CN115197141B - Fluorescent probe NI-CO-HCYS for cystathionine gamma lyase detection - Google Patents

Fluorescent probe NI-CO-HCYS for cystathionine gamma lyase detection Download PDF

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CN115197141B
CN115197141B CN202110381567.8A CN202110381567A CN115197141B CN 115197141 B CN115197141 B CN 115197141B CN 202110381567 A CN202110381567 A CN 202110381567A CN 115197141 B CN115197141 B CN 115197141B
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fluorescent probe
hcys
cse
lyase
cystathionine gamma
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CN115197141A (en
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韩克利
贾燕
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Dalian Institute of Chemical Physics of CAS
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
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    • 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"
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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

A fluorescent probe NI-CO-HCYS for detecting cystathionine gamma lyase. The invention provides a fluorescent probe for detecting cystathionine gamma lyase (Cystathionine gama lyase, CSE for short). The probe4 amino-1, 8-naphthalimide is taken as a fluorescent parent, and a linker ligase recognition site homocysteine constructed through a carbamate structure is used. CSE can selectively recognize and cut off NI-CO-HCYS to generateThe fluorescence difference between the reactant and the product is utilized to realize the selective detection of cystathionine gamma lyase. The probe can be used for qualitatively and quantitatively determining the content of CSE in animal cells and tissues and even living bodies, and for screening CSE inhibitors.

