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Cyanine compound, composition containing same and application in cell detection thereof

A technology of compounds and compositions, applied in the field of fluorescent dyes, can solve the problems of unsatisfactory accuracy of nucleated red blood cell counting, basophil differential counting, NRBC counting and other problems, and achieve good cell classification effect Effect

Active Publication Date: 2011-07-06
SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there are also defects: although a suitable hemolytic agent component only destroys the NRBC membrane, it does not damage the WBC membrane, so that the dye only enters the interior of the NRBC and binds to the NRBC nucleus
Due to the small differences in size and shape between nucleated red blood cells and lymphocytes, the accuracy of the count of nucleated red blood cells measured by this method is not ideal, and this method does not mention the differential count of basophils
[0013] As can be seen from the above description, most of the existing technologies for counting leukocytes cannot realize the counting of NRBC; among the existing technologies for counting NRBC, most of them cannot realize the counting of leukocytes

Method used

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  • Cyanine compound, composition containing same and application in cell detection thereof
  • Cyanine compound, composition containing same and application in cell detection thereof
  • Cyanine compound, composition containing same and application in cell detection thereof

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preparation example Construction

[0079] The preparation method of the compound of the present invention

[0080]The compounds of the present invention can be synthesized by general methods well known in the art. Specifically, some intermediates of the compounds of the present invention can be synthesized through the following schemes.

[0081] By unsubstituted or substituted compound of formula IV as raw material, respectively with formula R 1 X or R 3 Halide reaction of X (X is F, Cl, Br or I):

[0082]

[0083] Obtain the quaternary ammonium salt intermediate of formula V and formula VI:

[0084]

[0085] where R 1 , R 2 , R 3 , X and A1 rings are defined as described for compounds of formula I.

[0086] For example, the corresponding quaternary ammonium salt intermediate is obtained by the following reaction.

[0087]

[0088] Then, the prepared quaternary ammonium salt intermediate is condensed with a linking molecule such as squarylium to obtain a compound of formula I:

[0089]

...

Embodiment 1

[0157] Preparation of Compound 1

[0158]

[0159] Add 0.1mol 2,3,3-trimethylindole, 0.12mol allyl bromide and 25mL acetonitrile into a 100mL three-necked flask equipped with a reflux condenser and a magnetic heating stirrer as solvents. Protected from light, the reaction was refluxed for 24 hours under the protection of argon. After the reaction was completed, part of the solvent was distilled off under reduced pressure, and an appropriate amount of petroleum ether was added thereto, and the product was precipitated by ultrasonic vibration to obtain a brownish-red oil, which was directly used in the next reaction.

[0160] Take 0.01mol of the brown-red product, 0.005mol of squaraine, 8mL of benzene, 6mL of n-butanol, and 6mL of pyridine as solvents and put them into a 50mL three-neck flask together, stir and heat to reflux under the protection of argon, and stop the reaction after 6 hours. After cooling to room temperature, excess diethyl ether was added to precipitate th...

Embodiment 2

[0163] Preparation of compound 2

[0164]

[0165] Add 0.1mol 2,3,3-trimethylindole, 0.12mol butyl bromide and 20mL toluene to a 100mL three-necked flask equipped with a reflux condenser and a magnetic heating stirrer as a solvent, avoid light, and protect it under argon Reflux for 24 hours. After the reaction was completed, part of the solvent was distilled off under reduced pressure, and an appropriate amount of petroleum ether was added thereto, and the product was precipitated by ultrasonic vibration to obtain a brownish-red lump, which was directly used in the next reaction.

[0166] Take 0.01mol of the brown-red product, 0.005mol of squaraine, 8mL of toluene, 6mL of n-butanol, and 6mL of pyridine as solvents and put them together into a 50mL three-neck flask, stir and heat to reflux under the protection of argon, and stop the reaction after 7 hours. After cooling to room temperature, excess diethyl ether was added to precipitate the product, filtered, washed with an ...

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Abstract

On one hand, the invention provides a compound with a structure of general formula I or a conjugate thereof, wherein each group is as defined in the description. On the other hand, the invention provides a composition comprising (i) the compound of formula I or the conjugate thereof, and (ii) at least one surfactant selected from cationic surfactants and nonionic surfactants. The invention also provides a preparation method of the composition and a kit containing the composition. The invention still provides a method for the simultaneous identification of nucleated erythrocyte, basophilic granulocyte and lymphocyte and the classification by using the composition disclosed in the invention.

Description

technical field [0001] The present invention relates to fluorescent dyes. Specifically, the present invention relates to a cyanine compound suitable for staining of biological samples, a composition comprising the cyanine compound and a method for detecting nucleated red blood cells and counting white blood cells simultaneously by using the composition. Background technique [0002] Nucleated red blood cells (NRBCs) are immature red blood cells found in the bone marrow. Under normal circumstances, a small amount of immature red blood cells can be seen in the blood of infants and young children within 1 week, while adult immature red blood cells are all present in the bone marrow. If they are found in peripheral blood, it is a pathological phenomenon. Once NRBC appears in the peripheral blood of adults, it is mostly pathological. It is common in some diseases such as hemolytic anemia, acute massive blood loss, severe tissue hypoxia, acute and chronic leukemia, malignant tumo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C07D277/64C07D263/56C07D209/60C09B23/16C09K11/06G01N33/48G01N33/49G01N21/49G01N21/64C12Q1/02
CPCC09B57/007C09K2211/1011C07D277/24C09K2211/1007C09K2211/1029C07D209/12C09K11/06C09B23/0066G01N33/56972C09K2211/1037C07D209/60G01N33/80C07D263/54G01N15/1459G01N2015/1006G01N2015/1402G01N2015/1486G01N2015/016
Inventor 赵玉梅邵建辉赵阳雷霆徐兵
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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