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Asymmetric cyanine fluorescent dye, composition and application in biological sample dyeing

A technology for fluorescent dyeing and biological samples, applied in the field of asymmetric cyanine fluorescent dyes, can solve the problems of long synthesis route, limited scope of use, complex molecular structure, etc., and achieve the effect of improving accuracy and avoiding fluorescence background interference.

Pending Publication Date: 2016-03-30
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 [K.M.Sovenyhazy, J.A.Bordelon, J.T.Petty.NucleicAcidsRes, 2003,31,2561], Their absorption and emission are in the near-infrared region (670-1000nm), but the molecular structure of this type of dye is relatively complex, the synthesis route is long, and the yield is low, so the price is high, which limits its scope of use.

Method used

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  • Asymmetric cyanine fluorescent dye, composition and application in biological sample dyeing
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  • Asymmetric cyanine fluorescent dye, composition and application 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 dyes of the present invention are generally synthesized by the following process: first, unsubstituted or substituted 2-methylbenzothiazole, 2-methylbenzothiazole or 2,3,3-tri Starting from raw materials such as methyl-3H-indoline, making it with the 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 salt int...

Embodiment 1

[0090] Synthesis of Dye-1

[0091]

[0092] In a mixed solution of 40mL methanol and 20mL ethanol, heat and stir 10mmol 1-hexanoic acid ethyl-2-methylbenzothiazole bromide quaternary ammonium salt and 30mmol N,N'-diphenylformamidine on an oil bath at 65°C 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 gel colum...

Embodiment 2

[0095] Synthesis of Dye-2

[0096]

[0097] In a mixed solution of 40mL methanol and 20mL ethanol, put 10mmol 1-(2-hydroxyethyl)-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 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 separated through a sil...

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Abstract

The invention provides an asymmetric cyanine fluorescent dye expressed in the formula I (please see the formula in the specification). X, n, R1, R2, R3, R4 and Y are defined in the specification. The dye can be used as an excellent nucleic acid dyeing agent, the spectrum of the dye is in a near infrared region of 600 nm to 900 nm, and interference of background fluorescence does not exist. Meanwhile, according to the dye, a small red semiconductor laser can be used as a light source (633 nm). The invention further provides a composition containing the fluorescent dye and a method for using the fluorescent dye or the composition of the fluorescent dye in biological dyeing.

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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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/06C09B23/08G01N1/30G01N21/64G01N33/52
CPCC09B23/06C09B23/083G01N1/30G01N33/52Y10S436/80Y10T436/14
Inventor 邵建辉
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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