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Nucleic acid dye compound and preparation method and application of nucleic acid dye compound

A nucleic acid dye and compound technology, applied in the field of fluorescent probe probes, can solve the problems of slow response speed of G-quadruplex DNA or RNA, affecting application value, high phototoxicity, etc. Biotoxic, selective effect

Active Publication Date: 2018-06-15
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, G-quadruplex DNA fluorescent probes and RNA fluorescent probes have some defects in practical imaging applications, such as slow response to G-quadruplex DNA or RNA, high phototoxicity and poor photostability. Defects affect its application value

Method used

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  • Nucleic acid dye compound and preparation method and application of nucleic acid dye compound
  • Nucleic acid dye compound and preparation method and application of nucleic acid dye compound
  • Nucleic acid dye compound and preparation method and application of nucleic acid dye compound

Examples

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preparation example Construction

[0051] The present invention also provides a preparation method of nucleic acid dye compound, comprising:

[0052] The compound of formula (II) structure is reacted with the compound of formula (III) structure to obtain the compound of formula (I) structure,

[0053] R 3 -CHO formula (III),

[0054] Among them, R 1 Alkylamino, piperidinyl, morpholinyl, pyrrolidinyl, piperazinyl or pyroxolinyl selected from C1-C6;

[0055] R 2 Aryl vinyl selected from C8-C20;

[0056] R 3 It is selected from a C8-C20 aryl group or a C8-C20 aryl vinyl group.

[0057] According to the present invention, according to the present invention, the present invention will react the compound of formula (II) structure with the compound of formula (III) structure, obtain the compound of formula (I) structure, wherein, the present invention does not have special requirement to the condition of reaction , those skilled in the art can select suitable reaction conditions according to common knowledg...

Embodiment 1

[0079] Embodiment 1: the synthesis of compound 1a

[0080] Weigh 0.2g (1.130mmol) of 4-chlorodimethylquinoline into a 25ml round bottom 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 After cooling, 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%.

[0081]

[0082] The compound 1a obtained in Example 1 is analyzed by nuclear magnetic resonance, and its hydrogen nuclear magnetic resonance spectrum result is 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, 1.3 Hz, 1H), 8.11 (dd, J = 13.4, 5.7 Hz, 1H), 4.43 (s, 3H), 3.07 (s, 3H).

[0083] Compound 1a obtained in Example 1 is analyzed by mass spectrometer, and its mass spectrometry resu...

Embodiment 2

[0084] Embodiment 2: the synthesis of compound 1b

[0085] Weigh 0.4g (1.56mmol) of 2-methylbenzothiazole and 0.4ml (2mmol) of 1,3-dibromopropane into a 25ml round-bottomed flask as a pinkish white solid, heat the mixture to 100°C, and react 12 After one hour, cool, shake after adding ethyl acetate, suction filter, solid is washed with ethyl acetate, weigh after vacuum drying, thin-layer chromatography preliminary shows that there is no by-product, chemical structural formula is as follows, pure product 1b, productive rate is 98.2%.

[0086]

[0087] Compound 1b obtained in Example 2 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), 8.57-8.51 (m, 2H), 8.33 (ddd, J = 8.7, 7.1, 1.3 Hz, 1H), 8.12 (t, J = 7.7 Hz, 1H), 4.43 (s, 3H), 3.07 (s, 3H).

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Abstract

The invention provides a nucleic acid dye compound and a preparation method and application of the nucleic acid dye compound. The provided compound, as a fluorescence probe, can selectively recognizeG-quadruplex DNA and RNA; compared with the fluorescence probe having similar functions, the probe has the characteristics of strong selectivity, low bio-toxicity, good membrane permeability, strong developing, good counterstaining compatibility, and stronger light stability, and the characteristics indicate that the compound has extensive applications as the G-quadruplex DNA and the nucleolus fluorescence probe, and is expected to be developed into a simple convenient intuitive biological detection agent for the related physiological and pathological studies of the G-quadruplex DNA and nucleolus.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a nucleic acid dye compound and its preparation method and application. Background technique [0002] Small-molecule probes refer to detectors developed for a specific target biomolecule or biological ion. Small-molecule probes can specifically interact with specific target molecules and can be detected by special detection techniques. Compared with ordinary detection technologies, probe technology has the advantages of high sensitivity, strong specificity, fast and accurate, and is suitable for molecular imaging and real-time monitoring. [0003] Live-cell imaging or staining with cell-specific molecular fluorescent probes is an important technique for studying cell nucleus distribution, migration, and transcription dynamics, and can be used in medical diagnosis and biomedical research. RNA molecules in living cells are known to be responsible for a variety of functions, inclu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14C09B23/10C09K11/06C12Q1/6876
CPCC09B23/105C09B23/107C09B23/145C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C12Q1/6876
Inventor 龙威张焜卢宇靖李莹杜现王聪蔡森源郑园园林丹敏
Owner GUANGDONG UNIV OF TECH
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