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Halogen-containing asymmetry phthalocyanines compound, preparation method and application thereof

A cyanine compound, halogen-containing technology, applied in asymmetric cyanine compound, fluorescent dye application, new compound field, can solve the problems of unsatisfactory detection sensitivity, low fluorescence detection efficiency, poor cell permeability, etc. Avoid fluorescence background interference, simple structure, good photostability

Active Publication Date: 2012-05-30
SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the spectra of these commercial dyes are in the ultraviolet-visible region (490-530nm), and biological samples have strong absorption and a certain intensity of fluorescence emission in this region, resulting in a strong fluorescence background, so that the detection efficiency of fluorescence Greatly reduced
Although the absorption and emission wavelengths of dyes can be red-shifted to the near infrared region (650-1000nm) by increasing the number of conjugated chains, such as TOTAB, TOTIN, TO-PRO-3, PO-PRO-2 and BO-PRO-2 [K.M.Sovenyhazy, J.A.Bordelon, J.T.Petty.Nucleic Acids Res, 2003, 31, 2561], but these dyes generally have large molecules, poor cell permeability, complex synthesis, and many steps
Or, even if some existing dyes have absorption and emission wavelengths in the near-infrared region, their ability to bind nucleic acids is insufficient, and the detection sensitivity is not ideal

Method used

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  • Halogen-containing asymmetry phthalocyanines compound, preparation method and application thereof
  • Halogen-containing asymmetry phthalocyanines compound, preparation method and application thereof
  • Halogen-containing asymmetry phthalocyanines compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Synthesis of new compound intermediate 1-ethyl-4-methylquinoline quaternary ammonium salt:

[0066] Add 20mmol of 4-methylquinoline and 40mmol of ethyl iodide into a 100ml round bottom flask containing 20ml of toluene under argon protection. The reaction was heated and refluxed for 24 hours and then stopped. The heating was based on the fact that the reaction system began to reflux, and the temperature was about 110 degrees. After the mixture was cooled, the precipitate was filtered and the filter cake was washed with ether. After drying, a light yellow solid powder was obtained with a crude yield of 85%.

Embodiment 2

[0068] Preparation of Compound A:

[0069]

[0070] 10mmol of 1-ethyl-4-methylquinoline quaternary ammonium salt and 30mmol of N, N'-diphenylformamidine in 50ml of acetic anhydride were heated and stirred on a C oil bath at 100°C for 1.5 hours. The yellow-brown oil obtained by the reaction was poured into diethyl ether to precipitate a yellow solid powder, which was filtered and dried. The crude product was separated through a silica gel column, and the yellow component was collected with the eluent dichloromethane:methanol=100:3, with a yield of 41%. 4 mmol of 1-fluoroethyl-2-methylbenzothiazole quaternary ammonium salt and 1 ml of triethylamine were added thereto, and stirred under reflux in 25 ml of ethylene glycol monomethyl ether for 1.5 hours. Wherein, 1-fluoroethyl-2-methylbenzothiazole quaternary ammonium salt can be prepared by a general synthesis method similar to the quaternary ammonium salt in Example 1. Then add 4mmol NaClO to the reaction solution 4 Dissolv...

Embodiment 3

[0072] Preparation of Compound B:

[0073]

[0074] 10mmol of 1-ethyl-4-methylquinoline quaternary ammonium salt and 30mmol of N,N'-diphenylformamidine in 50ml of acetic anhydride were heated and stirred on an oil bath at 100°C for 1.5 hours. The yellow-brown oil obtained by the reaction was poured into diethyl ether to precipitate a yellow solid powder, which was filtered and dried. The crude product was separated through a silica gel column, and the yellow component was collected with the eluent dichloromethane:methanol=100:3, with a yield of 41%. 4 mmol of 1-chloroethyl-2-methylbenzothiazole quaternary ammonium salt and 1 ml of triethylamine were added thereto, and stirred in 25 ml of ethylene glycol monomethyl ether at room temperature for 12 hours. Wherein, 1-chloroethyl-2-methylbenzothiazole quaternary ammonium salt can be prepared by the general synthesis method of quaternary ammonium salt similar to Example 1. The reaction solution was poured into diethyl ether, a...

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Abstract

The invention provides a halogen-containing asymmetry phthalocyanines compound and a preparation method thereof. The compound has long emission wavelength, high molar extinction coefficient and sensitivity and good light stability, can be used for fluorescent dye, is particularly suitable for minitype cheap red semiconductor laser as a light source, and can be used in the fields such as nucleic acid molecular recognition, clinical medical diagnosis, immunoassay detection, and the like.

Description

technical field [0001] The invention relates to a new class of compounds in the field of fine chemicals, in particular to a class of halogen-containing asymmetric cyanine compounds, a preparation method thereof and an application as a fluorescent dye. Background technique [0002] As functional pigments, fluorescent dyes have been widely used in various fields of science and technology, especially as molecular probes in life sciences, clinical medical diagnosis, immunoassay and detection, etc., which have attracted worldwide attention. The earliest fluorescent dyes used in biological analysis are new methylene blue (NMB), acridine orange (AO), ethidium bromide (EB), propidium iodide (PI), basic yellow 7 (CPO) and so on. However, these dyes have their own application limitations, mainly in the fact that the fluorescence of the dye itself will cause a high fluorescence background and interfere with the detection; acridine and phenanthridine dyes such as ethidium bromide have g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D413/06C07D421/06C07D401/06C09B23/00C09K11/06
CPCC09B23/06C09B23/105C09B23/141C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104
Inventor 彭孝军吴彤樊江莉孙世国徐兵邵建辉
Owner SHENZHEN MINDRAY BIO MEDICAL ELECTRONICS CO LTD
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