CN107652220A - A kind of preparation method and application technology for the fluorescence probe for detecting cysteine - Google Patents

A kind of preparation method and application technology for the fluorescence probe for detecting cysteine Download PDF

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CN107652220A
CN107652220A CN201710854736.9A CN201710854736A CN107652220A CN 107652220 A CN107652220 A CN 107652220A CN 201710854736 A CN201710854736 A CN 201710854736A CN 107652220 A CN107652220 A CN 107652220A
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cysteine
fluorescence probe
preparation
probe
detection
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CN107652220B (en
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韩得满
陈逢灶
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Taizhou University
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • 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
    • G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom

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Abstract

The technical field of the present invention, which belongs to, analyzes detection field in analytical chemistry, be related to a kind of preparation method of novel fluorescence probe and its application in detection cysteine (Cys).The preparation method is obtained including probe by the phenylpropen aldehyde derivatives of 3 cyano-acetamide indoles and chloro by gram Novi's Na Gaier condensation reactions, and its preparation method is simple, probe structure is stable.The probe can be applied to high selectivity, rapidly high sensitivity, Visual retrieval cysteine by sepectrophotofluorometer.In addition, the probe is also successfully applied to the imaging of living biological cell.The invention provides a kind of preparation method of the fluorescence probe of new detection cysteine, there is good application prospect.

