CN106831781B - A kind of fluorescence probe NASA and its preparation and application - Google Patents
A kind of fluorescence probe NASA and its preparation and application Download PDFInfo
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Abstract
A kind of fluorescence probe NASA and its preparation and application.The present invention provides the fluorescence probes that one kind can be used for detecting external Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homocysteine hydrolase, abbreviation SAHH).Primary synthetic methods are to be keyed 1,8- naphthalimide generation structure by C-S on the site of action adenosine of SAHH to beCompound；Under SAHH effect, generate
Description
Technical field
The present invention relates to fluorescence probe fields, and in particular to one kind can be used for detecting Adenosylhomocysteinase EC3.3.1.1
The fluorescence probe of (S-adenosyl-L-homocysteine hydrolase, abbreviation SAHH).It is introduced on 1,8- naphthalimide
Adenosine molecule selectively detects Adenosylhomocysteinase EC3.3.1.1 using the realization of the difference in fluorescence of reactant and product.
Background technique
Adenosylhomocysteinase EC3.3.1.1 (SAHH, EC:3.1.3.1) is a kind of enzyme being widely present into the cell, it
It is catalyzed AdoHcy (AdoHcy) hydrolysis and generates adenosine and homocysteine.SAHH is inhibited to will lead into the cell
The accumulation of methylation mortifier AdoHcy generates feedback inhibiting effect to react transmethylase.And it methylates for maintaining
The activity of cell is required.The core status in the transmethylated reaction of organism is being adjusted in view of SAHH, it is made by selection
For the important target spot of a variety of new drug developments, including immunosuppressor, antiviral agent, prevention and treatment atherosclerosis and Alzheimer
Medicine.The completely new chemical structure of SAHH inhibitor, good function and effect and unique action target spot have caused to grind both at home and abroad
The extensive interest of the person of studying carefully.
Fluorescence probe is one of the means of SAHH in effective detection life entity, has detection sensitive excellent compared to absorbance method
Gesture.One fluorescence probe with application prospect should have change in fluorescence before and after effect obviously, to target molecule to respond fast, selection
Property it is good, synthesis it is simple the advantages that.The fluorescence probe for being applied to detection SAHH at present is very few, and access is only shown in same using S- adenosine
The metabolite Hcy of type cysteine carrys out the method for detecting SAHH indirectly.Therefore exploitation has the probe of its SAHH and chooses greatly very much
War property.
Summary of the invention
The present invention addresses the above problem, provides a kind of fluorescence spy that can be used for the intracellular SAHH of selective enumeration method
Needle, this probe can be acted on selectively with SAHH in physiological conditions, and fluorescence significantly increases after effect.
The present invention adopts the following technical scheme:
The present invention provides one kind can be used for detecting Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homoc
Ysteine hydrolase, abbreviation SAHH) fluorescence probe.Primary synthetic methods are to lead on the site of action adenosine of SAHH
Cross C-S key connection 1,8- naphthalimide；The compound generates 4- sulfydryl -1,8- naphthalimide, utilizes reaction under SAHH effect
The difference of front and back photoluminescent property realizes the selective enumeration method to SAHH.
The structure of the probe compound of synthesis is indicated with code name NASA.
The structural formula I of the fluorescence probe is as follows.
The fluorescence probe the preparation method comprises the following steps: on the site of action adenosine of SAHH pass through C-S be keyed 1,8- naphthalene
Acid imide；Specific preparation process is as follows,
1) triphenylphosphine (cas:603-35-0) 3.76g, stirring to Quan Rong are added in dry THF 50ml.Condition of ice bath
Under, diethylazodicarboxylate (cas:1972-28-7) 2.2ml is slowly added dropwise in 5min.After stirring 30min, 2', 3'- is added
Isopropylidene adenosine (cas:362-75-4) 2.1g.Maintain 0 degree of stirring 10min.Thioacetic acid (cas:507- is slowly added dropwise in 5min
09-5)1.0ml.After 0 degree is reacted 1 hour, it is spin-dried for solvent, obtained yellow solid chromatographs (CHCl with column2-MeOH,100:0,
95:5,90:10) separate.Obtain compound 11.62g, yield 65%.
