CN108484622B - Synthesis of multi-signal fluorescent probe and application thereof in simultaneous differential detection of Hcy, Cys and GSH - Google Patents
Synthesis of multi-signal fluorescent probe and application thereof in simultaneous differential detection of Hcy, Cys and GSH Download PDFInfo
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Abstract
The invention discloses a multi-signal fluorescent molecular probe for simultaneously distinguishing and detecting homocysteine (Hcy), cysteine (Cys) and Glutathione (GSH) in cells through three different fluorescent emission signals of blue, green and yellow, wherein the general formula of the chemical structure of the multi-signal fluorescent molecular probe is as follows:
Description
Technical Field
The invention belongs to the technical field of analytical chemistry, and particularly relates to synthesis of a multi-signal fluorescent probe, and application of the multi-signal fluorescent probe in simultaneously distinguishing, quantitatively detecting Hcy, Cys and GSH in an environment and three-channel fluorescence imaging of the Hcy, Cys and GSH in cells.
Background
Small molecule biological thiols such as cysteine (Cys), homocysteine (Hcy) and Glutathione (GSH) play an extremely important role in biological systems. Hcy can be synthesized by methionine in mammals under the assistance of various enzymes, the normal concentration of Hcy in serum is 5-12 μ M, and too high content of Hcy can cause folic acid and VB12Deficiency, senile dementia and other diseasesDisease (Chemical Communication,2014, 50, 6967-69669); in addition, intracellular Cys can be synthesized by Hcy at normal intracellular concentrations of 30-200. mu.M, and abnormal Cys content can lead to slow growth, cardiovascular and liver damage, and other diseases (Chemical Communication, 2013, 49, 9176-9178). GSH is the most abundant low molecular weight biological thiol in cells, can be synthesized in vivo by Cys, glutamic acid and glycine, has a normal concentration of 0.5-10 mM, can scavenge cytotoxin and free radicals as an antioxidant in cells, and maintain the in vivo redox reaction balance, and simultaneously maintain the normal function of Stem cells (Stem Cell Reports, 2018, 10, 600-. Because the three biological thiols have similar structures and reactivity, a biological metabolic process of converting Hcy into Cys and converting Cys into GSH exists in cells, the change of one content can cause the related change of the other two, and the occurrence of a plurality of diseases is closely related to the change of the content of the three biological thiols, so that the development of an efficient detection method/technology for simultaneously distinguishing, detecting and quantifying the three biological thiols Hcy, Cys and GSH, particularly the quantification of the endogenous Hcy, Cys and GSH in cells has very important significance for deeply understanding the action mechanism and the function of the three biological thiols and the early diagnosis of the diseases.
In recent years, multi-signal fluorescent probes have received much attention because they are capable of simultaneously monitoring and visualizing two or more analytes in living cells, as they provide a non-destructive, highly selective and sensitive, visualized, easy-to-operate analytical method. Although the structures and reactivity of the small molecule biological thiol homocysteine (Hcy), cysteine (Cys) and Glutathione (GSH) are similar, some single/double fluorescent channel fluorescent probes have been developed for detecting 1 or 2 of Hcy, Cys and GSH (e.g., Chinese patents CN105524055A, CN105588823A, CN105601658A, Journal of the American Chemical Society, 2014, 136, 574-577, Chemical Science, 2016, 7, 256-260, Analytical Chemistry, 2015, 87, 3460-3466, Chemistry-An Asian Journal, 2017, 12, 2098-2103, etc.). However, the reported thiol fluorescent probe cannot simultaneously distinguish and detect three biological thiols Hcy, Cys and GSH by using three channels, and particularly, the three channels of Hcy, Cys and GSH with different endogenous cell concentrations are analyzed and detected by using three-channel fluorescence imaging.
Disclosure of Invention
In view of the above circumstances, the present invention overcomes some deficiencies in the prior art, and an object of the present invention is to provide a fluorescent molecular probe for simultaneously detecting Hcy, Cys and GSH by using three-channel fluorescent signals, which can analyze Hcy, Cys and GSH in an imaging cell by using different fluorescent signals (colors), and provide some analysis and detection methods and ideas for the fields of analysis and detection, medical early diagnosis, etc.
The invention also aims to provide a synthesis and application method of the multi-signal thiol fluorescent molecular probe, which is simple in preparation method.
