CN110357867B - Glutathione ratio fluorescence sensor based on disulfide bond and preparation and application thereof - Google Patents
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Abstract
A glutathione ratio fluorescence sensor based on disulfide bonds, and preparation and application thereof, belonging to the technical field of organic chemistry and analytical chemistry. The preparation of the ratiometric fluorescence sensor comprises the steps of firstly reacting a compound 4-bromo-1, 8-naphthalic anhydride and morpholine in ethylene glycol monomethyl ether to obtain a compound 1; then reacting the compound 1 with cystine diamine hydrochloride and triethylamine to obtain a compound 2; finally, the compound 2 and coumarin derivative are reacted to obtain NAP-CR. According to the invention, the coumarin fluorophore with blue light emission and the naphthalimide organic fluorophore with green light emission are connected through the disulfide bond and integrated into one fluorescent sensor molecule through reasonable and ingenious design, and after glutathione is added, the disulfide bond is broken to increase the distance between the two fluorophores, so that the energy resonance transfer efficiency is reduced, the fluorescence generation ratio is changed, and the dual-channel fluorescent recognition of the glutathione is further realized.
Description
Technical Field
The invention belongs to the technical field of organic chemistry and analytical chemistry, and particularly relates to a glutathione ratio fluorescence sensor based on a disulfide bond, and preparation and application thereof.
Background
Glutathione exists in almost every cell of a body, is an important metabolic substance for regulating cells, is indispensable to maintaining a normal immune system and a biochemical defense system in a human body, and has important significance for monitoring diseases and early diagnosis and treatment by realizing the real-time and rapid detection of the glutathione.
The fluorescence sensor has high detection sensitivity, is real-time and quick, and is widely applied to various fields of biology, clinical medicine and the like. In particular, fluorescence ratio sensors can detect targets by using the ratio of two different internal emission wavelengths, and compared with sensors that rely solely on fluorescence intensity detection, the fluorescence ratio sensors avoid interference of instruments, biological environments, sensor concentrations and autofluorescence in organisms, and are more and more favored by researchers (Chemical Society Reviews,2016.45(10): 2976-. The fluorescence probe adopts two energy-matched fluorophores as a fluorescence donor and a fluorescence acceptor respectively, realizes dual-wavelength fluorescence detection through a proper connection mode, and is widely applied to detection in organisms at present.
One of the major problems often faced when fluorescent probes are used in practical applications for detecting analytes in environmental and biological systems is the accuracy of fluorescence measurement, because the fluorescence intensity of fluorescent probes is often affected by a series of factors, such as probe concentration, excitation light intensity, detection efficiency, photobleaching, probe leakage, cell thickness, etc., when detecting analytes. Therefore, when the fluorescence intensity is measured at a single wavelength, the fluorescence signal data is often distorted in practical applications, thereby causing errors in the measurement result. To solve the problem of fluorescence signal artifacts encountered with this single wavelength fluorescence intensity variation based fluorescence measurement method, fluorescence ratiometric probes are commonly used.
Disclosure of Invention
Aiming at the defects, the invention provides the glutathione ratio fluorescence sensor based on the disulfide bond, which can realize the fluorescence detection of glutathione in cells and has the characteristics of quick response and high sensitivity.
The technical scheme adopted by the invention for solving the technical problems is as follows: a glutathione ratio fluorescence sensor based on disulfide bonds has a structure shown as a formula I:
the synthetic route of the preparation reaction of the glutathione ratio fluorescence sensor based on disulfide bonds is shown as follows.
The preparation method of the compound comprises the following steps:
a. the compound 4-bromo-1, 8-naphthalic anhydride and morpholine with three times of molar weight are added into ethylene glycol monomethyl ether (the added amount is based on 4-bromo-1, 8-naphthalic anhydride, and is 1 mmol: 10-15 ml), heated at 100 ℃ for reaction for two hours, cooled to room temperature, and filtered to obtain a crude product compound 1.
b. Dissolving the compound 1 in ethanol (the addition amount is based on the compound 1, and 1 mmol: 10-15 ml), adding five times of mol of cystine diamine hydrochloride and ten times of triethylamine, reacting for six hours at 80 ℃, cooling, concentrating, precipitating, filtering, and separating the crude product by column chromatography to obtain a yellow compound 2.
c. And reacting the compound 2 and an equimolar amount of the compound 3 (coumarin derivative) and an equimolar amount of triethylamine in dichloromethane (the added amount is based on the compound 2 and is 1 mmol: 10-15 ml) at normal temperature for two hours, and after the TLC determines that the reaction is finished, carrying out column chromatography to separate a target product NAP-CR.
