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Asymmetric cyanine fluorochrome composition and use in biological sample dyeing

A compound and alkyl technology, applied in the field of fluorescent dyes, can solve the problems of limited use range, long synthesis route, complex molecular structure, etc., to avoid fluorescence background interference and improve accuracy.

Inactive Publication Date: 2009-07-08
SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Currently used cyanine fluorescent dyes, such as TOTAB, TOTIN, TO-PRO-3, PO-PRO-2 and BO-PRO-2 etc. ], their absorption and emission are all in the near-infrared region (670-1000nm), but the molecular structure of this class of dyes is more complex, the synthesis route is longer, and the yield is lower, so the price is high, which limits its scope of use

Method used

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  • Asymmetric cyanine fluorochrome composition and use in biological sample dyeing
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  • Asymmetric cyanine fluorochrome composition and use in biological sample dyeing

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preparation example Construction

[0064] The preparation method of the compound of the present invention

[0065] The compound of the present invention can be synthesized by general methods well known in the art, see for example the co-pending Chinese patent application CN200710137258.6 belonging to the present applicant. Said patent application is incorporated herein by reference. Specifically, the asymmetric cyanine fluorescent dye of the present invention is generally synthesized by the following process: firstly, by unsubstituted or substituted 2-methylbenzothiazole, 2-methylbenzoxazole or 2,3,3- Starting from raw materials such as trimethyl-3H-indoline, it can be compared with formula R 3 X (X is F, Cl, Br or I) halide reaction, the molar ratio of the two is 1:1-2, refluxed in toluene for 12-36 hours, the quaternary ammonium salt intermediate II can be obtained:

[0066]

[0067] where X, R 1 , R 3 and Y - as defined in the compound of formula I;

[0068] Then, the prepared quaternary ammonium sa...

Embodiment 1

[0090] Synthesis of Dye-1

[0091]

[0092] In a mixed solution of 40mL methanol and 20mL ethanol, put 10mmol 1-hexanoic acid ethyl-2-methylbenzothiazole bromide quaternary ammonium salt and 30mmol N, N'-diphenylformamidine on an oil bath at 65°C Heat and stir for 6 hours. After the reaction, the solvent was distilled off under reduced pressure, and then a certain amount of diethyl ether was added and stirred to precipitate an orange solid powder, which was filtered and dried. The crude product was recrystallized from ethyl acetate-hexane to obtain an orange-red solid product with a yield of 42%. Take 4.0 mmol of the reaction product, add 4.2 mmol of 1-benzyl-4-methylquinoline quaternary ammonium salt and 10 ml of pyridine, and heat and stir on an oil bath at 90° C. for 1.5 hours. After cooling to room temperature, the reaction solution was poured into ether, and a dark purple solid was precipitated, which was filtered and dried. The dye was separated through a silica ...

Embodiment 2

[0095] Synthesis of Dye-2

[0096]

[0097] In a mixed solution of 40mL methanol and 20mL ethanol, 10mmol 1-(2-hydroxyethyl)-2-methylbenzothiazole bromide quaternary ammonium salt and 30mmol N, N'-diphenylformamidine were dissolved in oil at 65°C Heat and stir on the bath for 6 hours. After the reaction, the solvent was distilled off under reduced pressure, and then a certain amount of diethyl ether was added and stirred to precipitate an orange solid powder, which was filtered and dried. The crude product was recrystallized from ethyl acetate-hexane to obtain an orange-red solid product with a yield of 41%. Take 4.0 mmol of the reaction product, add 4.5 mmol of 1-(ethylbutyrate)-4-methylquinoline quaternary ammonium salt and 10 ml of pyridine, and heat and stir on an oil bath at 90° C. for 1.5 hours. After cooling to room temperature, the reaction solution was poured into ether, and a purple-red solid was precipitated, which was filtered and dried. The dye was separat...

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Abstract

The invention provides asymmetrical cyanine fluorescent dye expressed by formula I, wherein X, n, R1, R2, R3, R4 and Y are defined as a specification. The dye can be used as excellent nucleic acid staining agent, and the spectrum of the dye is in a near infrared region of 600 to 900 nanometers and has no interference of background fluorescence. Simultaneously, the dye can utilize a small red semiconductor laser as a light source (633 nanometers). The invention also provides a composition comprising the fluorescent dye and a method for performing biological stain by using the fluorescent dye or the composition thereof.

Description

technical field [0001] The present invention relates to fluorescent dyes, in particular, the present invention relates to asymmetric cyanine fluorescent dyes suitable for dyeing biological samples, a composition containing the fluorescent dyes and its use in dyeing biological samples. Background technique [0002] Due to the introduction and rapid development of some new science and technology such as laser, microprocessor and electronics, fluorescence analysis technology has greatly promoted the wide application of fluorescence analysis. Especially in recent years, the emergence of biochips using fluorescent dyes as markers makes this technology have broad application prospects in cellular immunology, microbiology, molecular biology, molecular genetics, pathology, clinical laboratory science, botany, etc. . The development of fluorescent dyes is a decisive factor in the development of fluorescence analysis technology. [0003] The dyes used in the early stage include new ...

Claims

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Application Information

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IPC IPC(8): C09B23/16G01N21/64G01N33/52
CPCG01N33/52G01N1/30C09B23/06C09B23/083Y10S436/80Y10T436/14
Inventor 邵建辉
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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