CN101149374A - Fluorescent probe for detecting hydrogen ion in cell and its synthesis method and uses - Google Patents
Fluorescent probe for detecting hydrogen ion in cell and its synthesis method and uses Download PDFInfo
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- CN101149374A CN101149374A CNA2007101132652A CN200710113265A CN101149374A CN 101149374 A CN101149374 A CN 101149374A CN A2007101132652 A CNA2007101132652 A CN A2007101132652A CN 200710113265 A CN200710113265 A CN 200710113265A CN 101149374 A CN101149374 A CN 101149374A
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Abstract
This invention provides the fluorescence probe to detect the pH indicator in cell and its preparation method and use. This method goes as the following steps: a. dissolves the B rhodamine B cyanine dyes in the organic solvent, then adds the oxygen chlorination phosphor at the situation of whisking, the proportion of fluorescence coloring matter and oxygen chlorination phosphor is1:2-5 in weight, then reacts in the protection at 40-60 degree centigrade for4-6hours; b. colds the reaction compound to the room temperature, decompresses to get rid of the solvent, first dissolves in the organic solvent, then add the pH indicator response base in the proportion that the fluorescence coloring matter: pH indicator response base =1:1-3 in weight, heats at 80-100 degree centigrade for1-2hours after mixing; c. colds to the room temperature, decompresses to get rid of the solvent and gets the crude product; d. gets the product after chromatography and separating by silica gel pole.
Description
Technical field:
The present invention relates to the detection technique field, relate in particular to and be used to detect hydrionic fluorescence probe in the cell; The invention still further relates to the synthetic method of this fluorescence probe; In addition, this invention also relates to the purposes of this fluorescence probe.
Background technology:
PH is as an important metabolism and an intracellular parameter, in many cell processes, play crucial regulating action, such as cell growth, regulation of calcium, enzymatic activity, signal conduction, endocytosis, chemotactism and other cell processes.Many reports think that some diseases such as cancer, kidney failure, tuberculosis etc. are relevant unusually with the pH in tenuigenin or the acid organelle.Therefore, the accurate measurement of internal pH is very important.
At present, many methods can be used for detecting pH.Such as microelectrode, nuclear-magnetism, absorption and fluorescence spectrum method.In these methods, fluorescence method is owing to the character of its non-invasion, high sensitivity and selectivity, and widely available fluorescent dye is more more superior than additive method when measuring pH.And the fluorescent microscopic imaging technology can capture hydrionic time-space resolution in the cell by using the fluorescent pH probe.
Now, two class fluorescent pH probes are developed, and a class is the probe that is used to detect pH in the tenuigenin, its working pH scope approximately is 6.8-7.4 (K.M.Sun, C.K.McLaughlin, D.R.Lantero and R.A.Manderville, J.Am.Chem.Soc.2007,129,1894-1895; M.S.Briggs, D.D.Bums, M.E.Cooper and S.J.Gregory, Chem.Commun., 2000,2323-2324; J.A.Thomas, R.N.Buchsbaum, A.Zimniak and E.Racker, Biochem.1979,18,2210-2218; A.H.Lee and I.F.Tannock, Cancer Res.1998,58,1901-1908; R.Pal and D.Parker, Chem.Commun.2007,474-476); Another kind of is to be used for detection of acidic organ such as lysosome, the probe of endosome etc., and its working pH scope approximately is 4.5-6.0. (H.-J.Lin, P.Herman, J.S.Kang and J.R.Lakowicz, Anal.Biochem.2001,294,118-125; F.Galindo, M.I.Burguete, L.Vigara, S.V.Luis, N.Kabir, J.Gavrilovic andD.A.Russell, Angew.Chem.Int.Ed.2005,44,6504-6508.); Bo Tang, Xia Liu, Kehua Xu, Hui Huang, Guiwen Yang and Liguo An,
As everyone knows, the subtle change of internal pH may cause the dysfunction of cell, the subtle change of the response internal pH that desirable fluorescence probe should be sensitive, and can avoid interference from cell biological itself.Yet available pH fluorescence probe has following shortcoming at present: low sensitivity, what have excites in the ultraviolet region.Exciting in the ultraviolet region can the damaged tissue sample and cause the interference of biological sample autofluorescence.In addition, it is less to be used for the intraorganic desirable pH probe of detection of acidic, and this is considered to the bottleneck of cell biology and medical development.
