CN1837789A - Near infrared fluorescent probe for detecting hydroxyl free radicals, synthesis method and use thereof - Google Patents
Near infrared fluorescent probe for detecting hydroxyl free radicals, synthesis method and use thereof Download PDFInfo
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- CN1837789A CN1837789A CN 200610043566 CN200610043566A CN1837789A CN 1837789 A CN1837789 A CN 1837789A CN 200610043566 CN200610043566 CN 200610043566 CN 200610043566 A CN200610043566 A CN 200610043566A CN 1837789 A CN1837789 A CN 1837789A
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- free radical
- fluorescent probe
- probe
- near infrared
- hydroxyl radical
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Abstract
This invention relates to a near infrared fluorescent probe for detecting hydroxyl free radicals, synthesis method and use thereof. The near-IR fluorescent probe, manufacture method and application for -OH Free Radical --a. adding the 2, 2, 6, 6-tetramethyl peridol and strong base by mole ratio as 1:0.5~2.5 into the DMF to dissolve and water-bath react for 25-40min with IG protection; b. adding Cyanine-7 into the solution by same mole rate with the DMF to obtain the Cyanine-7 solution; adding former mixed liquid into the current solution slowly within 10-20min for reaction 25-35min in dried brash ice; c. vacuum evaporating the product to remove the DMF, cleaning with aether, and vacuum drying to obtain the coarse product; d. separating with silica gel column chromatography for the deep-blue solid pure product.
Description
Technical field
The present invention relates to Measurement for Biotechnique and clinical medicine detection range, relate in particular to the near-infrared fluorescent molecular probe that is used for the hydroxyl radical free radical detection; The invention still further relates to the synthetic method of this fluorescent molecular probe; In addition, the invention still further relates to the purposes of this fluorescent molecular probe.
Background technology
Produce numerous active oxygen radicals in the biological metabolic processes, comprise ultra-oxygen anion free radical (O
2 -), hydrogen peroxide (H
2O
2), hydroxyl radical free radical (HO), nitrogen monoxide (NO), peroxide nitroso-(ONOO
-) etc., the morbidity of these free radicals and cancer and inflammation, organize peroxidating, protein cross sex change, nucleic acid damaging and signal conduction (Wiseman, H.; Halliwell, B.Biochem.J.1996,313,17-29; McCord, J.M.; Science.1974,185,529-531; Dobashi, K.; Ghosh, B.; Orak, J.K.; Singh, I.Biochem.2000,205,1-11; Nishida, M.; Maruyama, Y.; Tanaka, R.; Kontani, K.; Nagao, T.:Hoshi, T.Nature.2000,408,492-495.) grade has direct relation, is unified to be called the oxidative stress to body.Yet, generation and the effect in vivo of these active oxygens, and the mechanism of causing a disease when excessive still awaits further probing into; In the biosome life-span of active oxygen very short, cause that generally Css is extremely low, the mensuration that means active oxygen is difficulty very.OH is as the strongest free radical of present known oxygen voltinism that produces in a kind of vital movement process, and its detection is particularly important.Fluorescence method demonstrates stronger superiority owing to highly sensitive in other method, and combining burnt micro-imaging technique of copolymerization and microscopic spectrum detection technique, is unique detection method that makes active somatic cell and in-house active oxygen " real-time, visible, quantitative ".Near-infrared region at 600-1000nm, biological substrate light absorption or fluorescence intensity are very little, and the light scattering of compact medium (as tissue) reduces greatly, the penetrability of exciting light is bigger, thereby the background interference of autofluorescence reduces greatly, and the low damage that reduces the illumination pair cell of energy is so near infrared fluorescent probe has bright development prospect.Existing at present interior NO of cell and the H of being used for
2O
2Detect near infrared fluorescent probe (Sasaki, the E. of also imaging; Kojima, H.; Nishimatsu, H.; Urano, Y.; Kikuchi, K.; Hirata, Y.; Nagano, T.J.Am.Chem.Soc.2005,127,3684-3685; Xu, K H.; Tang, B.; Huang, H.; Yang, G.W.; Chen, Z.Z.; Li, P.; An, L.G.; Chem.Commun.2005,48,5974-5976), and the near infrared fluorescent probe that is used for being detected as at HO in the cell picture does not appear in the newspapers as yet.