2) in 20ml ethyl alcohol, bromo- 1,8- naphthalene anhydride (cas:81-86-7) 1g of 4- and 1- butylamine (cas:109-73-9) is added
353uL, 78 degree are flowed back 4 hours.It is spin-dried for solvent after having reacted, obtains product 21.2g, yield 100%.
3) in dry methanol, product 453mg in product 1500mg and step 2) is added in step 1), cools to -20
Sodium methoxide (cas:124-41-4) 147mg is added in degree.Solution slowly rises to room temperature, sustained response 20h.It revolves after reaction
Dry solvent, column chromatography for separation (CHCl2- MeOH, 100:0,95:5,90:10), obtain product 3
314mg, yield 40%.
4) in the solution 2ml of water and formic acid 1:1, product 3100mg in 0 degree of lower addition step 3) slowly rises to room temperature
4h is reacted, 50 degree of reaction 2h are warmed to.Solvent is spin-dried for after having reacted.Column chromatographs to obtain fluorescence probe NASA50mg, yield 53%.
Triphenylphosphine described in step 1), diethylazodicarboxylate, 2', 3'- isopropylidene adenosine, thioacetic acid plus
Entering amount is 2:2:1:2；The additional amount of compound 1 and sodium methoxide is 1:2.2 in step 3).
In the step 1), solvent used is anhydrous tetrahydro furan；The step 1) -4) in stir mode be
Magnetic agitation.
The fluorescence probe can be by Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homocys
Teine hydrolase, abbreviation SAHH) it is metabolized and generates change in fluorescence.I.e. after the fluorescence probe and SAHH effect, fluorescence
To from 470nm, and there is significant fluorescence enhancement at peak from 500nm blue shift.
When the fluorescence probe is applied to detection SAHH, change in fluorescence is because generating the chemical combination with structure I I
Object；
The probe can be used for the inhibitor screening of Adenosylhomocysteinase EC3.3.1.1.
Beneficial effects of the present invention:
Compound fluorescence in the presence of SAHH significantly changes, and can be used for high sensitivity, detects SAHH with high throughput.
Especially, which can be used for the inhibitor screening of Adenosylhomocysteinase EC3.3.1.1.
The present invention can be used for detecting external Adenosylhomocysteinase EC3.3.1.1 (S-adenosyl-L-homoc
Ysteine hydrolase, abbreviation SAHH) fluorescence probe.Primary synthetic methods are to lead on the site of action adenosine of SAHH
Crossing C-S key connection 1,8- naphthalimide generation structure isCompound；It is raw under SAHH effect
AtThe detection to SAHH is realized using the difference of reaction front and back photoluminescent property, which can be with high sensitivity, high pass
Amount ground is used for the screening of SAHH inhibitor.
Detailed description of the invention
The synthetic route chart of the fluorescence probe NASA provided in Fig. 1 embodiment 1；
The schematic illustration of Fig. 2 fluorescence probe NASA detection SAHH provided by the invention；
The probe NASA's synthesized in Fig. 3 embodiment 11H NMR (a),13C NMR(b)；
Fluorescence excitation spectrum (a), the emission spectrum (b) of fluorescence probe NASA aqueous solution in Fig. 4 embodiment 2；
Fluorescence excitation spectrum (a), the emission spectrum of the hydrolysate aqueous solution of fluorescence probe NASA in Fig. 5 embodiment 3
(b)；
The linear relationship chart of spectrum 470nm peak value at any time after fluorescence probe NASA and SAHH response in Fig. 6 embodiment 4；
Spectrum change figure after the SAHH of fluorescence probe NASA and various concentration response in Fig. 7 embodiment 5；
The dynamics schematic diagram of fluorescence probe NASA and SAHH reaction detection 470nm fluorescence intensity in Fig. 8 embodiment 6；
Using fluorescence probe NASA as substrate in Fig. 9 embodiment 7, Dznep is able to suppress the enzymatic activity of SAHH；
Using fluorescence probe NASA as substrate in Figure 10 embodiment 8, the IC50 value of four kinds of inhibitor of SAHH is detected.
