CN113979973A - Design, synthesis and activity research of in-situ cysteine detection fluorescent probe - Google Patents
Design, synthesis and activity research of in-situ cysteine detection fluorescent probe Download PDFInfo
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims description 4
- 239000005695 Ammonium acetate Substances 0.000 claims description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 claims description 4
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- 229940125904 compound 1 Drugs 0.000 claims description 4
- 229940126214 compound 3 Drugs 0.000 claims description 4
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 claims description 2
- -1 Cys small-molecule Chemical class 0.000 claims description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 claims description 2
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/001—Preparation for luminescence or biological staining
- A61K49/0013—Luminescence
- A61K49/0017—Fluorescence in vivo
- A61K49/0019—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules
- A61K49/0021—Fluorescence in vivo characterised by the fluorescent group, e.g. oligomeric, polymeric or dendritic molecules the fluorescent group being a small organic molecule
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
Abstract
The invention discloses design, synthesis and activity research of a cysteine fluorescent probe for in-situ detection, wherein the synthetic route is as follows:
Description
Technical Field
The invention belongs to the fields of molecular biology, medicine and the like, and particularly relates to a preparation method of a cysteine fluorescent probe and application of the cysteine fluorescent probe in detecting overexpressed cysteine in an environment in a tumor.
Background
Cysteine (Cys) plays an important biological role in a variety of physiological and pathological processes, including protein synthesis, detoxification, cellular redox homeostasis, and metabolism. An imbalance of Cys in vivo is often indicative of several diseases. For example, low levels of Cys are considered important biomarkers of edema, liver damage, and skin lesions, while elevated Cys levels have been reported to be closely associated with neurotoxicity, cardiovascular disease, and alzheimer's disease. Therefore, developing a reliable method for Cys detection in a concentration-dependent manner would be advantageous for studying the biological functions involved in Cys and for clinical diagnosis of Cys-related diseases.
Fluorescence imaging is a powerful technique for monitoring biological analytes and processes in living systems. The developed fluorescent probes make a great contribution to the great progress of cell biology and medical diagnostic imaging. Near Infrared (NIR) fluorescent probes are particularly advantageous because near infrared light has significant advantages, including deep tissue penetration, low background noise, and minimal light damage to biological samples. However, the construction of small molecule-based near-infrared fluorescent probes is a very challenging task.
Based on the design, a fluorescent probe taking Cys as a target spot is designed and synthesized, and the probe enables the structure to be changed through the redox action of Cys according to the over-expression of Cys at a tumor part, releases a fluorophore with near infrared emission, and achieves the effect of early tumor detection. The present invention also provides a method for evaluating the biological activity of the fluorescent probe.
Disclosure of Invention
The purpose of the invention is as follows:
1. provides a new compound responding to cysteine so as to develop a new small molecule fluorescent probe.
2. Provides a preparation method of the small molecular fluorescent probe.
3. Provides a primary application of the probe in detecting the concentration of Cys in the environment in the tumor.
The technical scheme is as follows: and (3) synthesizing and characterizing the Cys small-molecule fluorescent probe:
aReagents and conditions：(a)CH2(CN)2，CH3CH2ONa，EtOH，50℃；(b)P-aminobenzaldehyde， Ammonium acetate，EtOH，rt；(c)Acrylic Chloride，THF，0℃.
synthesis of Compound 1:
sodium ethoxide (90mg, 1.3mmol) was added to a solution of 3-hydroxy-3-methyl-2-butanone (900mg, 8.8mmol) and malononitrile (1.2g, 18.1mmol) in ethanol (10mL), and stirred at room temperature for 1 h. Then, 30mL of ethanol was added to the reaction system, and the mixture was refluxed at 50 ℃ for one hour and then cooled to room temperature. The solid precipitate was filtered and washed with a small amount of cold ethanol to give off-white crystals (1.89g, 90%).
