CN106496156A - Conjugation benzothiazole derivant, near infrared fluorescent probe and its preparation and application - Google Patents
Conjugation benzothiazole derivant, near infrared fluorescent probe and its preparation and application Download PDFInfo
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- CN106496156A CN106496156A CN201610884031.7A CN201610884031A CN106496156A CN 106496156 A CN106496156 A CN 106496156A CN 201610884031 A CN201610884031 A CN 201610884031A CN 106496156 A CN106496156 A CN 106496156A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- 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
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- 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
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Abstract
The present invention relates to a kind of conjugation benzothiazole derivant, near infrared fluorescent probe and its preparation and application.Described conjugation benzothiazole derivant, it is characterised in that its structure is：Conjugation benzothiazole derivant preparation method in the present invention is simple, transmitting near-infrared fluorescent, fluorescence quantum yield are high, Stokes shift is big, and there is in development near infrared fluorescent probe and bioluminescence imaging important application prospect.
Description
Technical field
The invention belongs to organic near infrared fluorescent dye preparation field, and in particular to a kind of conjugation of transmitting near-infrared fluorescent
Benzothiazole derivant and preparation method thereof and fluorescence imaging application.
Background technology
Fluorescent technique has simple and quick, Non-Destructive Testing, sensitivity high, easy to automate and visualizes the spies such as ball picture
Put and receive much concern.Especially quickly grow in terms of bioluminescence imaging, fluorescent probe technique has been developed as dynamic monitoring
One of important tool of active somatic cell and diagnosis imaging.But as the background fluorescence of organism itself is disturbed, it is necessary to develop
Fluorescent dye of the fluorescence emission wavelengths near infrared region (650-900nm), so can not only reduce the interference of biological context fluorescence,
And which has relatively low light injury and deeper tissue penetration to biological tissue samples.The near-infrared for having developed at present has
Or its Stokes shift of machine fluorescent dye is typically small, it is 10-20nm or so, part transmitting luminous energy can be caused by self-priming
Receive, cause fluorescent quenching；Fluorescence quantum yield is low, and less than 10%, these can all cause the contrast in bioluminescence imaging
Degree is greatly reduced.Therefore development has the near-infrared organic fluorescent dye of big Stokes shift and high quantum production rate, can pole
The earth improves the accuracy of fluorescence imaging, is very important.
Content of the invention
It is an object of the invention to provide the near-infrared fluorescent that a kind of Stokes shift is big, fluorescent emission quantum yield is high is visited
Pin and preparation method thereof and fluorescence imaging application.
In order to achieve the above object, the invention provides a kind of conjugation benzothiazole derivant, it is characterised in that its structure
For：
Present invention also offers the preparation method of above-mentioned conjugation benzothiazole derivant, it is characterised in that include：
Step 1：Under inert gas shielding, 4- methylphenols are returned for 70-75 DEG C in trifluoroacetic acid with hexamethylenetetramine
Stream reaction 12-48 hours, are cooled to room temperature, and are poured in water, and with chloroform extraction 2-4 time, merging organic phase is simultaneously rotated except dechlorination
Imitative, obtain 3,5- diformyl -4- methylphenols；
Step 2：Under inert gas shielding, by gained 3 in step 1,5- diformyl -4- methylphenols and 2- methyl benzos
Thiazole 140-145 DEG C of backflow 6-24 hour in acetic anhydride, adds NaOH after cooling, little in 80-95 DEG C of stirring 0.5-1.5
When, room temperature is cooled to, pH=6-7 is adjusted with concentrated hydrochloric acid, filtered, gained solid is purified by chromatographed on silica gel post, obtain final product altogether
Yoke benzothiazole derivant.
Preferably, in described step 1 4- methylphenols, hexamethylenetetramine, the proportioning of trifluoroacetic acid are 1mmol:
2mmol∶1ml.
Preferably, in described step 23,5- diformyl -4- methylphenols, 2- methylbenzothiazoles, acetic anhydride
Proportioning is 1mmol: 2mmol: 2ml.
Preferably, when the silica gel chromatograph column chromatography for separation in described step 2 is purified, eluant, eluent is that volume ratio is 10: 1
N-hexane and ethyl acetate.
Preferably, conjugation maximum absorption wave of the benzothiazole derivant in dimethyl sulfoxide in described step 2 is a length of
340nm, maximum emission wavelength is 690nm, fluorescence quantum yield 42%.There is development near infrared fluorescent probe and be used for giving birth to
The application prospect of thing fluorescence imaging.
