Fluorescent probe and preparation method thereof

A fluorescent probe, selected technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of rigidity and low selectivity of G-quadruplex

Active Publication Date: 2017-06-13
GUANGDONG UNIV OF TECH
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  • 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.
At present, the dyes that have been found include porphyrins, cyanines, styrenes, etc., but their synthetic dyes do not provide a simple, reliable and mature reference for future work and provide a basis for the next step of synthesis. Guiding significance, and its response rigidity and selectivity to G-quadruplex are not high

Method used

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  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof
  • Fluorescent probe and preparation method thereof

Examples

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preparation example Construction

[0059] The present invention also provides a method for preparing the above-mentioned fluorescent probe, comprising:

[0060] The compound shown in formula (II) is reacted with aromatic aldehyde to obtain the fluorescent probe shown in formula (I);

[0061]

[0062] Among them, R 1 with R 2 Each is independently selected from H or an aromatic vinyl group, and at least one is an aromatic vinyl group;

[0063] R 3 selected from H, F, Cl, Br, OH, OCH 3 , N(CH 3 ) 2 Or C1~C6 alkyl;

[0064] R 4 Alkyl group selected from C1~C6;

[0065] R 12 with R 13 each independently selected from H or CH 3 , and not H at the same time.

[0066] where the R 1 ~R 11 All are the same as above, and will not be repeated here.

[0067] According to the present invention, the compound described in the formula (II) is preferably prepared according to the following method:

[0068] The compound shown in formula (III) is reacted with alkyl iodide to obtain the compound shown in formula...

Embodiment 1

[0087] Embodiment 1: the synthesis of compound 1a

[0088] Weigh 0.2g (1.400mmol) of 2-dimethylquinaldine into a 25ml round-bottomed flask, add about 1.2g of methyl iodide and 5.0ml of sulfolane, and heat the mixture to 70°C for 6 hours of reaction After cooling, shake after adding anhydrous diethyl ether, suction filter, wash the solid with anhydrous diethyl ether, weigh after vacuum-drying, thin-layer chromatography preliminarily shows that there is no by-product, obtains 0.355g pure product 1a, chemical structure formula is as follows, yield was 89.0%.

[0089]

[0090] Utilize nuclear magnetic resonance to analyze the compound 1a obtained in embodiment 1, obtain its proton nuclear magnetic resonance spectrum result: 1 H NMR (400MHz, DMSO) δ9.11(d, J=8.5Hz, 1H), 8.60(d, J=9.0Hz, 1H), 8.38(t, J=15.7Hz, 1H), 8.23(t, J =7.5Hz, 1H), 8.13(d, J=8.5Hz, 1H), 7.99(t, J=7.5Hz, 1H), 4.46(s, 3H), 3.09(s, 3H).

[0091] Compound 1a obtained in Example 1 is analyzed by mass spectromet...

Embodiment 2

[0092] Embodiment 2: the synthesis of compound 1b

[0093] The preparation method of this example is the same as that of Example 1 except that 4-dimethylquinaldine is used instead of 2-dimethylquinaldine. It is a brown solid with the following chemical structure and a yield of 91.7%.

[0094]

[0095] Utilize nuclear magnetic resonance to analyze the compound 1b that obtains in embodiment 2, obtain its proton nuclear magnetic resonance spectrum result: 1 H NMR (400MHz, DMSO) δ9.38(d, J=6.0Hz, 1H), 8.53(d, J=8.4Hz, 1H), 8.49(d, J=8.9Hz, 1H), 8.27(t, J =7.9Hz, 1H), 8.07(t, J=6.3Hz, 2H), 4.59(s, 3H), 3.00(s, 3H).

[0096] The compound 1b obtained in Example 2 is analyzed by a mass spectrometer, and its mass spectrometry result is obtained: ESI-MS m / z: 158.2[M+H] + .

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Abstract

The invention provides a fluorescent probe represented by the formula (I), wherein R1 and R2 are independently selected from H or an aromatic vinyl group, and at least one of R1 and R2 is the aromatic vinyl group; R3 is selected from H, F, Cl, Br, OH, OCH3, N(CH3)2 or C1-C6 alkyl; and R4 is selected from C1-C6 alkyl. Compared with the prior art, because the fluorescent probe provided by the invention has a relatively large electronic conjugated system and plane, the intensity of the intramolecular charge transfer effect can affect the molecular fluorescence emission intensity; when the fluorescent probe and the G-quadruplex generate a specific action, the flexibility of intramolecular rotatable double bonds is restricted, the intramolecular charge transfer effect is enhanced, and the fluorescence is also enhanced significantly; moreover, the fluorescent probe provided by the invention has the advantages of low biotoxicity, phototoxicity and photobleaching property, good light stability, good water solubility and good cell membrane permeability.

Description

technical field [0001] The invention belongs to the technical field of nucleic acid detection, and in particular relates to a fluorescent probe and a preparation method thereof. Background technique [0002] Nucleic acid is not only the basic component of all biological cells, but also plays a dominant role in the growth, development, reproduction, inheritance and variation of organisms and other major life phenomena. Nucleic acid macromolecules are divided into two categories: deoxyribonucleic acid (DNA) and ribonucleic acid (RNA), which play a role in storing and transmitting genetic information in the replication and synthesis of proteins. [0003] G-quadruplex (G-quadruplex) is a special nucleic acid secondary structure. Many guanine-rich regions in the human genome have the ability to form this structure, including the guanine repeat sequence at the end of the telomeric, and the promoter regions of various genes, such as c-kit, c-myc, c-myb, Bcl-2 , Pdgf, Hras, ​​Vegf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/06G01N21/64
CPCC07D401/06C09K11/06C09K2211/1018G01N21/6428
Inventor 卢宇靖郭晓路张焜黄宝华郑园园
Owner GUANGDONG UNIV OF TECH
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