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Yellow fluorochrome and synthetic method and use thereof

A technology of yellow fluorescence and synthesis method, applied in luminescent materials, benzoxanthene dyes, chemical instruments and methods, etc., can solve the problems of difficult labeling reagents, difficult selection of excitation wavelength, low fluorescence quantum yield, etc. The effect of large Stokes shift, good fluorescence labeling ability, and high fluorescence quantum yield

Inactive Publication Date: 2009-06-10
NORTHWEST UNIV
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0004] How to obtain different kinds of labeling reagents is very difficult in the field of protein labeling
First, it is difficult to find fluorescent reagents that do not have overlapping emission wavelengths, because the half emission wavelength of typical organic fluorescent dyes is generally 40-80nm, while the visible wavelength range is generally only 350-400nm
Secondly, even if there are fluorescent reagents with non-overlapping emission spectra, they cannot be applied to fluorescent labeling due to their very low fluorescence quantum yield. The absorption wavelength band of a fluorescent reagent will be very wide and cannot be separated

Method used

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  • Yellow fluorochrome and synthetic method and use thereof
  • Yellow fluorochrome and synthetic method and use thereof
  • Yellow fluorochrome and synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Embodiment 1: 4,7,2`, the synthesis of 7`-tetrachloro-6-(6-carboxycaproylamido)-fluorescein

[0066] (1) compound 4,7,2`, the synthesis of 7`-tetrachloro-5(6)-carboxyfluorescein, the synthetic steps are as follows:

[0067]

[0068] Add 1.39g (5.33mmol) 3,6-dichlorobenzene triacid anhydride, 1.70g (11.80mmol) 4-chlororesorcinol and 5.00ml concentrated sulfuric acid in a 50mL three-necked flask equipped with a reflux condenser and a drying tube , magnetically stirred, heated up to 190° C. for 24 h, cooled to room temperature, poured the reaction solution into ice-water mixture in batches, and stirred vigorously. A brown-yellow filter cake was obtained by suction filtration, and dried to obtain 2.50 g of a crude product with a yield of 91.20%.

[0069] MALDI-TOF MS, m / z: 515.55 (calcd. 514.09);

[0070] Infrared FT-IR (KBr), υ / cm -1 : 3421, 1759, 1608, 1434, 1212.

[0071] (2) Synthesis of compound 4,7,2`,7`-tetrachloro-5(6)-carboxyfluorescein pivalate

[0072] ...

Embodiment 2

[0104] Example 2: 2', 4, 4', 5', 7, 7'-hexachloro-6-(amidocaproylamido)fluorescein

[0105] (1) Synthesis of compound 2`, 4, 4`, 5`, 7,7`-hexachloro-5(6)-carboxyfluorescein

[0106]

[0107] Take 41.10g (0.23mol) of 2,4-dichlororesorcinol and 26.10g (0.01mol) of 3,6-dichloro-4-carboxyphthalic anhydride into a 500mL three-necked flask, add 200mL of concentrated sulfuric acid, The reaction was carried out at 170° C. for 36 hours under the protection of nitrogen. After the reaction was completed, the reaction mixture was poured into ice water, and a large amount of brick red precipitates were precipitated. After suction filtration, a pink solid was obtained with a yield of 75.00%.

[0108] MALDI-TOF MS, m / z: 581.90 (Calcd: 582.99);

[0109] Infrared FT-IR (KBr), υ / cm -1 : 3480, 1768, 1709, 1478, 1433.

[0110] (2) Synthetic compound of 2`, 4, 4`, 5`, 7,7`-hexachloro-5(6)-carboxyfluorescein pivalate

[0111]

[0112] Take 9.00g (15.00mmol) of 2`, 4,4`, 5`,7,7`-hexachlor...

Embodiment 3

[0140]Example 3: Synthesis of compound 4,7-dichloro-2`, 7`-difluoro-6-(6-carboxyhexanoyl)-fluorescein

[0141] (1) The synthesis of compound 4,7-dichloro-2`,7`-difluoro-5(6)-carboxyfluorescein is similar to Example 1 step (1), except that 2-fluororesorcinol Instead of 2-chlororesorcinol, the yield is 70.00%.

[0142] (2) The synthesis of compound 4,7-dichloro-2',7'-difluoro-5(6)-carboxyfluorescein pivalate is similar to step (2) of Example 1.

[0143] (3) Compound 4, the synthesis of 7-dichloro-2`, 7`-difluoro-tetrachloro-6-carboxyfluorescein pivalate diisopropylammonium salt is similar to Example 1 step (3), producing Rate 35.50%.

[0144] (4) The synthesis of compound 4,7-dichloro-2',7'-difluoro-6-carboxyfluorescein pivalate was similar to step (4) of Example 1, with a yield of 90.00%.

[0145] (5) Compound 4,7-dichloro-2`, 7`-difluoro-di-tert-valeryl-6-carboxyfluorescein-N-hydroxyl succinimidyl carbonate synthesis and embodiment 1 step (5 ) similar, yield 82.60%.

[01...

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Abstract

The invention discloses a yellow fluorescent dye, a method for synthesizing the same and application. The fluorescent dye has a structure shown as the general formula (I), wherein R1 and R2 are selected from chlorine, fluorine, bromine or hydrogen; and n is a positive integer between 3 and 7. The fluorescence emission spectrum of the yellow fluorescent dye is positioned in a yellow light region of visible spectrum; and the yellow fluorescent dye has high fluorescence quantum yield and good fluorescence labeling capacity, and can be used for protein labeling.

Description

technical field [0001] The invention belongs to the field of fluorescent dye synthesis, and in particular relates to a fluorescent dye with yellow light emission and a synthesis method and application thereof. Background technique [0002] With the rapid development of information technology, people have higher requirements for high-density and high-definition display technology. Fluorescence was discovered as early as the 16th century, but the principle and conditions of fluorescence were not clear until the middle of the 19th century. From 1867 when Goppetsroder used morin as a fluorescent reagent to detect aluminum by fluorescence method, until the beginning of the 20th century, people have known that more than 600 compounds including rhodamine, fluorescein, fused-ring aromatic hydrocarbons and eosin have fluorescence. Then Wawwillous measured the fluorescence yield (1924), and Gavila measured the fluorescence lifetime (1926). After the development of instruments combin...

Claims

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Application Information

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IPC IPC(8): C09B57/14C09K11/06G01N33/52
Inventor 田敏武祥龙第五振军史真
Owner NORTHWEST UNIV
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