CN109251160A - A kind of fluorescent probe compounds and preparation method thereof for selenoprotein detection - Google Patents
A kind of fluorescent probe compounds and preparation method thereof for selenoprotein detection Download PDFInfo
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Abstract
The present invention relates to a kind of fluorescent probe compounds for selenoprotein detection, and the compound structure is as shown in formula I.Compared with traditional sensing techniques, the fluorescence probe of Noninvasive detects simple, convenient, quick, high sensitivity, and selectivity is good, and the response time is short, can carry out in situ, real-time monitoring to detection object, and have wide range of applications.Formula I.
Description
Technical field
The invention belongs to high organic synthesis fields, and in particular to a kind of fluorescent probe compounds for selenoprotein detection
And preparation method thereof.
Background technique
Selenoprotein is intracellular important anti-oxidant species, can protect cell from oxidative damage.Active selenium species are anti-
Oxidation mechanism directly removes ROS by ping-pong mechanism.Active selenium species in body mainly exist in the form of containing selenoaminoacid, such as
Selenocysteine (CysSeH, Sec), seleno glutathione (GSeH), seleno over cure cysteine (CysSSeH), seleno
Over cure glutathione (GSSeH), selenium-methyl selenium substituted aminothiopropionic and selenomethionine etc., they are typically incorporated into albumen
Active site in matter as glutathione peroxidase (GPx) and thioredoxin reductase (Trx).In human body at least
There are 25 kinds of different selenoproteins (SePs), these selenoproteins have extensive physiological function.Body lack selenium will lead to it is immune
Hypofunction and cancer stricken risk increase.But the risk that excessive Selenium Supplement substance will lead to type II diabetes increases, and even results in
Acute or chronic selenosis because the RSeS of high concentration can be enhanced by electric charge transfer to oxygen intracellular super oxygen yin from
The content of son.Therefore, RSeS supply appropriate is most important to health.
Due to selenoprotein important biomedical meaning in vivo, for detecting point of selenoprotein concentration level variation
Analysis method is extremely important.Currently, detection method needs the pretreatment of sample, complicated operational means and large-scale instrument are needed.Cause
This, it is extremely urgent to find a kind of convenient and efficient detection method.
Summary of the invention
To solve the deficiencies in the prior art, the present invention provides a kind of fluorescence probe for being conveniently and quickly used for selenoprotein detection
Compound.
The present invention relates to a kind of fluorescent probe compounds for selenoprotein detection, and the compound structure is as shown in formula I:
Formula I.
The present invention also provides a kind of preparation method of fluorescent probe compounds for selenoprotein detection, step includes:
(1) the bromo- beta naphthal of 6- is reacted under catalytic action with methylamine hydrochloride, so that hydroxyl converts methylamino, obtains chemical combination
Object one；
Compound one
(2) compound one is reacted again with CuCN and generates cyano, obtain compound two；
Compound two
(3) compound two is reacted with diisobutyl aluminium hydride, so that cyano is converted into aldehyde radical, obtains compound three；
Compound three
(4) by 2,3,3- trimethyl -3H- indoles (24.8g, 0.156mol), after iodoethane reaction, half flower cyanines of synthesis, i.e. chemical combination
Object four；
Compound four
(5) compound three is reacted with compound four, synthesizes fluorogen, i.e. compound five；
Compound five
(6) by compound five and triphosgene, N, the reaction of N- diisopropylethylamine；Add anhydrous methylene chloride, N, N- diisopropyl
Base ethamine, 4-dimethylaminopyridine, the reaction of 2,2'- bis- thiodiethanols obtain the yellow product such as formula I.
The present invention also provides a kind of two-photon fluorescence probe, such as above-mentioned compound is glimmering as the two-photon of detection selenoprotein
Light probe.
The utility model has the advantages that the fluorescence probe detection of Noninvasive is simple, convenient, quick compared with traditional sensing techniques,
High sensitivity, selectivity is good, and the response time is short, can carry out in situ, real-time monitoring to detection object, and have wide range of applications.
Detailed description of the invention
Fig. 1 is the change in fluorescence before the fluorescence probe used in test example 1 of the present invention detects selenoprotein.
Fig. 2 is the change in fluorescence after the fluorescence probe used in test example 1 of the present invention detects selenoprotein.
Fig. 3 is applied in cell biological model for organic compound obtained in embodiment 1, and cell handles 2h with selenoprotein
Afterwards, (10 μM) of the compound shown in formula I incubations, the fluorogram shot later with laser co-focusing.
