CN101747355A - Fluorescent probe, synthetic method and use thereof - Google Patents
Fluorescent probe, synthetic method and use thereof Download PDFInfo
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- CN101747355A CN101747355A CN200910157126A CN200910157126A CN101747355A CN 101747355 A CN101747355 A CN 101747355A CN 200910157126 A CN200910157126 A CN 200910157126A CN 200910157126 A CN200910157126 A CN 200910157126A CN 101747355 A CN101747355 A CN 101747355A
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- fluorescent probe
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- column chromatography
- intermediate product
- boron trifluoride
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- 239000007850 fluorescent dye Substances 0.000 title claims abstract description 23
- 238000010189 synthetic method Methods 0.000 title claims abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000013067 intermediate product Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims abstract description 8
- MFFMQGGZCLEMCI-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC(C)=C1 MFFMQGGZCLEMCI-UHFFFAOYSA-N 0.000 claims abstract description 7
- PAPNRQCYSFBWDI-UHFFFAOYSA-N DMP Natural products CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims abstract description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 26
- 238000010898 silica gel chromatography Methods 0.000 claims description 14
- 238000004821 distillation Methods 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000012074 organic phase Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 claims description 3
- 238000001514 detection method Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 5
- 239000001301 oxygen Substances 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 206010021143 Hypoxia Diseases 0.000 abstract description 4
- 238000003384 imaging method Methods 0.000 abstract description 4
- 230000035945 sensitivity Effects 0.000 abstract description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 4
- 229910015900 BF3 Inorganic materials 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 238000004440 column chromatography Methods 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- 239000000377 silicon dioxide Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000001146 hypoxic effect Effects 0.000 abstract 1
- 239000012266 salt solution Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 239000000523 sample Substances 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 3
- 230000007954 hypoxia Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000011953 bioanalysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000003364 immunohistochemistry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000009666 routine test Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention discloses a fluorescent probe for hypoxic detection, a synthetic method and use thereof. The synthetic method comprises the following steps: 1) under the protection of nitrogen, by taking dichloromethane as solvent, butanedioic anhydride, 2, 4-dimethyl pyrrole and boron trifluoride ethyl etherate with the molar ratio of 1:2-10:1 are added and react with each other; triethylamine and boron trifluoride ethyl etherate with the molar ratio of 5:6-8 are sequentially added and react; and the obtained product is washed by saturated salt solution, is dried and is distilled to remove the solvent under reduced pressure, and intermediate product is obtained through silica column chromatography method; and 2) by taking dichloromethane as solvent, the intermediate product, 4-amino-2, 2, 6, 6-tetramethylpiperidine-1-oxygen free radical, dicyclohexylcarbodiimide and 4-dimethylamino pyridine with the molar ratio of 1:1-1:1-2:0.1-0.2 are added and react; and the obtained product is filtered and is distilled to remove the solvent under reduced pressure, and the fluorescent probe is obtained through silica column chromatography method. The fluorescent probe of the invention has the advantages that the synthesis is simple and convenient, the cost is low, the detection sensitivity is very high and the prospect of application in the fluorescence molecular imaging field is good.
Description
Technical field
The present invention relates to chemical analysis, bioanalysis, the clinical medicine detection range relates in particular to a kind of fluorescent probe and preparation method and use thereof.
Background technology
Weary oxygen is a key character of noumenal tumour, many studies show that, and the resistance of tumour and weary oxygen are closely related.Research to tumor hypoxia has very important significance.
Have in many bodies at present or the method for vitro detection tumor hypoxia tissue, as the responsive microelectrode method of oxygen, immunohistochemistry technology etc., these methods are damaging detection method.In addition, some Dynamic Non-Destruction Measurements such as mr (MRI) molecule imaging technique, PET molecule imaging technique etc., also be applied to the video picture research of tumor hypoxia, but its apparatus expensive, and detect the exploitation that effect is limited by probe to a great extent, therefore the practical application in fundamental research is restricted.At prior art and deficiency, the invention provides a kind of fluorescent probe that weary oxygen detects that is used for, its detection means is easy, and is highly sensitive, is suitable for being equipped with the Routine Test Lab application of fluoroscopic examination instrument.