Summary of the invention:
One of purpose of the present invention is intended to overcome the weak point of prior art fluorescence probe, provide a kind of have high sensitivity, good selectivity, good light stability and working pH at acid range, be applicable to and detect hydrionic fluorescence probe in the cell; Two of purpose provides the synthetic method of technology this fluorescence probe simple, with low cost; Three of purpose provides the purposes of this fluorescence probe.
One of purpose of the present invention can realize by following technical measures:
This fluorescence probe has following general structure:
Two of purpose of the present invention can realize by following technical measures:
This synthetic method is carried out as follows:
A. earlier the rhodamine fluorochrome is dissolved in the organic solvent, again according to the rhodamine fluorochrome: phosphorous oxychloride=1: 2-5 weight portion proportioning slowly adds phosphorous oxychloride down in stirring, then in 40-60 ℃ of heating reflux reaction hour;
B. be cooled to room temperature after reaction finishes, removal of solvent under reduced pressure, after adding organic solvent dissolution earlier, again according to the rhodamine fluorochrome: hydrogen ion response group=1: 1-3 weight portion proportioning adds hydrogen ion response group, mixes the back in 80-100 ℃ of reflux 1-2 hour;
C. be cooled to room temperature then, decompression is removed organic solvent and is obtained thick product;
D. silica gel column chromatography separates to such an extent that general structure is
Two of purpose of the present invention also can realize by following technical measures:
Described rhodamine fluorochrome is selected from rhodamine B, rhodamine 6G, rhodamine 800, rhodamine 110.Described hydrogen ion response group is selected from benzoyl hydrazine, p-methylphenyl benzoyl hydrazine, o-methyl-benzene formylhydrazine, a toluyl hydrazine.Said organic solvent is selected from methylene chloride, methenyl choloride, acetonitrile, ethanol.
In the representational compound exhibits of the present invention synthetic schemes below
Rhodamine fluorochrome and phosphorous oxychloride are dissolved in the methylene chloride, after reaction finishes, and removal of solvent under reduced pressure.Product is dissolved in the acetonitrile, constantly stirs to add benzoyl hydrazine down, and mixture heated refluxes and obtains probe molecule, at last through separation the fluorescence probe product.
The present invention detects the interior hydrionic fluorescence probe of cell does not have special restriction in use, usually, probe molecule can be dissolved in physiological saline, damping fluid or, add in the suitable damping fluid that contains cell tissue then and test by water-miscible organic solvents such as ethanol, acetonitrile, dimethyl sulfoxides.
Three of purpose of the present invention can realize by following technical measures:
Hydrionic novel fluorescence probe is used for the hydrionic detection of chemical simulation living things system in the detection cell of the present invention, hydrionic analyzing and testing in biological living cells and the living tissue and fluorescence imaging detect, and medically hydrionic detection in the pathological tissues.
The present invention is a raw material with rhodamine fluorochrome, phosphorous oxychloride and benzoyl hydrazine, synthetic fluorescence probe
1HNMR (CDCl
3, 300MHz) δ (ppm): 1.71 (12H), 3.33 (8H), 6.38 (4H), 6.72 (2H), 7.18 (1H), 7.42 (3H), 7.53 (4H), 8.00 (1H)
13C?NMR(CDCl
3，300MHz)δ(ppm)：12.7，44.5，66.5，97.8，104.6，108.2，123.7，124.4，127.6，128.5，129.4，129.5，131.7，132.8，133.3，149.2，151.5，154.0，165.6.
Significant contribution of the present invention is that the fluorescent probe molecule that synthesizes has high sensitivity and selectivity, and good light stability and cell permeability can effectively be avoided the interference of autofluorescence in the cell, reduce the damage to life entity, helps live body and detects; The design of fluorescent probe molecule of the present invention does not have the open loop structure of fluorescence closed loop configuration and hyperfluorescence based on rhodamine.The pH titration experiments shows that can increase by 100 times in the pH of 4.2-6.0 scope fluorescence intensity under the acid condition has a surplus, and pKa is 4.85, and this is very significant to studying intracellular acid organ; In addition, we are applied to probe (HepG2 cells) in the hepatoma carcinoma cell of animal further proved this probe by the laser co-focusing micro-imaging technique value.
