CN116003341A - Fluorescent probe and preparation method and application thereof - Google Patents
Fluorescent probe and preparation method and application thereof Download PDFInfo
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- CN116003341A CN116003341A CN202111231391.4A CN202111231391A CN116003341A CN 116003341 A CN116003341 A CN 116003341A CN 202111231391 A CN202111231391 A CN 202111231391A CN 116003341 A CN116003341 A CN 116003341A
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- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- -1 rhodamine lactam compounds Chemical class 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 238000001514 detection method Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 2
- 238000006555 catalytic reaction Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 abstract description 11
- 230000004044 response Effects 0.000 abstract description 6
- 150000002443 hydroxylamines Chemical class 0.000 abstract description 2
- 125000000879 imine group Chemical group 0.000 abstract description 2
- 150000002466 imines Chemical class 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 239000000523 sample Substances 0.000 description 6
- 238000003384 imaging method Methods 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- NCGICGYLBXGBGN-UHFFFAOYSA-N 3-morpholin-4-yl-1-oxa-3-azonia-2-azanidacyclopent-3-en-5-imine;hydrochloride Chemical compound Cl.[N-]1OC(=N)C=[N+]1N1CCOCC1 NCGICGYLBXGBGN-UHFFFAOYSA-N 0.000 description 3
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004113 cell culture Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000035790 physiological processes and functions Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- DYKFCLLONBREIL-KVUCHLLUSA-N minocycline Chemical compound C([C@H]1C2)C3=C(N(C)C)C=CC(O)=C3C(=O)C1=C(O)[C@@]1(O)[C@@H]2[C@H](N(C)C)C(O)=C(C(N)=O)C1=O DYKFCLLONBREIL-KVUCHLLUSA-N 0.000 description 2
- 229960004023 minocycline Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
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- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
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- 239000001963 growth medium Substances 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
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- 229940049954 penicillin Drugs 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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Abstract
The invention discloses a fluorescent probe and a preparation method and application thereof. The structure of the compound serving as the fluorescent probe is shown as a formula I: wherein R is 1 ‑R 6 Is H or a straight-chain or branched alkyl group having 1 to 6 carbon atoms. According to the invention, rhodamine compounds directly react with hydroxylamine compounds under alkaline conditions to obtain novel imine compounds. The structure breaks the original conjugated structure of rhodamine and has spectrum property completely different from rhodamine compounds and rhodamine lactam compounds. The imine group can react with active oxygen to generate a fluorophore with a novel conjugated structure, and fluorescence enhancement response is generated in a near infrared band.
Description
Technical Field
The invention relates to a fluorescent probe and a preparation method and application thereof, belonging to the technical field of biochemical analysis.
Background
Reactive oxygen species are a class of molecules with a relatively high oxidative activity. They have important physiological functions in organisms, for example, they can damage physiological species such as proteins, lipids and nucleic acids, and thus affect normal physiological functions of cells, causing a series of diseases such as cardiovascular diseases, alzheimer's disease, cancer, etc. In recent years, probes for detecting living body active oxygen play an important role in the study of the physiological functions of active oxygen, particularly in the cell imaging analysis. However, most of them have the disadvantage of shorter wavelength and higher background fluorescence, and their use in biological systems is limited. Further development of an active oxygen fluorescent probe excellent in properties is required. Rhodamine compounds have good spectral properties and biocompatibility and are often used for the design and preparation of fluorescent probes. The typical reaction is that carboxyl on rhodamine reacts with hydroxylamine nucleophilic reagent to generate rhodamine lactam structure containing five-membered ring. However, the analysis wavelength of such fluorescent probes is still relatively short, and thus a fluorescent probe having a longer analysis wavelength based on rhodamine structure has yet to be developed.
Disclosure of Invention
The invention aims to provide a fluorescent probe and a preparation method and application thereof.
