CN109810107A - A kind of fluorescence probe and preparation method thereof identifying mercaptoamino acid - Google Patents
A kind of fluorescence probe and preparation method thereof identifying mercaptoamino acid Download PDFInfo
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- CN109810107A CN109810107A CN201910157973.9A CN201910157973A CN109810107A CN 109810107 A CN109810107 A CN 109810107A CN 201910157973 A CN201910157973 A CN 201910157973A CN 109810107 A CN109810107 A CN 109810107A
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Abstract
A kind of fluorescence probe and preparation method thereof the invention discloses detection based on naphthalimide indoles containing mercaptoamino acid, structure is as follows:The probe is selectively good for detecting cysteine, homocysteine and glutathione, strong antijamming capability, and fast response time；There is long wavelength emission and big stoke shift in detection process simultaneously, the sensitivity and lesser background interference of detection can be improved.The probe can be used for biological sample and the intracellular detection containing mercaptoamino acid.
Description
Technical field
The invention belongs to chemical analysis detection technique fields, and in particular to a kind of fluorescence spy of the detection containing mercaptoamino acid
The application of needle and the probe in detection mercaptoamino acid.
Background technique
Cysteine (Cys), homocysteine (Hcy) and reduced glutathione (GSH) are main biological thiols,
It is the amino acid containing sulfydryl, plays an important role in the physiology of mammal life system and pathologic process.Half Guang ammonia
The concentration abnormality of acid and a variety of diseases have the concentration of cysteine in relationship, such as human body it is too low when can cause slow growth,
The diseases such as hepatic injury, research shows that the exception of semicystinol concentration is also related with the diseases such as skin injury, drowsiness and oedema；Homotype
The concentration of cysteine increases related with diseases such as cardiovascular disease, Alzheimer disease and osteoporosis；Reduced glutathione
It is main antioxidant in human body, human body can be protected from the damage of free radical, the redox state of organism is dense with it
Spending has direct relation, and the concentration abnormality of the diseases such as oligoleukocythemia, cancer, AIDS and reduced glutathione also has closely
Relationship.Therefore, it is meaningful that exploitation, which has high selection, highly sensitive method of the detection containing mercaptoamino acid,.
In recent years, fluorescence probe has become common method of the detection containing mercaptoamino acid, and being primarily due to fluorescence probe can
To realize the non-destructive testing of high-spatial and temporal resolution, and it is easy to operate at low cost.Currently, having some about glimmering containing mercaptoamino acid
The document report of light probe, but such most of fluorescence probe launch wavelength is in blue light or yellow region, and Stokes position
It moves and is less than 100nm.The background interference of long wavelength emission (feux rouges or near infrared light) in the detection process is small, and penetration into tissue is strong,
Detection in vivo has very big advantage.The fluorescence probe of big Stokes shift in the detection process excitation wavelength and
The difference comparsion of launch wavelength is big, can reduce self-absorption and the interference of autofluorescence, to improve the sensitivity of detection.Mesh
Before, research and development can be realized quickly detection mercaptoamino acid, and the fluorescence probe with long wavelength emission, big Stokes shift
It is still challenge.
Summary of the invention
In order to overcome the deficiencies of the prior art, one of the object of the invention is to provide a kind of while having red emission and this big support
Ke Si displacement, and quickly detect the fluorescence probe containing mercaptoamino acid；The second purpose is to provide preparation method.