Synthesis of Compound 2:
compound 1(1.99g, 150mmol) and p-aminobenzaldehyde (1.81g, 15mmol) were weighed, dissolved in 30mL of anhydrous ethanol, and ammonium acetate (0.39g, 5mmol) was added to the reaction system, and after refluxing at 50 ℃ for 6 hours, suction filtration and washing with cold ethanol gave a deep purple solid (3.19g, 83.9%).1H NMR(500MHz， Chloroform)δ7.58-7.46(m，2H)，7.30(s，1H)，6.76(s，1H)，6.38-6.25(m，2H)， 4.27(s，2H)，1.45(s，6H).13C NMR(125MHz，Common NMR Solvents)δ165.86(s， 1H)，165.46(s，1H)，149.29(s，2H)，142.95(s，2H)，130.61(s，2H)，124.55(s，2H)， 121.31(s，3H)，115.62(s，2H)，114.34(s，4H)，110.37(s，2H)，93.94(s，1H)，93.72(s， 1H)，60.68(s，1H)，24.58(s，7H).
Synthesis of Compound 3:
compound 3(200mg, 0.6mmol) was weighed out and dissolved in an appropriate amount of anhydrous tetrahydrofuran, followed by addition of acryloyl chloride (70. mu.L) at 0 ℃ and stirring reaction for 1 hour, and the resulting mixture was further stirred at room temperature for 8 hours. The reaction was quenched with 3mL water and washed with ethyl acetate (15mL x 3), anhydrous Na2SO4And (5) drying. Column chromatography was carried out at PE: EA 5: 1 to give an orange-red solid powder (100mg, 42.3%).1H NMR(500MHz，DMSO)δ8.80 (s，5H)，7.76(d，J＝7.5Hz，11H)，7.56(d，J＝7.4Hz，11H)，7.01(d，J＝15.0Hz，5H)， 6.24(s，1H)，6.15(d，J＝64.7Hz，11H)，5.85(s，5H)，5.03(s，5H)，1.41(s，32H).13C NMR(125MHz，Common NMR Solvents)δ165.90(d，J＝11.6Hz，2H)，165.46(s， 1H)，142.95(s，2H)，139.23(s，2H)，130.80(s，2H)，129.10(s，2H)，123.25(s，2H)， 122.83(s，2H)，121.31(s，3H)，121.14(s，4H)，115.62(s，2H)，110.37(s，2H)，93.94(s， 1H)，93.72(s，1H)，60.68(s，1H)，24.58(s，7H).
Drawings
FIG. 1 is a schematic diagram of the hydrogen nuclear magnetic resonance spectrum of the present invention
FIG. 2 is a schematic diagram of the nuclear magnetic resonance carbon spectrum of the present invention
FIG. 3 is a schematic diagram of the selectivity test of the present invention
FIG. 4 is a schematic diagram of the interference test of the present invention
Hydrogen spectrum of compound 3:
see attached figure 1
Carbon spectrum of compound 3:
see figure 2
Preliminary evaluation of biological Activity
And (3) selective testing:
see figure 3
Description of the drawings: this probe (1mM) responded only to Cys and was almost non-responsive to other substrates.
Interference testing:
see figure 4
Description of the drawings: the probe (1mM) was not interfered with by other substrates.
Preliminary evaluation of the biological activity of the small-molecule fluorescent probe shows that the probe has the function of detecting cysteine and can be applied to in-situ detection of Cys over-expressed cancer cells.
