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Green fluorescence cyanine dye and preparation method as well as application thereof

A technology of fluorescent dyes and green cyanines, which is applied in a class of green fluorescent cyanine dyes, preparation and application fields, can solve problems such as complex structures, large molecules, and impermeability of living cells, and achieve a suitable spectral range, Effect of High Fluorescence Quantum Yield

Inactive Publication Date: 2012-10-03
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these commercial dyes have large molecules and complex structures, and are impermeable to living cells, so they can only be applied to the identification and detection of nucleic acids in vitro

Method used

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  • Green fluorescence cyanine dye and preparation method as well as application thereof
  • Green fluorescence cyanine dye and preparation method as well as application thereof
  • Green fluorescence cyanine dye and preparation method as well as application thereof

Examples

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preparation example Construction

[0057] In another aspect, the present invention also provides a preparation method of the above-mentioned compound, the method comprising:

[0058] Prepare the first quaternary ammonium salt intermediate and the second quaternary ammonium salt intermediate respectively, wherein the first quaternary ammonium salt comprises quinoline substituted compounds and 4-chloroquinoline substitutes as raw materials to prepare respective quaternary ammonium salts, and then the first quaternary ammonium salt The ammonium salt reacts with the second quaternary ammonium salt intermediate in the presence of an organic base to obtain the final compound. The specific synthesis scheme is described below.

[0059] First is to prepare the first quaternary ammonium salt intermediate, that is, the compound of formula IIa or IIb and R 4 Z reaction, prepare the first quaternary ammonium salt intermediate IIIa or IIIb respectively, wherein Z is halogen or OTs, Z - Halogen anions or OTs generated for t...

Embodiment 1

[0104] Synthesis of the first quaternary ammonium salt intermediate 1-ethyl-4-iodoquinoline quaternary ammonium salt:

[0105] Add 10mmol of 4-chloroquinoline and 20mmol of ethyl iodide into a 100ml round bottom flask containing 20ml of toluene. Under the protection of nitrogen, the reaction was stopped after heating to reflux for 10 h. After the mixture was cooled to room temperature, the precipitate was filtered and the filter cake was washed with ethyl acetate. After drying, a yellow solid powder was obtained with a crude yield of 98%.

Embodiment 2

[0107] Synthesis of the second quaternary ammonium salt intermediate 1-diethylaminobutyl-2-methylbenzothiazole quaternary ammonium salt:

[0108] 10mmol of 2-methylbenzothiazole and 20mmol of 1-diethylamino-4-bromobutane were added to a 100ml round bottom flask containing 20ml of toluene. Under the protection of nitrogen, the reaction was stopped after heating to reflux for 18h. After the mixture was cooled to room temperature, the precipitate was filtered and the filter cake was washed with ether. After drying, a white solid powder was obtained with a crude yield of 75%.

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Abstract

The invention provides a green fluorescence cyanine dye, which has a structural general formula I shown in the specification, wherein in the formula, X is C(CH3)2, O, S or Se; R1 and R2 are independently selected form H, C1-18 alkyl groups, OR6, C1-6 alkyl group OR6 or halogen respectively; R3 is N(R5)(R7); R4 is selected from C1-18 alkyl groups, benzyl groups and substituted benzyl groups; the substituted benzyl groups are arbitrarily substituted by the following groups: C1-18 alkyl groups, CN, COOH, NH2, NO2, OH, SH, C1-6 alkoxy groups, C1-6 alkyl amino groups, C1-6 acylamino groups, halogen or C1-6 halogenated alkyl groups; R5 and R7 are independently selected from H or C1-18 alkyl groups respectively; R6 is H or C1-18 alkyl groups; and Y is negative ions. The fluorescence dye can be used for DNA (Deoxyribonucleic Acid) quantitative detection and biological dyeing, and is applied to the fields of nucleic acid marking, blood cell analysis, clinic medical diagnosis, immune analysis detection and the like.

Description

technical field [0001] The present invention relates to a new class of fluorescent dyes in the field of fine chemicals, their preparation methods and applications, in particular to a class of single-charged nitrogen-containing cyanine fluorescent dyes, their preparation methods, and the use of the fluorescent dyes, their conjugates or their Compositions for biological applications. Background technique [0002] DNA (deoxyribonucleic acid) is a class of biological macromolecules that carry genetic information. Normal cells in organisms have a relatively stable DNA diploid content, and only when cancerous or precancerous lesions with malignant potential occur, it is accompanied by abnormal changes in cellular DNA content. Therefore, the specific recognition and precise measurement of DNA, especially the detection in living cells, is of great significance in the early diagnosis of cancer. The quantitative analysis of DNA by fluorescence technology has the advantages of high s...

Claims

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Application Information

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IPC IPC(8): C09B23/04C09K11/06C12Q1/68G01N1/30G01N21/64
CPCC09B23/04C12Q1/68C12Q2563/107C12Q2563/173
Inventor 彭孝军刘涛樊江莉王静云宋锋玲孙世国
Owner DALIAN UNIV OF TECH
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