Specific embodiment
Following embodiments are for further illustrating the present invention, but the present invention is not limited to embodiments.
Embodiment 1 (synthesis of probe):
As shown in Figure 1, the synthesis of NASA is divided into 4 steps (as above), the identification of compound 1 are as follows: MS:366.12 (positive
mode).1HNMR (400MHz, Chloroform-d) δ (ppm): 8.37 (s, 1H), 8.19 (s, 1H), 6.07 (d, 1H, J=
2.08Hz), 5.77 (s, 2H), 5.51 (d, 1H, J=6.36Hz), 4.97 (d, 1H, J=6.36Hz), 4.34 (t, 1H, J=
6.88Hz), 3.29 (d, 1H, J=7.2Hz), 3.08 (d, 1H, J=6.64Hz), 1.60 (s, 3H), 1.39 (s, 3H).Compound
3 identification: MS:575.20 (positive mode)1HNMR(400MHz,Chloroform-d)δ(ppm):8.59(d,1H,J
=7.28Hz), 8.55 (d, 1H, J=8.48Hz), 8.37 (d, 1H, J=7.76Hz), 8.27 (s, 1H), 7.78 (s, 1H),
7.71 (t, 1H, J=8.16Hz), 7.57 (d, 1H, J=7.8Hz), 6.08 (s, 1H), 5.56 (d, 1H, J=6.2Hz), 5.20
(d, 1H, J=6.12Hz), 4.52 (t, 1H, J=6.76Hz), 4.16 (t, 2H, J=7.64Hz), 3.55 (m, 1H), 3.41 (m,
1H), 1.70 (m, 2H), 1.58 (s, 3H), 1.46 (m, 2H), 1.39 (s, 3H), 0.97 (t, 3H, J=7.32Hz).Target chemical combination
Object NASA (yellow solid).MS:535.17(positive mode).1HNMR(500MHz,Dime thylsulfoxide-d6)
δ (ppm): 8.53 (d, 1H, J=8.4Hz), 8.52 (d, 1H, J=6.9Hz), 8.36 (s, 1H), 8.32 (d, 1H, J=
7.85Hz), 8.13 (s, 1H), 7.87 (d, 1H, J=8.05Hz), 7.83 (d, 1H, J=8.00Hz), 7.26 (s, 2H), 5.93
(d, 1H, J=5.5Hz), 5.56 (d, 1H, J=5.95Hz), 5.43 (d, 1H, J=5.15Hz), 4.87 (m, 1H), 4.33 (m,
1H),4.18(m,1H),4.03(m,1H),3.75(m,1H),3.68(m,1H),1.61(m,2H),1.35(m,2H),0.92(t,
3H, J=7.3Hz).13CNMR(100MHz,Dimethylsulfoxide-d6)δ(ppm):163.10,163.03,156.01,
152.53,149.29,143.69,139.95,130.96,130.21,129.63,128.75,127.49,127.19,123.58,
122.68,119.16,118.71,87.77,82.19,72.87,72.51,34.19,29.58,19.70,13.61.(Fig. 3 is to change
The hydrogen for closing object NASA composes (a), and carbon composes (b))
Embodiment 2
As shown in figure 4, NASA is dissolved in the PBS buffer solution of 10mM, it is configured to the solution of 20uM.Use fluorescence microplate reader
(Thermofisher) fluorescence excitation spectrum (a), the fluorescence emission spectrum (b) of detector detection NASA aqueous solution；As the result is shown
Maximum excitation/launch wavelength of probe NASA is 400nm/512nm.
Embodiment 3
As shown in figure 5, NI-SH is dissolved in the PBS buffer solution of 10mM, it is configured to the solution of 20uM.Use fluorescence microplate reader
(Thermofisher) fluorescence excitation spectrum (a), the fluorescence emission spectrum (b) of detector detection NASA aqueous solution；As the result is shown
Maximum excitation/launch wavelength of NASA metabolite is 380/470nm.
