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Bifunctional probe, its preparation method, and its application in detection of orthographic parallel conformation G-quadruplex

A dual-function, quadruplex technology, applied in the field of biological probes, can solve the problems of high price and cannot be widely used, and achieve the effects of simple preparation, stable structure and enhanced fluorescence

Inactive Publication Date: 2015-06-17
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are very few probes that can identify the conformation of the G-quadruplex. In vitro experiments detect the conformation of the G-quadruplex mainly by means of instruments, such as methods such as circular dichroism chromatography and nuclear magnetic resonance. and technical operation requirements are higher, and the price is more expensive, basically can not be widely used

Method used

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  • Bifunctional probe, its preparation method, and its application in detection of orthographic parallel conformation G-quadruplex
  • Bifunctional probe, its preparation method, and its application in detection of orthographic parallel conformation G-quadruplex
  • Bifunctional probe, its preparation method, and its application in detection of orthographic parallel conformation G-quadruplex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Embodiment 1: the synthesis of compound 2

[0044] Dissolve 2.0g of 4-diethylamino salicylaldehyde in 30mL of absolute ethanol, add 3.20g of diethyl malonate and 1mL of piperidine, and react at 80°C for 6h. Then evaporate the solvent, add 20mL acetic acid and 20mL concentrated hydrochloric acid, continue to reflux for 6h, cool to room temperature, pour the reaction solution into ice water, adjust the pH to 5 with sodium hydroxide solution, precipitate a large amount of precipitate, vacuum filter and dry to obtain Crude. Purified by silica gel chromatography using petroleum ether / ethyl acetate (volume ratio 1 / 10) as the eluent to obtain 0.81 g of pure product 2 with a yield of 37.3%: 1 H NMR (400MHz, CDCl 3 )δ7.53(d, J=9.3Hz, 1H), 7.24(d, J=8.8Hz, 1H), 6.56(dd, J=8.8, 2.1Hz, 1H), 6.49(d, J=1.6Hz, 1H), 6.03(d, J=9.3Hz, 1H), 3.41(q, J=7.1Hz, 4H), 1.21(t, J=7.1Hz, 6H).ESI-MS m / z: 218.1[M+ H] + .

Embodiment 2

[0045] Embodiment 2: the synthesis of compound 3

[0046] Under nitrogen protection, 1.5mL POCl 3 Add dropwise to 1mL DMF and stir at room temperature for 20min. Then 0.77g of 2 dissolved in 4mL DMF was added dropwise to the above mixture, and reacted at 60°C for 10h. After cooling to room temperature, the reaction solution was poured into ice water, and the pH was adjusted to neutral with sodium hydroxide solution, and pumped under reduced pressure. Filter, wash with water and ethanol several times, dry in vacuo to obtain orange-yellow solid 30.50g, productive rate 58.3%: 1 H NMR (400MHz, CDCl 3 )δ10.13(s,1H),8.26(s,1H),7.41(d,J=9.0Hz,1H),6.64(dd,J=9.0,2.5Hz,1H),6.49(d,J=2.4 Hz,1H),3.48(q,J=7.1Hz,4H),1.26(t,J=7.1Hz,6H).ESI-MS m / z:246.1[M+H] + .

Embodiment 3

[0047] Embodiment 3: the synthesis of compound 5a

[0048] Dissolve 4,4'-difluorobenzil in DMSO (about 0.15M), add 3 times the molar amount of N-methylpiperazine and K 2 CO 3 , after heating and reacting in an oil bath at 90°C for 20h, add an appropriate amount of ether, wash away DMSO with water, and wash with anhydrous Na 2 SO 4 After drying, the solvent was evaporated and dried in vacuo to obtain a yellow solid with a yield of 95%; 1 HNMR (400MHz, CDCl 3 )δ7.85(d, J=9.0Hz, 4H), 6.85(d, J=9.1Hz, 4H), 3.41(t, J=5.0Hz, 2H), 2.53(t, J=5.0Hz, 2H) ,2.34(s,2H). 13 C NMR (101MHz, CDCl 3 )δ193.59, 154.84, 132.14, 123.32, 113.21, 54.58, 46.84, 46.05. MS (ESI+) m / z 407 [M+H] + .

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Abstract

The invention provides a bifunctional probe. The concrete structural formula of the probe is shown in the specification. In the formula, R1 is F or an N-methylpiperazinyl group, R2 is F or an N-methylpiperazinyl group, and R1 and R2 cannot simultaneously be F; and R3 is a methoxy group, a diethylamino group, a dimethylamino group, an N-methylpiperazinyl group, F or H. The probe has the advantages of simple preparation steps, easily available raw materials and stable structure, can be used for the specific detection of the orthographic parallel conformation G-quadruplex nucleic acid secondary structure, can rapidly detect the orthographic parallel conformation G-quadruplex nucleic acid secondary structure in a nucleic acid sample through an ultraviolet spectrophotometer, a fluorospectrophotometer or an enzyme linked immunosorbent assay instrument, and even naked eye observation under sunlight or an ultraviolet lamp, and overcomes the disadvantages of difficult distinguishing of many different conformations of G-quadruplex nucleic acid, high price, high device requirements and complex technical operation of other detection methods.

Description

technical field [0001] The invention belongs to the technical field of biological probes. More specifically, it relates to a bifunctional probe, its preparation method and its application in detecting the G-quadruplex in the orthoparallel conformation. Background technique [0002] 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 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 G-quadruplex structure is polymorphic. The number and orientation of the chains, the connection mode of the loop, the glycoside torsion angle of guanine, and the metal ion coordinated with the carbonyl negative center determine the type of the G-quadruplex. And conformation, these differences also provide multiple recognition sites for proteins ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D405/04G01N21/64G01N21/78C12Q1/68
Inventor 黄志纾谭嘉恒胡命豪陈硕斌
Owner SUN YAT SEN UNIV
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