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Asymmetric cyanine compound, preparation method and application thereof

A compound and composition technology, applied in the field of asymmetric cyanine compounds, can solve the problems of reducing the accuracy of detection results, incompatibility, and increasing the cost of instruments, and achieve the effects of avoiding fluorescence background interference, improving accuracy, and good dyeing effect

Active Publication Date: 2013-10-16
SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

During the stable operation of the instrument, the ambient temperature will reach 40°C, and the wavelength of the laser will increase to about 640nm at this time, which cannot match the maximum absorption peak of the fluorescent dye well, reducing the accuracy of the detection results.
On this basis, if in order to eliminate the influence of temperature on the test results, it is necessary to add a constant temperature device, which will greatly increase the cost of the instrument

Method used

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  • Asymmetric cyanine compound, preparation method and application thereof
  • Asymmetric cyanine compound, preparation method and application thereof
  • Asymmetric cyanine compound, preparation method and application thereof

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preparation example Construction

[0071] The preparation method of the compound of the present invention

[0072] 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 compound of the present invention is generally synthesized by the following scheme: first, unsubstituted or substituted 2-methylbenzothiazole, 2-methylbenzoxazole or 2,3,3-trimethyl Base-3H-indoline and other starting materials, make 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:

[0073]

[0074] where X, R 1 , R 3 and Y - as defined in the compound of formula I;

[0075] Then, the prepared quaternary ammonium salt intermediate II is c...

Embodiment 1

[0097] Synthesis of 4-methyl-7-chloroquinoline

[0098] Add 32.8g (0.2mol) of 3-chloroaniline hydrochloride, 81g of ferric chloride hexahydrate (0.3mol) , 3.0 g of re-dried anhydrous zinc chloride and 150 mL of 95% ethanol were stirred and heated to 60°C. Slowly add 12.6 g (0.18 mol) of methyl vinyl ketone from a constant pressure dropping funnel, keep the temperature at 60-70°C, raise the temperature to reflux after the addition, and keep the reflux state for 2 hours. After cooling, 25% aqueous sodium hydroxide solution was added to it to make it alkaline, the solvent was distilled off under reduced pressure to dryness, and the solid was taken out and extracted with anhydrous ether repeatedly. The combined extracts were dried with anhydrous potassium carbonate, filtered, and purified by silica gel column chromatography using hexane / ethyl acetate (3:1) as the mobile phase to obtain 11.38 g of the product.

Embodiment 2

[0100] Synthesis of 4-methyl-7-bromoquinoline

[0101] The title compound was obtained using a similar synthesis method to 4-methyl-7-chloroquinoline starting from 3-bromoaniline.

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Abstract

Asymmetric cyanine compounds represented by general formula I are provided, wherein X, n, R1, R2, R3, R4 and Y− are as defined in the specification. They have a maximum absorption peak at about 640 nm which may not change with ambient temperature. When the compounds bind a nucleic acid to form a dye / nucleic acid complex, the fluorescence intensity of the complexes will increased rapidly, so that they can be used as a staining agent for nucleic acids in flow cytometers. Their spectra are in the near-infrared region, which can effectively reduce the interference from background fluorescence and improve the accuracy of detection. Moreover, the compounds provided can also be used as a staining agent for blood reticulocytes.

Description

technical field [0001] The present invention relates to an asymmetric cyanine compound and its use for staining biological samples. Background technique [0002] Reticulocytes are transitional cells between late denucleated erythrocytes in bone marrow and fully mature erythrocytes. After reticulocytes are released from bone marrow to peripheral blood, as they mature, the RNA content in the cells gradually decreases. until it disappears completely. Therefore, the amount of intracellular RNA indicates the degree of maturation of reticulocytes. Reticulocytes are the basic test for assessing erythropoietic ability in hematological diagnosis, and are the basis for anemia diagnosis, typing, and curative effect detection. They can confirm the curative effect of bone marrow chemotherapy and transplantation, and detect the curative effect of EPO (erythropoietin). [0003] Early detection of reticulocytes was mainly by manual microscopic examination, but there were cumbersome steps ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06G01N21/25
CPCY10S436/80C07D417/06Y10T436/14
Inventor 邵建辉
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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