Specific embodiment
Embodiment 1
A kind of preparation method of the fluorescent probe compounds (as shown in formula I) for selenoprotein detection, step include:
Formula I
(1) preparation of compound one
The bromo- beta naphthal of 6- (10g, 0.0426mol) is dissolved in 40ml water, Sodium Metabisulfite (16.5g,
0.0868mol) and under sodium hydroxide (9g, 0.225mol) catalysis and at 140 DEG C of methylamine hydrochloride (15g, 0.222mol) react
96 hours.Reaction is cooled to room temperature, and is cleaned up with sodium hydrate aqueous solution (2mol/L), is used recrystallizing methanol after dry, is obtained
To brown color product, yield 83.2%.
Compound one:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 2.84 (s, 3H), 3.79 (s,
1H), 6.660-6.682 (d, 1H), 6.775-6.910 (q, 1H), 7.635-7.400 (q, 1H), 7.430-
7.465 (d, 2H), 7.760-7.790 (d, 1H). 13C NMR (125 MHz, CDCl3-D1) δ(ppm):
147.28, 133.84, 129.65, 129.48, 128.53, 127.98, 127.69, 118.83, 114.98,
103.56, 30.68。
Compound one
(2) preparation of compound two
Compound one (2g, 8.5mmol) is dissolved in 50ml pyridine, CuCN(1.1g, 12.3mmol) is added in reaction kettle,
4h is reacted under the conditions of 220 DEG C.Product is cooled to room temperature, is extracted with ethyl acetate, while being washed with 10% ethylenediamine, uses nothing later
Aqueous sodium persulfate is dry.After concentration, with silica gel column purification.Obtain yellow product, yield 71%.
Compound two:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 2.96 (s, 3H), 4.27 (s,
1H), 6.71-6.75 (d, 1H), 6.90-6.96 (q, 1H), 7.43-7.48 (q, 1H), 7.59-7.65 (q,
2H), 7.97-8.01 (s, 1H). 13C NMR (125 MHz, CDCl3-D1) δ(ppm): 149.31, 137.19,
133.82, 129.47, 127.11, 126.68, 125.97, 120.25, 119.22, 104.15, 103.02,
30.36.
Compound two
(3) preparation of compound three
Compound two (0.84g, 4.62mmol) is dissolved in 50ml toluene, reaction flask is added in diisobutyl aluminium hydride (9ml)
In, 30min is reacted under the conditions of -78 DEG C, reacts at room temperature 4h.With saturated ammonium chloride and aqueous sulfuric acid quenching reaction.Methylene chloride
It is dry with anhydrous magnesium sulfate after extraction.After concentration, with silica gel column purification.Obtain yellow product, yield 41%.
Compound three:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 2.48-2.52 (m, 1H), 2.78-
2.94 (d, 3H), 6.71-6.75 (d, 1H), 7.01-7.07 (q, 1H), 7.62-7.72 (q, 2H), 7.77-
7.83 (d, 1H), 8.24 (s, 1H), 9.94 (s, 1H). 13C NMR (125 MHz, CDCl3-D1) δ(ppm):
192.23, 151.11, 139.46, 135.11, 130.90, 129.99, 126.53, 125.37, 123.45,
119.36, 102.00, 29.84。
Compound three
In the preparation of compound three, -78 DEG C of reaction temperature are important the yield of compound three in the present invention.
(4) preparation of compound four
By 2,3,3- trimethyl -3H- indoles (24.8g, 0.156mol), iodoethane (30g, 0.192) is dissolved in 50ml acetonitrile,
It is heated to reflux 12h under protection of argon gas.After being cooled to room temperature, with filtered on buchner funnel, pink product is obtained after ether washing,
Yield 81%.
Compound four:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 1.06(s, 3H), 1.41 (t, 3H),
1.49 (s, 6H), 4.07 (q, 2H), 7.30 (d, 1H), 7.37 (t, 1H), 8.02 (t, 1H), 8.92
(d, 1H). 13C NMR (125 MHz, CDCl3-D1) δ(ppm): 196.5, 148.1, 141.4, 128.3,
125.0, 120.1, 111.0, 45.1, 43.0, 26.9, 26.9, 13.7, 8.8. LC-MS (API-ES): m/z
C13H18N+ Calcd 188.14, found [M+H] +188.15.
Compound four
(5) preparation of compound five
By compound four (1g, 0.00317mol), compound three (0.5g, 0.0027mol) is dissolved in n-butanol and toluene (volume
Than 7:3) in system, it is heated to reflux 4h.Column purified by silica gel chromatography is used after concentration.Obtain purple product, yield 78%.