Embodiment 4:
Add the DMSO solution (500uM) of 2ul NASA, the enzyme (10mg/ml) of 2ul in the PBS buffer solution of 196ul.It uses
The multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates measure, and sweep an emission spectra within every two minutes.λ ex=380nm,
Raster width is 5nm, at λ em=470nm, 470nm fluorescent value map at any time be it is linear, as a result as shown in Figure 6.
Embodiment 5
By the SAHH enzyme stock concentrations gradient dilution of 100mg/ml, 50/25/10/5/2.5/1/0.5/0.25/ is obtained
The enzyme liquid storage of 0.1mg/ml.Each reaction adds 2ul NASA (500uM) and 20ul difference dense in the PBS buffer solution of 178ul
The enzyme of degree measures after being incubated for 20min.It is measured using the multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates.Measurement
The fluorescence emission spectrum of the working solution, λ ex=380nm, raster width 5nm, transmitting range is from 400nm-600nm.As a result it shows
Show that such as Fig. 7, with the growth of enzyme concentration, the fluorescence intensity at 470nm enhances therewith.
Embodiment 6:
By the SAHH enzyme stock concentrations gradient dilution of 100mg/ml, 50/25/10/5/2.5/1/0.5/0.25/ is obtained
The enzyme liquid storage of 0.1mg/ml.Each reaction adds 2ul NASA (500uM) and 20ul difference dense in the PBS buffer solution of 178ul
The enzyme of degree, every 2min sweeps the fluorescent value (λ ex=380nm) of a 470nm at 37 DEG C.It is glimmering at such as Fig. 8 as the result is shown, 470nm
Luminous intensity enhances at any time, with enzyme concentration.
Embodiment 7:
It configures SAHH specific inhibitor Dznep (5mM), adds 2ul NASA (500uM) in the PBS buffer solution of 176ul,
The inhibitor of 2ul or the enzyme of 2ul buffer (control) and 20ul, every 2min sweeps the fluorescent value of a 470nm under 37 DEG C of incubations
(λ ex=380nm).As Fig. 9, NASA can be pressed down completely by the catalytic action of SAHH by 50uM Dznep (SAHH classics inhibitor)
System, demonstrates again that NA SA is the probe substrate of SAHH.
Embodiment 8:
Configure NASA specific inhibitor Dznep (5mM)/Adenosine (100mM)/3-deazaadenosine
(100mM)/2-Deoxyadenosine (100mM) liquid storage and ten times of diluted inhibitor liquid storages, each reaction is in 176ul
PBS buffer solution (10mM) in plus 2ul NASA (500uM) and 20ul enzyme (10mg/ml) and 2ul inhibitor.It uses
The multi-functional readout instrument of full wavelength scanner formula and 96 hole elisa Plates measure.Measure the fluorescence emission spectrum of the working solution, λ ex=
380nm, raster width 5nm, λ em=470nm.As shown in Figure 10, with log (inhibitor concentration) and enzyme percentage remaining activity
Mapping, the IC50 value for obtaining four kinds of compounds is Dznep:0.88uM respectively；Adenosine:8.02uM；2'-De
oxyadenosine 56.77uM；3'-Deazaadenosine 11.02uM.
Claims (7)
1. a kind of fluorescence probe NASA, it is characterised in that: the structure of the fluorescence probe be structure I shown in,
Structure I
Structure code name: NASA；
R is hydrogen atom or phenyl or substituted-phenyl, the alkyl that the substituent group on substituted-phenyl is C1-C5, substituent group on phenyl
Number be 1-5.
2. a kind of application of fluorescence probe according to claim 1, it is characterised in that: the fluorescence probe is applied to non-
When diagnosing the detection SAHH of non-treatment purpose, change in fluorescence is because generating the compound with structure I I；
Structure I I.
3. a kind of application of fluorescence probe described in claim 1, it is characterised in that: the fluorescence probe is for non-diagnostic non-
The detection of the Adenosylhomocysteinase EC3.3.1.1 (SAHH) of therapeutic purposes.