Although the preferred embodiments of the present invention and the evaluation of biological activity have been described in detail, the present invention is not limited to the details of the above embodiments, and various equivalent changes can be made to the technical solution of the present invention within the technical spirit of the present invention, and these equivalent changes are within the scope of the present invention. It should be noted that the various features described in the above embodiments may be combined in any suitable manner without departing from the scope of the invention. The invention is not described in detail in order to avoid unnecessary repetition. In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (1)
- The synthetic route and the method of the Cys small-molecule fluorescent probe comprise the following steps:
aReagents and conditions：(a)CH2(CN)2，CH3CH2ONa，EtOH，50℃；(b)P-aminobenzaldehyde，Ammonium acetate，EtOH，rt；(c)Acrylic Chloride，THF，0℃.synthesis of Compound 1:sodium ethoxide (90mg, 1.3mmol) was added to a solution of 3-hydroxy-3-methyl-2-butanone (900mg, 8.8mmol) and malononitrile (1.2g, 18.1mmol) in ethanol (10mL), and stirred at room temperature for 1 h. Then, 30mL of ethanol was added to the reaction system, and the mixture was refluxed at 50 ℃ for one hour and then cooled to room temperature. The solid precipitate was filtered and washed with a small amount of cold ethanol to give off-white crystals (1.89g, 90%).Synthesis of Compound 2:compound 1(1.99g, 150mmol) and p-aminobenzaldehyde (1.81g, 15mmol) were weighed, dissolved in 30mL of anhydrous ethanol, and ammonium acetate (0.39g, 5mmol) was added to the reaction system, and after refluxing at 50 ℃ for 6 hours, suction filtration and washing with cold ethanol gave a deep purple solid (3.19g, 83.9%).Synthesis of Compound 3:compound 3(200mg, 0.6mmol) was weighed out and dissolved in an appropriate amount of anhydrous tetrahydrofuran, followed by addition of acryloyl chloride (70. mu.L) at 0 ℃ and stirring reaction for 1 hour, and the resulting mixture was further stirred at room temperature for 8 hours. The reaction was quenched with 3mL water and washed with ethyl acetate (15mL x 3), anhydrous Na2SO4And (5) drying. Column chromatography was carried out at PE: EA 5: 1 to give an orange-red solid powder (100mg, 42.3%).
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100029952A1 (en) * | 2008-05-23 | 2010-02-04 | Kent State University | Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems |
| CN107417638A (en) * | 2017-05-04 | 2017-12-01 | 河南牧业经济学院 | A kind of glutathione and cysteine fluorescence probe based on 7 nitrobenzofurazans and preparation method thereof |
| JP2017222609A (en) * | 2016-06-16 | 2017-12-21 | 東ソー株式会社 | Xanthene derivative, production method thereof, and method of detecting cancer cells using the derivative |
-
2021
- 2021-10-29 CN CN202111296746.8A patent/CN113979973A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100029952A1 (en) * | 2008-05-23 | 2010-02-04 | Kent State University | Fluorogenic compounds converted to fluorophores by photochemical or chemical means and their use in biological systems |
| JP2017222609A (en) * | 2016-06-16 | 2017-12-21 | 東ソー株式会社 | Xanthene derivative, production method thereof, and method of detecting cancer cells using the derivative |
| CN107417638A (en) * | 2017-05-04 | 2017-12-01 | 河南牧业经济学院 | A kind of glutathione and cysteine fluorescence probe based on 7 nitrobenzofurazans and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| LI, ZHEN ET AL.，: "In vivo tracking cystine/glutamate antiporter-mediated cysteine/cystine pool under ferroptosis", 《ANALYTICA CHIMICA ACTA》, pages 66 - 75 * |
| ZHANG, BAOXIN ET AL.: "A novel off-on fluorescent probe for specific detection and imaging of cysteine in live cells and in vivo", 《CHINESE CHEMICAL LETTERS》, vol. 31, no. 1, pages 133 - 135, XP085974421, DOI: 10.1016/j.cclet.2019.05.061 * |
| ZHANG, RONG-RONG ET AL.: "Novel pyrazoline-based fluorescent probe for detecting thiols and its application in cells", 《SPECTROCHIMICA ACTA, PART A: MOLECULAR AND BIOMOLECULAR SPECTROSCOPY》, pages 450 - 455 * |
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