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Compound and preparation method, fluorescent dye and fluorescent probe thereof

A technology of fluorescent dyes and fluorescent probes, applied in the field of nucleic acid detection, to achieve good fluorescence response, enhanced fluorescence intensity, water solubility and improved cell permeability

Inactive Publication Date: 2018-01-16
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] With the development of biotechnology, the requirements for nucleic acid labeling are getting higher and higher. The previous method of sequencing DNA molecules through isotope effects has been unable to meet the needs. The marking technology with the advantages of less amount and no radiation has been widely valued and has achieved rapid development.

Method used

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  • Compound and preparation method, fluorescent dye and fluorescent probe thereof
  • Compound and preparation method, fluorescent dye and fluorescent probe thereof
  • Compound and preparation method, fluorescent dye and fluorescent probe thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0066] The invention provides a preparation method of a compound, comprising:

[0067] The compound shown in formula (III) is reacted with the group shown in formula (II) to obtain the compound shown in formula (I);

[0068]

[0069] Among them, R 1 with R 2 Each is independently selected from H or an aromatic amine group, and at least one is an aromatic amine group;

[0070] R 3 selected from H, F, Cl, Br, OH, OCH 3 , N(CH 3 ) 2 Or C1~C6 alkyl;

[0071] R 4 Alkyl group selected from C1~C6;

[0072] R 7 with R 8 each independently selected from H or CH 3 , and not H at the same time, and cannot be CH at the same time 3 .

[0073] where the R 1 ~R 8 All are the same as above, and will not be repeated here.

[0074] According to the present invention, the compound represented by the formula (III) is prepared according to the following method:

[0075] The compound shown in formula (IV) is reacted with alkyl iodide to obtain the compound shown in formula (III)...

Embodiment 1

[0105] Embodiment 1: the synthesis of compound 1a

[0106] Weigh 0.2g (1.130mmol) of 4-chlorodimethylquinoline into a 25ml round-bottomed flask, add about 1.2g of methyl iodide and 5.0ml of sulfolane, and heat the mixture to 60°C for 6 hours of reaction Afterwards, cool, shake after adding ethyl acetate, suction filter, wash the solid with ethyl acetate, weigh after vacuum drying, thin-layer chromatography preliminary shows that there is no by-product, obtains 1.82g pure product 1a, chemical structural formula is as follows, yield was 88.6%.

[0107]

[0108] Compound 1a obtained in Example 1 was analyzed by nuclear magnetic resonance, and its hydrogen nuclear magnetic resonance spectrum result was obtained: 1H NMR (400MHz, DMSO) δ8.67 (d, J=9.0Hz, 1H), 8.58–8.50 (m, 2H), 8.33 (ddd, J = 8.7, 7.1, 1.3Hz, 1H), 8.11 (dd, J = 13.4, 5.7Hz, 1H), 4.43 (s, 3H), 3.07 (s, 3H).

[0109] Compound 1a obtained in Example 1 is analyzed by mass spectrometer, and its mass spectrometry res...

Embodiment 2

[0110] Embodiment 2: the synthesis of compound 1b

[0111] The preparation method of this example is the same as that of Example 1 except that 4-chloroquinoline is used instead of 4-chlorodimethylquinoline. It is a reddish-brown solid with the following chemical structure and a yield of 90.5%.

[0112]

[0113] Compound 1b obtained in Example 2 is analyzed by nuclear magnetic resonance, and its hydrogen nuclear magnetic resonance spectrum result is obtained: 1H NMR (400MHz, DMSO) δ9.12 (d, J=6.1Hz, 1H), 8.87 (d, J= 6.1Hz, 1H), 8.50(dd, J=13.4, 7.6Hz, 2H), 8.37–8.28(m, 1H), 8.13(t, J=7.7Hz, 1H), 4.55(s, 3H).

[0114] The compound 1b obtained in Example 2 is analyzed by a mass spectrometer, and its mass spectrometry result is obtained: ESI-MS m / z: 178.04[M+H] + .

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Abstract

The invention provides a compound. The compound is shown in a formula (I), wherein R1 and R2 are selected from H or groups shown in a formula (II) independently, and at least one of the R1 and R2 is agroup selected from the formula (II); R3 is selected from groups consisting of H, F, Cl, Br, OH, OCH3, N(CH3)2 or C1-C6 alkyl groups, and R4 is selected from the C1-C6 alkyl groups. Compared with anexisting embedded fluorescent probe, since a fluorescent probe provided by the invention is provided with a large electron conjugated system and a large plane, the fluorescence emission intensity of the molecule of the fluorescent probe can be influenced by the intensity of a charge transfer effect in the molecule of the fluorescent probe, and when the fluorescent probe combines with G-quadruplexRNA specifically, the flexibility of rotary intramolecular double bonds is limited, so that the effect of intramolecular charge transfer is enhanced, and thus the fluorescence intensity is increased;the fluorescent probe provided by the invention has no biological toxicity, no phototoxicity and no fluorescence quenching, meanwhile, the solubility in water and the cellular permeability are greatlyimproved, and the fluorescent probe has a high binding constant in detection and an extremely low limit of detection.

Description

technical field [0001] The invention relates to the technical field of nucleic acid detection, in particular to a compound, a preparation method thereof, a fluorescent dye and a fluorescent probe. Background technique [0002] Fluorescent dye is a widely used fluorescent labeling agent, which has the advantages of fast detection speed, good repeatability, less dosage and no radiation. Fluorescent dyes commonly used for cell labeling can be divided into two types according to the way fluorescent dyes and probe molecules mark cells: one type is fluorescent probes containing active groups, which bond with the labeled substances, such as rhodamines, Fluoresceins, acridine, and stilbene, etc.; the other is embedded fluorescent probes, which interact with nucleic acids by inserting affinity into the structure of nucleic acids, such as thiazole orange (TO), oxazole yellow (YO ) series of cyanine dyes, they do not emit light when they are not combined with nucleic acid, and there i...

Claims

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Application Information

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IPC IPC(8): C07D417/06C09K11/06C09B23/04C12Q1/68
Inventor 龙威张焜卢宇靖王聪蔡森源郑园园林丹敏
Owner GUANGDONG UNIV OF TECH
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