The specific technical scheme adopted for solving the problems is that a multi-signal fluorescent probe is synthesized and is simultaneously used for distinguishing and detecting Hcy, Cys and GSH, and the chemical structural general formula of the probe is as follows:
The method for simultaneously distinguishing and detecting the synthesis of the multi-signal fluorescent probe for Hcy, Cys and GSH is characterized in that the preparation method of the fluorescent molecular probe comprises the following steps:
step 1 Synthesis of 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one
a. Adding proper amount of diphenyl malonate and 8-hydroxy julolidine into anhydrous toluene, reacting for 8-12 hours at 100 ℃,
b. after the reaction is cooled to room temperature, filtering, washing the solid with diethyl ether, and then drying in vacuum to obtain a gray-green solid 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one;
step 2, synthesizing 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-formaldehyde
step 3. Synthesis of multiple Signal fluorescent probes (E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2, 3-f)]Pyrido [3,2,1-ij]Quinolin-10-yl) -2-cyanoacrylic acid (ester)
The invention discloses a using method for simultaneously distinguishing and detecting Hcy, Cys and GSH by using a multi-signal fluorescent molecular probe, which comprises the following steps: without specific reference, the probe molecules are typically dissolved at room temperature in an environment with a volume ratio of organic phase to aqueous phase of 4:6, the organic phase being dimethyl sulfoxide (DMSO) and the aqueous phase being Phosphate Buffered Saline (PBS) at pH = 7.4 and an aqueous solution of the analyte for analytical detection.
The multi-signal mercaptan fluorescent probe is characterized in that: the molecular fluorescent probe is dissolved by dimethyl sulfoxide (DMSO), probe molecules are dissolved in organic phase and aqueous phase (4:6, v/v) solutions, and after reacting with Hcy for 15 minutes at room temperature, 467nm strong blue fluorescence is emitted under 375nm excitation wavelength; after reacting with Cys at room temperature for 15 minutes, emitting strong green fluorescence of 503nm at the excitation wavelength of 400 nm; after 15 minutes of interaction with GSH, 568nm yellow fluorescence is emitted at an excitation wavelength of 500 nm. The probe itself has no significant fluorescence, and excitation at 375nm produces strong blue fluorescence when detecting Hcy, and excitation at the excitation wavelength (400/500 nm) of Cys/GSH has no fluorescence or very weak fluorescence, as do the other two. Therefore, the specific excitation and fluorescence emission signals are realized to detect the specific analyte, and when three kinds of biological thiol exist, the three kinds of biological thiol can be well distinguished by using different excitation and fluorescence emission signals. The fluorescent molecular probe realizes the simultaneous distinguishing and detection of Hcy, Cys and GSH under the same detection condition, and can detect NAC, Gly, Ala, His, Met, Thr, Lys, Asp, Glu, Pro, Ser, NaHS and NaHSO3Amino acids, sulfur-containing derivatives and amine derivatives such as EtSH, PhSH, n-Butylamine and anilineThe substances have no obvious response, and the detection limits on Hcy, Cys and GSH are respectively as low as 0.2 nM, 0.7 nM and 1 nM. Therefore, the multi-signal fluorescent molecular probe disclosed by the invention can realize high-sensitivity distinguishing quantitative detection of the three.
Drawings
FIG. 1 is a fluorescence image of L-02 (normal liver cell) endogenous Hcy, Cys and GSH of the multi-signal fluorescent probe of the present invention by blue, green and red fluorescence imaging.
Fig. 2 is a nuclear magnetic resonance hydrogen spectrum (R = ethyl) of the multi-signal fluorescent probe of the present invention.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
The general synthetic route of the multi-signal fluorescent molecular probe is shown as the following formula:
EXAMPLE 1 Synthesis of 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one
a. 16.3 g (63.4 mmol) of diphenyl malonate and 10.0 g (52.8 mmol) of 8-hydroxy julolidine are added into 100 mL of anhydrous toluene, and the mixture is stirred and reacted at 100 ℃ for 8 to 12 hours,
b. after the reaction was completed, the reaction solution was cooled to room temperature and then filtered, the filter cake was washed with diethyl ether, and the obtained solid was dried under vacuum to obtain 11.0 g of 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one as a pale green solid, with a yield of 80.9%.
