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Method for preparing and purifying water-soluble cyanine dye (Cy5.5)

A purification method and technology of cyanine dyes, which are applied in the field of preparation and purification of water-soluble cyanine dyes Cy5.5, can solve problems such as separation difficulties, and achieve the effect of simple operation and low cost

Active Publication Date: 2011-04-13
TIANJIN SUNGENE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Indole water-soluble cyanine dyes Cy3.5, Cy5.5, Cy7.5, etc. are commonly used fluorescent dyes for biochips and molecular beacons, but due to the above-mentioned preparation, separation difficulties and other reasons, and there is no corresponding synthesis literature report so far

Method used

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  • Method for preparing and purifying water-soluble cyanine dye (Cy5.5)
  • Method for preparing and purifying water-soluble cyanine dye (Cy5.5)
  • Method for preparing and purifying water-soluble cyanine dye (Cy5.5)

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Embodiment 1

[0027] 1) Preparation of 1,1,2-trimethylbenzindole 1,3-disulfonate:

[0028] Add 6g of 6-naphthylhydrazine-1,3-disulfonic acid, 6.4mL of methyl isopropyl ketone, 5.88g of potassium acetate, and 30mL of acetic acid into a 100mL single-necked bottle, heat and reflux for 24 hours, and spin evaporate after cooling to obtain an earth-colored solid. Methanol was added for extraction, and the extract was concentrated by rotary evaporation to obtain a light yellow solid, which was 1,1,2-trimethylbenzindole 1,3-disulfonate.

[0029] 2) Preparation of N-ethyl-2,3,3-trimethylbenzindole 5,7-disulfonate:

[0030] Add 1g of 1,1,2-trimethylbenzindole 1,3-disulfonate, 3mL of iodoethane, 10mL of o-dichlorobenzene into a 25mL single-necked bottle, heat to 100°C for 24h and react after cooling , poured out o-dichlorobenzene, dissolved in methanol, and separated by preparative thin-layer chromatography to obtain a purple-red product.

[0031] 3) Preparation of N-(ε-carboxypentyl)-2,3,3-trimethy...

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Abstract

The invention discloses a method for preparing and purifying a water-soluble cyanine dye (Cy5.5), which comprises the following steps of: reacting 1,3-disulfonic acid-6-naphthylhydrazine serving as an initiative raw material with methyl isopropyl ketone to generate 1,1,2-trimethyl-benzindole-1,3-disulphonate; reacting the 1,1,2-trimethyl-benzo-indole-1,3-disulfonate with ethyl iodide and 6-bromocaproic acid respectively to generate N-ethyl-2,3,3-trimethyl-benzindole-5,7-disulphonate (product 1) and N-(epsilon-carboxy-pentyl)-2,3,3-trimethyl-benzindole-5,7-disulphonate (product 2); reacting the product 1 with beta-anilino-acraldehyde-anil-hydrochloride and then directly reacting the product 1 with the product 2 to prepare the Cy5.5; and preparing a thin layer chromatogram, and repeatedly purifying and separating the Cy5.5 to obtain a pure product of the Cy5.5. The method is easy and convenient to operate and has a high yield, the product does not need expensive high performance liquid chromatography (HPLC) (C-18 reverse column) for separation, and the method has great significance for meeting requirements of domestic autonomous production.

Description

technical field [0001] The invention relates to the technical field of biosynthesis, in particular to a method for preparing and purifying a water-soluble cyanine dye Cy5.5. Background technique [0002] Cyanine dyes refer to the amidine ion intercalates between the N-N atoms at both ends of the chromophore conjugated system, which have a good planar rigid structure or a large planar conjugated system, high fluorescence quantum yield, and long fluorescence wavelength. It is well distinguished from the light blue fluorescence of DNA itself, and the fluorescence quantum yield is enhanced after interacting with DNA. Therefore, cyanine dyes have received more and more attention. [0003] Water-soluble cyanine dyes are excellent fluorescent labeling dyes, widely used in the labeling and detection of antibodies, nucleic acids and other biomolecules. By changing the length of the methine chain, its fluorescence emission wavelength can be changed. Amershan Pharmacia Biotech first...

Claims

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Application Information

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IPC IPC(8): C09B23/08C09B67/54
Inventor 郗日沫赵秀杰王文虎
Owner TIANJIN SUNGENE BIOTECH
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