Description

A kind of preparation method and application technology for the fluorescence probe for detecting cysteine
Technical field
The present invention relates to the fluorescence probe field of sensing technologies in analytical chemistry, is related to a kind of quick, high selectivity, Gao Ling The preparation method and applications of the fluorescence probe of sensitivity detection cysteine.
Background technology
With the development of life science, the detection of biological micromolecule, which seems, to be even more important.Such as biological small point of sulfydryl Son, including cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) are all played the part of in physiology and pathologic process Highly important effect, such as：Cys synthesized with the detoxication, metabolism and protein of body it is close contact, and Abnormal Cys contents may give rise to diseases, such as：Growth retardation, cutaneous lesions, hematopoietic disorder, Achromotrichia etc.. As Cys presoma, Hcy is then relevant with the disease such as angiocardiopathy, Alzheimer's disease, phrenoblabia.GSH and AIDS The diseases such as disease, cancer, angiocardiopathy are relevant.In addition, Cys also has important utilization in medicine, cosmetics and food, than Such as：For acrylonitrile, the postacidotic removing toxic substances of aromatic series；For treating the medicine of bronchitis；It is mainly used in terms of cosmetics Permanent wave solution, after shave lotion, sunproof skin care cream etc.；It is mainly used in terms of food in bread material and fruit juice.Therefore, for The detection of these biological sulfydryl small molecules is highly important.But due to the similitude of structure, it is difficult to by Cys/Hcy and GSH Distinguish.Because internal Cys content is more than ten times of Hcy contents, Cys and GSH differentiation are focused primarily upon at present Detection.Traditional assay method depends primarily on liquid chromatography, AAS, isotope method, Immunological Method etc..These Although method can realize qualitative or quantitative measure, there is also it is certain the defects of, such as sample preparation is complicated, operation is multiple Miscellaneous, expensive equipment, the testing time is tediously long, is not easy popularization and application.Therefore, developing one kind being capable of high selectivity, high sensitivity, quick The method for easily detecting Cys is of great significance to the preliminary clinical diagnosis tool of some major diseases.
The present invention relates to a kind of preparation method and applications technology for the fluorescence probe for detecting cysteine.We use 3- The phenylpropen aldehyde derivatives of cyano-acetamide indoles and chloro obtain fluorescence probe by gram Novi's Na Gaier condensation reactions, and it is made Preparation Method is simple, Stability Analysis of Structures.By testing in vitro, experiment shows that the fluorescence probe can be used for high selectivity, high sensitivity, fast Fast ground Visual retrieval cysteine.In addition, the fluorescence probe is also successfully applied to the imaging of living biological cell, experiment shows It can monitor endogenous cellular and exogenous Cys.Therefore, the probe has potential application prospect.
The content of the invention
It is an object of the invention to provide a kind of preparation method and applications technology for the fluorescence probe for detecting cysteine.
According to the present invention, the phenylpropen aldehyde derivatives condensation reaction by 3- cyano-acetamides indoles and chloro obtains Fluorescence probe, its synthesis step specifically include：(1) indoles and cyanoacetic acid are dissolved in acid anhydrides, are heated to reflux under argon gas protection Reaction 4 hours, question response terminates, and processing obtains white solid product 3- cyano-acetamide indoles；(2) by N,N-dimethylformamide It is placed in ice bath and is precooled to 0-5 DEG C, is then slowly added into POCl3, is stirred 1 hour under ice bath, be then slowly added into 3,4, 5- trimethoxy acetophenones, then be stirred at room temperature 3 hours, question response terminates, and reaction solution is poured into trash ice, is adjusted with sodium carbonate PH value is saved to 7~8, there is yellow mercury oxide generation in reaction solution, filtering, separating-purifying obtain the phenyl of yellow solid product chloro Propenal derivative；(3) the 3- cyano-acetamides indoles in (1) and (2) and the phenylpropen aldehyde derivatives of chloro are dissolved in anhydrous In ethanol, base catalyst is added, at room temperature stirring reaction, there is yellow solid precipitation in reaction solution, filtering, separating-purifying obtain To final product, i.e., the fluorescence probe of detection cysteine of the present invention.
The art of this patent has advantages below compared with prior art：
1. high selectivity, related substances has little to no effect to it；
2. high sensitivity, the detection to micro object can be achieved；
3. quick response, quick detection can be achieved；
3. synthesis is simple, cost is low, pollution-free.
Brief description of the drawings
Fig. 1 is the fluorescence titration figure of probe in detecting cysteine
Fig. 2 is the response time fluorescence spectra of probe in detecting cysteine
Fig. 3 is the selective experimental fluorescence spectrogram of probe
Fig. 4 is that the pH of detection environment optimizes fluorescence spectra
Embodiment