Description

Fluorescent probe NI-CO-HCYS for cystathionine gamma lyase detection
Technical Field
The invention relates to the field of fluorescent probes, in particular to a fluorescent probe NI-CO-HCYS which can be used for detecting cystathionine gamma lyase (Cystathionine gama lyase, CSE for short). The probe uses 4 amino-1, 8-naphthalimide as a fluorescent matrix, and is constructed through a carbamate structure to form a linker ligase recognition site homocysteine. CSE can selectively recognize and cut off NI-CO-HCYS. The fluorescence difference between the reactant and the product is utilized to realize the selective detection of cystathionine gamma lyase.
Background
Cystathionine gamma lyase (Cystathionine gama-lyase, CSE EC4.4.1.1) belongs to the class of lyases, catalyzes the cleavage of cystathionine gamma, and after removal of alpha ketoglutarate and NH3, produces L-cysteine, a penultimate step in methionine biosynthesis in animals. In addition, cystathionine gamma lyase is also the main pathway for the production of hydrogen sulfide, which has been demonstrated to be an important molecule in the signal transduction process in cell signaling pathways. Therefore, it is of great importance to detect and quantify CSE in animals. The novel chemical structure, good action effect and unique action target point of the CSE inhibitor have attracted extensive interest of researchers at home and abroad.
The fluorescent probe is one of means for effectively detecting CSE in a living body, and compared with an absorbance method and a liquid phase mass spectrometry, the isotope labeling method has the advantages of convenience and sensitivity in detection. A fluorescent probe with application prospect has the advantages of obvious fluorescence change before and after action, quick response to target molecules, good selectivity, simple synthesis and the like. There is no fluorescent probe for detecting CSE, and developing a fluorescent probe for CSE is very challenging.
Disclosure of Invention
The invention aims at the problems and provides a fluorescent probe NI-CO-HCYS which can be used for selectively detecting the intracellular CSE, and the probe can selectively act with the CSE under physiological conditions, and the fluorescence change is obvious after the probe acts. The probe can be used for detecting the activity of CSE and screening inhibitors.
The invention adopts the following technical scheme:
the invention provides a fluorescent probe NI-CO-HCYS which can be used for detecting cystathionine gamma lyase (Cystathionine gama-lyase, CSE). NI-CO-HCYS uses 4 amino-1, 8-naphthalimide as a fluorescent matrix, and is constructed through a carbamate structure. CSE can selectively recognize and cut off NI-CO-HCYS. The fluorescence difference between the reactant and the product is utilized to realize the selective detection of cystathionine gamma lyase.
The structure of the synthesized probe compound is represented by the code NI-CO-HCYS. The structural formula I of the fluorescent probe is as follows.
Structural code: NI-CO-HCYS.
R may be a hydrogen atom, or a substituted alkyl group having 1 to 10 carbon atoms, or a phenyl group, or a substituted phenyl group, wherein the substituent on the substituted phenyl group is a C1-C5 alkyl group, and the number of substituents on the phenyl group is 1 to 5.
The specific preparation method of the fluorescent probe comprises the following steps:
1) To 50ml of dry ethanol was added 4 amino-1, 8 naphthalene dicarboxylic anhydride (cas: 6492-86-0) 2.13g, and stirring to complete dissolution. 0.87g of n-butylamine (cas: 109-73-9) was added, heated under reflux for 12 hours, refluxed for 12 hours, ethanol and excess n-butylamine were dried by chromatography on a silica gel column with an elution gradient of (petroleum ether: ethyl acetate=3:1). The yield of compound 1 was about 80%. And after the obtained product is obtained, the product is put into use.
2) To anhydrous methylene chloride in an ice bath, 0.293g of triphosgene was added, 0.01N of triethylamine was added and stirred to promote the decomposition of triphosgene, then 0.268g of methylene chloride solution of 4 amino-1, 8 naphthalimide was added dropwise, stirring was continued, the reaction was monitored by a spot plate, after the complete conversion thereof was completed, 1N methyl N- (tert-butyloxycarbonyl) -S- (2-hydroxyzyl) homocysteine was added, stirring was continued, the reaction was monitored by a spot plate, and after the completion of the reaction, the reaction was separated by silica gel column chromatography (methylene chloride: methanol=20:1), to give product 2 in about 53% yield.
