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Near-infrared fluorescent probe with maximum Stoke displacement

A fluorescent probe and near-infrared technology, applied in the field of near-infrared fluorescent probes, can solve problems such as poor stability, large molecular weight of phycobiliprotein, and affecting use

Inactive Publication Date: 2011-07-20
江苏迈健生物科技发展股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the molecular weight of phycobiliprotein is huge, ranging from 17,000 to 18,000, and its stability is relatively poor. When the temperature exceeds 40°C, it will be denatured, which affects the use to a certain extent.

Method used

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  • Near-infrared fluorescent probe with maximum Stoke displacement
  • Near-infrared fluorescent probe with maximum Stoke displacement
  • Near-infrared fluorescent probe with maximum Stoke displacement

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] Example 1 Extraction of Phycocyanin

[0070] First, weigh 1 g of Porphyra zebra, add an appropriate amount of phosphate buffer, and mash the tissue. The mashed liquid is refrigerated and centrifuged at 10,000 g for 20 minutes, and the supernatant is taken. The supernatant was precipitated with 25% and 50% saturated ammonium sulfate segmented precipitation method, and the final precipitate was still dissolved in phosphate buffer solution, refrigerated and centrifuged at 15000g for 30min, the precipitate was taken out, and impurity ions were removed after dialyzing with distilled water for a period of time to obtain a crude extract. of phycocyanin. The obtained phycocyanin was cracked with 10 mol / L concentrated hydrochloric acid at 80° C. for 30 minutes, and then extracted with chloroform. The extracted solutions were combined and rotatively evaporated to remove the chloroform to obtain phycocyanin.

Embodiment 2

[0071] Example 2 Activation of Phycocyanin

[0072] 2mmol phycocyanin, 20mmol N-hydroxysuccinimide and 40mmol dicyclohexylcarbodiimide (DCC) were added to 5ml anhydrous DMF, and stirred at room temperature for 36 hours in the dark. After the reaction solution was filtered, the filtrate was added to diethyl ether to precipitate the product. Then the product was centrifuged in a centrifuge to remove the supernatant, and the solid in the lower layer was washed three times with ether, and then centrifuged in a centrifuge to remove the supernatant to obtain a crude solid. The crude product was purified by normal-phase silica gel column chromatography to obtain activated phycocyanin, which was stored in a refrigerator protected from light.

Embodiment 3

[0073] The synthesis of embodiment 3 NIR-1

[0074] Synthesis of Intermediate II

[0075] Add 10mmol of 3-(4-benzoyl)-2,3-dimethyl-3H-indole-5-sodium sulfonate (intermediate I) and 13mmol of propane sultone into a dry and clean three-necked flask , using o-dichlorobenzene as a solvent, magnetically heated and stirred to reflux under light-shielding conditions, stopped heating after 18 hours of reflux reaction, and washed the product with ether three times after the solvent was removed to obtain a reddish-brown solid product 3-(4-benzoic acid base)-2,3-dimethyl-1-(3-sulfonic acid propyl)-3H-indole-5-sodium sulfonate (intermediate II).

[0076] Synthesis of Intermediate IV

[0077] Add 10mmol of 2,3,3-trimethyl-5-nitro-3H-indole (intermediate III) and 13mmol of propane sultone into a dry and clean three-necked flask, using o-dichlorobenzene as a solvent, Under the condition of avoiding light, magnetically heat and stir to reflux, stop heating after 15 hours of reflux reaction...

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Abstract

The invention relates to a near-infrared fluorescent probe with maximum Stoke displacement, belonging to the technical field of specific molecular recognition diagnostic reagents. The invention provides a fluorescent dye with maximum Stoke displacement, which is prepared by coupling phycocyanobilin in phycobiliprotein with a near-infrared fluorescent dye. The fluorescent dye has maximum Stoke displacement reaching above 300nm, has the characteristic of smaller molecular weight, can be used for marking matters with small molecular weight, such as folic acid and the like, and is used for specific fluorescence detection of a tumor marker, an antibody and the like.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe with a large Stoke shift, which can be used for specific fluorescent detection of tumor markers, antibodies, etc., and belongs to the technical field of specific molecular recognition diagnostic reagents. Background technique [0002] Malignant tumors have become the number one cause of human death, and more than 10 million people die from various cancers every year. With the rapid development of modern industry and changes in lifestyles, the incidence and mortality of tumors are on the rise. In the current clinical research on tumors, no effective cure method has been found for the treatment of middle and advanced tumors, but early tumors are not associated with metastasis and are easy to resect, which can win more chances of survival for patients. Therefore, people focus on the early stage of tumors. Diagnostic and preventive research. With the continuous development of molecular biomarker t...

Claims

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Application Information

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IPC IPC(8): C07D403/14C07D403/06G01N33/52G01N33/577
Inventor 邵建辉
Owner 江苏迈健生物科技发展股份有限公司
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