A polyaryl-substituted imidazole fluorescent probe and its preparation method and application in specific detection of g-quadruplexes

A technology of fluorescent probes and quadruplexes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effects of low cost, easy storage, and stable structure

Active Publication Date: 2019-10-01
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the detection of single-sequence G-quadruplexes (such as c-MYC) in vivo and in vitro has not been reported yet

Method used

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  • A polyaryl-substituted imidazole fluorescent probe and its preparation method and application in specific detection of g-quadruplexes
  • A polyaryl-substituted imidazole fluorescent probe and its preparation method and application in specific detection of g-quadruplexes
  • A polyaryl-substituted imidazole fluorescent probe and its preparation method and application in specific detection of g-quadruplexes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the synthesis of compound 1b

[0048] The raw material 4,4-difluorobenzil (2.5g, 10mmol) was dissolved in DMSO, 5 equivalents of N-methylpiperazine and 2 equivalents of potassium carbonate were added thereto, and reacted at 80°C for 24 hours. After the reaction, DMSO and potassium carbonate were removed by washing with water to obtain a yellow solid (2.6 g, 60%). 1 H NMR (400MHz, CDCl 3 )δ7.77(d, J=8.9Hz, 4H), 6.77(d, J=9.0Hz, 4H), 3.34(m, 8H), 2.40–2.52(m, 8H), 2.30(s, 6H). 13 C NMR (100MHz, CDCl 3 )δ193.59,154.84,132.14,123.32,113.21,54.58,46.84,46.05.ESI-MS m / z:407.2[M+H] + .

Embodiment 2

[0049] Embodiment 2: the synthesis of compound 1c

[0050] Mix 1b (0.8g, 2mmol) with 1.05 equivalents of p-propargyloxybenzaldehyde and dissolve in acetic acid, add 10 equivalents of ammonium acetate, and reflux at 115°C for 20 hours. Sodium hydroxide solution adjusted Ph to weakly alkaline, extracted with ethyl acetate, mixed with silica gel, and passed through the column with dichloromethane:methanol=20:1 eluent to obtain a light yellow solid (0.7g, 65%) . 1 H NMR (400MHz, CDCl 3 )δ7.78(d, J=8.7Hz, 2H), 7.41(d, J=8.6Hz, 4H), 6.95(d, J=8.8Hz, 2H), 6.83(d, J=8.7Hz, 4H) ,4.68(s,2H),3.41(s,1H),3.35–3.04(m,8H),2.73–2.47(m,8H),2.33(s,6H). 13 CNMR (101MHz, CDCl 3 )δ157.74, 150.05, 145.27, 128.59, 126.73, 124.03, 115.68, 115.13, 78.37, 75.77, 55.88, 55.06, 48.72, 46.10. ESI-MSm / z: 547.3[M+H] + .

Embodiment 3

[0051] Embodiment 3: the synthesis of compound 2b

[0052] Fluorescein 2a (3.3 g, 10 mmol) was dispersed in 100 mL of ethanol, 2 mL of concentrated sulfuric acid was added dropwise thereto, and refluxed for 20 hours. Then part of the ethanol was removed by rotary evaporation, and water was added to adjust Ph=5, that is, a large amount of yellow solids were precipitated. The target product (3.0 g, 83%) was obtained by suction filtration. 1 H NMR (400MHz, DMSO) δ8.18 (dd, J = 7.8, 1.1Hz, 1H), 7.86 (td, J = 7.5, 1.3Hz, 1H), 7.77 (td, J = 7.7, 1.3Hz, 1H) ,7.49(dd,J=7.5,0.9Hz,1H),6.81(s,1H),6.79(s,1H),6.73–6.37(m,4H),3.96(q,J=7.1Hz,2H), 0.86(t,J=7.1Hz,3H). 13 C NMR(101MHz,DMSO)δ165.48,150.82,134.07,133.43,131.10,131.04,130.50,130.38,103.77,61.32,13.77.ESI-MS m / z:361.1[M+H] + .

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Abstract

The invention discloses a polyaryl-substituted imidazole fluorescence probe. The structural formula of the polyaryl-substituted imidazole fluorescence probe is shown in the formula (I). The invention further discloses a preparation method of the polyaryl-substituted imidazole fluorescence probe and application of the polyaryl-substituted imidazole fluorescence probe in the specific detection of a G-quadruplex. The fluorescence probe is simple to prepare, stable in structure and can be applied to the specific detection of a wild c-MYC G-quadruplex nucleic acid secondary structure, the raw materials are easily available, the wild c-MYC G-quadruplex nucleic acid secondary structure in a solution can be rapidly detected by virtue of a fluorescence spectrometer, and the fluorescence probe has no fluorescent responsiveness to mutational c-MYC G-quadruplexes or other DNA secondary structures. The method for the specific detection of the wild c-MYC G-quadruplex nucleic acid secondary structure has the beneficial effects that the operation is simple and convenient, the sensitivity and the specificity are strong, and disadvantages of other detection methods that the cost is high, the equipment requirement is high, the technical operation is relatively complex, and the like can be overcome.

Description

technical field [0001] The present invention relates to a novel fluorescent probe, more specifically to a polyaryl-substituted imidazole fluorescent probe, its preparation method and its application in specific detection of G-quadruplexes. 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 telomeric terminal guanine repeat sequence, and the promoter regions of various genes, such as c-KIT, c-MYC, BCL-2, PDGF, KRAS , VEGF 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 and small molecule compounds. According ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/14C09K11/06G01N21/64
Inventor 黄志纾谭嘉恒胡命豪陈硕斌
Owner SUN YAT SEN UNIV
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