Probe molecule of the present invention has extremely important using value.It is very high that particularly this probe molecule is measured sensitivity, and light stability is very good; And have good selectivity, the good penetrability and the toxic and side effect of cell are little.In addition should the series probe molecule simple in structure, synthesis technique be simple and easy and efficient is high, with low cost, be applicable to and detect hydrionic fluorescence probe in the cell;
Description of drawings:
Fig. 1 is the mono-crystalline structures of this probe.
Fig. 2 be the fluorescent probe molecule of the embodiment of the invention in acidic buffer solution, the relation of its fluorescence intensity and pH and pH titration curve.Horizontal ordinate is wavelength (nm), and ordinate is a fluorescence intensity.
Fig. 3 is the light stability of the fluorescent probe molecule of the embodiment of the invention.Horizontal ordinate is time (s), and ordinate is a fluorescence intensity.
Fig. 4 is that the fluorescent probe molecule of the embodiment of the invention has good selectivity to hydrogen ion.1:H
+2:H
++ Cu
2+3:H
++ Zn
2+4:H
++ Ca
2+5:H
++ Mg
2+. horizontal ordinate is various ions, and ordinate is for adding the fluorescence intensity of various ions front and back probe solution.
Fig. 5 is the laser co-focusing micro-imaging of the fluorescent probe molecule of the embodiment of the invention hepatoma carcinoma cell (HepG2 cells) of zoologizeing.(left side) hatches 30 minutes laser co-focusing photo for the hepatoma carcinoma cell of animal with fluorescence probe under 37 ℃, (right side) is that the bright field photo is to show cell viability.
Embodiment:
Synthesizing of probe
Embodiment 1:
A. earlier rhodamine B is dissolved in the organic solvent, again according to rhodamine B: phosphorous oxychloride=the weight portion proportioning slowly added phosphorous oxychloride down in stirring in 1: 2, then in 40 ℃ of heating reflux reactions 6 hours;
B. reaction is cooled to room temperature after finishing, removal of solvent under reduced pressure, add the acetonitrile dissolving earlier after, again according to rhodamine B: benzoyl hydrazine=the weight portion proportioning added benzoyl hydrazine in 1: 1, mixed the back in 100 ℃ of reflux 1 hour;
C. be cooled to room temperature then, decompression is removed organic solvent and is obtained thick product; Use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets product.
Embodiment 2:
A. earlier rhodamine B is dissolved in the organic solvent, again according to rhodamine B: phosphorous oxychloride=the weight portion proportioning slowly added phosphorous oxychloride down in stirring in 1: 5, then in 60 ℃ of heating reflux reactions 4 hours;
B. reaction is cooled to room temperature after finishing, removal of solvent under reduced pressure, add the acetonitrile dissolving earlier after, again according to rhodamine B: benzoyl hydrazine=the weight portion proportioning added benzoyl hydrazine in 1: 3, mixed the back in 80 ℃ of reflux 2 hours;
C. be cooled to room temperature then, decompression is removed organic solvent and is obtained thick product; Use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets product.
Embodiment 3:
A. earlier rhodamine B is dissolved in the organic solvent, again according to rhodamine B: phosphorous oxychloride=the weight portion proportioning slowly added phosphorous oxychloride down in stirring in 1: 3, then in 50 ℃ of heating reflux reactions 5 hours;
B. reaction is cooled to room temperature after finishing, removal of solvent under reduced pressure, add the acetonitrile dissolving earlier after, again according to rhodamine B: benzoyl hydrazine=the weight portion proportioning added benzoyl hydrazine in 1: 2, mixed the back in 90 ℃ of reflux 1.5 hours;
C. be cooled to room temperature then, decompression is removed organic solvent and is obtained thick product; Use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets product.