Summary of the invention
The objective of the invention is to overcome the deficiencies in the prior art, a kind of fluorescent probe and preparation method and use thereof are provided.
Fluorescent probe has following structural formula:
The synthetic method of fluorescent probe comprises the steps:
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 2～10: 1 a Succinic anhydried, 2,4-dimethyl pyrrole and boron trifluoride diethyl etherate, reaction 12～24h; Under 5～10 ℃, drip mol ratio successively and be 5: 6～8 triethylamine and boron trifluoride diethyl etherate,, nitrogen protection continues reaction 24～36h down; With saturated common salt washing 2～3 times, organic phase anhydrous Na
2SO
4Drying, underpressure distillation removes and desolvates, and obtains intermediate product with silica gel column chromatography;
2) with the methylene dichloride be solvent, the adding mol ratio is 1: 1～2: 1～2: 0.1～0.2 above-mentioned intermediate product, 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical, dicyclohexylcarbodiimide and 4-Dimethylamino pyridine, reaction 1～2h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe with silica gel column chromatography.
Fluorescent probe is used for the check and analysis of anoxic cell.
Advantage of the present invention is: 1) fluorescent probe is synthetic easy, and raw material is easy to get, and is with low cost; 2) this fluorescent probe has very high detection sensitivity, is fit to trace detection, and good prospects for application is arranged; 3) this probe is fit to multiple fluoroscopic examination instruments such as fluorescent microscope, flow cytometer, spectrophotometer, fluorescence microplate reader.
Description of drawings
Fig. 1 is the change in fluorescence situation after probe is reduced, and vitamin c solution is prepared with phosphoric acid buffer PBS (pH7.4), and final concentration is respectively 0 μ M, 50 μ M, and 100 μ M, 150 μ M (from left to right) add probe, and making its final concentration is 5 μ M.React ultraviolet excitation after 5 minutes, clap and establish image;
Fig. 2 (a) is that cell is handled 48h with cobalt chloride (concentration 50 μ M), after PBS washes, adds probe solution (concentration 5 μ M), takes under fluorescent microscope after 15 minutes;
Fig. 2 (b) is that cell is handled 48h with PBS, adds probe solution (concentration 5 μ M), takes under fluorescent microscope after 15 minutes, in contrast group.
Embodiment
Synthetic equation of the present invention:
Embodiment 1
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 10: 1 a Succinic anhydried (10mmol), 2,4-dimethyl pyrrole (100mmol), boron trifluoride diethyl etherate (10mmol), reaction 24h; Drip triethylamine (50mmol), boron trifluoride diethyl etherate (80mmol) under 5～10 ℃ successively, nitrogen protection continues reaction 36h down; With saturated common salt washing 3 times, organic phase anhydrous Na 2SO4 drying, underpressure distillation removes and desolvates, and obtains intermediate product 0.25g with silica gel column chromatography, productive rate 7.8%;
2) with the methylene dichloride be solvent, adding mol ratio is 1: 2: 2: 0.2 above-mentioned intermediate product (0.2mmol), 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical (0.4mmol), dicyclohexylcarbodiimide (0.4mmol), 4-Dimethylamino pyridine (0.04mmol), reaction 2h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe 0.020g with silica gel column chromatography, productive rate 18.6%.
Embodiment 2
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 2: 1 a Succinic anhydried (10mmol), 2,4-dimethyl pyrrole (20mmol), boron trifluoride diethyl etherate (10mmol), reaction 12h; Drip triethylamine (50mmol), boron trifluoride diethyl etherate (60mmol) under 5～10 ℃ successively, nitrogen protection continues reaction 24h down; With saturated common salt washing 2 times, organic phase anhydrous Na 2SO4 drying, underpressure distillation removes and desolvates, and obtains intermediate product 0.22g with silica gel column chromatography, productive rate 6.8%;
2) with the methylene dichloride be solvent, adding mol ratio is 1: 1: 1: 0.1 above-mentioned intermediate product (0.2mmol), 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical (0.2mmol), dicyclohexylcarbodiimide (0.2mmol), 4-Dimethylamino pyridine (0.02mmol), reaction 1h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe with silica gel column chromatography.Finally obtain intermediate product 0.019g, productive rate 18.5%.
