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Preparation method of quinoxaline type fluorescent probe and application of quinoxaline type fluorescent probe in detection of G-quadruplex

A technology of fluorescent probes and quadruplexes, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve low cost, stable structure, and simple preparation

Active Publication Date: 2019-01-18
SHENZHEN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the research on G-quadruplexes at this stage only involves a small number of gene sequences, and there are still a large number of G-quadruplex potential sequences (PQS) to be experimentally verified

Method used

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  • Preparation method of quinoxaline type fluorescent probe and application of quinoxaline type fluorescent probe in detection of G-quadruplex
  • Preparation method of quinoxaline type fluorescent probe and application of quinoxaline type fluorescent probe in detection of G-quadruplex
  • Preparation method of quinoxaline type fluorescent probe and application of quinoxaline type fluorescent probe in detection of G-quadruplex

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of compound 2

[0036] Dissolve the raw material 3,6-dibromo-9,10-phenanthrenequinone in 20mL DMSO (2.0g), add 5 times the molar equivalent of N-methylpiperazine and 1 times the molar equivalent of K2CO3, in an oil bath at 90°C After heating and reacting for 24 hours, the reaction solution was poured into 200 mL of ice water, a large amount of solids were precipitated, filtered under reduced pressure, and dried in vacuo to obtain a purple solid with a yield of 80%. Mass spectrometry confirmed the structure. MS(ESI)m / z405.2[M+H]+.

Embodiment 2

[0037] Embodiment 2: the synthesis of compound 3 (BQX-1)

[0038] Disperse compound 2 in 100mL ethanol (1.0g), add 2 times the molar equivalent of 4,5-difluoro-o-phenylenediamine, add 5 drops of glacial acetic acid as a catalyst to the reaction system, and reflux for 20 hours; after the reaction, After natural cooling, solids were precipitated, vacuum filtration under reduced pressure, and the filter cake was washed 3 times with a small amount of ethanol to obtain a brownish-yellow solid with a yield of about 60%. 1H NMR (500MHz, CDCl3) δ9.11 (d, J = 8.8Hz, 2H), 7.93 (t, J = 9.5Hz, 2H), 7.87–7.77 (m, 2H), 7.37–7.30 (m, 2H) ,3.66–3.49(m,8H),2.95–2.71(m,8H),2.50(s,6H).13C NMR(126MHz,CDCl3)δ152.50,151.83,142.09,138.48,133.15,127.40,122.02,116.73,113.71 ,107.21,77.37,77.11,76.86,54.75,48.04,45.77.MS(ESI)m / z 513.3[M+H]+.

Embodiment 3

[0039] Embodiment 3: the synthesis of compound BQX-2

[0040] Compound 3 (BQX-1) was dissolved in 10 mL of DMF (0.5 g), and 5 molar equivalents of N-methylpiperazine and 1 molar equivalent of K 2 CO 3, heated and reacted in an oil bath at 80°C for 24h, then poured into ice water, solids were precipitated, filtered under reduced pressure, and dried in vacuo. Then it was separated by column chromatography, and the eluent was dichloromethane / methanol (volume ratio 30:1) to obtain a yellow solid with a yield of about 50%. 1H NMR (500MHz, CDCl3) δ9.14(d, J=6.1Hz, 2H), 7.87–7.74(m, 3H), 7.61(d, J=8.5Hz, 1H), 7.35(d, J=8.2Hz ,2H),3.60–3.47(m,8H),3.47–3.35(m,4H),2.86–2.71(m,12H),2.48(s,9H).13C NMR(126MHz,CDCl3)δ157.46,152.30,152.21 ,143.14,141.64,140.83,139.98,138.44,133.03,132.81,127.23,127.16,122.90,122.86,117.11,117.04,114.96,112.70,107.58,107.55,77.34,77.08,76.83,54.88,50.23,48.42,48.38,45.91 ,45.88.MS(ESI)m / z 593.3[M+H]+.

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Abstract

The invention provides a preparation method of a quinoxaline type fluorescent probe and application of the quinoxaline type fluorescent probe in detection of a G-quadruplex. The structural formula ofthe quinoxaline type fluorescent probe is as shown in the specification. In the formula, R1 adopts at least one of N-methylpiperazinyl, morpholinyl and diethylamino, R2 adopts F and methyl, and R3 adopts at least one of F, methyl, N-methylpiperazinyl and triazolyl. Compared with the prior art, the probe provided by the invention has the following advantages: (1) the probe is simple in preparation,easily available, stable in structure and convenient to store; (2) the probe provided by the invention can specifically detect a G-quadruplex structure to distinguish the G-quadruplex structure fromother secondary structures, the secondary structure of a nucleic acid sample can be identified by using a simple fluorescence spectrophotometer or even can be observed with naked eyes without any instrument, the process is fast, the operation is simple and convenient, the cost is low, and field inspection can be realized; and (3) the probe has no obvious influence on the secondary structure of thenucleic acid to be detected, and can accurately detect the original structure of the nucleic acid.

Description

technical field [0001] The invention relates to a preparation method of a novel G-quadruplex fluorescent probe and its application in detecting the secondary structure of G-quadruplex nucleic acid. Background technique [0002] The G-quadruplex is a special nucleic acid higher-order structure formed by self-assembly of guanine (G)-rich nucleic acid sequences. Studies such as bioinformatics have shown that there are a large number of potential sequences that can form G-quadruplexes (putative quadruplex sequence, PQS), and more and more evidences show that G-quadruplexes participate in the regulation of many important biological processes, such as telomere end protection, DNA replication, transcription and translation, etc., and in cell proliferation, apoptosis and aging, It plays an important regulatory role in the occurrence and development of tumors. The G-quadruplex is considered to function as a molecular switch, and its formation and disassembly may involve a series of...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/38C07D403/04C09K11/06G01N21/64
CPCC07D241/38C07D403/04C09K11/06C09K2211/1044C09K2211/1059G01N21/6428
Inventor 胡命豪靳广毅
Owner SHENZHEN UNIV
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