Summary of the invention
One of purpose of the present invention provides function admirable, is applicable to that the interior hydroxyl radical free radical of biosome is detected as the near infrared fluorescent probe of the detection hydroxyl radical free radical of picture, early diagnosis and prevention that hydroxyl radical free radical detects, the discussion human diseases reaches aging machine-processed and some major disease for low content in the biological sample provide good supplementary means; Two of purpose provides the synthetic method of this fluorescence probe that technology is simple, cost is low, easy to operate; 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:
R＝CH
2CH
2CH
3，CH
2CH
3，CH
2CH
2SO
3Na，CH
2CH
2SO
3，CH
2CH
2CH
2SO
3Na，CH
2CH
2CH
2SO
3；
X＝I，SO
3。
Two of purpose of the present invention can realize by following technical measures:
This synthetic method is carried out as follows:
A. according to 2,2,6, the 6-tetramethylpiperidinol: the mol ratio of highly basic=1: 0.5～2.5 adds anhydrous N respectively, and dinethylformamide mixes two lysates then to dissolving fully, under inert gas shielding and ice-water bath condition, reacted 25～40 minutes, after return to room temperature;
B. will be with 2,2,6, colored cyanines 7 (Cy.7.Cl) dyestuff of mol ratios such as 6-tetramethylpiperidinol adds anhydrous N, and dinethylformamide must be spent cyanines 7 solution to dissolving fully; Then with a operation gained mixed liquor slowly adding in flower cyanines 7 solution in 10～20 minutes under the inert gas shielding, in the trash ice of doing, reacted 25～35 minutes;
C. with b operation products therefrom evaporated under reduced pressure, steam and remove N, dinethylformamide, with the ether washing, vacuum drying obtains crude product then;
D. with silica gel column chromatography separate the bluish violet solid pure product.
Two of purpose of the present invention also can realize by following technical measures:
The slow joining day described in the b operation generally is controlled to be 10～20 minutes;
Evaporated under reduced pressure described in the c operation is to adopt the oil pump decompression, and the mode of 35～45 ℃ of rotary evaporations realizes;
It is that (3: 7～5: 5v/v) be eluant, eluent, the mode of 35～45 ℃ of rotary evaporation removal solvent final vacuum dryings realizes employing methyl alcohol-methenyl choloride that silica gel column chromatography described in the d operation separates.
Three of purpose of the present invention can realize by following technical measures:
The near infrared fluorescent probe of detection hydroxyl radical free radical of the present invention is used for the detection of chemical system, chemical simulation living things system hydroxyl radical free radical, the analyzing and testing and the fluorescence imaging of the hydroxyl radical free radical in biological living cells and the living tissue detect, and the detection of hydroxyl radical free radical in the pathological tissues on the clinical medicine.
The present invention has following good effect:
Probe molecule can selectivity be caught chemistry and the interior methyl free radicals of living things system, and methyl free radicals is to be generated by the dimethyl sulfoxide fast quantification of hydroxyl radical free radical in the system and adding, therefore, reaction be equal to probe molecule quantitatively, selectivity catches hydroxyl radical free radical.For for simplicity, the following narration of the present invention all is described as measuring the probe molecule of hydroxyl radical free radical.
1. probe molecule of the present invention excite with emission spectrum in near-infrared region, belong near infrared fluorescent probe, excite and be positioned at 780nm, emission is positioned at 802nm, can effectively avoid the interference of cell autofluorescence, improve the selectivity and the sensitivity of detection method, reduce damage, help live body and detect life entity.
2. the design of probe molecule of the present invention makes fluorophor fluorescent quenching based on the piperidine NO free radical spin labeling, and probe molecule is caught the principle of being recovered by fluorescence behind hydroxyl radical free radical and the quantitatively quick methyl free radicals that generates of dimethyl sulfoxide.Fluorescent probe molecule shows good selectivity, and other active oxygen radical can not make its fluorescence strengthen.Fluorescent probe molecule is insensitive to pH in addition, and in 8.00 scopes, pH changes not influence of fluorescent emission at pH6.80.
3. probe molecule of the present invention is 3.0 * 10 to the sensing range of hydroxyl radical free radical
-5～5.0 * 10
-6M can detect hydroxyl radical free radical in the cell of nanomolar concentration.The probe molecule cell permeability is good, and itself does not have toxic and side effect pair cell, is suitable for the detection that hydroxy free radical concentration changes in the cell.