Present invention also offers a kind of near infrared fluorescent probe, it is characterised in that its structure is：
Present invention also offers the preparation method of above-mentioned near infrared fluorescent probe, it is characterised in that include：
Above-mentioned conjugation benzothiazole derivant is dissolved in chloroform, in the presence of triethylamine, 2,4- dinitro benzene sulphurs is added dropwise
Acyl chlorides, stirs 4-8 hours under room temperature, and with chloroform extraction 2-4 time after adding water, merging organic phase simultaneously rotates removing chloroform, and gained is thick
Product is through by silica gel chromatographic column chromatographic purifying, obtaining final product near infrared fluorescent probe.
Preferably, described conjugation benzothiazole derivant, 2,4- dinitrophenyl chlorides, the proportioning of triethylamine are
1mmol∶2mmol∶1ml.
Present invention also offers the application process of above-mentioned near infrared fluorescent probe, it is characterised in that include：Will in gradient
The aqueous solution of the cysteine of change be separately added into above-mentioned near infrared fluorescent probe phosphate buffer solution (containing 50% ethanol,
PH=7.4), using XRF fluorescence intensity, with semicystinol concentration as abscissa, the change of fluorescence intensity turns to vertical
Coordinate is mapped, and obtains linear work curve, can read the content of cysteine in solution by determining fluorescence intensity from figure,
Wherein excitation wavelength 340nm, launch wavelength 670nm, response time are 20 minutes.
Preferably, described XRF is Edinburgh FS5.
Compared with prior art, the invention has the beneficial effects as follows：
The conjugation benzothiazole derivant of the present invention is a kind of new benzothiazole derivant with conjugated structure, has
Fluorescence emission wavelengths are located near infrared region, fluorescent emission quantum yield is high, Stokes shift is big, preparation method is simple and quick
Feature, and can be used to develop near infrared fluorescent probe to detect cysteine and carry out active somatic cell fluorescence imaging, new in development
There is in type organic molecule near infrared fluorescent probe and high-contrast bioluminescence imaging important application prospect.
The present invention prepare conjugation benzothiazole derivant can launch closely red fluorescence (＞ 650nm), with Stokes position
The characteristics of moving big (＞ 200nm), fluorescent emission quantum yield height (＞ 10%).Nearly near infrared fluorescent probe pair according to the present invention
There is cysteine highly sensitive and high selectivity to respond, and can be applicable to active somatic cell fluorescence imaging.
Description of the drawings
Fig. 1 is that the synthetic route of conjugation benzothiazole derivant I and near infrared fluorescent probe II involved in the present invention is shown
It is intended to；
Fig. 2 is conjugation absorption spectrum and near-infrared of the benzothiazole derivant I in dimethyl sulfoxide involved in the present invention
Fluorescence spectrum；
Fig. 3 is the fluorescence light of near infrared fluorescent probe II involved in the present invention to cysteine (Cys) selective response
Spectrum；
Fig. 4 is near infrared fluorescent probe II involved in the present invention to fluorescence titration spectrum (a) of cysteine and corresponding
Linear relationship (b) between fluorescence intensity and semicystinol concentration；
Fig. 5 is fluorescence imagings of the near infrared fluorescent probe II according to the present invention to cysteine in live body L929 cells
Figure, cell light field (a) that was cultivated with fluorescence probe II and details in a play not acted out on stage, but told through dialogues (b) image.
Specific embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the present invention.In addition, it is to be understood that after the content for having read instruction of the present invention, people in the art
Member can be made various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited
Scope.
Embodiment 1
A kind of conjugation benzothiazole derivant, its structure such as Formulas I, as shown in figure 1, its preparation method is：
(1), under nitrogen protection, 4- methylphenols (15mmol) and hexamethylenetetramine (30mmol) are dissolved in 15ml trifluoros
In acetic acid, 70-75 DEG C of back flow reaction 48 hours is cooled to room temperature (25 DEG C), and is poured in 60ml water, with chloroform extraction three times,
Merge organic phase and rotate removing chloroform, solid obtains 3,5- diformyl -4- methylphenols after drying, and is directly used in next step
Reaction；
(2) under nitrogen protection, by gained 3 in step (1), 5- diformyls -4- methylphenols (1mmol) and 2- methylbenzenes
And thiazole (2mmol) flows back 12 hours for 140-145 DEG C in 2ml acetic anhydride, adds NaOH 1.5g, in 80-95 after cooling
DEG C stirring 1 hour, is cooled to room temperature, adjusts pH=6-7 with concentrated hydrochloric acid, filter, will filter gained solid crude product and pass through silica gel color
Spectrum column chromatography, solvent is ethyl acetate, and eluant, eluent is 10: 1 n-hexane and ethyl acetate, obtains final product conjugation benzothiazole and spreads out
Biological I, characterize data are as follows.