3) Dissolving the product 2 in ice-bath anhydrous dichloromethane, slowly dropwise adding trifluoroacetic acid, and slowly dropwise adding saturated sodium bicarbonate solution until no bubbles are generated after the reaction is completed at room temperature. Silica gel column chromatography (dichloromethane: methanol=20:1) gave 45mg of the product NI-CO-HCYS in about 11% yield.
The addition amount of the 4-amino-1, 8-naphthalene dicarboxylic anhydride and the n-butylamine in the step 1) is 1:1.2; the addition of the compound triphosgene, triethylamine, 4 amino-1, 8 naphthalimide in step 2) was 1:0.01:1.
In the step 1), the solvent is ethanol, and in the steps 2) to 3), the solvent is dichloromethane; the stirring mode in the steps 1) to 3) is magnetic stirring.
The fluorescent probe can be metabolized by cystathionine gamma lyase (Cystathionine gama-lyase, CSE) to produce a fluorescence change. Namely, after the fluorescent probe acts with CSE, the fluorescence peak is red-shifted from 467nm to 542nm, and the phenomenon that the short-wave fluorescence is weakened and the long-wave fluorescence is enhanced is remarkable.
When the fluorescent probe is applied to detecting CSE, the fluorescence change is caused by generating a compound with a structure II;
the probe can be used for screening inhibitors of cystathionine gamma lyase.
The fluorescent probe can be used for detecting cystathionine gamma lyase (Cystathionine gama lyase, CSE for short).
The fluorescent probe can be used for detecting cystathionine gamma lyase in an aqueous solution.
The probe can be used for screening inhibitors of cystathionine gamma lyase in an aqueous solution.
The probe can be used for quantitative detection and/or qualitative detection of one or more than two cystathionine gamma lyase in animal cells (whether the animal cells are retired or living), animal tissues (whether the animal cells are retired or living) and animal living.
The probe can be used for quantitative detection and/or qualitative detection of cystathionine gamma lyase in liquid (such as water).
The invention has the beneficial effects that: the compound has obviously changed fluorescence in the presence of cystathionine gamma lyase CSE, and can be used for detecting the CSE enzyme activity with high sensitivity and high flux. In particular, the compounds are useful in screening inhibitors of cystathionine gamma lyase.
The invention can be used for detecting the fluorescent probe of cystathionine gamma lyase (Cystathionine gama-lyase, CSE) in vitro or in vivo. NI-CO-HCYS4 amino-1, 8-naphthalimide is taken as a fluorescent parent, and a linker ligase recognition site homocysteine constructed through a carbamate structure is used. CSE can selectively recognize and cut off NI-CO-HCYS. Under the action of CSE, generate +.>The probe can be used for detecting the activity of the CSE and screening inhibitors with high sensitivity and high flux.
Drawings
FIG. 1 is a synthetic route diagram of the fluorescent probe NI-CO-HCYS provided in example 1;
FIG. 2 is a schematic diagram of the principle of detecting CSE by using the fluorescent probe NI-CO-HCYS;
FIG. 3 probe NI-CO-HCYS synthesized in example 1 1 H NMR(a)， 13 C NMR(b)；
FIG. 4 HRMS of probe NI-CO-HCYS synthesized in example 1;
FIG. 5 UPLC-MS analysis of the probe of example 2 after metabolic conversion of NI-CO-HCYS;
FIG. 6 is a graph showing the response of the fluorescent probes NI-CO-HCYS and CSE with time in example 3;
FIG. 7 response of fluorescent probes NI-CO-HCYS to different enzyme species in example 4;
FIG. 8 is a graph showing the response of fluorescent probe NI-CO-HCYS to CSE at various concentrations in example 5;
FIG. 9 response of fluorescent probes NI-CO-HCYS and CSE with different concentrations of inhibitor (PAG) in example 6.
Detailed Description
The following detailed description of the invention is provided merely to more clearly illustrate the invention and is not to be construed as limiting the invention.
All procedures and steps, substrate reaction conditions, etc., are designed and practiced according to methods well known to those of ordinary skill in the art throughout the experiment.
Example 1
The specific preparation method of the fluorescent probe comprises the following steps:
1) To 50ml of dry ethanol was added 4 amino-1, 8 naphthalene dicarboxylic anhydride (cas: 6492-86-0) 2.13g, and stirring to complete dissolution. 0.87g of n-butylamine (cas: 109-73-9) was added, heated and refluxed for 12 hours, ethanol and excess n-butylamine were dried by silica gel column chromatography, and elution gradient was (petroleum ether: ethyl acetate=3:1, v/v). The yield of compound 1 (4 amino-1, 8 naphthalimide) was about 80%. And after the obtained product is obtained, the product is put into use.
