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Radix stemonae alkaloid analogue near-infrared fluorescent probe and preparation method thereof

A fluorescent probe and near-infrared technology, applied in the field of optical imaging, can solve the problems of short emission wavelength, complex synthesis route, and long response time, and achieve the effects of rapid fluorescence detection, easy availability of raw materials, and low cost

Active Publication Date: 2020-07-10
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The currently reported fluorescent probes for the detection of biothiols still have certain limitations, such as complex synthetic routes, long response times, and short emission wavelengths.

Method used

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  • Radix stemonae alkaloid analogue near-infrared fluorescent probe and preparation method thereof
  • Radix stemonae alkaloid analogue near-infrared fluorescent probe and preparation method thereof
  • Radix stemonae alkaloid analogue near-infrared fluorescent probe and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: The specific synthetic process of fluorescent probe of the present invention

[0028] (1) The specific synthetic steps of compound 2 are as follows:

[0029]

[0030] 2,6-bis(hydroxymethyl)-p-cresol (5g, 29mmol) and MnO 2 (20 g, 229 mmol) in 400 ml of acetone was stirred overnight at room temperature, filtered and the filtrate was concentrated to give a residue. Separation by column chromatography (PE:EA=2:1) ​​gave compound 5 (53%) as a white solid.

[0031]

[0032] Compound 5 (278 mg, 1.67 mmol), cyclopent-2-en-1-one (compound 6) (0.280 mL, 3.35 mmol) and 1-H-imidazole (120 mg, 1.67 mmol) were dissolved in tetrahydrofuran (THF, 2.5 mL) and distilled water (2.5mL). The mixture was stirred at room temperature for 96 h, the final mixture was diluted with 10 mL of HCl solution (1 mol / L), extracted with ethyl acetate (3×15.27 mL). The resulting residue was concentrated from the filtrate and separated by silica gel column chromatography (PE:EA=1:2) ...

Embodiment 2

[0036] Embodiment 2. The concrete synthetic steps of fluorescent probe are as follows:

[0037]

[0038] Compound 2 (32 mg, 139 μmol, 1 eq), compound 3 (58 mg, 167 μmol, 1.2 eq) and DMAP (57 mg, 470 μmol, 3.38 eq) were dissolved in 0.64 mL of pyridine and stirred overnight at 45 °C under argon. The reaction was monitored by TLC spot plate until the reaction of the raw materials was completed, the reaction solution was precipitated with diethyl ether, and the diethyl ether layer was dried, the filtrate was concentrated to obtain the residue, and separated by silica gel column chromatography (PE:EA=2:1, 5% triethylamine) Obtained 49 mg of fluorescent probe. 1 H NMR (600MHz, CDCl 3 )δ7.40(s,2H),7.18(d,J=2.5Hz,1H),7.08(d,J=2.2Hz,1H),7.00(d,J=2.2Hz,1H),6.69(s, 2H), 6.63(s, 2H), 5.29(s, 1H), 5.21(ddd, J=9.6, 7.5, 2.5Hz, 2H), 2.95(s, 12H), 2.70(dt, J=12.3, 8.1Hz ,1H),2.61(dd,J=18.5,9.0Hz,1H),2.35(ddd,J=18.6,12.7,8.7Hz,1H),2.26(s,3H),2.16(ddd,J=12.5,9.1 ,3.5Hz,1H). 13 C NMR (1...

Embodiment 3

[0039] Embodiment 3: before and after the reaction of the fluorescent probe of the present invention and Cys, the ultraviolet and fluorescence spectrograms:

[0040] Add 140 μM Cys (stirring) to the fluorescent probe solution of the present invention (10 μM, PBS:DMSO=1:1), and measure the changes of ultraviolet and fluorescence intensity after 10 min. The results can be found in image 3 with Figure 4 , all UV and fluorescence intensities were normalized.

[0041] Such as image 3As shown, the pictures of color changes visible to the naked eye without adding (left) and adding (right) Cys to the fluorescent probe solution of the present invention. After adding Cys, the fluorescence changes obviously, from colorless to blue, indicating that the probe reacts with Cys and can be used to trace Cys.

[0042] Such as image 3 Shown is the ultraviolet-visible absorption spectrum of the fluorescent probe solution of the present invention before and after adding Cys. It can be fo...

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Abstract

The invention relates to the field of optical imaging, in particular to a radix stemonae alkaloid analogue near-infrared fluorescent probe and a preparation method thereof. The near-infrared fluorescent probe is applied to rapid detection of biological mercaptan, and is applied to imaging of the biological mercaptan in cells and living bodies. Existing reported fluorescent probes for detecting thebiological mercaptan have certain limitations, such as complex synthetic routes, long response time, short emission wavelength and the like. The preparation method of the near-infrared fluorescent probe comprises the following steps: 5-(hydroxymethyl)-7-methyl-3, 3 a-dihydrocyclopenta [ b ] chroman cyclo-1 (2H)-one and 3, 7-bis (dimethylamino)-10H-benzothiazine-10-carbonyl chloride react under the action of 4-dimethylamino pyridine and pyridine to generate (7-methyl-1-oxy-1, 2, 3, 3 a-tetrahydrocyclopenta [ b ] chroman cyclo-5-yl)-methyl-3, 7-bis (dimethylamino)-10H-benzothiazine-10-carboxylate.

Description

technical field [0001] The invention relates to the field of optical imaging, in particular to a near-infrared fluorescent probe of a basilica alkaloid analogue and a preparation method thereof. Background technique [0002] It is well known that small molecule biothiols in the body, such as cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH), play a very important role in physiological substrates. For example, Cys and Hcy are essential biomolecules necessary for the growth of cells and tissues in living systems. Cysteine ​​deficiency can lead to various health problems such as growth retardation, hair loss, lethargy, liver damage, loss of muscle and fat, and skin damage. Elevated Hcy levels in human plasma are risk factors for Alzheimer's disease, cardiovascular disease, neural tube defects, inflammatory bowel disease, and osteoporosis. GSH, the most abundant intracellular non-proteinogenic thiol, plays a key role in maintaining the reducing environment in cells ...

Claims

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Application Information

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IPC IPC(8): C07D417/12C09K11/06G01N21/64A61K49/00
CPCA61K49/003C07D417/12C09K11/06C09K2211/1037C09K2211/1088G01N21/6428G01N21/6486
Inventor 马开庆赵玲玲阴彩霞
Owner SHANXI UNIV
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