Compound I:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 1.18(t, 1H), 1.47 (t, 3H),
1.99 (s, 1H), 2.505-2.525 (m, 1H), 2.850-2.990 (d, 3H), 3.360 (s, 1H), 4.000-
4.050 (m, 1H), 4.640-4.760 (q, 2H), 6.800 (d, 1H), 6.890-6.970 (q, 1H),
7.040-7.110 (d, 1H), 7.515-7.690 (m, 4H), 7.695-7.795 (q, 2H), 7.835-7.915 (d,
2H), 8.175-8.250 (d, 1H), 8.495-8.600 (d, 2H). 13C NMR (125 MHz, CDCl3-D1) δ
(ppm): 180.15, 154.89, 151.19, 143.36, 140.47, 138.70, 135.92, 130.80,
128.90, 128.45, 127.22, 126.23, 125.39, 124.98, 122.93, 118.84, 114.27,
108.31, 102.12, 51.57, 41.37, 29.27, 25.92, 20.68, 13.47. LC-MS (API-ES): m/z
C25H27N2 + Calcd 355.22, found [M+H] +355.42.
Compound five
Compound five is important the present invention as new fluorogen, and the application fluorogen is used as probe after connecting response group
It is Promethean to prepare a new probe.
N-butanol in the preparation of compound five: toluene system, and volume ratio be 7:3 when, the production to the compound of the present invention
Amount is important.
(6) preparation of formula I
Compound five (0.0357g, 0.1mmol) and triphosgene (0.09g, 0.3mmol) are dissolved in 50ml anhydrous methylene chloride,
By N, N- diisopropylethylamine (1ml) is added dropwise to above-mentioned reaction solution.Reaction system is protected with argon gas, is reacted and is continued in ice bath
30min.50ml anhydrous methylene chloride, n,N-diisopropylethylamine (1ml) and 4- dimethylamino is added after being spin-dried in residue
Reaction mixture is added in pyridine (20mg).2,2'- bis- thiodiethanols (0.03g, 0.2mmol) are dissolved in 2ml anhydrous methylene chloride
It is added in above-mentioned solution middlely.TCL monitoring reaction, until raw material has reacted completely.Column purified by silica gel chromatography is used after concentration.?
To the yellow product of such as formula I, yield 34%.
Compound six:1H NMR (500 MHz, CDCl3-D1) δ (ppm): 1.41(t, 3H), 1.49 (s, 6H),
2.75 (t, 2H), 2.84 (t, 2H), 3.25 (s, 3H), 3.26 (t, 2H), 3.65 (t, 1H), 3.96
(t, 2H), 4.07 (q, 2H), 5.67 (d, 1H), 6.79 (d, 1H), 7.30 (d, 1H), 7.37 (t, 1H),
7.39 (d, 1H), 7.49(d, 1H), 7.52 (d, 1H), 7.71 (s, 1H), 7.74 (s, 1H), 7.84 (d,
1H), 8.02 (t, 1H), 8.92 (d, 1H). 13C NMR (125 MHz, CDCl3-D1) δ(ppm): 173.1,
155.1, 141.6, 141.4, 141.2, 138.1, 133.1, 129.0, 128.7, 128.3, 127.1, 126.6,
126.2, 126.2, 125.0, 124.8, 124.7, 120.1, 113.3,111.0, 60.6, 60.4, 54.9,
45.5, 40.1, 36.5, 29.6, 24.7, 24.7, 13.8,LC-MS (API-ES): m/z C30H35N2O3S2 + Calcd
535.21, found [M+H] + 535.21。
Test example 1
Compound shown in gained formula I will be prepared as fluorescence probe and be applied to aqueous systems, simulation physiological environment and intracellular progress
Detection to selenoprotein, simulate physiological condition, the following terms experiment under the conditions of pH=7.4 carry out (HEPES buffer solution, it is dense
Degree is 10 mM).
Response of the compound to selenoprotein shown in formula I obtained by above-mentioned preparation:
PH is controlled using HEPES buffer solution.Compound shown in formula I is added in 10 ml colorimetric cylinders, is then added pre-assigned
Selenoprotein, 10 mM HEPES constant volumes to 10 ml shake up solution, after balancing 10 min, will, working solution is poured into glimmering in colorimetric cylinder
Fluorescence spectrum is measured in light ware.It is the fluorescent emission before probe reaction such as Fig. 1, Fig. 2 is the fluorescent emission after probe reaction.This change
Closing object can be used for realizing the detection of selenoprotein of in vitro.Meanwhile embodiment 1 provide probe reacted with selenoprotein after production
Object structure is as follows:
The fluorescence imaging intracellular in SH-SY5Y of compound shown in Formulas I: selecting SH-SY5Y cell as biological model, firstly,
At 37 DEG C, cell with selenoprotein handle 2h, (10 μM) of compound shown in Formulas I be incubated for after with laser co-focusing carry out cell at
Picture.There is apparent fluorescence to generate in collection channel, such as Fig. 3.Therefore, probe can be used to directly detect the selenium egg in living cells
It is white.
