CN105820810B - A kind of synthesis and application for identifying cysteine and homocysteine novel fluorescence probe - Google Patents
A kind of synthesis and application for identifying cysteine and homocysteine novel fluorescence probe Download PDFInfo
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- CN105820810B CN105820810B CN201610267757.6A CN201610267757A CN105820810B CN 105820810 B CN105820810 B CN 105820810B CN 201610267757 A CN201610267757 A CN 201610267757A CN 105820810 B CN105820810 B CN 105820810B
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Abstract
The present invention relates to a kind of preparation method and application for being used to detect the fluorescence probe of cysteine and homocysteine, belong to chemical analysis detection technique field.Its molecular structure is as follows：The probe molecule maximum absorption wavelength is in 368nm, after probe molecule acts on cysteine or homocysteine, for intensity by nothing to having and constantly strengthening, the sensitivity of detection can be improved to fluorescence spectrum by showing larger Stokes shift (Stokes shifts) at 585nm；The light injury of background fluorescence and living cells of the launch wavelength during near-infrared can reduce probe in detecting.Probe molecule detection sensitivity of the present invention is higher, and strong to recognition capability containing mercaptoamino acid, response speed is very fast, strong antijamming capability, and such probe has important application value in fields such as biochemistries.
Description
Technical field
The invention belongs to chemical analysis detection technique field, and in particular to one kind can detect cysteine and the Guang of homotype half
The preparation method of new feux rouges-near infrared fluorescent probe of propylhomoserin and its in vitro with living cells inside detection cysteine and
Application in terms of homocysteine.
Background technology
Biological sulfhydryl compound, cysteine (Cysteine, Cys), homocysteine (Homocysteine, Hcy)
With glutathione (Glutataione, GSH) etc. important adjustment effect is played in the physiology of biology and pathologic process.Half
Cystine is the essential amino acid of the protein synthesis for participating in life entity, detoxication and metabolic processes.Research shows,
Cysteine is too high to have substantial connection with neurotoxicity, and cysteine is too low with slow-growing, drowsiness, hepatic injury, skin
Infringement etc. is associated.Homocysteine is relevant with various blood vessels and kidney trouble.Too high can increase of homocysteine obtains the heart
The risk of vascular diseases and Alzheimers disease.Glutathione be people's vivo oxidation reduction and detoxication whether normal operation
Indicator, and and Neuroleptic Leukocytopenia, cancer, AIDS viral infection etc. have close ties.Therefore effective biological sulphur is studied
The detection technique of alcohol is all extremely important in chemistry, biology, and medical domain.Because fluorescence probe has simple to operate, nothing
Radiation, high sensitivity and high-resolution advantage, become the ideal chose of detection biological thiol.At present, it has been reported that
A variety of fluorescence probes with high-sensitivity detection biological thiol.But most of this kind of probe is the strong nucleophilic based on sulphur atom
Property, therefore their detections to cysteine and homocysteine are difficult to the interference for resisting other mercaptan.And it is most this
Class probe also has the shortcomings that short launch wavelength and small Stokes shift (Stokes shifts).But grow launch wavelength energy
The light injury of background fluorescence and living cells enough during reduction probe in detecting, big Stokes shift can improve the spirit of detection
Sensitivity.So far it is not yet reported that excessively a kind of have big Stokes shift, for detecting cysteine and homocysteine, base
In feux rouges-near infrared fluorescent probe of acryloyl fat.
The content of the invention
One of present invention purpose is to provide that a kind of synthesis is simple, reaction is gentle, yield is higher, lower-cost fluorescence is visited
Pin synthetic method；Another object of the present invention is to provide a kind of good selectivity, high sensitivity, strong anti-interference ability, big stoke
This displacement (Stokes shifts), launch wavelength, can be to the cysteines inside external or living cells and same in near-infrared
Type cysteine is monitored or the fluorescence probe of cell fluorescence imaging.
The technical scheme of the present invention that solves the problems, such as to take is, a kind of fluorescent switch (off-on) method identification cysteine and same
The novel fluorescence probe of type cysteine, its molecular structural formula are as follows：Synthetic route is as follows：Specific synthetic method is as follows：(a) exist
In 50ml round-bottomed flasks, by 3- nitrophthalonitriles (2.0g, 11.6mmol), K2CO3(1.8g, 12.7mmol) and NaNO2
(0.8g, 11.6mmol) is dissolved in dimethyl sulfoxide (DMSO) (30mL), and 130 DEG C of oil baths are stirred at reflux 30min, and reaction is completed.It is cooled to
Room temperature, 90ml distilled water diluting reaction solutions are added, be acidified to PH=3 with 2M hydrochloric acid, produce precipitation, filter, with distilled water and first
Alcohol washs filter cake, vacuum drying, and glacial acetic acid recrystallization is further purified to obtain brown crystal.Produce intermediate product 3- hydroxyl neighbour's benzene
Dimethoxy nitrile.Yield：0.9g.Yield 54%.(b) in 25ml round-bottomed flasks, by upper step products therefrom (288mg, 2mmol), 2-
Aminopyridine (385mg, 4.1mmol) and CaCl2(46mg, 0.41mmol) is dissolved in n-butanol (6mL).Argon gas is protected, 110 DEG C
Oil bath heating flows back 5 days, and reaction is complete, is cooled to room temperature, and vacuum revolving removes n-butanol, washing, natural filtration, filter cake vacuum
Dry, purify to obtain product through column chromatography, be dried in vacuum overnight, obtain crocus powder.Produce intermediate product hydroxy dye 4.
