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Unsymmetrical cyanines fluorochrome

A technology of fluorescent dyes and dyes, which is applied in the direction of organic dyes, methine/polymethine dyes, analytical materials, etc., and can solve the problems of expensive and high equipment costs

Active Publication Date: 2009-01-14
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

This fluorescent dye requires an expensive helium-neon laser, and the equipment cost for practical applications is high

Method used

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  • Unsymmetrical cyanines fluorochrome
  • Unsymmetrical cyanines fluorochrome
  • Unsymmetrical cyanines fluorochrome

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] Synthesis of intermediate 1-benzyl-2-methylbenzothiazole quaternary ammonium salt

[0093] Add 20mmol of 2-methylbenzothiazole and 22mmol of benzyl bromide into a 50ml round bottom flask containing 20ml of toluene under argon protection. The reaction was stopped by heating to reflux for 24 hours. After the mixture was cooled, the precipitate was filtered and the filter cake was washed with ether. After drying, a pale pink solid powder was obtained with a crude yield of 58%.

Embodiment 2

[0095] Preparation of Compound A

[0096]

[0097] In 60ml of acetic acid, 10mmol of 1-benzyl-2-methylbenzothiazole quaternary ammonium salt and 30mmol of N,N'-diphenylformamidine were heated and stirred on an oil bath at 90°C for 1.5 hours. The red oil obtained by the reaction was suspended and washed 3 times with petroleum ether to remove acetic acid. Then add a certain amount of ether to precipitate an orange solid powder, filter and dry. The crude product was separated through a silica gel column, and the yellow component was collected with the eluent dichloromethane:methanol=100:3, and the yield was 42%. 4 mmol of 1-benzyl-4-methylquinoline quaternary ammonium salt and 10 ml of pyridine were added thereto, and heated and stirred on an oil bath at 90° C. for 1.5 hours. The reaction solution was poured into ether, and small dark purple particles were precipitated, which were filtered and dried. The dye was separated by silica gel column, and the eluent was dichlorom...

Embodiment 3

[0100] Preparation of Compound B

[0101]

[0102] In 60ml of acetic acid, heat and stir 10mmol 1-(4-fluoro)-benzyl-2-methylbenzothiazole quaternary ammonium salt and 30mmol N,N'-diphenylformamidine on an oil bath at 90°C for 1.5 hours . The red oil obtained by the reaction was suspended and washed 3 times with petroleum ether to remove acetic acid. Then add a certain amount of ether to precipitate an orange solid powder, filter and dry. The crude product was separated by a silica gel column, and the yellow component was collected with the eluent dichloromethane:methanol=100:3, and the yield was 47%. 5 mmol of 1-(4-fluoro)-benzyl-4-methylquinoline quaternary ammonium salt and 10 ml of pyridine were added thereto, and heated and stirred on an oil bath at 90° C. for 1.5 hours. The reaction solution was poured into ether, and small dark purple particles were precipitated, which were filtered and dried. The dye was separated by silica gel column, and the eluent was dichlo...

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PUM

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Abstract

The invention provides type I unsymmetrical cyanine fluorescent dye, wherein X, n, R1, R2, R3, R4, R5 and Y<-> are defined as in the instruction book. The invention also provides the conjugate and the preparation method of the fluorescent dye, the combination containing the fluorescent dye and the biological dyeing method by using the fluorescent dye or the combination.

Description

technical field [0001] The present invention relates to dyes suitable for nucleic acid staining, more specifically to asymmetric cyanine fluorescent dyes. Background technique [0002] The wide application of fluorescence detection technology in DNA hybridization test, gene recombination test, immune detection, blood cell analysis and early diagnosis of tumor cells has greatly promoted the development of fluorescent dyes. The earliest fluorescent dyes used in biological analysis were acridine and phenanthridine dyes, such as acridine orange and ethidium bromide, etc. They combined with small DNA molecules through intercalation or electrostatic attraction, and the fluorescence was greatly enhanced after combination. However, autofluorescence of unconjugated dye can cause high fluorescence background, which interferes with detection. At the same time, ethidium bromide, etc. have great toxicity and carcinogenicity, so they have been gradually replaced by other fluorescent dyes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/00G01N1/30
CPCY10S436/80C09B23/06C09B23/083Y10T436/145555Y10T436/141111
Inventor 彭孝军吴彤樊江莉孙世国王炳帅徐兵邵建辉
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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