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Half cyanine dye compound, preparation method and application of half cyanine dye compound

A technology of cyanine dyes and compounds, which is applied in the field of fine chemicals, can solve the problems that dyes are difficult to enter cells (such as requiring 24 hours of incubation, cannot enter the nucleus, etc.), and achieve the effects of avoiding fluorescence background interference, simple structure, and high sensitivity

Active Publication Date: 2013-05-22
SICHUAN ANKERUI NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because of the negative charge on the RNA phosphate backbone, most of the reported RNA probes have one or more positive charges, which makes it difficult for the dye to enter the cell (e.g., requires 24 hours of incubation) or not at all to enter the nucleus

Method used

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  • Half cyanine dye compound, preparation method and application of half cyanine dye compound
  • Half cyanine dye compound, preparation method and application of half cyanine dye compound
  • Half cyanine dye compound, preparation method and application of half cyanine dye compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Synthesis of new compound intermediate N-methyl-2-methylbenzothiazole quaternary ammonium salt (compound 1):

[0047]

[0048] Add 20mmol of 2-methylbenzothiazole and 40mmol of methyl 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, an off-white solid powder was obtained with a crude yield of 85%.

Embodiment 2

[0050] Preparation of Compound A:

[0051]

[0052] (1) Synthesis of intermediate 4-dimethylamino-1,3-benzaldehyde (compound A)

[0053] 50 g (326 mmol) POCl 3 It was added dropwise to 81.2 g (1.11 mmol) of DMF to obtain a pale yellow solution. Add the obtained solution dropwise to 12.1g (100mmol) N,N-dimethylaniline solution under ice bath condition. After the dropwise addition, move the solution into an oil pan and react at 80-90°C for 10h. After the reaction, the reaction solution was poured into a mixture of 600 g of ice and 150 mL of 38% NaOH and stirred to obtain a brown precipitate, which was filtered and the obtained mixture was separated by a silica gel column. Compound A (4.5g) was obtained by washing with petroleum ether: ethyl acetate (5:1-4:1), with a yield of 25%. 1 H NMR (400MHz, CDCl 3 )δ=10.04(s,1H), 9.86(s,1H), 7.92(d,J=8.8,1H), 7.03(d,J=8.8,1H).

Embodiment 3

[0055] Preparation of Compound B:

[0056]

[0057] Add 11 mmol of piperidine to an ethanol solution of 3.3 g (11.0 mmol) 1,2,3,3-tetramethylindole quaternary ammonium salt and stir for 30 min, then add 890 mg (5.0 mmol) of compound A to an ethanol solution for 1 h Dropped into the refluxing above-mentioned mixed solution, the reaction continued for 6 hours, a dark brown precipitate was produced and filtered, and recrystallized in ethanol to obtain 1.5 g of the product, with a yield of 40.4%. 1 H NMR (400MHz, CDCl 3 )δ=9.53(d,J=1.9,1H),8.72(d,J=16.0,1H),8.60(dd,J=9.0,1.9,1H),8.24(d,J=16.0,1H),8.14 (d,J=16.0,1H),7.96(d,J=16.0,1H),7.70–7.43(m,8H),7.28(s,1H),7.17(d,J=9.0,1H),4.56( s,3H),4.44(s,3H),3.18(s,6H),1.97(s,6H),1.89(s,6H). 13 C NMR (100MHz,D 2 O)δ=182.3, 182.2, 159.1, 154.7, 150.9, 143.4, 143.2, 141.4, 137.0, 136.6, 129.8, 129.6, 129.3, 129.2, 126.7, 124.3, 122.8, 122.71, 118.2, 1133.8, 5, 1 52.4, 45.4, 37.5, 36.9, 27.4, 27.2. HRMS (TOF-MS EI + ) calculated for C...

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PUM

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Abstract

The invention discloses a half cyanine dye compound, a preparation method and an application of the half cyanine dye compound. The half cyanine dye compound has the structural general formula I as shown in the specification. The half cyanine dye compound has a near-infrared emission function, is large in Stokes displacement, simple in structure, easy to prepare and low in toxicity, and can be used as a fluorescent dye. The half cyanine dye compound has response to nucleic acid, is an RNA (ribonucleic acid) selective fluorescent probe and can be used for RNA dying in cells.

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 semicyanine dye compounds containing two similar electron-withdrawing groups, 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. With the establishment of the genetic code, RNA is considered to be an important biomolecule closely linked with some important processes in the cell. Therefore, capturing the temporal-spatial morphologies of RNA synthesis, transport, and processing is critical to our understanding of cellular function and behavior in disease, health, and external stimuli. Live-cell imaging of RNA can provide a complete spatio-tem...

Claims

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Application Information

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IPC IPC(8): C07D209/14C07D277/64C07D263/56C09B23/14C09K11/06C12Q1/68C12Q1/02G01N21/64
Inventor 彭孝军孙世国李志勇张思
Owner SICHUAN ANKERUI NEW MATERIAL CO LTD
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