Cyanine dye probe of the present invention is water-soluble fine, usually, probe molecule can be dissolved in physiological saline, damping fluid or the dimethyl sulfoxide, add in the suitable damping fluid that contains cell tissue then and test, avoid the use of a large amount of organic solvents in the system.
The concrete feature of fluorescence probe of the present invention is as follows:
Probe is made of by covalent bonds near-infrared fluorescent group flower cyanines 7 and piperidine NO free radical, and the excitation-emission wavelength can improve the sensitivity of method at near-infrared band, the detectability of reduction method.In pH value scope was 6.80 to 8.00 scope, probe used and not influenced by the environment potential of hydrogen, was applicable in the biosome and used.The active oxygen and the reductibility enzyme of other kind that exists in the body do not cause interference to detection.The cell permeability of laser confocal microscope imaging experiment proof probe molecule is good, and itself does not have toxic and side effect pair cell, and the HO content of micromole's level detects in can pair cell.
The conventional method that hydroxyl radical free radical detects in the cell is with cultured cell separated into two parts, and a part is stimulated with phorbol myristate (PMA), makes and produces a large amount of O in the cell
2 -, free chain reaction afterwards can generate HO, after the nutrient solution flushing, carries out the laser co-focusing micro-imaging.Stimulated cells does not obtain blank contrast images with the laser confocal microscope imaging.
The probe molecule that the present invention relates to has extremely important using value.Particularly its excitation wavelength of this probe molecule is positioned at the near-infrared region, and extremely insensitive to the pH variation, the response time is short, mensuration sensitivity is high, the good penetrability of pair cell, toxic and side effect is little, makes this class probe as the reagent of measuring hydroxyl radical free radical in the biosome good actual value be arranged.In addition should the series probe molecule simple in structure, synthetic method be simpler, and equipment input and production run cost are all very low, easy to operate and production efficiency is high, are suitable for large-scale industrial production.
Description of drawings
Fig. 1 is the excitation-emission spectrogram of fluorescent probe molecule of the present invention and combined with radical afterproduct, and the experimental system component adds fashionable excitation-emission spectrogram in twos.Horizontal ordinate is wavelength (nm), and ordinate is a fluorescence intensity.
Fig. 2 is the fluorescence intensity and the pH variation relation of fluorescent probe molecule of the present invention and combined with radical afterproduct.Horizontal ordinate is pH, and ordinate is a relative intensity of fluorescence.
Fig. 3 is the fluorescence intensity of fluorescent probe molecule of the present invention and combined with radical afterproduct and the relation in reaction time.Horizontal ordinate is the time, and ordinate is a relative intensity of fluorescence.
Fig. 4 is the fluorescence intensity of fluorescent probe molecule of the present invention and combined with radical afterproduct and the relation of concentration and probe concentration.Horizontal ordinate is a concentration and probe concentration, and ordinate is a relative intensity of fluorescence.
Fig. 5 is the laser co-focusing micro-imaging of HO in the fluorescent probe molecule research Turnover of Mouse Peritoneal Macrophages of the present invention.
Embodiment
Be described further with reference to accompanying drawing 1～5 and table 1:
Probe is to the hydroxyl free based selective
Contrasted the reaction of probe to HO and other free radical and biological substance in vivo.Probe (0.1mM) in the HEPES of pH 7.4 buffering is mixed with 10% the dimethyl sulfoxide solution of 10 μ M, and the probe excitation wavelength is 780nm, and emission wavelength is 802nm, and test result is shown in the table 1.As can be seen from the table, produce very big fluorescence intensity after probe and the combined with radical, and the interference of the active oxygen fluorescence background of other kind is extremely low.
Show that by table 1 fluorescent probe molecule of the present invention has good selectivity to hydroxyl radical free radical.
