Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of fluorescent probe and its preparation method and application

A technology of fluorescent probes and probes, which is applied in the field of probes, can solve the problems of high price and inability to be widely used, and achieve the effects of low cost, easy operation and stable structure

Active Publication Date: 2016-08-17
SUN YAT SEN UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application
  • A kind of fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of compound 2

[0039] Dissolve 2.01g 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

[0040] Embodiment 2: the synthesis of compound 3

[0041] Under nitrogen protection, 1.5mL POCl 3 Add dropwise to 1mL DMF and stir at room temperature for 20min. Then 0.77g2 dissolved in 4mL DMF was added dropwise to the above mixture, reacted at 60°C for 10h, cooled to room temperature, poured the reaction solution into ice water, adjusted the pH to neutral with sodium hydroxide solution, and filtered under reduced pressure , washed with water and ethanol several times, and dried in vacuo to obtain 30.50 g of an orange-yellow solid, with a yield of 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

[0042] Embodiment 3: the synthesis of compound 5a

[0043] Dissolve 4,4'-difluorobenzil in DMSO (about 0.15M), add 0.5 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 H NMR (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 / z407[M+H] + .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a fluorescent probe, as well as preparation method of the fluorescent probe, and applications of the fluorescent probe in detecting conformation of G-quadruplex nucleic acid. The specific structural formula is as shown in specification, wherein R1 in the formula is F or N-methylpiperazine, and R2 is N-methylpiperazine. The probe is simple to prepare and easily available, and stable in structure, and can be used for specifically detecting the secondary structure of the orthographically parallel conformed G-quadruplex nucleic acid, and the secondary structure of a DNA sample in a solution can be rapidly detected through a fluorospectro photometer. A method for detecting the secondary structure of the orthographically parallel conformed G-quadruplex nucleic acid through the probe has the advantages of being simple and convenient to operate, and good in selectivity, and the defects that other detection methods are difficult for various conformations of the G-quadruplex nucleic acid to distinguish, expensive in price, high in equipment requirement, relatively complicated in technical operations, and the like can be overcome.

Description

technical field [0001] The present invention relates to probes, more specifically, to a fluorescent probe and its preparation method and application. 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 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 to the different orientations of the chains, G-quadruplexes can be divid...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04G01N21/64
CPCC07D405/04G01N21/64
Inventor 黄志纾谭嘉恒吴伟彬陈硕斌胡命豪
Owner SUN YAT SEN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com