CN113185506B - Synthesis of multi-signal fluorescent probe and application thereof in detection of Cys, GSH and Hcy - Google Patents
Synthesis of multi-signal fluorescent probe and application thereof in detection of Cys, GSH and Hcy Download PDFInfo
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Abstract
The invention discloses a synthesis of a multi-signal fluorescent probe and an application method thereof in quantifying serum total cysteine (Cys) and homocysteine (Hcy) and simultaneously distinguishing Cys, Glutathione (GSH) and Hcy in a fluorescence imaging cell/living body, wherein the molecular probe has the following chemical structural formula:
. The fluorescent probe disclosed by the invention has a plurality of reaction sites with controllable activity, and can realize that three channels of blue, green and yellow are used for respectively detecting Cys λ ex/λ em=360/453 nm）、GSH（λ ex/λ em=415/513 nm) and Hcy (c: λ ex/λ em=488/542 nm). The kit has good selectivity, high sensitivity and strong anti-interference performance, and can be used for directly and simultaneously quantifying the total Cys and Hcy level in blood plasma and distinguishing Cys, GSH and Hcy in fluorescence imaging cells/living bodies.
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 probe in preparation of devices for directly quantifying total Cys and Hcy in blood plasma, simultaneously quantifying and detecting Cys, GSH and Hcy in an environment, and simultaneously distinguishing Cys, GSH and Hcy in fluorescence imaging in a biological sample.
Background
Homocysteine is an amino acid of a sulfur-containing molecule, belongs to a non-essential amino acid of a human body, and is an intermediate product for metabolizing methionine in protein taken by the human body into glutathione (the most important antioxidant in the body) and S-adenosylmethionine (SAMe). Normally, the Hcy in plasma is at a low level, but when the Hcy in blood is increased (more than or equal to 10 mu mol/L), the Hcy has a great influence on the health of a human body, and in recent years, the research finds that the prediction accuracy of the Hcy level in blood on myocardial infarction is almost 40 times of that of cholesterol; high concentrations of Hcy are independent risk factors for coronary artery disease, cerebrovascular disease, and peripheral vascular disease. Meanwhile, Hcy can be vitamin B in vivo6As a coenzyme, inβCystathionine is formed under catalysis of cystathionine synthase (CBS) and cleaved to cysteine (Cys) under catalysis of cystathionine lyase. Cys is involved in protein synthesis, detoxification, metal binding, post-translational modification of proteins, and metabolism as an antioxidant in vivo. However, Cys deficiency can cause a variety of diseases, such as growth retardation, skin damage, lethargy, liver damage and physical weakness in infants, and the concentration of Cys in plasma is 150-300. mu. mol/L. The existing methods for quantifying the Hcy and the Cys in the blood plasma mainly comprise chromatography, enzyme-linked immunosorbent assay, chemiluminescence, a circulating enzyme method and the like, but the methods have the defects of long time consumption, high cost, special instruments and the like, so that the detection of the Hcy and the Cys levels in the blood serum is often ignored in health examination. Therefore, an efficient detection method/technology is developed for simultaneously quantifying the total Hcy and Cys levels of the plasma, and the method has very important clinical significance and wide application prospect.
In recent years, fluorescent probes have attracted much attention because they have high selectivity, high sensitivity, and easy operation, and can monitor and visualize biomolecules in living cells. To date, several fluorescent probes have been reported for the selective detection of Hcy or Cys in plasma (e.g., chinese patent CN 105524055A;J. Am. Chem. Soc., 2004, 126, 3400-3401；J. Am. Chem. Soc., 2005, 127, 15949-15958；Nat. Protocols, 2006, 1, 2759-2762；Chem. Commun., 2014, 50, 3071-3073；Chem. Commun., 2014, 50, 13668-13671；Chem. Commun.2014, 50, 6967-69669, etc.). However, the reported fluorescent probes can only detect the Hcy added in the plasma, have the problems of low sensitivity, poor selectivity and the like, and do not realize direct and accurate quantification of the Hcy and Cys in the plasma/serum. Meanwhile, several small-molecule fluorescent probes are reported to be used for distinguishing Cys, GSH and Hcy at the same time, but the sensitivity and the imaging signal-to-back ratio are low, and the requirements of endogenous mercaptan and the like in cells/living bodies imaged at the same time cannot be met.