Table 1:
| compounds | RFI a compounds | RFI a |
| blank | 10 t-BuOOH h | 25 |
| ·OH b(·CH 3) | 336 esterase i | 23 |
| ·OH(·CH 3)/mannitol c | 13 ascorbic acid j | 11 |
| O 2 -·(X/XO) d | 30 1，4-Hydroquinone k | 12 |
| H 2O 2 e | 10 GSH 1 | 17 |
| NO· f | 17 ·OCl m | 15 |
| ONOO -g | 11 |
The applicability of probe under physiological pH
Estimate the applicability of probe under physiological pH.As can be seen from Figure 3 at pH6.80 in 8.00 scopes, pH changes not have to influence to fluorescence intensity substantially.Therefore probe can be used for detection of zinc ions under the physiological condition.
Cellular incubation:
It is 1 * 10 that the Turnover of Mouse Peritoneal Macrophages of collecting is adjusted cell concentration with the nutrient solution that contains 10% bovin serum albumin
6Individual/ml.At 37 ℃, CO
2Concentration is under 5% the condition cell attachment to be hatched 12 hours, takes out and washes not attached cell with nutrient solution, hatches 20min with probe solution, and with the cell separated into two parts, a part (2ng/ml) stimulates with phorbol myristate (PMA).Stimulated cells is not taken fluorescence micrograph as blank with the laser co-focusing imaging.
The laser co-focusing imaging
As can be seen from Figure 5, the amount of the HO that the macrophage inside that stimulates without phorbol myristate (PMA) is contained is very little, be difficult to carry out fluorescent imaging (Fig.5a), the macrophage of hatching with probe sends strong fluorescence (Fig.5b) after stimulating through phorbol myristate (PMA), shows that the HO that the cell internal stimulus generates is transformed into CH
3The back is successfully caught.Fig.5c is the cell image under the bright field.
Embodiment 1:
Synthesizing of probe
Flower cyanines 7 (Cy.7.Cl) probes (Cy.7.TEMPO)
With 382.7mg (2.15mmol) 2,2,6, the 6-tetramethylpiperidinol joins the 100ml there-necked flask under the nitrogen protection, and the ice-water bath cooling is the anhydrous N of 10ml down, dinethylformamide (DMF) stirring and dissolving.The NaOH 65mg of pulpous state (2.15mol, 80%, be stored in the kerosene, clean with normal hexane) is dissolved in the anhydrous N of 5ml, in the dinethylformamide (DMF), stirs down and adds in the flask, returns to room temperature after reacting on 30 minutes.Flower cyanines 7 (Cy.7.Cl) 378mg (2.15mmol) are dissolved in the anhydrous N of 50ml; among the dinethylformamide DMF; above-mentioned gained solution is dropwise joined the anhydrous N of Hua Jing 7 (Cy.7.Cl) under the room temperature nitrogen protection; in dinethylformamide (DMF) solution; finished reinforcedly in 15 minutes, 30 minutes afterreactions finish in the trash ice of doing.The oil pump decompression, 40 ℃ of rotary evaporations are with N, and dinethylformamide (DMF) evaporate to dryness washs gains with ether, the silicagel column separation component is used in vacuum drying, and eluant, eluent is methyl alcohol-methenyl choloride (3: 7v/v), 40 ℃ of rotary evaporations are removed solvent, and vacuum drying gets bluish violet solid (C
45H
59O
8S
2N
3), 1.486g, productive rate 83%.Results of elemental analyses (theoretical value): C, 64.6 (64.8); H, 6.9 (7.1); N, 5.1 (5.0);
1H NMR(DMSO-d
6，300MHz)δ8.00(d，2H)，7.52(d，2H)，7.42(d，2H)，7.37(t，2H)，7.21(t，2H)，6.27(d，2H)，4.17(t，4H)，3.80(m，1H)，1.96(m，2H)，1.76(m，8H)，1.62(m，2H)，1.32(s，12H)，1.08(t，12H)，0.86(d，4H)。
Claims (4)
1, detect the near infrared fluorescent probe of hydroxyl radical free radical, it is characterized in that this fluorescence probe has following general structure:
R＝CH
2CH
2CH
3，CH
2CH
3，CH
2CH
2SO
3Na，CH
2CH
2SO
3，CH
2CH
2CH
2SO
3Na，CH
2CH
2CH
2SO
3；
X＝I，SO
3。
2, detect the synthetic method of the near infrared fluorescent probe of hydroxyl radical free radical, it is characterized in that this synthetic method carries out as follows:
A. according to 2,2,6, the 6-tetramethylpiperidinol: the mol ratio of highly basic=1: 0.5～2.5 adds anhydrous N respectively, and the dinethylformamide dissolving then with two lysate mixings, was reacted 25～40 minutes under inert gas shielding and ice-water bath condition;
B. will be with 2,2,6, the colored cyanines 7 of mol ratios such as 6-tetramethylpiperidinol add anhydrous N, and the dinethylformamide dissolving must be spent cyanines 7 solution; Then a operation gained mixed liquor is slowly added under inert gas shielding in flower cyanines 7 solution and in dry crushing ice and reacted 25～35 minutes;
C. with b operation products therefrom evaporated under reduced pressure, steam and remove N, dinethylformamide, with the ether washing, vacuum drying obtains crude product then;