Embodiment 3
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 2: 1 a Succinic anhydried, 2,4-dimethyl pyrrole, boron trifluoride diethyl etherate, reaction 12h; Drip triethylamine, boron trifluoride diethyl etherate under 5～10 ℃ successively, mol ratio is 5: 6, and nitrogen protection continues reaction 24h down; With saturated common salt washing 2 times, organic phase anhydrous Na
2SO
4Drying, underpressure distillation removes and desolvates, and obtains intermediate product with silica gel column chromatography;
2) with the methylene dichloride be solvent, adding mol ratio is 1: 1: 1: 0.1 above-mentioned intermediate product, 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical, dicyclohexylcarbodiimide, 4-Dimethylamino pyridine, reaction 1h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe with silica gel column chromatography.
Embodiment 4
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 10: 1 Succinic anhydried, pyrroles, a boron trifluoride diethyl etherate, reaction 24h; Drip triethylamine, boron trifluoride diethyl etherate under 5～10 ℃ successively, mol ratio is 5: 8, and nitrogen protection continues reaction 36h down; With saturated common salt washing 3 times, organic phase anhydrous Na
2SO
4Drying, underpressure distillation removes and desolvates, and obtains intermediate product with silica gel column chromatography;
2) with the methylene dichloride be solvent, adding mol ratio is 1: 2: 2: 0.2 above-mentioned intermediate product, 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical, dicyclohexylcarbodiimide, 4-Dimethylamino pyridine, reaction 2h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe with silica gel column chromatography.
Embodiment 5
1) with Succinic anhydried (10mmol), 2,4-dimethyl pyrrole (20mmol), BF
3OEt
2(10mmol) join in the three-necked flask, the 100ml methylene dichloride is injected in nitrogen protection down; Behind the stirring reaction 12 hours, carefully drip triethylamine (50mmol), boron trifluoride diethyl etherate (60mmol) successively under 5～10 ℃, nitrogen protection continues reaction 36h down; After reaction finishes, reaction soln with twice of saturated common salt washing (2 * 20mL), the organic phase anhydrous sodium sulfate drying, vacuum is spin-dried for organic solvent afterwards.(eluent is selected sherwood oil for use to the dark oil thing that obtains: ethyl acetate=1: 1) with the silica gel column chromatography separation.Finally obtain intermediate product 0.32g, productive rate 10%.mp?190-192℃；
1H?NMR(400MHz，CDCl
3)6.09(s，2H)，3.33(t，J＝8.8Hz，2H)，2.64(t，J＝8.8Hz，2H)，2.53(s，6H)，2.46(s，6H)；
13C?NMR(100MHz，CDCl
3)：δ173.1，154.0，144.9，141.4，131.0，122.3，35.3，23.8，16.2，14.5；IR(film)v/cm
-1：2913，1702，1549，1510，1475，1305，1199，1155，1076，974；MS(ESI)：m/z＝319.2；HRMS(ESI)：m/z?calcd?for(M-H)
-319.1435，found?319.1433.
2) with above-mentioned intermediate product (0.2mmol), dicyclohexylcarbodiimide (0.2mmol), 4-Dimethylamino pyridine (0.02mmol), 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical is dissolved in (10ml) in the exsiccant methylene dichloride. and stirring reaction is 1 hour under the room temperature.The rotation solvent evaporated, silica gel column chromatography separates, and gets final product 21mg, productive rate 19%.MS(ESI)：m/z＝475.5
Embodiment 6
Change in fluorescence situation after probe is reduced.Vitamin c solution is prepared with phosphoric acid buffer PBS (pH7.4), and final concentration is respectively 0 μ M, 50 μ M, 100 μ M, 150 μ M.Add probe, making its final concentration is 5 μ M.React ultraviolet excitation after 5 minutes, clap and establish image.