Disclosure of Invention
In view of the above, the present invention overcomes some deficiencies of the prior art, and aims to provide a synthesis of a multi-signal fluorescent probe, and an application method of the probe in direct quantification of total Cys and Hcy in plasma, and an application of the probe in preparation of a device for simultaneously and quantitatively detecting Cys, GSH and Hcy in an environment and simultaneously distinguishing Cys, GSH and Hcy in fluorescence imaging in a biological sample.
The specific technical scheme adopted by the invention for solving the problems is that the synthesis of a multi-signal fluorescent probe and the application of the multi-signal fluorescent probe in the detection of Cys, GSH and Hcy are as follows:
the synthesis of the multi-signal fluorescent probe for simultaneously distinguishing Cys, GSH and Hcy is characterized in that the preparation method of the fluorescent molecular probe comprises the following steps:
step 1. Synthesis of 3,3' - ((4- (butylsulfanyl) -3-formyl-2-oxo-2)H-pyran-7-yl) azepindiyl) dipropionic acid dimethyl ester
The use method of the multi-signal fluorescent molecular probe for simultaneously distinguishing Cys, GSH and Hcy 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 for detection of Cys and GSH, a volume ratio of organic phase to aqueous phase of 7:3 for detection of Hcy, an organic phase of dimethyl sulfoxide (DMSO), an aqueous phase of Phosphate Buffered Saline (PBS) at pH = 7.4, and an aqueous solution of the analyte.
The specific characteristics of the multi-signal fluorescent probe for detecting Cys, GSH and Hcy are as follows: the molecular probe is dissolved by dimethyl sulfoxide (DMSO), the probe is dissolved in an organic phase and aqueous phase (4: 6, v/v) solution, and after the probe reacts with Cys at room temperature for 30 minutes, strong blue fluorescence at 453 nm is emitted under the excitation wavelength of 360 nm; after reacting with GSH for 30 minutes at room temperature, emitting strong green fluorescence at 513 nm under the excitation wavelength of 415 nm; the probe molecules are dissolved in organic phase and aqueous phase (7: 3, v/v) solutions, and after reacting with Hcy at room temperature for 60 minutes, strong yellow-green fluorescence at 542 nm is emitted under the excitation wavelength of 488 nm. The probe has no obvious fluorescence, the selectivity is better under different conditions, the detection limit and the quantification limit of Hcy detection of the probe are respectively 0.5 nM and 1.7 nM, and the detection limit and the quantification limit of GSH detection are respectively 8.0 nM and 27.5 nM. Therefore, specific excitation and fluorescence emission signals are realized to detect specific analytes, and no obvious response is generated to other common amino acids, active oxygen and active nitrogen species.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of the fluorescent probe of the present invention.
FIG. 2 shows the fluorescence emission spectrum of the fluorescent probe of the present invention in the system of DMSO and aqueous solution (volume ratio of 4: 6) as a function of cysteine concentration, with wavelength on the abscissa and fluorescence intensity on the ordinate.
FIG. 3 shows the fluorescence emission spectrum of the fluorescent probe of the present invention in the system of DMSO and aqueous solution (volume ratio of 7: 3) as the change of homocysteine concentration, with the abscissa as wavelength and the ordinate as fluorescence intensity.
FIG. 4 shows the simultaneous imaging of Cys, GSH and Hcy in SH-SY5Y cells by the fluorescent probe of the present invention.
Detailed Description
The invention is further described below with reference to the accompanying drawings.