The invention also claims the application of the glutathione ratio fluorescence sensor based on the disulfide bond. Before glutathione is added, the fluorescence of the compound NAP-CR solution only shows fluorescence emission at 532nm of naphthalimide, while the fluorescence of coumarin at 463nm is hardly seen, because the fluorescence of coumarin disappears due to fluorescence resonance energy transfer between the compound coumarin and the naphthalimide. When glutathione was added, the fluorescence gradually decreased at 532nm and increased at 463nm, indicating that the energy transfer between the two fluorophores, naphthalimide and coumarin, gradually decreased. Namely, after glutathione is added, the disulfide bond in the ratio fluorescence sensor NAP-CR is broken, so that the distance between coumarin and naphthalimide is obviously changed, and the fluorescence resonance energy transfer between two fluorophores is controlled by reasonably regulating and controlling the distance, so that the fluorescence of the ratio fluorescence sensor is obviously changed before and after glutathione identification.
Has the advantages that:
the invention designs a ratiometric fluorescent molecular probe taking naphthalimide and coumarin fluorophore as a donor-acceptor system based on a fluorescence resonance transfer mechanism by taking a disulfide bond as a glutathione recognition site. The energy of the naphthalimide and the energy of the coumarin fluorophore are matched, the photophysical property is excellent, and the recognition of the glutathione by using the naphthalimide and the coumarin fluorophore as the fluorescence resonance energy transfer fluorescent probe of a fluorescence donor-acceptor provides more valuable information for the recognition of the glutathione in organisms.
According to the invention, the coumarin fluorophore with blue light emission and the naphthalimide organic fluorophore with green light emission are connected through the disulfide bond and integrated into one fluorescent sensor molecule through reasonable and ingenious design, and after glutathione is added, the disulfide bond is broken to increase the distance between the two fluorophores, so that the energy resonance transfer efficiency is reduced, the fluorescence generation ratio is changed, and the dual-channel fluorescent recognition of the glutathione is further realized.
Drawings
FIG. 1 is a hydrogen spectrum of Compound 2;
FIG. 2 is a carbon spectrum of Compound 2;
FIG. 3 is a hydrogen spectrum of Compound NAP-CR;
FIG. 4 is a carbon spectrum diagram of Compound NAP-CR;
FIG. 5 is an ultraviolet absorption spectrum of Compound NAP-CR;
FIG. 6 is a graph showing a change in fluorescence spectrum of Compound NAP-CR;
FIG. 7 is a graph showing the relationship between the fluorescence intensity at 463nm and 532nm of the compound NAP-CR with time.
Detailed Description
The invention is described in more detail below with reference to specific examples, without limiting the scope of the invention. Unless otherwise specified, the experimental methods adopted by the invention are all conventional methods, and experimental equipment, materials, reagents and the like used in the experimental method can be purchased from chemical companies.
Synthesis of the Compound of example 1
(a) Synthesis of Compound 1
Morpholine (4.74g, 54.3mmoL) was slowly dropped into 30 ml of ethylene glycol monomethyl ether containing 4-bromo-1, 8-naphthalenic anhydride (5g, 18.1mmoL), and the mixture was heated at 100 ℃ for two hours, and the TLC trace point plate was used to find that the reaction of the starting material was complete, and the mixture was cooled and left to stand to precipitate yellow needle-like crystals, which were filtered to obtain 3.48g of crude product with a yield of 68%. The crude product was directly subjected to the next reaction without treatment.