Yield：141.6mg.Yield 25%.(c) upper step products therefrom (79.25mg, 0.25mmol) is dissolved in 10mL anhydrous methylene chlorides
In, triethylamine (0.07mL, 0.5mmol) is added, the acryloyl chloride for being dissolved in 4ml anhydrous methylene chlorides is added dropwise under ice bath
(58.16mg, 0.31mmol), argon gas protection, lower reaction 10 minutes is stirred at room temperature, reaction is complete, and dichloro is evaporated off in ice bath backspin
Methane, the isolated yellow powder of rapid column chromatography.Produce probe molecule.Yield：75.31mg.Yield：81.2%.
The mechanism of action of the fluorescence probe of the present invention is as follows, due to the Photo-induced electron transfer (PET) of acrylate part,
Probe molecule does not have fluorescence.Cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) can be with probe molecules
The double bond of middle acrylate occurs nucleophilic addition and obtains sulfide derivative, cysteine (Cys) and homocysteine
(Hcy) sulfide derivative obtained after reacting can be sloughed polysulfide moiety by intramolecular cyclization and recover hydroxy dye 4, probe point
Son becomes very strong red fluorescence by unstressed configuration, and the sulfide derivative obtained after glutathione (GSH) reaction is because intermediate product
Dynamics prohibit and can not occur intramolecular cyclization reaction.So as to realize specific detection cysteine (Cys) and homotype half
The purpose of cystine (Hcy).The response process of probe molecule is as follows：
High performance liquid chromatography demonstrates this Response Mechanism, each in probe molecule and the liquid chromatogram of corresponding hydroxy dye 4
Occur within comfortable 15 minutes and 24.57 minutes unimodal.After probe molecule is handled with 0.5 times of equivalent cysteine (Cys), 15 minutes
Probe molecule peak weaken while, there is the unimodal of dyestuff 4 within 24.57 minutes.Visited with 5 times of equivalent cysteine (Cys) processing
After pin molecule, the probe molecule peak of 15 minutes is wholly absent, and leaves behind the dye molecule peak of 24.57 minutes.
Fluorescence probe of the invention acts near infrared emission, itself and cysteine (Cys) and homocysteine (Hcy)
Preceding unstressed configuration, fluorescence emission peak is at 585nm after effect.
The fluorescence probe of the present invention has a big Stokes shift (Stokes shifts), absorption maximum in 368nm, with
Emission maximum is in 585nm, Stokes shift (Stokes after cysteine (Cys) and homocysteine (Hcy) effect
Shifts) it is 217nm.
The fluorescence probe of the present invention is selectively good.The test system of probe molecule is the cetyl front three containing 1.0mM
Base ammonium bromide (CTAB), PH are 7.4 10mM PBS cushioning liquid, are measured at room temperature.Probe molecule does not have fluorescence in itself,
Add after 5 times of equivalent cysteines (Cys), fluorescence intensity increases 86 times at maximum emission wavelength 585nm, adds 5 times
After equivalent cysteine (Hcy), fluorescence intensity increases 84 times.And adding the GSH and other physiology amino of same equivalent
After sour (Asp, Ala, Val, Phe, His, Leu, Ser, IIe, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, andThr),
Fluorescence only has almost negligible increase.
The fluorescence probe strong antijamming capability of the present invention, other physiology amino acid (Asp, Ala, Val, Phe, His, Leu,
Ser, IIe, Trp, Lys, Arg, Pro, Gly, Met, Tyr, Glu, and Thr) presence do not influence probe molecule and half Guang ammonia
The effect of sour (Cys).
The fluorescence probe high sensitivity of the present invention, the fluorescence intensity of probe molecule is with the increasing of cysteine (Cys) concentration
Add gradual increase, until reaching maximum.Cysteine (Cys) concentration is strong in the fluorescence of low concentration (0-7uM) and probe molecule
Spend into good linear relationship.Detection is limited to 5.6nM.It can be seen that probe molecule of the invention can be used for detecting half Guang in aqueous phase
Propylhomoserin (Cys) and homocysteine (Hcy).
