Dual-functional probe and preparation method and application in detection of G-quadruplex structure thereof

A dual-function, quadruplex technology, which is applied in chemical instruments and methods, color/spectral property measurement, color-changing fluorescent materials, etc. Effect

Active Publication Date: 2014-07-02
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the detection of the G-quadruplex structure in in vitro experiments is mainly through the means of instruments, such as circular dichroism, nuclear magnetic resonance, surface plasmon resonance, fluorescence resonance energy transfer and other methods. These methods have relatively high requirements for instruments and technical operations. High, and the price is relatively expensive, basically cannot be widely used

Method used

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  • Dual-functional probe and preparation method and application in detection of G-quadruplex structure thereof
  • Dual-functional probe and preparation method and application in detection of G-quadruplex structure thereof
  • Dual-functional probe and preparation method and application in detection of G-quadruplex structure thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Embodiment one : Synthesis of Compound 2

[0056] Dissolve 2.01g of 4-diethylamino salicylaldehyde in 30 mL of absolute ethanol, add 3.20 g of diethyl malonate and 1 mL of piperidine, and react at 80°C for 6 h. Then distill off the solvent, add 20 mL of acetic acid and 20 mL of concentrated hydrochloric acid, and continue to reflux for 6 h. After cooling to room temperature, pour the reaction solution into ice water, adjust the pH to 5 with sodium hydroxide solution, and precipitate a large amount of precipitates. Filter and dry to obtain the crude product. Purification by silica gel chromatography using petroleum ether / ethyl acetate (volume ratio 1 / 10) as the eluent gave 0.81 g of pure product 2 with a yield of 37.3%: 1 H NMR (400 MHz, CDCl 3 )δ7.53 (d, J = 9.3 Hz, 1H), 7.24 (d, J = 8.8 Hz, 1H), 6.56 (dd, J = 8.8, 2.1 Hz, 1H), 6.49 (d, J = 1.6 Hz, 1H), 6.03 (d, J = 9.3 Hz, 1H), 3.41 (q, J = 7.1 Hz, 4H), 1.21 (t, J = 7.1 Hz, 6H). ESI-MS m / z: 218.1 [M+ H] + .

Embodiment 2

[0057] Embodiment two : Synthesis of compound 3

[0058] Under nitrogen protection, 1.5 mL POCl 3 Add it dropwise to 1 mL DMF, and stir at room temperature for 20 min. Then 0.77 g of 2 dissolved in 4 mL DMF was added dropwise to the above mixture, reacted at 60 oC for 10 h, cooled to room temperature, poured the reaction solution into ice water, adjusted the pH to neutral with sodium hydroxide solution, and reduced Pressure suction filtration, rinse with water and ethanol several times, and dry in vacuo to obtain 30.50 g of orange-yellow solid, yield 58.3%: 1 H NMR (400 MHz, CDCl 3 )δ10.13 (s, 1H), 8.26 (s, 1H), 7.41 (d, J = 9.0 Hz, 1H), 6.64 (dd, J = 9.0, 2.5 Hz, 1H), 6.49 (d, J = 2.4 Hz, 1H), 3.48 (q, J = 7.1 Hz, 4H), 1.26 (t, J = 7.1 Hz, 6H). ESI-MS m / z: 246.1 [M+H] + .

Embodiment 3

[0059] Embodiment three : Synthesis of compound 5a

[0060] Mix 3 ml of 2-pyrrolidone with 2.64 g of anthranilic acid, and slowly add 45 ml of phosphorus oxychloride dropwise under ice cooling. Then reflux for 7 h. After cooling, distill out phosphorus oxychloride, add ethyl acetate to dilute, adjust the solution to be weakly alkaline with sodium hydroxide solution, extract with ethyl acetate several times, collect the organic layer, dry with anhydrous magnesium sulfate, suction filter, and rotary evaporate , to get crude products. Purification by silica gel chromatography using petroleum ether / ethyl acetate (volume ratio 4 / 1) as the eluent afforded 1.51 g of white solid 5a in a yield of 42.1%: 1 H NMR (400 MHz, CDCl 3 )δ8.28 (d, J = 7.9 Hz, 1H), 7.77 - 7.69 (m, 1H), 7.65 (d, J = 8.1 Hz, 1H), 7.49 - 7.42 (m, 1H), 4.21 (t, J = 7.3 Hz, 2H), 3.19 (t, J = 7.9 Hz, 2H), 2.36 - 2.23 (m, 2H). ESI-MS m / z: 187.1 [M+H] + .

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Abstract

The invention discloses a bifunctional probe, its preparation method and its application in detecting the G-quadruplex structure. This type of probe is easy to prepare, easy to obtain, and has a stable structure. It can be used to specifically detect the secondary structure of G-quadruplex nucleic acid. It can be quickly detected by ultraviolet-visible absorption spectroscopy, fluorescence spectrophotometer, or directly by naked eye observation. The secondary structure of a DNA sample in solution is detected. This type of probe has the advantages of simple operation, good selectivity, quickness, and visible to the naked eye for the detection of the secondary structure of G-quadruplex nucleic acid, and overcomes the disadvantages of other detection methods such as expensive, high equipment requirements, and relatively complicated technical operations. .

Description

technical field [0001] The invention relates to a novel bifunctional probe and its preparation method, as well as its application in detecting the secondary structure of G-quadruplex nucleic acid. Background technique [0002] G-quadruplex (G-quadruplex) is a special DNA secondary structure. Many guanine-rich regions in the human genome have the ability to form this structure, including the guanine repeat at the end of the telomeric region, and the promoter regions of various genes, such as c-kit, c-myc, c-myb, bcl-2 , PDGF, kRAS, VEGF, Rb and insulin genes, etc. The latest research shows that RNA sequences in many non-coding regions can also form a G-quadruplex structure. The G-quadruplex structure of RNA is more stable than that of DNA. This structure may prevent gene translation or participate in the process of protein binding and recognition. To achieve the effect of inhibiting tumor growth. The formation of G-quadruplex structure regulates a series of physiological p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C09K9/02C07D487/04G01N21/31G01N21/64C12Q1/68
Inventor 黄志纾古练权谭嘉恒颜金武叶文杰
Owner SUN YAT SEN UNIV
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