D. with silica gel column chromatography separate the bluish violet solid pure product.
3, synthetic method according to claim 1 is characterized in that:
The slow joining day described in the b operation generally is controlled to be 10～20 minutes; Evaporated under reduced pressure described in the c operation is meant oil pump decompression, 35～45 ℃ of rotary evaporations; Silica gel column chromatography separation described in the d operation is meant that with methyl alcohol-methenyl choloride be eluant, eluent, and 35～45 ℃ of rotary evaporations are removed solvent final vacuum dryings.
4, the near infrared fluorescent probe of the described detection hydroxyl radical free radical of claim 1 is used for the detection of chemical system, chemical simulation living things system hydroxyl radical free radical, the analyzing and testing and the fluorescence imaging of the hydroxyl radical free radical in biological living cells and the living tissue detect, and the detection of hydroxyl radical free radical in the pathological tissues on the clinical medicine.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101413896B (en) * | 2008-12-02 | 2011-05-18 | 上海理工大学 | Method for measuring hydroxy free radical |
| CN101791414B (en) * | 2010-01-19 | 2011-11-23 | 华东理工大学 | Multifunctional EPR bio-probe based on magnetic nano particle and application thereof |
| CN106610372A (en) * | 2015-10-23 | 2017-05-03 | 清华大学 | Probe and method for detecting catechol and/or hydroquinone |
| CN108624081A (en) * | 2018-05-29 | 2018-10-09 | 苏州百源基因技术有限公司 | A kind of fluorescent dye and the preparation method and application thereof |
| CN114031546A (en) * | 2021-10-21 | 2022-02-11 | 广西师范大学 | Photoacoustic imaging probe of hydroxyl free radical and preparation method and application thereof |
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| CN105154065B (en) * | 2015-08-19 | 2017-03-15 | 济南大学 | A kind of fluorescent probe of quick specific recognition hydroxyl radical free radical and its preparation method and application |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1412553A (en) * | 2002-11-28 | 2003-04-23 | 武汉大学 | Detection method of hydroxyl free radical |
| CN100473653C (en) * | 2005-06-06 | 2009-04-01 | 大连理工大学 | Near infrared meso-position nitrogen and sulfur substituted hepta-methyl-cyanine fluorochrome for bioanalysis |
| CN1715919A (en) * | 2005-07-12 | 2006-01-04 | 大连理工大学 | Fluoroboric dye fluorescent probe for cell zinc ion detection |
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2006
- 2006-04-07 CN CNB2006100435668A patent/CN100486966C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101413896B (en) * | 2008-12-02 | 2011-05-18 | 上海理工大学 | Method for measuring hydroxy free radical |
| CN101791414B (en) * | 2010-01-19 | 2011-11-23 | 华东理工大学 | Multifunctional EPR bio-probe based on magnetic nano particle and application thereof |
| CN106610372A (en) * | 2015-10-23 | 2017-05-03 | 清华大学 | Probe and method for detecting catechol and/or hydroquinone |
| CN108624081A (en) * | 2018-05-29 | 2018-10-09 | 苏州百源基因技术有限公司 | A kind of fluorescent dye and the preparation method and application thereof |
| US11859087B2 (en) | 2018-05-29 | 2024-01-02 | Suzhou Baiyuan Gent. Co., Ltd. | Fluorescent dye, preparation method therefor, and application thereof |
| CN114031546A (en) * | 2021-10-21 | 2022-02-11 | 广西师范大学 | Photoacoustic imaging probe of hydroxyl free radical and preparation method and application thereof |
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