EXAMPLE 2 Synthesis of 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-carbaldehyde
Example 3 Synthesis of multiple Signal fluorescent probes: (E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2, 3-f)]Pyrido [3,2,1-ij]Quinolin-10-yl) -2-cyanoacrylate (R = ethyl)
Example 4 Synthesis of multiple Signal fluorescent probes: (E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ]]Pyrido [3,2,1-ij]Quinolin-10-yl) -2-cyanoacrylic acid (R = hydrogen)
A. 1.0 g (3.29 mmol) of 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-carbaldehyde and 0.56 g (6.58 mmol) of cyanoacetic acid are mixed and added to 10 mL of anhydrous dichloromethane, 0.05 mL of triethylamine is added dropwise, and the reaction is stirred at room temperature;
B. after the reaction is completed, dropwise adding the reaction solution obtained in the step A into 50 mL of absolute ethyl alcohol, filtering, and drying the solid to obtain the fluorescent molecular probe (R = hydrogen) of claim 1E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ]]Pyrido [3,2,1-ij]Quinolin-10-yl) -2-cyanoacrylic acid 0.7 g, yield 57.3%.
Example 5 application of multiple-signal fluorescent molecular probe (R = ethyl probe is taken as an example here, no special description is provided, and other probe operation steps are similar) to distinguishing Hcy, Cys and GSH in-vitro environment
The spectrum property experiment of the multi-signal fluorescent molecular probe comprises the following steps: the probe was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1mM probe solution, and 1mM Cys, Hcy, and GSH aqueous solutions were prepared, respectively. The specific test mode is as follows: taking 20. mu.L of 1mM probe solution, 780. mu.L of analytically pure DMSO, the required amount of 1mM Cys/Hcy/GSH aqueous solution and the required amount of PBS buffer aqueous solution in a 2 mL sample tube, all tests were kept with a volume ratio of organic phase to aqueous phase of 4:6 (total volume of 2 mL per test sample), for example, fluorescence intensity after reaction of probe with Hcy when the required concentration of Hcy was 20. mu.M, samples were prepared: after 20. mu.L of 1mM probe solution, 780. mu.L of analytically pure DMSO, 40. mu.L of 1mM Hcy aqueous solution and 1160. mu.L of PBS buffer solution were put in a 2 mL sample tube and shaken at room temperature for 15 minutes, the fluorescence emission intensity of the sample can be measured at an excitation wavelength of 375nm, and other test operations are similar to the above steps. The multi-signal probe molecule realizes the distinguishing and detection of three biological thiols Hcy, Cys and GSH by using different excitation wavelengths and fluorescence emission signals, has high sensitivity, has detection limits as low as 0.2 nM, 0.7 nM and 1 nM respectively, and is very suitable for the imaging/quantitative analysis of endogenous Hcy, Cys and GSH of living cells.
Example 6L-02 (Normal liver cells) endogenous Hcy, Cys and GSH three-channel fluorescence imaging analysis
The L-02 cells are subcultured in a confocal dish cell culture medium, after 24 hours of culture under a standard growth condition, a proper amount of probe (5 mu M) is added to continue to be cultured for 30 minutes under the standard growth condition, then photography is carried out under a confocal fluorescence microscope, fluorescence imaging is carried out on endogenous Hcy, Cys and GSH of the L-02 cells by using blue, green and red fluorescence channels respectively, as can be seen from figure 1, the multi-signal fluorescence probe successfully realizes three-channel fluorescence imaging analysis of endogenous Hcy, Cys and GSH in the cells, reflects the content of Hcy, Cys and GSH to a certain extent in the fluorescence intensity, has the potential capability of quantifying Hcy, Cys and GSCyH, and has great application value in the fields of biochemistry, analysis and detection, early diagnosis of diseases and the like.
The synthesis of the multi-signal fluorescent probe and the application thereof in simultaneous distinguishing and detecting Hcy, Cys and GSH develop a high-efficiency simple multi-channel thiol detecting probe which can be used for simultaneously distinguishing and detecting Hcy, Cys and GSH, and different fluorescent substances are generated by utilizing different chemical reactions of the probe with Hcy, Cys and GSH under the same probe and the same detection condition, so that the fluorescent probes emit blue, green and yellow fluorescence under specific excitation wavelength to achieve the purpose of simultaneously distinguishing and detecting, successfully realize the endogenous Hcy, Cys and GSH in a three-channel simultaneous fluorescence imaging cell, and have the potential capability of quantifying Hcy, Cys and GSH. It is expected to provide some ideas for the development of multi-signal biological thiol fluorescent probes in the future. While the present invention has been described in detail with reference to the preferred embodiments, it should be understood that the above description should not be taken as limiting the invention. Various modifications and alterations to this invention will become apparent to those skilled in the art upon reading the foregoing description. Therefore, the synthesis of multi-signal fluorescent probe with the technical characteristics described herein and the application thereof in simultaneously distinguishing and detecting Hcy, Cys and GSH are all within the protection scope of the present patent.