2) To 10ml of anhydrous methylene chloride in an ice bath, 0.293g of triphosgene was added, 2mg of triethylamine was added and stirred to promote the decomposition of triphosgene, then, 10ml of methylene chloride solution of 0.268g of 4 amino-1, 8 naphthalimide was added dropwise, stirring was continued, the reaction was monitored by a dot plate, and after the complete conversion thereof, 0.28g of methyl N- (tert-butyloxycarbonyl) -S- (2-hydroxyyethyl) homocysteine was added, stirring was continued, the reaction was monitored by a dot plate, and after the completion of the reaction, the reaction was separated by silica gel column chromatography (methylene chloride: methanol=20:1, v/v) to give product 2 in about 53% yield.
3) After the completion of the reaction at room temperature, 24mg of trifluoroacetic acid was slowly added dropwise to 50ml of anhydrous dichloromethane in an ice bath to dissolve the product 2, and then a saturated solution of sodium hydrogencarbonate was slowly added dropwise until bubbling did not occur. Silica gel column chromatography (dichloromethane: methanol=20:1, v/v) gave 45mg of the product NI-CO-HCYS, approximately 11% yield. HRMS m/z C 24 H 29 N 3 O 6 S[M+H] + 488.3.1HNMR:(400MHz，MeOD)δ(pp):8.48(m,2H),8.40(d,1H,J＝8.4Hz),8.18(d,1H,J＝8.4Hz),7.73(m,1H),4.41(t,2H,J＝6.8Hz),4.09(t,2H,J＝7.6Hz),3.72(s,3H),3.62(t,1H,J＝5.2Hz),,2.91(t,2H,J＝6.8Hz),2.74(t,2H,J＝7.6Hz),2.09(m,1H),1.90(m,1H),1.66(m,2H),1.43(m,2H),0.99(t,3H,J＝7.6Hz) 13 CNMR(100MHz，MeOD)δ(pp):175.42,164.05,163.54,154.18,140.58,131.58,130.72,128.43,128.08,126.00,123.64,122.29,117.34,116.96,64.33,52.69,51.20,39.61,33.98,30.05,29.81,27.71,19.97,12.81.
Example 2
As shown in FIG. 5, NI-CO-HCYS was dissolved in 10mM borax borate buffer solution at pH (8-9) to prepare 20uM solution, which was incubated with 1mg/ml CSE for 10 hours and then filtered, and the conversion of NI-CO-HCYS was detected by UPLC-MS, and FIG. 5 (a-c) is respectively an ion flow chart, an ultraviolet absorption chart, and a mass spectrum of NI-CO-HCYS, and FIG. 5 (d-f) is an ion flow chart, an ultraviolet absorption chart, and a mass spectrum of metabolites, indicating the production of the target product.
Example 3
As shown in FIG. 6, 193ul of borax borate buffer was added with 2ul of DMSO solution (20 uM) of NI-CO-HCYS, 5ul of CSE enzyme (1 mg/ml). The measurement was performed using a full-wavelength scanning type multifunctional reader and a 96-well elisa plate. By excitation wavelength lambda ex =438 nm, using emission wavelength λ em The results, shown in the figure, show that the fluorescence intensity at 540nm increases gradually over time, representing the constant production of the product.
Example 4:
as shown in FIG. 7, 2 was added to 193ul of borax borate buffer solution, respectivelyA DMSO solution (20 uM) of ul NI-CO-HCYS, and 10ul of different enzymes and active substances (1 mg/ml), including CSE (cystathionine gamma lyase), CBL (cystathionine beta lyase), BSA (bovine serum albumin), cys (cysteine), hcy (homocysteine), ascoic acid (ascorbic acid), chymotorypsin (chymotrypsin), peppanA (pepsin A), after incubation for 3 hours, lambda is detected ex ＝438nm，λ em Fluorescence intensity=540 nm, NI-CO-HCYS was found to respond selectively only to CSE, and not affected by other species including the syngeneic enzyme CBL.
Example 5
As shown in FIG. 8, the concentration of the CSE enzyme stock solution was diluted in a gradient of 1.3mg/ml to obtain 1, 0.75, 0.5, 0.25, 0.1mg/ml enzyme stock solution. Each reaction was measured after incubation for 1h with 2ul of NI-CO-HCYS (20 uM) and 20ul of enzyme stock solutions of different concentrations, respectively, in 178ul of PBS buffer. The measurement was performed using a full-wavelength scanning type multifunctional reader and a 96-well elisa plate. Measuring fluorescence emission spectrum of the working solution, and detecting lambda ex ＝438nm，λ em Emission values at 542nm, the results are shown in graph 8,F 540nm The results show that NI-CO-HCYS can be used for quantitative detection of in vitro CSE as the enzyme concentration increases linearly.
Example 6
As shown in FIG. 9, 5ul of CSE (final concentration 1 mg/ml), 1ul of D, L-proparylglycoline (classical inhibitor PAG of CSE) and 1ul of DMSO solution of NI-CO-HCYS (final concentration 20 uM) were added to 193ul of borax borate buffer, respectively, and incubated together for 3h. The measurement was performed using a full-wavelength scanning type multifunctional reader and a 96-well elisa plate. Measuring fluorescence emission spectrum of the working solution, and detecting lambda ex ＝438nm，λ em Emission at 542nm, results show that as the inhibitor concentration increases, F, representing CSE enzyme activity, is shown in FIG. 8 540nm The results also show that NI-CO-HCYS can be used for inhibitor screening and inhibition ability evaluation.