Fluorescence probe in the present invention, structure are as follows:
Fluorescence probe in the present invention is prepared by following reaction, and synthesis process is as follows:
Specific synthetic method is as follows: (a) compound 1 is dissolved in glycol monoethyl ether, is heated to 115 DEG C until reaction solution
Become clarification, hydrazine hydrate (80%) is then added dropwise dropwise into above-mentioned mixed liquor, is added dropwise to complete rear mixed liquor and continues to be heated to reflux instead
It answers 3 hours, to after the reaction was completed, be cooled to room temperature, a large amount of crocus precipitatings is precipitated, filtration washing obtains compound 2.(b) will
Intermediate 2 is dissolved in 3- methyl -2- butanone, and the concentrated sulfuric acid is then slowly added dropwise, and reaction mixture flows back stir under nitrogen protection
It mixes 4 hours, 3- methyl -2- butanone is evaporated off to after completion of the reaction, depressurize rotation, obtains crude product, is separated with silica gel column layer pure
Change obtains light yellow solid product 3.(c) compound 3 and parahydroxyben-zaldehyde are dissolved in dry toluene, are stirred and evenly mixed then
Glacial acetic acid and piperidines is successively added dropwise into above-mentioned mixed liquor, after being added dropwise, return stirring 6 is small under nitrogen protection for mixed liquor
When, decompression rotation is evaporated toluene, obtains crude product, uses column chromatography purifying and obtain red solid product 4.(d) by compound 4
It is dissolved in 2,4- dinitrophenyl chloride in dry methylene chloride, adds triethylamine, stirred 4 hours under ice-water bath, it will be anti-
Liquid decompression rotation solvent evaporated is answered, crude product is obtained, is purified to obtain crocus solid product, i.e. probe with chromatography.
The testing mechanism of fluorescence probe of the invention is as follows:
Fluorescence probe unstressed configuration itself, reacts with mercaptoamino acid, and 2,4- dinitrobenzene parts are left away from probe, launches red
Color fluorescence.
The maximum absorption band of fluorescence probe of the invention exists in 453nm with maximum emission peak after mercaptoamino acid reacts is contained
590nm, stoke shift 137nm.
The excitation wavelength that fluorescence probe of the invention selects during the test is 488nm.
Fluorescence probe of the invention is selectively good.The PBS buffer solution packet that the test system of probe is the 10mM that pH is 7.4
CTAB containing 1.0mM is tested at 25 DEG C.Probe itself is in fluorescent quenching state, is being separately added into 3.5 times of equivalent cysteines
(Cys), after homocysteine (Hcy) and reduced glutathione (GSH), the fluorescence intensity at maximum emission wavelength 590nm
Increase 24 times.And be added its detectable substance (Arg, Ile, Ser, His, Ala, Phe, Glu, Trp, Thr, Val, Lys, Asp,
Tyr, Leu, Gly, Pro, Met) after, fluorescence intensity is almost without increase.
Fluorescence probe strong antijamming capability of the invention, other detectable substances (Arg, Ile, Ser, His, Ala, Phe,
Glu, Trp, Thr, Val, Lys, Asp, Tyr, Leu, Gly, Pro, Met) in the presence of do not influence cysteine (Cys), homotype
The detection effect of cysteine (Hcy) and reduced glutathione (GSH).
Fluorescence probe detection speed of the invention is fast.It is being separately added into 3.5 times of equivalent cysteines (Cys), half Guang of homotype
After propylhomoserin (Hcy) and reduced glutathione (GSH) effect, fluorescence enhances immediately, reaches maximum value in 5min.
Fluorescence probe of the invention can be to cysteine (Cys), homocysteine (Hcy) and reduced glutathione
(GSH) quantitative detection is carried out respectively.Fluorescence probe of the invention is linearly preferable, and linearly dependent coefficient is respectively as follows: cysteine
(Cys) R=0.9857, homocysteine (Hcy) R=0.9969, reduced glutathione (GSH) R=0.9805.
Fluorescence probe of the invention has lower cytotoxicity, is measured by MTT method, dark to cultivate within 20 μM
For 24 hours, survival rate is 95% or more.
Fluorescence probe of the invention has good cell membrane penetration, can be used for endogenous cellular containing mercaptoamino acid
Detection.
Probe pH application range of the present invention is wider, detectable from pH=5.0 to pH=10.0.
Fluorescence probe of the invention also can be used for the detection that living body includes mercaptoamino acid.