Below with reference to embodiment, the present invention will be further described, and embodiments of the invention are merely to illustrate the present invention's Technical scheme, and the non-limiting present invention.
Embodiment 1
Indoles (2.00g, 17.02mmol) and cyanoacetic acid (1.59g, 18.69mmol) are dissolved in 15mL acid anhydrides, The lower heating reflux reaction of argon gas protection 4 hours, reaction terminates, and question response liquid is cooled to room temperature, and reaction solution is poured into 100mL water In, ethyl acetate extraction, organic phase solution, anhydrous sodium sulfate drying are collected, revolving obtains crude product, then by column chromatography for separation Obtain final product i.e. 3- cyano-acetamides indoles (2.13g, yield 68%).Nuclear-magnetism characterize data：1H NMR(400MHz,DMSO- d6,TMS):δ 12.18 (s, 1H), 8.38 (d, J=4.0Hz, 1H), 8.14 (dd, J1=2.0Hz, J2=7.1Hz, 1H), 7.51 (m,1H),7.24(m,2H),4.50(s,2H)。
Embodiment 2
5mL DMF is placed in ice bath and is precooled to 0-5 DEG C, is then slowly added into 2mL trichlorine Oxygen phosphorus, stir 1 hour under ice bath, be then slowly added into 3,4,5- trimethoxy acetophenones (1.00g, 4.76mmol), then in room The lower stirring of temperature 3 hours, question response terminates, and reaction solution is poured into trash ice, is 7 with sodium carbonate regulation pH value, there is yellow mercury oxide Generation, be filtrated to get crude product, then column chromatography for separation obtain the i.e. chloro of final product phenylpropen aldehyde derivatives (588mg, Yield 48%).Nuclear-magnetism characterize data：1H NMR(400MHz,CDCl3,TMS):δ 10.20 (d, J=7.0Hz, 1H), 6.98 (s, 2H), 6.63 (d, J=6.9Hz, 1H), 3.91 (s, 9H).
Embodiment 3
By the phenylpropen aldehyde derivatives of above-mentioned 3- cyano-acetamides indoles (150mg, 0.82mmol) and chloro (209mg, 0.82mmol) it is dissolved in 10mL absolute ethyl alcohol, adds three drop pyridines, at room temperature stirring reaction, has yellow to consolidate in reaction solution Body separates out, and filtering, separating-purifying obtain final product (152mg, yield 44%), i.e., detection cysteine of the present invention Fluorescence probe.Nuclear-magnetism characterize data：1H NMR(400MHz,CDCl3,TMS):δ 8.85 (s, 1H), 8.60 (d, J=11.52Hz, 1H), 8.53 (d, J=3.2Hz, 1H), 8.47 (d, J=5.0,1H), 7.46 (d, J=4.0Hz, 1H), 7.36 (m, 3H), 7.04 (s, 2H), 3.94 (d, J=7.2Hz, 9H).High resolution mass spectrum：[M+H]+=423.1102 (Calcd=423.1111).
Application example 1：Such as Fig. 1, the fluorescence titration figure of probe in detecting cysteine.It is molten in the mixing of dimethyl sulfoxide (DMSO) and water 5 μM of probe is added in liquid, excites the lower probe fluorescence of itself very weak in wavelength 430nm light, but probe is dense with difference After the cysteine response of degree, fluorescence intensity changes significantly at 655nm, glimmering with being incremented by for semicystinol concentration Luminous intensity also strengthens therewith, and is in good linear relationship (R2=0.994), test limit reaches 240nmol/L.Experiment proves should Probe can be applied to the detection of cysteine with sensitivity.
Application example 2：Such as Fig. 2, the response time fluorogram of probe in detecting cysteine.In dimethyl sulfoxide (DMSO) and water Probe (5 μM) is added in mixed solution, excites the lower probe fluorescence of itself very weak in wavelength 430nm light, but adds 50 μM After cysteine, over time, the fluorescence intensity at 480nm starts gradually to strengthen, and is rung within 10 minutes Should be complete, fluorescence intensity no longer changes.Prove that the probe can realize the quick detection to cysteine with this.
Application example 3：Such as Fig. 3, the selective experimental fluorescence spectrogram of probe.In identical test system and test condition Under be separately added into different chaff interferences (1~27 be respectively：Probe in itself, alanine, arginine, aspartic acid, glycine, paddy Propylhomoserin, proline, phenylalanine, threonine, leucine, histidine, serine, tryptophan, methionine, S2O3 2-、SO4 2-、Mg2 +、Ca2+、Ba2+、K+、CO3 2-、NO3 -、NO2 -、HS-、GSH、Cys、Hcy).The results show, probe is to cysteine/homotype half Cystine has high selectivity, shows as the fluorescence intensity at 480nm and obvious enhancing occurs.But for other related dry Disturb thing to be almost not responding to, show as fluorescence intensity and keep constant
Application example 4：As Fig. 4, the pH for detecting environment optimize fluorescence spectra.Respectively different pH's (pH=3~10) 5 μM of probe and 50 μM of cysteine is added in dimethyl sulfoxide (DMSO)/water buffer solution, keeps other test conditions consistent, is surveyed Obtain the situation of probe response cysteine under different pH.As seen from the figure, probe keeps higher steady in this different pH environment certainly Qualitative, fluorescence intensity is almost unchanged.In addition, the fluorescence intensity between pH=3~7 after probe response cysteine gradually increases By force, optimum efficiency is reached when pH is neutral, and the fluorescence intensity between pH=7~10 after probe response cysteine is then Gradually reduce.Comprehensive Experiment data are understood：Probe can keep self stability under different pH environment, in the range of larger pH Cysteine can be preferably responded, and the optimum efficiency of measurement is issued in neutral environment, is advantageous to it in biological sample Application in detection.

