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A kind of preparation method of quinoxaline fluorescent probe and its application in detecting g-quadruplex

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

Active Publication Date: 2021-06-29
SHENZHEN UNIV
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  • Summary
  • 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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  • A kind of preparation method of quinoxaline fluorescent probe and its application in detecting g-quadruplex
  • A kind of preparation method of quinoxaline fluorescent probe and its application in detecting g-quadruplex
  • A kind of preparation method of quinoxaline fluorescent probe and its application in detecting 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 fluorescent probe and its application in detecting G-quadruplexes. At least one of ethylamino, R2 adopts F, methyl, and R3 adopts at least one of F, methyl, N-methylpiperazinyl and triazolyl. Compared with the prior art, the present invention has the following advantages: (1) The probe is easy to prepare, easy to obtain, stable in structure and convenient for storage. (2) The probe provided by the present invention can specifically detect the G-quadruplex structure, realize the distinction between the G-quadruplex structure and other secondary structures, and use a simple fluorescence spectrometer, even without any instrument, to observe with the naked eye The secondary structure of the nucleic acid sample can be identified, which is fast, easy to operate, low in cost, and can realize on-site detection. (3) The probe has no obvious influence on the secondary structure of the nucleic 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 Patents(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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