(b) Synthesis of Compound 2
Taking compound 1(1g, 3.53mmol) and five times molar amount of cystine diamine hydrochloride, placing in 50 ml ethanol, heating and refluxing at 80 ℃, then adding ten times molar amount of triethylamine, after about six hours of reaction, TLC tracing point plate finds that the raw material is completely reacted, decompression and spin-drying, column chromatography separation, and distillate is mixed solvent of dichloromethane and methanol (V)Methylene dichloride：VMethanol20: 1) rf value 0.4, product 884mg, yield 60%.1H NMR(500MHz,CDCl3):δ(ppm)8.6(s,2H,-NH2),8.46-8.52(m,2H,-ArH), 8.35(t,1H,J＝6.8Hz,-ArH),7.65(1H,-ArH),7.18(1H,-ArH),4.41(2H, -CH2CH2-),4.01(m,4H,-CH2CH3),3.47(m,2H,-CH2CH2-),2.24-3.29(m,6H),3.00 (2H,-CH2CH2-).13C NMR(125MHz,CDCl3):δ(ppm)164.32,163.86,155.94, 133.04,131.53,130,45,129.77,125.90,125.88,122.71,116.35,115.04,66.94,53.40, 39.34,38.99,35.49,35.33.
(c) Synthesis of Compound NAP-CR
Dissolving 100mg of Compound 2 inAn equimolar amount of triethylamine was added to 10 ml of dichloromethane, and stirred at room temperature, an equimolar amount of a solution of compound 3 (coumarin derivative, tetrahedron.2010; 66: 9762-.1H NMR(500MHz,CDCl3) δ (ppm)9.10 (broad peak, 1H, -NH),8.70(s,1H, -ArH),8.60(d,1H, J-7.0 Hz, -ArH),8.55(d,1H, J-8.0 Hz, -ArH),8.44(d,1H, J-8.5 Hz, -ArH),7.72(d,1H, J-7.8 Hz, -ArH),7.44(d, 1H, J-8.5 Hz, -ArH),7.24(d,1H, J-8.0 Hz, -ArH),6.67(d,1H, J-8.5 Hz, -ArH), 6.52(s,1H, -ArH),4.56(t,2H, J-7.2, -CH, t,2H, J-7.2, -CH, -NH), 8.5Hz, and-ArH2CH2-),4.03(m,4H,-CH2CH2-),3.80 (t,2H,J＝6.8Hz,-CH2CH2-),3.47(m,4H,J＝7.0Hz,-CH2CH3),3.29(m,4H, -CH2CH2-),3.10(t,2H,J＝7.2Hz,-CH2CH2-),3.02(t,2H,J＝6.8Hz,-CH2CH2-), 1.26(t,6H,J＝7.0Hz,-CH2CH3).13C NMR(125MHz,CDCl3):δ(ppm)164.35, 163.86,163.34,162.65,157.66,155.74,152.43,148.08,132.75,131.39,131.17, 130.22,129.96,126.15,125.90,123.16,116.97,115.02,110.34,109.99,108.48, 96.71,67.00,53.45,45.18,39.46,38.77,37.52,35.98,12.43.
Ultraviolet absorption Spectroscopy of the Compound of example 2
Weighing compound 3 (coumarin derivative), compound 2 (naphthalimide derivative) and compound NAP-CR, and respectively preparing into 10-5The ultraviolet absorption spectrum of the ethanol solution with the diameter of mu m is measured, and the test result is shown in figure 5. As can be seen from FIG. 5, the UV absorption of the compound NAP-CR covers the UV absorption spectrum of the naphthalimide and coumarin derivatives constituting it, since the absorption peaks of the two are relatively close to each other, and finally a broad absorption peak is formed, indicating that there is no significant interaction between the naphthalimide and coumarin derivatives in the ground state.
EXAMPLE 3 fluorescence Spectroscopy of the Compound NAP-CR at different excitation wavelengths
The compound NAP-CR of example 1c was weighed and formulated into 10-5μ m solution (DMSO: H)2O9: 1), the fluorescence change with time after 100 molar times of glutathione was added is shown in fig. 6, and the fluorescence intensity ratio at 463nm and 532nm is shown in fig. 7. Before glutathione is added, the fluorescence of the compound NAP-CR solution only shows the fluorescence emission at 532nm of naphthalimide, because the fluorescence of coumarin disappears due to the fluorescence resonance energy transfer of the compounds coumarin and naphthalimide. When glutathione was added, the fluorescence gradually decreased at 532nm and increased at 463 nm. This indicates that the addition of glutathione results in the cleavage of the disulfide bond and an increase in the distance between coumarin and naphthalimide fluorophores beyond the range where fluorescence resonance energy transfer can occur, at which time coumarin fluorescence is released.