The fluorescence probe of the present invention is to cysteine (Cys) and homocysteine (Hcy) fast response time, probe molecule
After the cysteine (Cys) of 5 times of equivalents of middle addition, fluorescence quickly strengthens, and maximum was reached at 10 minutes, 5 times of equivalents of addition
After homocysteine (Hcy), reached maximum at 15 minutes.And the significant change of fluorescence can be observed in 30 seconds.
The fluorescence probe of the present invention shows wider application, and probe molecule all may be used in the range of being 7 to 10 in pH
With to cysteine Selective recognition.
Probe molecule synthetic route of the present invention is simple, and yield is higher, and cost is relatively low, to cysteine (Cys)
With the launch wavelength of homocysteine (Hcy) in near-infrared, stoke shift is big, the good, strong antijamming capability of selectivity, sensitive
Degree is high, fast response time, has wider application, and the fluorescence probe has real in fields such as biochemistry, environmental sciences
The application value on border.
Brief description of the drawings
Fig. 1 be fluorescence probe of the present invention selectivity, fluorescence probe (5.0 × 10-6Mol/L) in PBS cushioning liquid
In (10mM, pH=7.4,1.0Mm CTAB), the fluorescence spectrum after being acted on variety classes amino acid, abscissa is wavelength, is indulged
Coordinate is fluorescence intensity.
Fig. 2 is the antijamming capability of fluorescence probe of the present invention, and glimmering when cysteine (Cys) and other amino acid coexist
Light probe (5.0 × 10-6Mol/L after) being acted in PBS cushioning liquid (10mM, pH=7.4,1.0Mm CTAB) with cysteine
Fluorescence intensity ratio (I/I0) block diagram.
Fig. 3 is the fluorescence probe (5.0 × 10 of the present invention-5Mol/L) high performance liquid chromatography (a) fluorescence at different conditions
The liquid chromatogram of probe.(b) fluorescence probe (5.0 × 10-5Mol/L the liquid chromatogram after) being acted on 0.5equiv. cysteines.
(c) fluorescence probe (5.0 × 10-5Mol/L the liquid chromatogram after) being acted on 5equiv. cysteines.(d) fluorescence probe and half Guang
The hydroxy dye 4 (5.0 × 10 generated after propylhomoserin effect-5Mol/L) liquid chromatogram.Abscissa is the time, and ordinate is response.
Fig. 4 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in PBS cushioning liquid (10mM, pH=7.4,1.0Mm
CTAB in), the fluorescence spectrum after being acted on various concentrations cysteine (Cys) changes, and abscissa is wavelength, and ordinate is fluorescence
Intensity.
Fig. 5 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in PBS cushioning liquid (10mM, pH=7.4,1.0Mm
CTAB in), the linear relationship with cysteine (Cys) concentration, abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 6 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in PBS cushioning liquid (10mM, pH=7.4,1.0Mm
CTAB in), the fluorescence spectrum after being acted on various concentrations homocysteine (Hcy) changes, and abscissa is wavelength, and ordinate is
Fluorescence intensity.
Fig. 7 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in PBS cushioning liquid (10mM, pH=7.4,1.0Mm
CTAB in), the linear relationship with homocysteine (Hcy) concentration, abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 8 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in PBS cushioning liquid (10mM, pH=7.4,1.0Mm
CTAB in), with fluorescence intensity in cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) mechanism with
The change of time, abscissa are the time, and ordinate is fluorescence intensity.
Fig. 9 is the fluorescence probe (5.0 × 10 of the present invention-6Mol/L) in different pH value cushioning liquid, with cysteine
(Cys) the front and rear fluorescence intensity of effect, abscissa pH, ordinate is fluorescence intensity.
Example is embodied
Embodiment 1：The synthesis of intermediate product 3- hydroxyl phthalonitriles
In 50ml round-bottomed flasks, by 3- nitrophthalonitriles (2.0g, 11.6mmol), K2CO3(1.8g,
12.7mmol) and NaNO2(0.8g, 11.6mmol) is dissolved in dimethyl sulfoxide (DMSO) (30mL), and 130 °C of oil baths are stirred at reflux 30 points
Clock, reaction are completed.Room temperature is cooled to, adds 90ml distilled water diluting reaction solutions, PH=3 is acidified to 2M hydrochloric acid, produces precipitation,
Filter, filter cake is washed with distilled water and methanol, be dried in vacuo, glacial acetic acid recrystallization is further purified to obtain brown crystal.Yield：
0.9g.Yield 54%.