The present invention detects the two-photon fluorescence probe of selenoprotein, and corresponding fluorescence intensity occurs obvious in the presence of selenoprotein
Variation, can be used for the detection of selenoprotein, and can substantially reduce the interference of external detection condition, improve detection accuracy, detect noise
Than high, sensitivity and selectivity are good.In addition, this kind of compound of the invention selenoprotein fluorescence probe, purple in the presence of selenoprotein
Significant change also occurs for outer absorption, can be detected with ultraviolet specrophotometer.This kind of compound can be used for as fluorescence probe
The detection of selenoprotein in complex biological sample, under this stimulates further investigation external factor, the cell of selenoprotein in vivo
Signal transduction has important biomedical meaning.The above content is combine specific preferred embodiment made for the present invention
It is further described, and it cannot be said that specific implementation of the invention is only limited to these instructions.Technology belonging to the present invention is led
For the those of ordinary skill in domain, without departing from the inventive concept of the premise, a number of simple deductions or replacements can also be made,
It all shall be regarded as belonging to protection scope of the present invention.It is a kind of purposes of noval chemical compound of the present invention as fluorescent dye, cannot recognizes
Determine the compound of the present invention and be only used for fluorescent dye, for those of ordinary skill in the art to which the present invention belongs, in base
Under the considerations of the compounds of this invention is used as the identical mechanism of action of fluorescent dye, several simple inferences can also be made, are obtained
The other application purposes of the compound of the present invention, all shall be regarded as belonging to protection scope of the present invention.
Claims (3)
1. a kind of fluorescent probe compounds for selenoprotein detection, which is characterized in that the compound structure is as shown in formula I:
Formula I.
2. a kind of preparation method of the fluorescent probe compounds for selenoprotein detection, which is characterized in that step includes:
(1) the bromo- beta naphthal of 6- is reacted under catalytic action with methylamine hydrochloride, so that hydroxyl converts methylamino, obtains chemical combination
Object one；
Compound one
(2) compound one is reacted again with CuCN and generates cyano, obtain compound two；
Compound two
(3) compound two is reacted with diisobutyl aluminium hydride, so that cyano is converted into aldehyde radical, obtains compound three；
Compound three
(4) by after 2,3,3- trimethyl -3H- indoles and iodoethane reaction, cyanines, i.e. compound four are spent in synthesis half；
Compound four
(5) compound three is reacted with compound four, synthesizes fluorogen, i.e. compound five；
Compound five
(6) by compound five and triphosgene, N, the reaction of N- diisopropylethylamine；Add anhydrous methylene chloride, N, N- diisopropyl
Base ethamine, 4-dimethylaminopyridine, the reaction of 2,2'- bis- thiodiethanols obtain the yellow product such as formula I.
3. a kind of two-photon fluorescence probe, which is characterized in that compound as described in claim 1 is double as detection selenoprotein
Photon fluorescence probe.
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| CN113045497A (en) * | 2021-06-02 | 2021-06-29 | 中国农业科学院北京畜牧兽医研究所 | Selenol reaction type naphthalimide fluorescent probe, preparation method thereof and application thereof in food detection |
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| CN104910060A (en) * | 2015-05-28 | 2015-09-16 | 中国科学院烟台海岸带研究所 | Fluorophore derivative and application thereof |
| CN108164450A (en) * | 2018-02-08 | 2018-06-15 | 赣南师范大学 | A kind of carboxy-lesterase fluorescence probe and its preparation method and application |
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| CN104910060A (en) * | 2015-05-28 | 2015-09-16 | 中国科学院烟台海岸带研究所 | Fluorophore derivative and application thereof |
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| CN113045497A (en) * | 2021-06-02 | 2021-06-29 | 中国农业科学院北京畜牧兽医研究所 | Selenol reaction type naphthalimide fluorescent probe, preparation method thereof and application thereof in food detection |
| CN113045497B (en) * | 2021-06-02 | 2021-09-28 | 中国农业科学院北京畜牧兽医研究所 | Selenol reaction type naphthalimide fluorescent probe, preparation method thereof and application thereof in food detection |
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