Claims (4)
1. The multi-signal fluorescent probe is characterized in that the chemical structural general formula of the fluorescent molecular probe is as follows:
2. The method for preparing the multi-signal fluorescent probe of claim 1, wherein the method for preparing the fluorescent molecular probe comprises the following steps:
step 1 Synthesis of 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one
a. Adding proper amount of diphenyl malonate and 8-hydroxy julolidine into anhydrous toluene, reacting for 8-12 hours at 100 ℃,
b. after the reaction is cooled to room temperature, filtering, washing the solid with diethyl ether, and then drying in vacuum to obtain a gray-green solid 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one;
step 2, synthesizing 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-formaldehyde
I. Under the protection of nitrogen, adding a proper amount of dry redistilled N, N-Dimethylformamide (DMF) slowly into equal volume of phosphorus oxychloride (POCl)3) In 20-5Stirring for 30 minutes at 0 ℃ to obtain a red solution,
II, dissolving 9-hydroxy-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinolin-11-one in an appropriate amount of N, N-dimethylformamide, dropwise adding the mixture into the mixed solution in the step I, and continuously stirring and reacting the mixture at 60 ℃ for 12 hours under the protection of nitrogen;
III, pouring the reaction liquid obtained in the step II into a proper amount of ice water, adjusting the pH value to 5-6 by using a 20% NaOH solution, generating a large amount of precipitates, filtering, washing the solids for 3 times by using a proper amount of deionized water, and drying in vacuum to obtain 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-formaldehyde;
step 3, synthesizing a multi-signal fluorescent probe (E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-f ] pyrido [3,2,1-ij ] quinoline-10-yl) -2-cyanoacrylate alkyl ester
i. Adding 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-formaldehyde and corresponding alkyl cyanoacetate into a proper amount of anhydrous dichloromethane, dropwise adding a proper amount of triethylamine, and stirring at room temperature for reaction;
ii, dropwise adding the reaction solution obtained in the step i into a proper amount of anhydrous ethanol, filtering, and drying the obtained solid in vacuum to obtain the fluorescent molecular probe (E) -3- (9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H-pyrano [2,3-f ] pyrido [3,2,1-ij ] quinolin-10-yl) -2-cyanoacrylate alkyl ester disclosed in claim 1.
3. The method of claim 2, wherein the molar ratio of 9-chloro-11-oxo-2, 3,6, 7-tetrahydro-1H, 5H, 11H pyrano [2,3-F ] pyrido [3,2,1-ij ] quinoline-10-carbaldehyde to alkyl cyanoacetate in step i is 1: 1.5-2.
4. The use of the multi-signal fluorescent probe of claim 1 in the context of its preparation for quantitative detection of Hcy, Cys and GSH, for simultaneous differential imaging of Hcy, Cys and GSH in a cell.
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| CN109912612B (en) * | 2019-04-04 | 2021-05-11 | 郑州大学 | Synthesis, preparation and application of fluorescent probe for identifying Cys, GSH and HOCl based on molecular logic gate |
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| CN111718319A (en) * | 2020-07-27 | 2020-09-29 | 山西大学 | Fluorescent probe for distinguishing and detecting mercaptan and monitoring Cys/GSH metabolism and preparation method thereof |
| CN113512034B (en) * | 2021-03-17 | 2022-08-09 | 湖南师范大学 | Synthesis of multi-signal fluorescent probe and simultaneous Cys and SO distinguishing thereof 2 GSH and Hcy |
| CN113121541B (en) * | 2021-03-17 | 2022-06-07 | 湖南师范大学 | Synthesis and application of fluorescent probe capable of distinguishing gold ions Au3+ and palladium simultaneously |
| CN113121552A (en) * | 2021-03-17 | 2021-07-16 | 湖南师范大学 | Synthesis and application of fluorescent probe for selectively detecting cysteine |
| CN114577929A (en) * | 2022-02-14 | 2022-06-03 | 北京优量云产业计量技术创新研究院有限公司 | Method for measuring reduced glutathione |
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