Embodiment 2：The synthesis of intermediate product dyestuff 4
In 25ml round-bottomed flasks, by upper step products therefrom 3- hydroxyls phthalonitrile (288mg, 2mmol), 2- amino pyrroles
Pyridine (385mg, 4.1mmol) and CaCl2(46mg, 0.41mmol) is dissolved in n-butanol (6mL).Argon gas is protected, and 110 DEG C of oil baths add
Heat backflow 5 days, reaction is complete, is cooled to room temperature, and vacuum, which rotates, removes n-butanol, washing, natural filtration, filter cake vacuum drying,
Purify to obtain product through column chromatography, be dried in vacuum overnight, obtain crocus powder.Yield：141.6mg.Yield 25%.Structure table
Sign is as follows：1H NMR (400MHz, CDCl3)δH13.70 (s, 1H), 8.62 (m, 2H), 7.78 (t, J=7.9Hz, 2H), 7.60
(s, 1H), 7.52 (d, J=7.3Hz, 2H), 7.38 (d, J=8.0Hz, 1H), 7.19-7.09 (m, 3H).13C NMR (101MHz,
CDCl3)δc160.10,159.34,155.81,155.59,153.70,147.98,147.76,138.12,138.08,
135.66,133.58,123.43,122.31,120.50,120.27,118.98,118.29,114.52.
Embodiment 3：The synthesis of probe molecule
Upper step products therefrom (79.25mg, 0.25mmol) is dissolved in 10mL anhydrous methylene chlorides, adds triethylamine
(0.07mL, 0.5mmol), the acryloyl chloride (58.16mg, 0.31mmol) for being dissolved in 4ml anhydrous methylene chlorides, argon are added under ice bath
Gas shielded, lower reaction 10 minutes is stirred at room temperature, reaction is complete, and dichloromethane is evaporated off in ice bath backspin, and rapid column chromatography separates
To yellow powder.Yield：75.31mg.Yield：81.2%.Probe molecule is characterized as below：1HNMR (400MHz, DMSO) δH
14.02 (s, 1H), 8.74 (d, J=4.6Hz, 2H), 8.02-7.95 (m, 2H), 7.91 (dd, J=14.1,7.2Hz, 1H),
7.82 (t, J=7.7Hz, 1H), 7.56 (d, J=7.9Hz, 1H), 7.48 (d, J=7.8Hz, 1H), 7.29 (dd, J=12.1,
6.9Hz, 2H), 7.19 (d, J=7.8Hz, 1H), 6.63 (d, J=8.0Hz, 2H), 6.29 (dd, J=7.8,3.0Hz, 1H).
Embodiment 4：The present invention:The application of fluorescence probe
Probe molecule is dissolved in PBS cushioning liquid (10mM, pH=7.4,1.0Mm CTAB) and is configured to 5.0 × 10- 6Mol/L solution, added into solution various amino acid (Asp, Ala, Val, Phe, His, Leu, Ser, IIe, Trp, Lys,
Arg, Pro, Gly, Met, Tyr, Glu, Thr and GSH) after do not cause the significant change of fluorescence, and add human amino acid
(Cys, Hcy) causes fluorescence significant changes, the fluorescence probe cysteine and homocysteine are shown high sensitivity,
The identification of high selectivity.When cysteine and interfering material (Asp, Ala, Val, Phe, His, Leu, Ser, IIe, Trp, Lys,
Arg, Pro, Gly, Met, Tyr, Glu, Thr and GSH) when coexisting, the influence of the interference-free factor of probe, show very
Strong antijamming capability.The probe molecule and cysteine fast response time, can be observed the change of fluorescence in 30 seconds.Probe
Molecule can show good biological adaptation ability in the range of being 7 to 10 in pH to cysteine Selective recognition.
Claims (1)
1. one kind identification cysteine and homocysteine fluorescence probe, its structure are：
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| WO2008014280A2 (en) * | 2006-07-25 | 2008-01-31 | Glumetrics, Inc. | Flourescent dyes for use in glucose sensing |
| WO2013126816A1 (en) * | 2012-02-23 | 2013-08-29 | Oregon State Board Of Higher Education On Behalf Of Portland State University | Selective detection of thiols |
| CN103773361A (en) * | 2014-02-25 | 2014-05-07 | 山东大学 | Cysteine fluorescence probe adopting coumarin as fluorophore and application of cysteine fluorescence probe |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008014280A2 (en) * | 2006-07-25 | 2008-01-31 | Glumetrics, Inc. | Flourescent dyes for use in glucose sensing |
| WO2013126816A1 (en) * | 2012-02-23 | 2013-08-29 | Oregon State Board Of Higher Education On Behalf Of Portland State University | Selective detection of thiols |
| CN103773361A (en) * | 2014-02-25 | 2014-05-07 | 山东大学 | Cysteine fluorescence probe adopting coumarin as fluorophore and application of cysteine fluorescence probe |
Non-Patent Citations (1)
| Title |
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| Highly selective red-em itting H2S fluorescent probe with a large Stokes shift;Wenqiang Chen等;《Dyes and Pigments》;20141002;596-601 * |
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