The synthetic route of the multi-signal fluorescent probe is as follows:
EXAMPLE 1 Synthesis of 3,3' - ((4- (butylsulfanyl) -3-formyl-2-oxo-2)H-pyran-7-yl) azepindiyl) dipropionic acid dimethyl ester
a. 3.0 g (5.68 mmol) of 3,3' - ((4-chloro-3-formyl-2-oxo)HDimethyl-pyran-7-yl) azepinyl) dipropionate was added to 20 mL of methylene chloride, and 615.2 mg (6.82 mmol) of n-butylmercaptan and 690.3 mg (5.68 mmol) of triethylamine were further added, and the mixture was stirred at room temperature for reaction for 6 hours;
b. after the reaction is completed, the solvent is spin-dried on a rotary evaporator, and the yellow solid product is obtained by column chromatography purification, wherein the yield is 2.0 g, and the yield is 78.3%.
Example 2 Synthesis of Probe dimethyl 3,3' - ((3- (2- (benzo [ b ], ])d]Thiazol-2-yl) -2-cyanovinyl) -4- (butylsulfanyl) -2-oxo-2H-pyran-7-yl) azepindiyl ((E)E) -dipropionic acid ester
Example 3 application of the multiple Signal fluorescent Probe of the present invention to simultaneously differentiate Cys, GSH and Hcy
The experiment for detecting the spectral properties of Cys, GSH and Hcy by using the fluorescent molecular probe disclosed by the invention comprises the following steps: the probe was dissolved in dimethyl sulfoxide (DMSO) to prepare a 1 mM probe solution, and 1 mM aqueous solutions of Cys, GSH, and Hcy were prepared, respectively. The specific test mode for detecting Cys/GSH is as follows: taking 20 mu L of probe solution (1 mM), 780 mu L of analytically pure DMSO, the required amount of 1 mM aqueous Cys/GSH solution and the required amount of PBS buffer aqueous solution in a 2 mL sample tube, keeping the final volume ratio of the organic phase to the aqueous phase of 4:6 (the total volume of each test sample is 2 mL) in all tests, shaking uniformly at room temperature for 30 minutes, and then measuring the fluorescence emission spectra of Cys and GSH by using excitation wavelengths of 360nm and 415 nm respectively; the specific test mode for detecting Hcy is as follows: mu.L of probe solution (1 mM), 1380. mu.L of analytically pure DMSO, the required amount of 1 mM aqueous homocysteine and the required amount of PBS buffer in 2 mL sample tubes were taken, the final volume ratio of the organic phase to the aqueous phase was maintained at 7:3 for all tests (total volume of 2 mL for each test sample), and the fluorescence emission spectra were measured at 488nm excitation wavelength after shaking at room temperature for 60 minutes.
Example 4 application of the fluorescent probes of the present invention to direct quantification of serum total Cys and Hcy
The protocol for direct quantification of total Cys and Hcy in plasma was as follows: take 0.5mL of fresh serum was reduced for 30 minutes by the addition of tris (2-carboxyethyl) phosphine (0.5 mL, 10 mM). 20. mu.L of the probe solution (1 mM), 780. mu.L of analytical DMSO, 1140. mu.L of PBS buffer and 60. mu.L of the above serum solution were reacted at room temperature for 30 minutes, and then the fluorescence emission spectrum was measured at an excitation wavelength of 360 nm; 20. mu.L of the probe solution (1 mM), 1380. mu.L of analytical DMSO, 780. mu.L of PBS buffer and 20. mu.L of the above serum solution were taken, reacted at room temperature for 60 minutes, and then fluorescence emission spectra thereof were measured at an excitation wavelength of 488nm, and the concentrations of total Cys and Hcy in the serum were calculated from a standard curve. The results of the 10 serum samples are shown in the following table:
| serial number | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 |
| Cys（μM） | 253.5 | 252.3 | 198.4 | 259.8 | 238.4 | 299.1 | 330.7 | 331.2 | 359.3 | 362.0 |
| Hcy（μM） | 7.9 | 12.0 | 14.2 | 14.5 | 16.8 | 22.3 | 26.6 | 24.1 | 28.5 | 39.5 |
Example 5 use of simultaneous differentiation of endogenous Cys, GSH and Hcy in imaged SH-SY5Y cells
SH-SY5Y cells are passaged into a confocal dish cell culture medium, after being cultured for 24 hours under standard growth conditions, a proper amount of probe (5 mu M) is added to continue culturing for 30 minutes under the standard growth conditions, then photography is carried out under a confocal fluorescence microscope, and fluorescence imaging is carried out by using blue, green and red fluorescence channels respectively. As can be seen from FIG. 4, the multi-signal fluorescent probe of the invention successfully realizes the triple-channel fluorescence imaging analysis of endogenous Cys, GSH and Hcy in cells, and has great application value in the fields of biochemistry, analytical detection, environmental science and the like.