In the invention, rhodamine compounds directly react with hydroxylamine compounds under alkaline conditions to obtain novel imine compounds (namely fluorescent probes). The structure breaks the original conjugated structure of rhodamine and has spectrum property completely different from rhodamine compounds and rhodamine lactam compounds. The imine group can react with active oxygen to generate a fluorophore with a novel conjugated structure, and fluorescence enhancement response is generated in a near infrared band.
The invention provides a compound, the structure of which is shown in formula I:
wherein R is 1 -R 6 Is H or a straight-chain or branched alkyl group having 1 to 6 carbon atoms.
In the above-mentioned compounds, R 1 -R 6 H or alkyl with 1-2 carbon atoms.
The structure of the compound is shown in the following formula II:
the invention also provides a preparation method of the compound shown in the formula I, which is characterized by comprising the following steps: mixing a compound shown in a formula III with a hydroxylamine compound in an organic solvent, and carrying out a base catalytic reaction to prepare the compound shown in the formula I;
r in III 1 -R 6 And R in the compound shown in the formula I 1 -R 6 The same applies.
In the preparation method, the organic solvent is at least one of methanol, ethanol, methylene dichloride, acetonitrile and tetrahydrofuran;
the hydroxylamine compound comprises hydroxylamine hydrochloride;
the base is triethylamine and/or sodium hydroxide.
In the preparation method, the molar ratio of the compound shown in the formula II to the hydroxylamine compound can be 1:5-25, and can be specifically 1:12, 1:5-12, 1:12-25 or 1:10-20;
the molar ratio of the compound shown in the formula II to the alkali can be 1:5-25, and can be specifically 1:21, 1:5-21, 1:21-25, 1:15-25 or 1:10-25.
In the preparation method, the reaction temperature of the reaction can be 45-90 ℃, specifically 85 ℃, 45-85 ℃, 85-90 ℃ or 65-90 ℃, and the reaction time can be 10-24 h, specifically 12h, 10-12 h, 12-24 h, 10-16 h or 11-20 h.
The invention also provides a fluorescent probe which comprises the compound shown in the formula I.
The fluorescent probe is applied to active oxygen detection.
In the above application, the active oxygen includes peroxynitroso group.
Specifically, peroxynitroso groups may undergo oxidation reactions with compounds of formula I, resulting in an increase in fluorescence signal. The concentration of peroxynitroso can be determined by detecting the fluorescence intensity at a wavelength of 672nm under excitation conditions at a wavelength of 620nm.
The invention has the following advantages:
1) The probe can perform specific fluorescence opening response on the peroxynitroso in the near infrared wavelength (672 nm) region, and is not interfered by other active oxygen species or physiologically active species;
2) The sensitivity of the probe is high, and the detection limit is as low as 6.3nM;
3) The probe has good biocompatibility and can be used for imaging peroxynitroso groups in cells;
4) The probe has simple preparation condition, can be prepared in large batch, has stable property, is easy to store, and has no obvious change in appearance and fluorescence intensity when being placed for more than one month at room temperature.
Drawings
FIG. 1 is a graph showing the fluorescence response of fluorescent probes of formula II to different concentrations of peroxynitroso.
FIG. 2 is a graph showing the fluorescence response intensity of the fluorescent probe of formula II to peroxynitroso group at 672nm wavelength versus the concentration of peroxynitroso group.
FIG. 3 is a fluorescent image of RAW264.7 cells with the fluorescent probe of formula II.
Detailed Description
The experimental methods used in the following examples are conventional methods unless otherwise specified.
Materials, reagents and the like used in the examples described below are commercially available unless otherwise specified.
Example 1 preparation of Compounds of formula II
This example provides a process for the preparation of a compound of formula II, which is synthesized as follows:
the method comprises the following specific steps:
the compound represented by formula IV (443 mg,1 mmol) and hydroxylamine hydrochloride (284 mg,12 mmol) were dissolved in 15mL of anhydrous methanol, and 3mL of triethylamine (21 mmol) was added thereto, and the mixture was refluxed at 85℃for 12 hours. After the reaction, the solvent is removed by reduced pressure distillation, 50mL of dichloromethane is used for dissolution, the same volume of water is used for extraction twice, the organic phase is remained, the solvent is removed, and column chromatography separation is carried out by taking dichloromethane/methanol as an eluent, so that orange solid (320 mg, 70%) is obtained, namely the compound shown as the formula II, namely the rhodamine B derivative.