Detailed description of the invention
Fig. 1 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, change with the fluorescence spectrum after various concentration cysteine (Cys) effect, abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 2 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, with fluorescence intensity at 590nm in cysteine (Cys) mechanism with the linear relationship of concentration, abscissa is concentration, indulges and sits
It is designated as fluorescence intensity.
Fig. 3 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, change with the fluorescence spectrum after various concentration homocysteine (Hcy) effect, abscissa is wavelength, and ordinate is fluorescence
Intensity.
Fig. 4 is fluorescence probe (10.0 μM) of the invention in PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
With for fluorescence intensity with the linear relationship of concentration, abscissa is concentration at 590nm in half homocysteine (Hcy) mechanism,
Ordinate is fluorescence intensity.
Fig. 5 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, change with the fluorescence spectrum after various concentration reduced glutathione (GSH) effect, abscissa is wavelength, and ordinate is fluorescence
Intensity.
Fig. 6 is fluorescence probe (10.0 μM) of the invention in PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
With for fluorescence intensity with the linear relationship of concentration, abscissa is concentration at 590nm in reduced glutathione (GSH) mechanism, indulge
Coordinate is fluorescence intensity.
Fig. 7 is the selectivity of fluorescence probe of the invention, and fluorescence probe is at (10.0 μM) in PBS buffer solution (10mM, pH
=7.4,1.0mM CTAB) with Cys, Hcy, GSH, Arg, Ile, Ser, His, Ala, Phe, Glu, Trp, Thr, Val, Lys,
Fluorescence spectrum after Asp, Tyr, Leu, Gly, Pro, Met effect, abscissa is wavelength, and ordinate is fluorescence intensity.
Fig. 8 is the anti-interference of fluorescence probe of the invention, cysteine (Cys) and analyte (Arg, Ile, Ser,
His, Ala, Phe, Glu, Trp, Thr, Val, Lys, Asp, Tyr, Leu, Gly, Pro, Met) when coexisting, exist with fluorescence probe
(10.0 μM) are strong with the fluorescence after cysteine (Cys) effect in PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
Spend ratio (IProbe+others/IProbe+Cys) histogram.
Fig. 9 is the anti-interference of fluorescence probe of the invention, homocysteine (Hcy) and analyte (Arg, Ile,
Ser, His, Ala, Phe, Glu, Trp, Thr, Val, Lys, Asp, Tyr, Leu, Gly, Pro, Met) when coexisting, with fluorescence probe
At (10.0 μM) in PBS buffer solution (10mM, pH=7.4,1.0mM CTAB) and after homocysteine (Hcy) effect
Fluorescence intensity ratio (IProbe+others/IProbe+Hcy) histogram.
Figure 10 is the anti-interference of fluorescence probe of the invention, reduced glutathione (GSH) and analyte (Arg, Ile,
Ser, His, Ala, Phe, Glu, Trp, Thr, Val, Lys, Asp, Tyr, Leu, Gly, Pro, Met) when coexisting, with fluorescence probe
At (10.0 μM) in PBS buffer solution (10mM, pH=7.4,1.0mM CTAB) and after reduced glutathione (GSH) effect
Fluorescence intensity ratio (IProbe+others/IProbe+GSH) histogram.
Figure 11 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, probe changes with time with fluorescence intensity at 590nm in cysteine (Cys) mechanism, and abscissa is the time, indulges and sits
It is designated as fluorescence intensity.
Figure 12 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, probe changes with time with fluorescence intensity at 590nm in homocysteine (Hcy) mechanism, and abscissa is the time,
Ordinate is fluorescence intensity.
Figure 13 is fluorescence probe (10.0 μM) of the invention at PBS buffer solution (10mM, pH=7.4,1.0mM CTAB)
In, probe changes with time with fluorescence intensity at 590nm in reduced glutathione (GSH) mechanism, and abscissa is the time,
Ordinate is fluorescence intensity.