By testing the Absorption and fluorescence spectrum (Fig. 2) in dimethyl sulfoxide, it is seen that I launches near-infrared fluorescent
(690nm), with big Stokes shift (＞ 200nm) and high fluorescence quantum yield (42%).
1H NMR (400MHz, DMSO-d6), δ (ppm)：9.88 (s, 1H), 8.11 (d, J=8Hz, 2H), 8.04 (s, 1H),
7.99 (t, J=4Hz, 3H), 7.69 (s, 2H), 7,59 (d, J=16Hz, 2H), 7.53 (t, J=8Hz, 2H), 7.45 (t, J=
8Hz, 2H), 2.34 (s, 3H)；13C NMR (100MHz, DMSO-d6), δ (ppm)：167.48,153.99,134.48,133.12,
129.27,125.19,122.94,122.63,122.10,20.67.MALDI-TOF-MS：m/z calcd 426.55；found
426.94.
Embodiment 2
A kind of near infrared fluorescent probe, its structure such as Formula II, as shown in figure 1, its preparation method is：
The conjugation benzothiazole derivant (1mmol) of embodiment 1 is dissolved in 10ml chloroforms, in the presence of triethylamine (1ml),
2,4- dinitrophenyl chlorides (2mmol) are added dropwise, are stirred 6 hours under room temperature, add water 20ml, with chloroform extraction three times, be associated with
Machine phase simultaneously rotates removing chloroform, and through by silica gel chromatographic column chromatographic purifying, solvent is ethyl acetate to gained crude product, and eluant, eluent is
10: 1 n-hexane and ethyl acetate, obtain final product near infrared fluorescent probe II, and characterize data is as follows.
1H NMR (400MHz, CDCl3), δ (ppm)：8.32 (s, 1H), 8.26 (d, J=8Hz, 1H), 8.10 (s, 1H),
8.07 (t, J=6Hz, 2H), 7.91 (d, J=8Hz, 2H), 7.72 (d, J=16Hz, 2H), 7.60 (t, J=6Hz, 4H), 7.51
(t, J=8Hz, 2H), 7.39 (d, J=16Hz, 2H), 2.52 (s, 3H)；13C NMR (100MHz, CDCl3), δ (ppm)：
150.35,143.87,138.86,134.48,133.60,131.09,130.54,128.94,127.06,126.46,126.30,
125.01,124.99,122.97,121.77,120.74,21.26.MALDI-TOF-MS：m/z calcd 656.71；found
656.62.
Embodiment 3
Near infrared fluorescent probe is to cysteine selective enumeration method and active somatic cell fluorescence imaging application.
Gained near infrared fluorescent probe in embodiment 2 is dissolved in PBS cushioning liquid (containing 50% ethanol, pH=7.4) and is matched somebody with somebody
Make 10 μM of solution, be separately added into in solution common amino acid (Ala, Arg, Asp, Cys, Glu, Gly, GSH, Hcy,
His, Ile, Leu, Lys, Met, Phe, Pro, Ser, Thr, Trp, Tyr, Val), strong using Edinburgh FS5 detection fluorescence
Degree, excitation wavelength 340nm, it is seen that only cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) are caused
Change in fluorescence, response time are 20 minutes, and other amino acid do not cause the significant change of fluorescence；And the fluorescence probe pair
Cysteine shows maximum sensitivity, therefore can be applicable to the selective determination (Fig. 3) of cysteine.With cysteine dense
The increase of degree, fluorescence gradually strengthen, and the concentration of fluorescence intensity and cysteine has linear relationship (figure in the range of 0-20 μM
4), equation of linear regression is Y=0.03765X+0.1097, and wherein Y is the fluorescence intensity at 670nm, and X is the dense of cysteine
Degree, according to the concentration that above-mentioned linear equation can directly calculate cysteine by the measure of fluorescence intensity.
By gained near infrared fluorescent probe in embodiment 2, (number of cells is that 20,000, concentration and probe concentration is with live body L929 cells
10 μM, culture medium be 10% hyclone, in 5%CO2With 95% humidity, cultivate 48 hours under the conditions of 37 DEG C) cultivate 30 minutes
Afterwards, it is placed under fluorescence microscope and can be clearly observable cell (Fig. 5), shows that the fluorescence probe of the invention design is biological in near-infrared
There is in fluorescence imaging important application prospect.