4. a kind of application of fluorescence probe as claimed in claim 3, it is characterised in that: the fluorescence probe is for detecting cell
In SAHH.
5. the application of fluorescence probe according to claim 3, the probe is for Adenosylhomocysteinase EC3.3.1.1
Inhibitor screening.
6. the application of fluorescence probe according to claim 3, the probe is for S- adenyhomotype in vitro erythrocyte half
The quantitative detection of cystine hydrolase.
7. a kind ofShown in fluorescence probe preparation method, specific preparation process is as follows,
1) triphenylphosphine (cas:603-35-0) 3.76g is added in dry THF 50ml, stirring is to Quan Rong, under condition of ice bath,
Diethylazodicarboxylate (cas:1972-28-7) 2.2ml is slowly added dropwise in 5min, after stirring 30min, is added
2.1g maintains that thioacetic acid (cas:507-09-5) 1.0ml is slowly added dropwise in 0 DEG C of stirring 10min, 5min, and 0 DEG C is reacted 1 hour
Afterwards, it is spin-dried for solvent, obtained yellow solid is chromatographed with column, CHCl2MeOH, 100:0,95:5,90:10 separation, obtain chemical combination
Object 11.62g, yield 65%；
2) in 20ml ethyl alcohol, bromo- 1,8- naphthalene anhydride (cas:81-86-7) 1g of 4- and 1- butylamine (cas:109-73-9) is added
353uL, 78 DEG C are flowed back 4 hours, are spin-dried for solvent after having reacted, are obtained product 21.2g, yield 100%；
3) in dry methanol, product 453mg in product 1500mg and step 2 is added in step 1), cools to -20 DEG C, adds
Enter sodium methoxide (cas:124-41-4) 147mg, solution slowly rises to room temperature, sustained response 20h；It is spin-dried for after reaction molten
Agent, column chromatography for separation, CHCl2MeOH, 100:0,95:5,90:10 obtain product 3
314mg, yield 40%；
4) in the solution 2ml of water and formic acid 1:1,3 100mg of product in step 3) is added at 0 DEG C, it is anti-to slowly rise to room temperature
4h is answered, 50 DEG C of reaction 2h is warmed to, solvent is spin-dried for after having reacted, column chromatographs to obtain fluorescence probe NASA50mg, yield 53%.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2006108678A2 (en) * | 2005-04-14 | 2006-10-19 | Rwth Aachen | New s-adenosyl-l-methionine analogs with extended activated groups for transfer by methyltransferases |
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| WO2006108678A2 (en) * | 2005-04-14 | 2006-10-19 | Rwth Aachen | New s-adenosyl-l-methionine analogs with extended activated groups for transfer by methyltransferases |
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| Title |
|---|
| 9-[(2s,3s)-3-formyl-2,3-dihydroxyproxypropyl]adenine:a facile affinity-labeling probe of human s-adenosyl-L-homocysteine hydrolase;Y.Kitade et al.;《Bioorganic & Medicinal Chemistry Letters》;19991231;第9卷;第2737-2740 * |
| An ICT-Based Approach to Ratiometric Fluorescence Imaging of Hydrogen Peroxide Produced in Living Cells;Duangkhae Srikun et al.;《J.Am.Chem.Soc》;20080313;第130卷;第4596-4597页 * |
| Substrate Binding Stabilizes S-Adenosylhomocysteine Hydrolase in a Closed Conformation;Dan Yin et al.;《Biochemistry》;20000714;第39卷(第20期);第9811-9818页 * |
| Thymine-based molecular beacon for sensing adenosine based on the inhibition of S-adenosylhomocysteine hydrolase activity;Chih-Chun Nieh et al.;《Biosensors and Bioelectronics》;20140521;第61卷;第404-409页 * |
| Using S-adenosyl-L-homocysteine capture compounds to characterize S-adenosyl-L-methionine and S-adenosyl-L-homocysteine binding proteins;Lindsey J.Brown et al.;《Analytical Biochemistry》;20140827;第467卷;第14-21页 * |
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