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Easy-to-combine xanthene fluorescent compound as well as preparation and application thereof

The technology of a kind of compound and general formula compound is applied in the fields of easy-to-combine xanthene-based fluorescent compounds and their preparation and application, which can solve the problems of influence on fluorescent properties, destruction of conjugated system, high production cost, etc., to reduce production cost, reduce Hazards to persons and the environment, effects of good fluorescent properties

Inactive Publication Date: 2020-01-21
罗宇峰
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, while the production cost of this type of compound remains high, it is difficult to ensure the accuracy of isothiocyanate modification on the fluorescein molecule, and it is easy to produce isomers modified at different positions on the aromatic ring of the molecule. The purity and performance of the synthetic product cannot be guaranteed, which is very unfavorable for the follow-up research and use of the probe
If the exposed carboxyl group is modified with a primary amine, it will form a cyclic lactam and destroy the conjugated system, which will seriously affect the fluorescence properties of the molecule under neutral and alkaline conditions.

Method used

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  • Easy-to-combine xanthene fluorescent compound as well as preparation and application thereof
  • Easy-to-combine xanthene fluorescent compound as well as preparation and application thereof
  • Easy-to-combine xanthene fluorescent compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1. Synthesis of fluorescein-proline methyl ester

[0024] Dissolve 333mg fluorescein and 1mmol DIEA HBTU HOBt in 20ml DMF, cool down to 5°C for 15 minutes; dissolve 1mmol proline methyl ester hydrochloride and 1mmol DIEA in 10ml DMF and stir, then add the previous solution and react at room temperature for 10h. After the reaction was completed, 200ml of water was added, and extracted twice with 100ml of ethyl acetate. The organic phases were combined, washed twice with water, dried over anhydrous sodium sulfate, and separated by column chromatography to obtain 273 mg of the product, with a yield of 61.5%.

[0025] Chemical formula: C 26 h 21 NO 6 . Electrospray ionization mass spectrometry: [M+H] + =443.17.

Embodiment 2

[0026] Example 2. Fluorescein-proline synthesis

[0027] In Example 1, 444 mg of the product was dissolved in 10 ml of THF, 4 eq LiOH and 10 ml of water were added, and the reaction was stirred for 3 h. After the reaction was completed, the THF was spun off, 50ml of water was added, and the pH was adjusted to 3 with 1M hydrochloric acid. Solids were precipitated and filtered. Rinse twice with petroleum ether, filter and dry to obtain 335 mg of the product with a yield of 78%.

[0028] Chemical formula: C 25 h 19 NO 6 . Electrospray ionization mass spectrometry: [M+H] + =430.16. 1H NMR (400 MHz, CDCl3): δ 7.78 – 7.59 (m, 3H), 7.44 – 7.38 (m, 1H), 7.37 – 7.32 (m, 1H), 7.24 (dd, J= 10.0, 7.9 Hz , 2H), 6.88 – 6.77 (m, 2H), 6.72 – 6.66 (m, 1H), 4.39 (dd, J =8.6, 4.7 Hz, 1H), 3.31 (ddd, J = 19.8, 14.1, 5.4 Hz, 1H ), 3.26 – 3.14 (m,1H), 2.21 – 2.07 (m, 1H), 1.93 (ddd, J = 40.5, 21.0, 12.0 Hz, 1H), 1.75 (d, J= 4.8 Hz, 2H).

Embodiment 3

[0029] Example 3. Fluorescein-proline NHS ester

[0030] 525 mg of the product in Example 2 was dissolved in 40 ml of THF, an equivalent amount of DCC and NHS were added, and the reaction was stirred for 3 h. After the reaction, the insoluble matter was removed by filtration, and then the filtrate was spin-dried under low pressure, and the obtained solid was recrystallized with ethanol to obtain 360 mg of pure product with a yield of 68.4%. Chemical formula: C 29 h 22 N 2 o 8 . Electrospray ionization mass spectrometry: [M+H] + =526.17.

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Abstract

The invention relates to xanthene structure derivatives of general formula 1 and salts thereof. In the general formula 1, R1 represents hydroxyl, dimethylamino or diethylamino, and R2 represents hydrogen, an NHS ester, or another carboxylic acid ester. The xanthene derivative is characterized in that carboxyl on a xanthene structure compound is connected with proline and derivatives thereof. The invention also relates to a preparation method and an application method of the compound.

Description

technical field [0001] The invention relates to a novel structurally modified xanthene fluorescent compound, a synthesis method thereof, and a method for combining other functional groups. Background technique [0002] Xanthene fluorescent compounds such as fluorescein and rhodamine b have large molar absorptance coefficients and high fluorescence quantum yields. They are excellent optical probe precursors and are widely used in fluorescence imaging of cells and organisms. A single fluorescein molecule is often used as a probe fluorophore linked to molecules with other functions, and is widely used in production and research. Proline is a cyclic imino acid that widely exists in animals and plants in nature. [0003] The synthesis of xanthene-based fluorescent compounds requires the use of phthalic anhydride as a raw material, and the molecules will have exposed carboxyl groups after the synthesis. In the process of actual use, it is usually necessary to connect other funct...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/10C09K11/06
CPCC07D405/10C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088
Inventor 罗宇峰
Owner 罗宇峰
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