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Synthesis method of pentamethine cyanine dye for mercapto labeling

A technology of pentamethanine and a synthesis method, which is applied in the directions of methine/polymethine dyes, peptide preparation methods, organic dyes, etc. The problem of uneven end distribution, etc., achieves the effect of low toxicity, reducing background fluorescence interference, and improving signal-to-noise ratio.

Inactive Publication Date: 2015-04-01
顾新华
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a kind of synthetic method that is used for the pentamethine cyanine dye of sulfhydryl label, it introduces a plurality of hydrophilic sulfonic acid groups into the compound of pentamethine cyanine, improves water solubility ; further reduce the distance between the connection site and the fluorescent group, and improve the rigidity of the probe; thereby solving the problem of uneven distribution of the hydrophilic and hydrophobic ends of the protein fluorescent probe and the long connection group of the probe

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  • Synthesis method of pentamethine cyanine dye for mercapto labeling
  • Synthesis method of pentamethine cyanine dye for mercapto labeling
  • Synthesis method of pentamethine cyanine dye for mercapto labeling

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specific Embodiment approach 1

[0019] Specific implementation mode 1: see Figure 1-Figure 4 , this specific embodiment adopts the following technical scheme: its synthesis step is as follows:

[0020] The first step, reaction 1: take 1 equivalent of the potassium salt of compound I and 1.2 equivalent of the sodium salt of compound II, add 1.5 equivalents of chloroacetic anhydride, and stir at room temperature for 0.5 hours; rotary evaporation to remove the solvent, column chromatography, using methanol: Acetone=1:7 elution to obtain the corresponding compound III;

[0021] The second step, reaction 2: the obtained 1 equivalent of compound III and 1.1 equivalent of sodium iodide were reacted in a solvent of methanol:chloroform=1:1 at 60°C for 24 hours, filtered, and the solvent was removed by rotary evaporation to obtain the corresponding The final product IV; confirmed by nuclear magnetic spectrum is consistent with the target product.

[0022] In the structure of compound I, the corresponding cation is ...

specific Embodiment approach 2

[0026] Specific embodiment two: the difference between this specific embodiment and specific embodiment one is: its synthesis step is as follows:

[0027] The first step, reaction 1: take 1 equivalent of the sodium salt of compound I and 1.1 equivalent of the sodium salt of compound II, add 2 equivalents of chloroacetic anhydride, heat and stir for 0.6 hours; remove the solvent by rotary evaporation, column chromatography, and methanol : acetone=1:5 elution to obtain the corresponding compound III;

[0028] The second step, reaction 2: the obtained 1 equivalent of compound III and 1.5 equivalents of sodium iodide were reacted in a solvent of methanol:chloroform=1:2 at 70°C for 20 hours, filtered, and the solvent was removed by rotary evaporation to obtain the corresponding The final product IV; the NMR showed that it was consistent with the target product.

specific Embodiment approach 3

[0029] Specific embodiment three: the difference between this specific embodiment and specific embodiment one is: its synthesis step is as follows:

[0030] The first step, reaction one: take 0.40 g of the potassium salt of compound I and 0.62 g of the potassium salt of compound II, dissolve in 0.21 g of acetic acid, heat and stir for 1 hour; remove the solvent by rotary evaporation, column chromatography, use methanol: acetone =1:5 elution to obtain the corresponding compound III;

[0031] The second step, reaction two: the obtained 0.42g of compound III and 0.11g of sodium iodide were reacted in a solvent of methanol:chloroform=1:10 at 65°C for 24 hours, filtered, and the solvent was removed by rotary evaporation to obtain the corresponding The final product IV was 0.42 g; the NMR and mass spectrometry showed that it was consistent with the target product.

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Abstract

The invention discloses a synthesis method of pentamethine cyanine dye for mercapto labeling and relates to the technical field of mercapto fluorescent labeling. The synthesis method comprises the following steps of 1, reaction 1: heating 1-1.5 equivalent of a compound I and 1-1.2 equivalent of a compound II in 1.5-3.5 equivalent of acetic anhydride with stirring for 0.5-1h to obtain an intermediate III, and 2, reaction 2: heating 1 equivalent of the intermediate III and 1.1-1.5 equivalent of sodium iodide in an organic solvent 1 to a temperature of 40-70 DEG C, and carrying out reflux for 2-24h to obtain a desired product IV which is a water-soluble fluorescent compound. A pentamethine cyanine compound is introduced with multiple hydrophilic sulfonic acid groups so that water solubility is improved. A distance between a connection locus and a fluorescent group is further reduced so that probe rigidity is improved and thus the problem that the existing protein fluorescent probe has nonuniform hydrophobic ends and hydrophilic ends and has long length of a probe connection group.

Description

Technical field: [0001] The invention relates to the technical field of fluorescent labeling of mercapto groups, in particular to a method for synthesizing thiol-labeled pentamethine dyes. Background technique: [0002] Wujiachuan cyanine compounds are an important class of organic dyes widely used in biological analysis, laser dyes, nanomaterials and other fields. This type of compound has a very high molar extinction coefficient, and its maximum absorption wavelength can be in the 600-700nm region, which can effectively filter the background fluorescence in the organism and improve the signal-to-noise ratio of experimental detection. [0003] The commercial products of fluorescent probes with an excitation wavelength of 600-700nm include GE’s Cy5-NHS-ester, Cy5Maleimide and other products. However, these products have poor water solubility, which is not conducive to labeling macromolecules in aqueous solution. The longer carbon chain of the biomacromolecule, its greater f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09K11/06G01N21/64C07K1/13
Inventor 顾新华郭大川
Owner 顾新华
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