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Solid phase synthesis process of thiazde orange cyanine dye

A technology for solid-phase synthesis and orange-like cyanine, which is applied in the field of solid-phase synthesis of cyanine dyes, can solve the problems that the solid-phase carrier cannot be cut automatically, and achieve the effects of easy purification, simple separation process, and low production cost

Inactive Publication Date: 2006-10-18
TIANJIN URBAN CONSTR COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2001, Jennie Isacsson of Sweden synthesized four kinds of asymmetric water-soluble thiazole orange cyanine dyes by solid-phase synthesis method. This method uses 2-mercaptobenzothiazole as the starting material and bonds it to the -NH-containing 2 Polystyrene polymer carrier, and then cut with HBTU and DIEA to synthesize band-COOH thiazole orange cyanine dye; but when this method synthesizes thiazole orange, the solid phase carrier cannot realize automatic cutting

Method used

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  • Solid phase synthesis process of thiazde orange cyanine dye
  • Solid phase synthesis process of thiazde orange cyanine dye
  • Solid phase synthesis process of thiazde orange cyanine dye

Examples

Experimental program
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Embodiment 1

[0029] The solid-phase synthesis of embodiment 1 thiazole orange (TO)

[0030] Step 1: Synthesis of polystyrene-supported 2-benzylbenzothiazole

[0031] Add 2.84g of 2-mercaptobenzothiazole into 30mL of acetone, stir and dissolve, then add 1.38g of potassium carbonate and 1.0g of polystyrene immobilized benzyl chloride, and react at 50°C for 6 hours. After the reaction is complete, unreacted potassium carbonate is removed by filtration, washed with water, dichloromethane and acetone for 3-5 times, and then dried at room temperature to obtain polystyrene-supported 2-benzylbenzothiazole.

[0032] Step 2: Synthesis of polystyrene-supported-3-methyl-2-benzylbenzothiazole p-toluenesulfonate

[0033] The above-mentioned polystyrene-immobilized 2-benzylbenzothiazole and 5.6 g of methyl p-toluenesulfonate were refluxed in toluene at 110 ° C for 72 hours, and then washed with toluene, dichloromethane and acetone for 3 After -5 times, place at room temperature to dry to obtain polysty...

Embodiment 2

[0038] The solid-phase synthesis of embodiment 2 TO-1 (chloro-substituted thiazole orange)

[0039] Step 1: Synthesis of polystyrene-immobilized-5-chloro-2-benzylbenzothiazole

[0040] Add 3.42g of 5-chloro-2-mercaptobenzothiazole into 30mL of acetone, stir to dissolve, add 1.38g of potassium carbonate and 1.0g of polystyrene-supported benzyl chloride, and react at 50°C for 6 hours. After the reaction is complete, unreacted potassium carbonate is removed by filtration, washed with water, dichloromethane and acetone for 3-5 times in sequence, and then dried at room temperature to obtain polystyrene-supported 5-chloro-2-benzylbenzothiazole.

[0041] Step 2: Synthesis of polystyrene-immobilized-5-chloro-3-methyl-2-benzylbenzothiazole p-toluenesulfonate

[0042] The compound obtained in Step 1 and 5.6 g of methyl p-toluenesulfonate were refluxed in toluene at 110°C for 72 hours, then washed with toluene, dichloromethane and acetone for 3-5 times, and then dried at room temperatur...

Embodiment 3

[0047] Example 3 The solid-phase synthesis of TO-2 (nitro-substituted thiazole orange)

[0048] Step 1: Synthesis of polystyrene-supported 5-nitro-2-benzylbenzothiazole

[0049] Add 3.61g of 5-nitro-2-mercaptobenzothiazole into 30mL of acetone, stir to dissolve, add 1.38g of potassium carbonate and 1.0g of polystyrene immobilized benzyl chloride, and reflux at 50°C for 6 hours. After the reaction is complete, unreacted potassium carbonate is removed by filtration, washed with water, dichloromethane and acetone for 3-5 times, and then dried at room temperature to obtain polystyrene-immobilized 5-nitro-2-benzylbenzothiazole .

[0050] Step 2: Synthesis of polystyrene-supported 5-nitro-3-methyl-2-benzylbenzothiazole p-toluenesulfonate

[0051]The above-mentioned polystyrene-immobilized 5-nitro-2-benzylbenzothiazole and 5.6 g of methyl p-toluenesulfonate were refluxed in toluene at 110 ° C for 72 hours, and then successively with toluene, dichloro After washing with methane and...

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Abstract

The present invention discloses the solid synthesis process of thiazole orange cyanine dye. The present invention is superior to liquid phase synthesis, and has simple separation and easy purification. Compared with available solid synthesis process, the present invention has the advantages of automatic cutting, simplified synthesis process and lowered production cost. The present invention has solid carrier without volatization, no toxicity, no bad smell and environment friendship.

Description

technical field [0001] The invention relates to a solid-phase synthesis technology of cyanine dyes, in particular to solid-phase synthesis and automatic cutting technology for preparing thiazole orange cyanine dyes and derivatives thereof. Background technique [0002] With the continuous development of biotechnology, people have made great progress in biological markers, such as nucleic acid markers. However, traditional biomarker dyes, such as acridine orange, ethidium bromide, and H33258, etc., all of them have strong fluorescence background interference, but there is no such interference when using thiazole orange (Thiazole orange, TO) cyanine dyes to label biomacromolecules. . Thiazole orange monomethylcyanine dyes have almost no fluorescence in the free state, but the fluorescence is significantly enhanced when combined with nucleic acid, and there is no fluorescence interference of the dye itself during fluorescence detection, which improves the sensitivity of detect...

Claims

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Application Information

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IPC IPC(8): C09B23/00C12Q1/68
Inventor 费学宁杨少斌张宝莲石博杰
Owner TIANJIN URBAN CONSTR COLLEGE
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