Embodiment 4:
Restrain (2.3 mmol) rhodamine Bs after the dissolving of 15mL methylene chloride with 1.0, dropwise drip phosphorous oxychloride 0.4mL, then in 60 ℃ of heating reflux reactions 4 hours, be cooled to room temperature, removal of solvent under reduced pressure, product is dissolved in the 125mL acetonitrile, constantly stir and add 0.31 gram benzoyl hydrazine down, potpourri is cooled to room temperature in 100 ℃ of reflux 1 hour, and removal of solvent under reduced pressure obtains the fluorescence probe crude product, use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets the fluorescence probe product.
Embodiment 5:
Restrain (2.3mmol) rhodamine Bs after the dissolving of 15mL methylene chloride with 1.0, dropwise drip phosphorous oxychloride 0.8mL, then in 40 ℃ of heating reflux reactions 6 hours, be cooled to room temperature, removal of solvent under reduced pressure, product is dissolved in the 125mL acetonitrile, constantly stir and add 0.93 gram benzoyl hydrazine down, potpourri is cooled to room temperature in 80 ℃ of reflux 2 hours, and removal of solvent under reduced pressure obtains the fluorescence probe crude product, use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets the fluorescence probe product.
Embodiment 6:
Restrain (2.3mmol) rhodamine Bs after the dissolving of 15mL methylene chloride with 1.0, dropwise drip phosphorous oxychloride 0.6mL, then in 50 ℃ of heating reflux reactions 5 hours, be cooled to room temperature, removal of solvent under reduced pressure, product is dissolved in the 125mL acetonitrile, constantly stir and add 0.60 gram benzoyl hydrazine down, potpourri is cooled to room temperature in 90 ℃ of reflux 1.5 hours, and removal of solvent under reduced pressure obtains the fluorescence probe crude product, use the silicagel column separation component at last, eluant, eluent is a methyl alcohol: methenyl choloride=1: 15 (v/v), and the evaporation under reduced pressure removed residual solvent, vacuum drying gets the fluorescence probe product.
Embodiment 7:
Rhodamine 6G is replaced rhodamine B, and other are respectively with embodiment 1-6.
Embodiment 8:
Rhodamine 110 is replaced rhodamine B, and other are respectively with embodiment 1-6.
Embodiment 9:
Rhodamine 800 is replaced rhodamine B,, other are respectively with embodiment 1-6.
Embodiment 10:
Methenyl choloride is replaced methylene chloride, and other are respectively with embodiment 1-9.
Embodiment 11:
Acetonitrile is replaced methylene chloride, and other are respectively with embodiment 1-9.
Embodiment 12:
Ethanol is replaced methylene chloride, and other are respectively with embodiment 1-9.
Embodiment 13:
To replace benzoyl hydrazine to the toluyl hydrazine, other are respectively with embodiment 1-12.
Embodiment 14:
The o-methyl-benzene formylhydrazine is replaced benzoyl hydrazine, and other are respectively with embodiment 1-12.
Embodiment 15:
The toluyl hydrazine is replaced benzoyl hydrazine between inciting somebody to action, and other are respectively with embodiment 1-12.
Claims (6)
1. hydrionic fluorescence probe in the detection cell is characterized in that this fluorescence probe has following general structure:
2. the synthetic method of hydrionic fluorescence probe in the described detection cell of claim 1 is characterized in that this method carries out as follows:
A. earlier the rhodamine fluorochrome is dissolved in the organic solvent, again according to the rhodamine fluorochrome: phosphorous oxychloride=1: 2-5 weight portion proportioning slowly adds phosphorous oxychloride down in stirring, then in 40-60 ℃ of heating reflux reaction 4-6 hour;
B. be cooled to room temperature after reaction finishes, removal of solvent under reduced pressure, after adding organic solvent dissolution earlier, again according to the rhodamine fluorochrome: hydrogen ion response group=1: 1-3 weight portion proportioning adds hydrogen ion response group, mixes the back in 80-100 ℃ of reflux 1-2 hour;
C. be cooled to room temperature then, decompression is removed organic solvent and is obtained thick product;
D. silica gel column chromatography separates to such an extent that general structure is
3. synthetic method according to claim 2 is characterized in that described rhodamine fluorochrome is selected from, rhodamine B, rhodamine 6G, rhodamine 800, rhodamine 110.