The prepared rhodamine B derivative was used as a fluorescent probe in examples 2 and 3 of the present invention.
The structure of the compound of formula II is confirmed as follows:
1 H NMR(600MHz,298K,DMSO-d 6 ):δ＝12.65(s,1H),7.73(d,J＝7.8Hz,1H),7.54-7.57(m,1H),7.48-7.51(m,1H),7.44(d,J＝7.2Hz,1H),6.99(d,J＝9Hz,1H),6.57(d,J＝9Hz,1H),6.48-6.50(m,3H),6.34-6.36(m,1H),3.33-3.36(m,8H),1.07-1.11(m,12H)；
13 C NMR(150MHz,298K,DMSO-d 6 ):δ＝169.16,162.04,161.36,152.38,151.08,147.55,142.01,133.69,131.29,130.32,130.07,129.67,128.92,128.86,128.28,115.47,108.25,106.91,103.07,102.10,43.84,43.76,12.38,12.32ppm；
high resolution mass spectrometry: c (C) 28 H 32 BN 3 O 3 + ，[M+H] + Calculated as 458.24382 and measured as 458.24406.
Example 2 determination of peroxynitroso groups in phosphate buffer
50. Mu.L of a stock solution of dimethyl sulfoxide (100. Mu.M) of the compound of the invention (fluorescent probe) of the formula II was taken in a 5mL graduated tube, 500. Mu.L of phosphate buffer solution of 200mM concentration and pH 7.4 was added thereto, followed by addition of different volumes of peroxynitroso mother liquor, volume fixation with water to 5mL and final fluorescent probe concentration of 1. Mu.M. After the reaction mixture was uniformly mixed, the mixture was reacted at 37℃for 10 minutes, and 3mL of the solution was taken out to measure the fluorescence spectrum thereof, with an excitation wavelength of 620nm.
FIG. 1 is a graph showing fluorescence response of a compound of formula II to peroxynitroso groups of different concentrations, wherein the fluorescence at 672nm is gradually increased with the increase of the peroxynitroso group concentration; FIG. 2 is a graph of fluorescence intensity at 672nm as ordinate and peroxynitroso concentration as abscissa, and the relationship between fluorescence intensity and peroxynitroso concentration is obtained, and it is understood from FIG. 2 that in the range of 0.05 to 2. Mu.M, the system fluorescence intensity and peroxynitroso concentration exhibit a good linear relationship F=1009.75 [ ONOO - ](μM)-21.61(R 2 =0.961) and the calculated limit of detection is as low as 6.3nM.
EXAMPLE 3 imaging of peroxynitroso groups in cells by Compounds of formula II
1) In a special glass bottom culture dish for a confocal laser fluorescence microscope, 37 ℃ and 5% (v/v) CO 2 RAW264.7 cells (commercially available from Jiangsu Kai Biotechnology Co., ltd.) were cultured under atmospheric conditions with DMEM medium (commercially available from Jiangsu Kai Biotechnology Co., ltd.) containing 10% (v/v) fetal bovine serum (commercially available from Yingsu Life technologies Co., ltd., product catalog number 10099141), 100U/mL penicillin, 100. Mu.g/mL streptomycin for 24 hours, and the cells were sufficiently attached to the bottom of the culture dish.
2) After the completion of the cell culture in step 1), the culture solution in the dish was aspirated, and then 1mL of DMEM medium containing 20. Mu.M probe was added thereto, followed by further culturing for 30 minutes.