Figure 14 is fluorescence probe (10.0 μM) of the invention in different pH value buffer solutions, with cysteine, homotype half
The fluorescence intensity of cystine and glutathione effect front and back, abscissa pH, ordinate is fluorescence intensity.
Figure 15 is the copolymerization coke cell imaging that fluorescence probe of the invention detects the intracellular mercaptoamino acid of MCF-7,37
DEG C when imaging effect.A1-A3First 15min is cultivated with cysteine Cys (0.5mM) for cell to cultivate with (10.0 μM) of probe again
The imaging of 15min；B1-B3First 15min is cultivated with homocysteine Hcy (0.5mM) for cell to cultivate with (10.0 μM) of probe again
The imaging of 15min；C1-C315min first, which is cultivated, with glutathione (0.5mM) for cell cultivates 15min's with (10.0 μM) of probe again
Imaging；D1-D3For the imaging of probe (10.0 μM) and cell culture 15min；E1-E3For cell first with NEM cultivate 15min again with
The imaging of probe cultivation 15min.
Figure 16 is the toxicity test of fluorescence probe of the invention to cell.In probe molecule concentration 1.0 × 10-5mol/L
When, cell survival rate is 95% or more.
Example is embodied
Embodiment 1: the synthesis of compound 2
Compound 1 (3.32g, 10.0mmol) is dissolved in 50mL glycol monoethyl ether, is heated to 115 DEG C until reaction solution becomes clear
Clearly, it is then added dropwise dropwise into above-mentioned mixed liquor 3.0mL hydrazine hydrate (80%), is added dropwise to complete rear mixed liquor and continues to be heated to reflux instead
It answers 3 hours, to after the reaction was completed, be cooled to room temperature, a large amount of crocus precipitatings is precipitated, filtration washing obtains compound 2.Yield:
2.32g；Yield: 81.9%.
Embodiment 2: the synthesis of compound 3
Intermediate 2 (1.98g, 7mmol) is dissolved in 3- methyl -2- butanone (100mL), the 3mL concentrated sulfuric acid is then slowly added dropwise,
Reaction mixture return stirring 4 hours under nitrogen protection, to after completion of the reaction, 3- methyl -2- butanone is evaporated off in decompression rotation,
Crude product is obtained, (petroleum ether/methylene chloride=1/10, v/v) is isolated and purified with silica gel column layer and obtains light yellow solid product 3.
Yield: 1.13g；Yield: 48.5%.
Embodiment 3: the synthesis of compound 4
Compound 3 (1.0g, 3mmol) and parahydroxyben-zaldehyde (0.37g, 3mmol) are dissolved in the dry toluene of 20mL, stirring
It mixes and glacial acetic acid (0.02mL) and piperidines (0.05mL) is then successively added dropwise into above-mentioned mixed liquor, after being added dropwise, mixed liquor
Return stirring 6 hours under nitrogen protection, decompression rotation is evaporated toluene, obtain crude product, use column chromatography purifying (ethyl alcohol/
Methylene chloride=1/50, v/v) obtain red solid product 4.Yield: 0.68g；Yield: 51.7%.
Embodiment 4: the synthesis of probe
Compound 4 (0.483g, 1mmol), 2,4- dinitrophenyl chlorides (0.563g, 2.11mmol) are dissolved in dry two of 15mL
It in chloromethanes, adds triethylamine (0.476g, 4.7mmol), is stirred 4 hours under ice-water bath, reaction solution decompression rotation is evaporated
Solvent obtains crude product, with chromatography purify (ethyl acetate/dichloromethane=0.3:10, v/v) obtain crocus solid produce
Product 5 are probe molecule.Yield: 1.13g；Yield: 48.5%.