Claims (10)
1. a kind of conjugation benzothiazole derivant, it is characterised in that its structure is：
2. as claimed in claim 1 conjugation benzothiazole derivant preparation method, it is characterised in that include：
Step 1：Under inert gas shielding, by 4- methylphenols, 70-75 DEG C of backflow in trifluoroacetic acid is anti-with hexamethylenetetramine
12-48 hours are answered, room temperature is cooled to, and is poured in water, with chloroform extraction 2-4 time, merged organic phase and simultaneously rotate removing chloroform, obtain
To 3,5- diformyl -4- methylphenols；
Step 2：Under inert gas shielding, by gained 3 in step 1,5- diformyl -4- methylphenols and 2- methylbenzothiazoles
140-145 DEG C of backflow 6-24 hour in acetic anhydride, adds NaOH, stirs 0.5-1.5 hours at 80-95 DEG C after cooling,
Room temperature is cooled to, pH=6-7 is adjusted with concentrated hydrochloric acid, filter, gained solid is purified by chromatographed on silica gel post, conjugation benzene is obtained final product
And thiazole.
3. as claimed in claim 2 conjugation benzothiazole derivant preparation method, it is characterised in that in described step 1
4- methylphenols, hexamethylenetetramine, trifluoroacetic acid proportioning be 1mmol: 2mmol: 1ml.
4. as claimed in claim 2 conjugation benzothiazole derivant preparation method, it is characterised in that in described step 2
3,5- diformyl -4- methylphenols, 2- methylbenzothiazoles, acetic anhydride proportioning be 1mmol: 2mmol: 2ml.
5. as claimed in claim 2 conjugation benzothiazole derivant preparation method, it is characterised in that in described step 2
Silica gel chromatograph column chromatography for separation purify when eluant, eluent be volume ratio for 10: 1 n-hexane and ethyl acetate.
6. a kind of near infrared fluorescent probe, it is characterised in that its structure is：
7. the preparation method of the near infrared fluorescent probe described in claim 6, it is characterised in that include：By described in claim 1
Conjugation benzothiazole derivant be dissolved in chloroform, in the presence of triethylamine, be added dropwise 2,4- dinitrophenyl chlorides, under room temperature stir
4-8 hours, with chloroform extraction 2-4 time after adding water, merge organic phase and simultaneously rotate removing chloroform, and gained crude product is passed through by silica gel color
Spectrum column chromatography purifying, obtains final product near infrared fluorescent probe.
8. the preparation method of the near infrared fluorescent probe described in claim 7, it is characterised in that described conjugation benzothiazole spreads out
Biology, the proportioning of 2,4- dinitrophenyl chlorides, triethylamine are 1mmol: 2mmol: 1ml.
9. the application process of the near infrared fluorescent probe described in claim 6, it is characterised in that include：By changed in gradient
The aqueous solution of cysteine is separately added into the phosphate buffer solution of above-mentioned near infrared fluorescent probe, is detected using XRF
Fluorescence intensity, with semicystinol concentration as abscissa, the change of fluorescence intensity turns to ordinate mapping, obtains linear work curve,
The content of cysteine in solution, wherein excitation wavelength 340nm, launch wavelength can be read by determining fluorescence intensity from figure
670nm, response time are 20 minutes.
10. the application process of near infrared fluorescent probe as claimed in claim 9, it is characterised in that described XRF
For Edinburgh FS5.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107782707A (en) * | 2017-10-12 | 2018-03-09 | 华南师范大学 | Application of the three benzothiazolyl benzene in nitryl aromatic explosive fluoroscopic examination |
| CN108299427A (en) * | 2018-03-22 | 2018-07-20 | 泰山医学院 | Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application |
-
2016
- 2016-10-10 CN CN201610884031.7A patent/CN106496156A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| XUAN ZHANG 等: "Near-infrared fluorescence of π-conjugation extended benzothiazole and its application for biothiol imaging in living cells", 《JOURNAL OF MATERIALS CHEMISTRY B》 * |
| XUAN ZHANG 等: "Solvent dependent photophysical properties and near-infrared solid-state excited state intramolecular proton transfer (ESIPT)fluorescence of 2,4,6-trisbenzothiazolylphenol", 《DYES AND PIGMENTS》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107782707A (en) * | 2017-10-12 | 2018-03-09 | 华南师范大学 | Application of the three benzothiazolyl benzene in nitryl aromatic explosive fluoroscopic examination |
| CN107782707B (en) * | 2017-10-12 | 2020-07-17 | 华南师范大学 | Application of triphenylthiazolyl benzene in fluorescence detection of nitro aromatic explosives |
| CN108299427A (en) * | 2018-03-22 | 2018-07-20 | 泰山医学院 | Imidazopyridine Ben Bing oxadiazole class cysteine ratio fluorescent probes and its application |
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