Claims (8)

1. a kind of fluorescence probe for detecting cysteine, it is characterised in that its molecular structural formula is：
2. a kind of preparation method of the fluorescence probe of detection cysteine according to claim 1, it is characterised in that prepare Process comprises the following steps：
a：Indoles and cyanoacetic acid are dissolved in acid anhydrides, the lower heating reflux reaction of argon gas protection 4 hours, question response terminates, processing Obtain white solid product 3- cyano-acetamide indoles；
b：DMF is placed in ice bath and is precooled to 0-5 DEG C, POCl3 is then slowly added into, is stirred under ice bath Mix 1 hour, be then slowly added into 3,4,5- trimethoxy acetophenones, then be stirred at room temperature 3 hours, question response terminates, will be anti- Answer liquid to pour into trash ice, adjust pH value with sodium carbonate, there is yellow mercury oxide generation in reaction solution, filtering, separating-purifying obtain Huang The phenylpropen aldehyde derivatives of color solid product chloro；
c：By a, the phenylpropen aldehyde derivatives of 3- cyano-acetamides indoles and chloro in b are dissolved in absolute ethyl alcohol, add alkali Property catalyst, stirring reaction at room temperature has yellow solid precipitation in reaction solution, and filtering, separating-purifying obtain final product, i.e., The fluorescence probe of the described detection cysteine of invention.
3. application of the fluorescence probe according to claim 1 in cysteine is detected.
A kind of 4. preparation method of the fluorescence probe of detection cysteine according to claim 2, it is characterised in that step The stoichiometric proportion of raw material indoles and cyanoacetic acid is 1 in a:0.1~10.
A kind of 5. preparation method of the fluorescence probe of detection cysteine according to claim 2, it is characterised in that step PH value after being adjusted in b is 7~8.
A kind of 6. preparation method of the fluorescence probe of detection cysteine according to claim 2, it is characterised in that step The base catalyst species used in c is pyridine or triethylamine.
7. application of a kind of fluorescence probe according to claim 3 in cysteine is detected, it is characterised in that during detection The wavelength of selected optimal exciting light is between 420nm~440nm.
8. application of the fluorescence probe according to claim 3 in cysteine is detected, it is characterised in that selected during detection Dicyandiamide solution is the mixed solution of dimethyl sulfoxide (DMSO) and water.
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CN108299427A (en) * 2018-03-22 2018-07-20 泰山医学院 Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application
CN110498795A (en) * 2018-05-18 2019-11-26 泰山医学院 The pyridine derived species cysteine fluorescence probe of imidazo [1,2-a] and its application
CN111747918A (en) * 2020-07-17 2020-10-09 南京师范大学 Biflavone derivative fluorescent probe, preparation method thereof and application thereof in brain glioma imaging
CN113527193A (en) * 2020-04-18 2021-10-22 中国科学院精密测量科学与技术创新研究院 Probe for nuclear magnetic fluorine spectrum detection and application of probe in detection of sulfhydryl compounds
US11658726B2 (en) 2019-05-08 2023-05-23 Apple Inc. Beam tracking using downlink data reception and motion sensing information

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108299427A (en) * 2018-03-22 2018-07-20 泰山医学院 Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application
CN110498795A (en) * 2018-05-18 2019-11-26 泰山医学院 The pyridine derived species cysteine fluorescence probe of imidazo [1,2-a] and its application
US11658726B2 (en) 2019-05-08 2023-05-23 Apple Inc. Beam tracking using downlink data reception and motion sensing information
CN113527193A (en) * 2020-04-18 2021-10-22 中国科学院精密测量科学与技术创新研究院 Probe for nuclear magnetic fluorine spectrum detection and application of probe in detection of sulfhydryl compounds
CN113527193B (en) * 2020-04-18 2022-06-10 中国科学院精密测量科学与技术创新研究院 Probe for nuclear magnetic fluorine spectrum detection and application of probe in detection of sulfhydryl compounds
CN111747918A (en) * 2020-07-17 2020-10-09 南京师范大学 Biflavone derivative fluorescent probe, preparation method thereof and application thereof in brain glioma imaging
CN111747918B (en) * 2020-07-17 2022-05-20 南京师范大学 Biflavone derivative fluorescent probe, preparation method thereof and application thereof in brain glioma imaging

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