Claims (7)

1. A fluorescent probe NI-CO-HCYS, characterized in that: the structure of the fluorescent probe is shown as a structure I,
，
structural code: NI-CO-HCYS; r is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
2. Use of a fluorescent probe according to claim 1, wherein: the fluorescent probe is used for detecting cystathionine gamma lyase (Cystathionine gama lyase, CSE for short) in an aqueous solution, and the application of the fluorescent probe is not suitable for diagnosing and treating diseases.
3. The use of a fluorescent probe according to claim 2, wherein: the probe is used for screening inhibitors of cystathionine gamma lyase in aqueous solution.
4. The use of a fluorescent probe according to claim 2, wherein: the probe is used for quantitative detection and/or qualitative detection of cystathionine gamma lyase in an aqueous solution.
5. The use of a fluorescent probe according to any one of claims 2-4, wherein: when the fluorescent probe NI-CO-HCYS is applied to detecting CSE, the fluorescence change is caused by generating a compound with a structure II;
，
r is a hydrogen atom or a substituted alkyl group having 1 to 10 carbon atoms.
6. A method for synthesizing a fluorescent probe according to claim 1, comprising the following steps,
1) Adding 2-2.2g of 4 amino-1, 8 naphthalene dicarboxylic anhydride into 40-60ml of dry ethanol, and stirring until the mixture is dissolved; adding 0.8-1g of n-butylamine, heating and refluxing for 8-24 hours, drying ethanol and redundant n-butylamine by spin, separating by silica gel column chromatography, and eluting with petroleum ether as gradient: ethyl acetate = 2:1-6:1, v/v; obtaining a compound 1;
2) Adding 0.28-0.3 g triphosgene into 10-20ml anhydrous dichloromethane with ice bath temperature of-4 ℃, adding 1-3mg triethylamine, stirring to promote triphosgene decomposition, then dropwise adding 10-20ml dichloromethane solution of 0.24-0.28g 4 amino-1, 8 naphthalimide, continuously stirring, performing spot-plate monitoring reaction, continuously adding 0.27-0.29g when the triphosgene is completely convertedBoc-S- (2-hydroxyethyl) -L-cysteine methyl ester (methyl N- (tert-butoxin carboyl) -S- (2-hydroxyyethyl) homocysteine), continuing to stir, monitoring the reaction by a dot plate, and after the reaction is complete, separating by silica gel column chromatography, and separating dichloromethane: methanol=16:1-25: 1, v/v to give product 2;
3) Dropwise adding trifluoroacetic acid 20-28 mg into 40-60ml of anhydrous dichloromethane with the ice bath temperature ranging from-4 ℃ to dissolve a product 2, and slowly dropwise adding sodium bicarbonate saturated solution until bubbling is avoided after the reaction is completed at room temperature; separating by silica gel column chromatography, and separating dichloromethane: methanol=16:1-25: 1, v/v to give the product.
7. The method of synthesis according to claim 6, wherein the temperature of the ice bath in step 2) and step 3) is in the range of-2 ℃ to 0 ℃.
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833615A (en) * 2015-12-04 2017-06-13 中国科学院大连化学物理研究所 A kind of fluorescence probe NACL and its preparation and application
CN110698401A (en) * 2019-10-30 2020-01-17 大连理工大学 Novel fluorescent probe for detecting biological thiol and preparation method and application thereof

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833615A (en) * 2015-12-04 2017-06-13 中国科学院大连化学物理研究所 A kind of fluorescence probe NACL and its preparation and application
CN110698401A (en) * 2019-10-30 2020-01-17 大连理工大学 Novel fluorescent probe for detecting biological thiol and preparation method and application thereof

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