The above description is only for the purpose of creating a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can substitute or change the technical solution and the inventive concept of the present invention within the technical scope of the present invention.
Claims (6)
1. A preparation method of a glutathione ratio fluorescence sensor based on disulfide bonds is characterized in that the synthetic route of the ratio fluorescence sensor is as follows:
the preparation method comprises the following specific steps:
s1, heating a compound 4-bromo-1, 8-naphthalic anhydride and morpholine in ethylene glycol monomethyl ether for reaction for two hours, cooling to room temperature, and filtering to obtain a crude product compound 1;
s2, dissolving the compound 1 in ethanol, adding cystine diamine hydrochloride and triethylamine, heating for reacting for six hours, cooling, concentrating, precipitating and filtering, and obtaining a yellow compound 2 from a crude product by using a column chromatography separation method;
s3, mixing the compound 2 with an equimolar amount of coumarin derivative,
equimolar triethylamine is put into dichloromethane to react for two hours at normal temperature, and after TLC determines that the reaction is finished, the target product NAP-CR is separated by column chromatography.
2. The method for preparing a glutathione-ratiometric fluorescence sensor based on disulfide bonds as claimed in claim 1, wherein the molar amount of morpholine added in step S1 is three times that of 4-bromo-1, 8-naphthalic anhydride; the amount of the added ethylene glycol monomethyl ether is based on 4-bromo-1, 8-naphthalic anhydride, and is determined according to the weight ratio of 4-bromo-1, 8-naphthalic anhydride: ethylene glycol monomethyl ether ═ 1 mmol: adding 10-15 ml of the mixture; the heating temperature was 100 ℃.
3. The method for preparing a glutathione ratiometric fluorescence sensor based on disulfide bonds as claimed in claim 1, wherein the ethanol in the step S2 is based on the compound 1, and the ratio of the glutathione to the glutathione is determined according to the following formula 1: ethanol 1 mmol: adding 10-15 ml of the mixture; the added molar amount of the cystine diamine hydrochloride is five times of the 1 molar amount of the compound; the adding amount of triethylamine is 10 times of the molar amount of the compound 1; the heating temperature was 80 ℃.
4. The method for preparing a glutathione ratiometric fluorescence sensor based on disulfide bonds as claimed in claim 1, wherein the amount of dichloromethane added in step S3 is determined according to the standard of compound 2, compound 2: dichloromethane ═ 1 mmol: 10-15 ml of the additive.
5. A glutathione ratiometric fluorescence sensor based on disulfide bonds, prepared by the method of claim 1, having the structural formula:
6. the application of the glutathione ratio fluorescence sensor based on disulfide bonds is characterized in that the glutathione ratio fluorescence sensor is used for identifying glutathione at the fluorescence intensity ratio change of 463nm and 532 nm.
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Citations (3)
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| CN104402853A (en) * | 2014-09-30 | 2015-03-11 | 天津理工大学 | Preparation method of specific fluorescent probe for identifying glutathione and application thereof |
| CN104673278A (en) * | 2015-02-15 | 2015-06-03 | 浙江理工大学 | Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe |
| CN104710979A (en) * | 2015-02-15 | 2015-06-17 | 浙江理工大学 | Fluorescent probe used for detecting glutathione as well as preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104402853A (en) * | 2014-09-30 | 2015-03-11 | 天津理工大学 | Preparation method of specific fluorescent probe for identifying glutathione and application thereof |
| CN104673278A (en) * | 2015-02-15 | 2015-06-03 | 浙江理工大学 | Fluorescence probe for detecting glutathione as well as preparation method and use method of fluorescence probe |
| CN104710979A (en) * | 2015-02-15 | 2015-06-17 | 浙江理工大学 | Fluorescent probe used for detecting glutathione as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
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| Constructing a FRET-based molecular chemodosimeter for cysteine over homocysteine and glutathione by naphthalimide and phenazine derivatives;Lin Yang等;《Analyst》;20141104;第140卷;第182-189页 * |
| Reduction-sensitive fluorescence enhanced polymeric prodrug nanoparticles for combinational photothermal-chemotherapy;Yuanyuan Zhang等;《Biomaterials》;20180209;第163卷;第14-24页 * |
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