Embodiment 6: probe molecule detects cysteine (Cys), homocysteine (Hcy) and reduction paddy Guang in cell
The application of sweet peptide (GSH)
MCF-7 cell is incubated for 15min with the PBS buffer solution (10.0mM, pH=7.4) containing NEM (1.0mM) first, is buffered with PBS
Liquid rinses 3 times；It is incubated for 15min with the PBS buffer solution containing probe (10.0 μM) again, after being rinsed 3 times with PBS buffer solution, uses laser
Confocal fluorescent microscopic carries out cell fluorescence imaging, can't see fluorescence signal.MCF-7 cell is used containing probe (10.0 μM)
PBS buffer solution be incubated for 15min, with PBS buffer solution rinse 3 times after, with laser confocal fluorescence microscope carry out cell fluorescence at
Picture, it is seen that red fluorescent.MCF-7 cell is incubated with the PBS buffer solution (10.0mM, pH=7.4) containing Cys (0.5mM) first
15min is educated, is rinsed 3 times with PBS buffer solution；It is incubated for 15min with the PBS buffer solution containing probe (10.0 μM) again, uses PBS buffer solution
After rinsing 3 times, cell fluorescence imaging is carried out with laser confocal fluorescence microscope, it is seen that intense red fluorescence signal.MCF-7 is thin
Born of the same parents are incubated for 15min with the PBS buffer solution (10.0mM, pH=7.4) containing Hcy (0.5mM) first, are rinsed 3 times with PBS buffer solution；
It is incubated for 15min with the PBS buffer solution containing probe (10.0 μM) again, after being rinsed 3 times with PBS buffer solution, with laser co-focusing fluorescence
Microscope carries out cell fluorescence imaging, it is seen that intense red fluorescence signal.MCF-7 cell is first with the PBS for containing GSH (0.5mM)
Buffer (10.0mM, pH=7.4) is incubated for 15min, is rinsed 3 times with PBS buffer solution；It is slow with the PBS containing probe (10.0 μM) again
Fliud flushing is incubated for 15min, after being rinsed 3 times with PBS buffer solution, carries out cell fluorescence imaging with laser confocal fluorescence microscope, sees
To intense red fluorescence signal.These are the result shows that fluorescence probe of the invention can be used for the inspection that cell includes mercaptoamino acid
It surveys.
Claims (1)
1. a kind of fluorescence probe for identifying biological thiol, structural formula are as follows:
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354584A (en) * | 2021-06-15 | 2021-09-07 | 郑州大学 | Naphthalimide fluorescent probe for distinguishing Cys, Hcy and GSH, and preparation method and application thereof |
| CN116840197A (en) * | 2022-03-23 | 2023-10-03 | 中国科学院苏州生物医学工程技术研究所 | 2' -O-methyltransferase activity detection method, kit and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105802606A (en) * | 2014-12-29 | 2016-07-27 | 苏州罗兰生物科技有限公司 | Preparation method and use of mercapto-containing amino acid fluorescent probe |
| CN108530446A (en) * | 2018-06-13 | 2018-09-14 | 郑州大学 | A kind of fluorescence probe of identification benzenethiol |
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2019
- 2019-03-02 CN CN201910157973.9A patent/CN109810107A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105802606A (en) * | 2014-12-29 | 2016-07-27 | 苏州罗兰生物科技有限公司 | Preparation method and use of mercapto-containing amino acid fluorescent probe |
| CN108530446A (en) * | 2018-06-13 | 2018-09-14 | 郑州大学 | A kind of fluorescence probe of identification benzenethiol |
Non-Patent Citations (1)
| Title |
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| BAOXIN ZHANG ET AL.: "Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications", 《J. AM. CHEM. SOC.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113354584A (en) * | 2021-06-15 | 2021-09-07 | 郑州大学 | Naphthalimide fluorescent probe for distinguishing Cys, Hcy and GSH, and preparation method and application thereof |
| CN113354584B (en) * | 2021-06-15 | 2023-05-16 | 郑州大学 | Naphthalimide fluorescent probe for distinguishing Cys, hcy and GSH, and preparation method and application thereof |
| CN116840197A (en) * | 2022-03-23 | 2023-10-03 | 中国科学院苏州生物医学工程技术研究所 | 2' -O-methyltransferase activity detection method, kit and application |
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