The synthesis of the multi-signal fluorescent probe and the application of the multi-signal fluorescent probe in detecting Cys, GSH and Hcy develop an application method for quantifying total Cys and Hcy in serum, which is high in efficiency, simple, low in cost and high in accuracy, and can rapidly quantify total Cys and Hcy in serum; meanwhile, the simultaneous detection and imaging analysis of Cys, GSH and Hcy in the environment and biological samples can be realized. 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 probes with the technical characteristics described herein and the application thereof in the detection of Cys, GSH and Hcy fall into the protection scope of the present patent.
Claims (5)
1. The multi-signal fluorescent probe for detecting Cys, GSH and Hcy is characterized in that the chemical structural formula of the fluorescent molecular probe is as follows:
2. the method for synthesizing a multi-signal fluorescent probe according to claim 1, wherein the method for preparing the fluorescent molecular probe comprises the following steps:
step 1. Synthesis of 3,3' - ((4- (butylsulfanyl) -3-formyl-2-oxo-2)H-pyran-7-yl) azepindiyl) dipropionic acid dimethyl ester
step 2. Synthesis of Probe dimethyl 3,3' - ((3- (2- (benzo [ b ], ])d]Thiazol-2-yl) -2-cyanovinyl) -4- (butylsulfanyl) -2-oxo-2H-pyran-7-yl) azepindiyl ((E)E) -dipropionic acid ester
3. Use of the multi-signal fluorescent probe of claim 1, wherein the fluorescent molecular probe is used for preparing a reagent for directly quantifying total Cys and Hcy in plasma.
4. The use of the multi-signal fluorescent probe for detecting Cys, GSH and Hcy according to claim 1, wherein the fluorescent molecular probe can be used for preparing a device for simultaneously and quantitatively detecting Cys, GSH and Hcy in an environment and simultaneously distinguishing Cys, GSH and Hcy in a biological sample for fluorescence imaging.
5. Use according to claim 3, wherein the method of direct quantitative containment comprises the steps of:
A. reduction of oxidized Cys and oxidized Hcy in serum: the serum was mixed with an equal volume of 10mM tris (2-carboxyethyl) phosphine and incubated at 37 ℃ for 20 minutes;
B. fluorescence detection: adding a proper amount of the serum solution obtained in the step A into a probe solution with the volume ratio of dimethyl sulfoxide to PBS buffer solution being 4/6 for quantifying the total Cys in the serum; adding a proper amount of the serum solution obtained in the step A into a probe solution with the volume ratio of dimethyl sulfoxide to PBS buffer solution being 7/3 for quantifying the total Hcy of the serum; oscillating the obtained test solution at room temperature for 30min, and measuring the fluorescence intensity of the maximum emission wavelength by 360nm excitation; the latter is oscillated for 60min at room temperature, and the fluorescence intensity of the maximum emission wavelength of the sample is measured by 488nm excitation;
C. and (4) calculating a result: and (4) calculating the concentrations of total Cys and Hcy in the serum according to the standard curve prepared by the experiment and the fluorescence intensity value detected in the step B by using mapping software.
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