Embodiment 7
The anoxic cell model of handling with cobalt chloride is an example, uses probe that anoxic cell is carried out imaging.Cell is handled 24h with cobalt chloride (concentration 50 μ M), after PBS washes, adds probe solution (concentration 5 μ M).Under fluorescent microscope, take after 15 minutes.
Claims (3)
1. fluorescent probe is characterized in that this fluorescent probe has following structural formula:
2. the synthetic method of fluorescent probe according to claim 1 is characterized in that comprising the steps:
1) under nitrogen protection, be solvent with the methylene dichloride, the adding mol ratio is 1: 2～10: 1 a Succinic anhydried, 2,4-dimethyl pyrrole and boron trifluoride diethyl etherate, reaction 12～24h; Under 5～10 ℃, drip mol ratio successively and be 5: 6～8 triethylamine and boron trifluoride diethyl etherate,, nitrogen protection continues reaction 24～36h down; With saturated common salt washing 2～3 times, organic phase anhydrous Na
2SO
4Drying, underpressure distillation removes and desolvates, and obtains intermediate product with silica gel column chromatography;
2) with the methylene dichloride be solvent, the adding mol ratio is 1: 1～2: 1～2: 0.1～0.2 above-mentioned intermediate product, 4-amino-2,2,6,6-tetramethyl piperidine-1-oxyradical, dicyclohexylcarbodiimide and 4-Dimethylamino pyridine, reaction 1～2h; Filter, underpressure distillation removes and desolvates, and obtains fluorescent probe with silica gel column chromatography.
3. the purposes of fluorescent probe according to claim 1 is characterized in that being used for the check and analysis of anoxic cell.
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|---|---|---|---|
| CN200910157126A CN101747355A (en) | 2009-12-22 | 2009-12-22 | Fluorescent probe, synthetic method and use thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910157126A CN101747355A (en) | 2009-12-22 | 2009-12-22 | Fluorescent probe, synthetic method and use thereof |
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ID=42475030
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013495A (en) * | 2012-12-14 | 2013-04-03 | 江苏大学 | Copper ion fluorescence probe and synthetic method thereof |
| CN103013496A (en) * | 2012-12-14 | 2013-04-03 | 江苏大学 | Sulfhydryl group ion fuorescence probe and synthesis method thereof |
| CN106432309A (en) * | 2015-08-12 | 2017-02-22 | 南京江原安迪科正电子研究发展有限公司 | Preparation method of alpha-amino acid boron trifluoride compound |
| CN108164509A (en) * | 2018-01-17 | 2018-06-15 | 浙江大学 | A kind of multi-mode molecular probe |
-
2009
- 2009-12-22 CN CN200910157126A patent/CN101747355A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013495A (en) * | 2012-12-14 | 2013-04-03 | 江苏大学 | Copper ion fluorescence probe and synthetic method thereof |
| CN103013496A (en) * | 2012-12-14 | 2013-04-03 | 江苏大学 | Sulfhydryl group ion fuorescence probe and synthesis method thereof |
| CN103013495B (en) * | 2012-12-14 | 2014-07-30 | 江苏大学 | Copper ion fluorescence probe and synthetic method thereof |
| CN106432309A (en) * | 2015-08-12 | 2017-02-22 | 南京江原安迪科正电子研究发展有限公司 | Preparation method of alpha-amino acid boron trifluoride compound |
| CN106432309B (en) * | 2015-08-12 | 2020-04-10 | 南京江原安迪科正电子研究发展有限公司 | Preparation method of α -amino acid-like boron trifluoride compound |
| CN108164509A (en) * | 2018-01-17 | 2018-06-15 | 浙江大学 | A kind of multi-mode molecular probe |
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Open date: 20100623 |