell, and then places two 6 orifice plates to cultivate for experiment used respectively with the nutrient solution dilution; A part is directly hatched 30min with 10 μ M target compound solution; A part is hatched the concentration of 2h with biological thiol in the reduction cell with 50 μ MNEM earlier, and then hatches 30min with 10 μ M target compound solution.Take the fluorescence micrograph of above-mentioned cell, excitation light source: green glow with laser confocal microscope; Before the laser co-focusing micro-imaging, remove nutrient solution, and then wash twice with PBS buffered soln.
Claims (2)
1. colorimetric fluorescence probe for high selectivity multiple biological thiol is characterized in that: with the selenazoles ring be identification receptor, with the multiple biological thiol colorimetric fluorescence probe of anthraquinone derivative as the report information functional group, its structural formula is as follows:
In the formula: R
1, R
2, R
3, R
4, R
5, R
6A kind of in hydrogen atom, alkyl, alkoxyl group, sulfonic group or the ester group; R
1, R
2, R
3, R
4, R
5, R
6Can be identical or different.
2. the preparation method of colorimetric fluorescence probe for high selectivity multiple biological thiol, it is characterized in that: in agate mortar, carry out griding reaction with corresponding diamino compounds of colorimetric fluorescence probe for high selectivity multiple biological thiol and tin anhydride and make, grinding temperature is 10～35 ℃, milling time is 15～90min, and the mol ratio of corresponding diamino compounds and tin anhydride is 1: 1～5; Its reaction structure formula is:
The colorimetric fluorescence probe for high selectivity multiple biological thiol that aforesaid method obtains can produce different absorption spectrum simultaneous distinct colors with halfcystine, homocysteine and gsh effect respectively to be changed and fluorescence emission spectrum, thereby realizes the selectivity identification to halfcystine, homocysteine and gsh; And all can not cause the obvious change of absorption spectrum and fluorescence emission spectrum with other non-mercaptan amino acid effects, and these occurrences of amino acid do not disturb to the quantitative assay of biological thiol; But hatch behind 10～60min just transfered cell with cell, thereby realize biological thiol Determination on content in the pair cell.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102585802A (en) * | 2012-01-31 | 2012-07-18 | 天津理工大学 | Novel water-soluble sulfydryl fluorescent probe, and preparation method and application thereof |
| CN103084073A (en) * | 2011-10-31 | 2013-05-08 | 中国科学院合肥物质科学研究院 | Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof |
| CN103088554A (en) * | 2011-10-31 | 2013-05-08 | 中国科学院合肥物质科学研究院 | Porous membrane mixed by 1,4-dihydroxy anthraquinone and cellulose, preparation method and usage |
| CN108101867A (en) * | 2017-12-15 | 2018-06-01 | 湖北大学 | A kind of preparation method and application technology for the fluorescence probe for detecting glutathione |
| CN108947994A (en) * | 2018-07-13 | 2018-12-07 | 济南大学 | A kind of biological thiol fluorescence probe and its application |
| CN112209942A (en) * | 2020-10-14 | 2021-01-12 | 中南大学 | Fluorescent probe for rapidly distinguishing and detecting cysteine, homocysteine and glutathione |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010028349A2 (en) * | 2008-09-08 | 2010-03-11 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010028349A2 (en) * | 2008-09-08 | 2010-03-11 | Enzo Life Sciences, Inc. | Fluorochromes for organelle tracing and multi-color imaging |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103084073A (en) * | 2011-10-31 | 2013-05-08 | 中国科学院合肥物质科学研究院 | Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof |
| CN103088554A (en) * | 2011-10-31 | 2013-05-08 | 中国科学院合肥物质科学研究院 | Porous membrane mixed by 1,4-dihydroxy anthraquinone and cellulose, preparation method and usage |
| CN103084073B (en) * | 2011-10-31 | 2015-06-03 | 中国科学院合肥物质科学研究院 | Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof |
| CN102585802A (en) * | 2012-01-31 | 2012-07-18 | 天津理工大学 | Novel water-soluble sulfydryl fluorescent probe, and preparation method and application thereof |
| CN108101867A (en) * | 2017-12-15 | 2018-06-01 | 湖北大学 | A kind of preparation method and application technology for the fluorescence probe for detecting glutathione |
| CN108947994A (en) * | 2018-07-13 | 2018-12-07 | 济南大学 | A kind of biological thiol fluorescence probe and its application |
| CN112209942A (en) * | 2020-10-14 | 2021-01-12 | 中南大学 | Fluorescent probe for rapidly distinguishing and detecting cysteine, homocysteine and glutathione |
| CN112209942B (en) * | 2020-10-14 | 2023-10-31 | 中南大学 | Fluorescent probe for distinguishing and detecting cysteine, homocysteine and glutathione |
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