3) After the incubation in step 2), the culture medium in the dish was aspirated, and cells were washed with 20mM phosphate buffer (pH 7.4), and a cell culture dish containing 50. Mu.M peroxynitroso donor SIN-1 (Chinese name: linxidormine, english name: 3-morpholinosydnomine) in DMEM culture broth, for 30min to cause an increase in the peroxynitroso content in the cells; in order to reduce the concentration of peroxynitroso in the control group, 50. Mu.M of the peroxynitroso scavenger minocycline was added at the same time as the SIN-1 incubation.
4) After the cell culture in step 3 was completed, the culture solution in the dish was aspirated, and the cells were washed with 20mM phosphate buffer (pH 7.4), and finally 1mL of 20mM phosphate buffer (pH 7.4) was added. The dishes were placed on a confocal fluorescence microscope for fluorescence imaging. The red excitation light source is a 635nm laser, the fluorescence signal collection range is 650-750nm, and the change in signal intensity represents the change in peroxynitroso level.
FIG. 3 is a fluorescence imaging diagram of the fluorescent probe shown in the formula II on RAW264.7 cells, and as can be seen from FIG. 3, the fluorescence signal of the system is enhanced after the peroxynitroso donor SIN-1 is added. Whereas for the control group to which the peroxynitroso scavenger minocycline was added, the fluorescence of the system was reduced, indicating that the fluorescent probe of the invention can be used for imaging peroxynitroso in cells.
Finally, it should be noted that the above examples only illustrate the preparation and application of the fluorescent probe shown in formula II, and the preparation methods, test conditions and the like of the other fluorescent probes are not listed because the structures and properties of the other fluorescent probes are similar.
The present invention is not limited to the above-mentioned embodiments, and any changes or substitutions that can be easily understood by those skilled in the art within the technical scope of the present invention are intended to be included in the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (10)
1. A compound, characterized in that the structure of the compound is shown in formula I:
wherein R is 1 -R 6 Is H or a straight-chain or branched alkyl group having 1 to 6 carbon atoms.
2. A compound according to claim 1, characterized in that: r is R 1 -R 6 H or alkyl with 1-2 carbon atoms.
3. A compound according to claim 1 or 2, characterized in that: the structure of the compound is shown as the following formula II:
4. a process for the preparation of a compound of formula I according to any one of claims 1 to 3, comprising the steps of: mixing a compound shown in a formula III with a hydroxylamine compound in an organic solvent, and carrying out a base catalytic reaction to prepare the compound shown in the formula I;
r in III 1 -R 6 And R in the compound shown in the formula I 1 -R 6 The same applies.
5. The method of manufacturing according to claim 4, wherein: the organic solvent is at least one of methanol, ethanol, dichloromethane, acetonitrile and tetrahydrofuran;
the hydroxylamine compound comprises hydroxylamine hydrochloride;
the base is triethylamine and/or sodium hydroxide.
6. The method of claim 4 or 5, wherein: the molar ratio of the compound shown in the formula II to the hydroxylamine compound is 1:5-25;
the molar ratio of the compound shown in the formula II to the alkali is 1:5-25.
7. The production method according to any one of claims 4 to 6, characterized in that: the reaction temperature is 45-90 ℃ and the reaction time is 10-24 h.
8. A fluorescent probe, characterized in that: the fluorescent probe comprises a compound shown in a formula I in any one of claims 1-3.
9. The use of the fluorescent probe according to claim 8 in active oxygen detection.
10. The use according to claim 9, characterized in that: the active oxygen includes a peroxynitroso group.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107973828A (en) * | 2016-10-21 | 2018-05-01 | 南京理工大学 | Based on glycosyloxy glycoside fluorescence probe, synthetic method and its application |
| CN113061140A (en) * | 2021-03-26 | 2021-07-02 | 辽宁大学 | Hexa-spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107973828A (en) * | 2016-10-21 | 2018-05-01 | 南京理工大学 | Based on glycosyloxy glycoside fluorescence probe, synthetic method and its application |
| CN113061140A (en) * | 2021-03-26 | 2021-07-02 | 辽宁大学 | Hexa-spiro rhodamine copper ion fluorescent probe containing hydroxyurea structure and preparation method and application thereof |
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