4. synthetic method according to claim 2 is characterized in that described hydrogen ion response group is selected from benzoyl hydrazine, p-methylphenyl benzoyl hydrazine, o-methyl-benzene formylhydrazine, a toluyl hydrazine.
5. synthetic method according to claim 2 is characterized in that said organic solvent is selected from methylene chloride, methenyl choloride, acetonitrile, ethanol.
6. hydrionic fluorescence probe is used for the hydrionic detection of chemical simulation living things system in the described detection cell of claim 1, hydrionic analyzing and testing in biological living cells and the living tissue and fluorescence imaging detect, and medically hydrionic detection in the pathological tissues.
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| CN102603782A (en) * | 2012-02-07 | 2012-07-25 | 山东师范大学 | Boron difluoride dye fluorescent probe, synthesizing method of boron difluoride dye fluorescent probe and application of boron difluoride dye fluorescent probe in detecting hydrogen ion in cell |
| CN101811870B (en) * | 2009-07-21 | 2012-09-05 | 哈尔滨理工大学 | Probe for quick tester of hydrogen content in aluminium alloy melt and manufacturing method thereof |
| CN103012418A (en) * | 2012-12-04 | 2013-04-03 | 山东大学 | 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof |
| CN103214494A (en) * | 2012-12-21 | 2013-07-24 | 厦门安特奥生物工程有限公司 | Acid-sensitive double light emission probe, preparation method and uses thereof |
| CN103232465A (en) * | 2013-04-11 | 2013-08-07 | 天津师范大学 | A preparation method and applications of a Schiff base compound of benzophenone rhodamine 6G hydrazide |
| CN103992791A (en) * | 2014-06-06 | 2014-08-20 | 福建师范大学 | Rhodamine-based pH value fluorescent probe with linear response in weak acid range and preparation method thereof |
| CN105400233A (en) * | 2015-12-31 | 2016-03-16 | 东华大学 | Functional reactive dye for zinc ion probe, and preparation method and application thereof |
| CN110551056A (en) * | 2019-09-29 | 2019-12-10 | 山东师范大学 | Cyanine compound, preparation method and application in detection of Golgi pH |
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2007
- 2007-10-26 CN CNA2007101132652A patent/CN101149374A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN101811870B (en) * | 2009-07-21 | 2012-09-05 | 哈尔滨理工大学 | Probe for quick tester of hydrogen content in aluminium alloy melt and manufacturing method thereof |
| CN102603782A (en) * | 2012-02-07 | 2012-07-25 | 山东师范大学 | Boron difluoride dye fluorescent probe, synthesizing method of boron difluoride dye fluorescent probe and application of boron difluoride dye fluorescent probe in detecting hydrogen ion in cell |
| CN103012418A (en) * | 2012-12-04 | 2013-04-03 | 山东大学 | 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof |
| CN103012418B (en) * | 2012-12-04 | 2014-12-10 | 山东大学 | 1,3,4-oxadizaole structure unit-containing Rhodamine B pH fluorescence probe and applications thereof |
| CN103214494A (en) * | 2012-12-21 | 2013-07-24 | 厦门安特奥生物工程有限公司 | Acid-sensitive double light emission probe, preparation method and uses thereof |
| CN103214494B (en) * | 2012-12-21 | 2015-07-15 | 厦门生光生物科技有限公司 | Acid-sensitive double light emission probe, preparation method and uses thereof |
| CN103232465A (en) * | 2013-04-11 | 2013-08-07 | 天津师范大学 | A preparation method and applications of a Schiff base compound of benzophenone rhodamine 6G hydrazide |
| CN103992791A (en) * | 2014-06-06 | 2014-08-20 | 福建师范大学 | Rhodamine-based pH value fluorescent probe with linear response in weak acid range and preparation method thereof |
| CN105400233A (en) * | 2015-12-31 | 2016-03-16 | 东华大学 | Functional reactive dye for zinc ion probe, and preparation method and application thereof |
| CN110551056A (en) * | 2019-09-29 | 2019-12-10 | 山东师范大学 | Cyanine compound, preparation method and application in detection of Golgi pH |
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