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Fluorescent molecular switch and fluorescent probe thereof, and applications of fluorescent probe

A technology of fluorescent molecules and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of rare organic fluorescent small molecule materials, and achieve the effect of reducing costs and time

Inactive Publication Date: 2015-07-15
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, apart from several common commercial nucleic acid-labeled organic small molecule fluorescent dyes, the research on organic fluorescent small molecule materials in the construction of molecular logic gates and logic devices is still rare.

Method used

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  • Fluorescent molecular switch and fluorescent probe thereof, and applications of fluorescent probe
  • Fluorescent molecular switch and fluorescent probe thereof, and applications of fluorescent probe
  • Fluorescent molecular switch and fluorescent probe thereof, and applications of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Synthesis of small molecule derivatives of fluorene (compound 5) (see figure 1 ):

[0050] Add 2 g of fluorene, 20 mL of chloroform, and 10.6 mg of iron powder to a 50 mL round-bottomed flask, cool it to below 0°C in an ice bath, and slowly add a mixture of 4.12 g of liquid bromine and 10 mL of chloroform dropwise. After the dropwise addition, the reaction is continued for 2 hours. Aqueous sodium bisulfite was added to remove excess bromine. The chloroform layer was separated, concentrated, the solid was filtered out, and then purified by recrystallization from chloroform to obtain 2.95 g of 2,7-dibromofluorene (compound 1) as white crystals, yield: 78.5%.

[0051] 1.5 g of 2,7-dibromofluorene, 0.009 g of triethylbenzyl ammonium chloride, and 30 mL of dimethyl sulfoxide were placed in a three-necked flask to form a suspension, and 1.5 mL of 50wt% sodium hydroxide aqueous solution was added dropwise, and the reaction was carried out for half an hour. , 1.59g of 1-bromo...

Embodiment 2

[0057] Design and Synthesis of Small Molecular Derivatives of Fluorene / DNA Probes

[0058] Dissolve compound 5 (100 mg) and N-hydroxysuccinimide (91.25 mg) obtained in Example 1 in 10 mL of anhydrous N,N-dimethylformamide (DMF), and then slowly add 1,3-dimethylformamide (DMF). The solution of cyclohexylcarbodiimide (DCC, 92.75mg) dissolved in 5mL DMF, after adding, react at room temperature for 24h, thin layer chromatography (TLC) detects the end of the reaction, the reaction solution is extracted with dichloromethane, and the solvent is removed under reduced pressure , and column chromatography (petroleum ether: ethyl acetate = 3:1) separated a light yellow solid (compound 6), and its nuclear magnetic detection results were as follows:

[0059] 1 H NMR (600MHz, CDCl 3 ):δ8.17(d,J=8.4Hz,4H),7.75(m,6H),7.59(t,J=7.2Hz,2H),7.54(s,2H),2.87(s,8H),2.00 (m,4H),1.26-0.62(m,22H).

[0060] The above-obtained compound 6 is connected to the 5'-terminal amino group of DNA through the a...

Embodiment 3

[0065] Example 3: Molecular switch construction based on fluorene-based small molecule derivatives (compound 5)

[0066] Compound 5 in Example 1 was dissolved in DMSO to obtain a concentration of 1.7×10 -3 M's mother liquor. The pH value of 2 mL of ultrapure water was adjusted to 1-14 with 5M NaOH and 12M HCl, and a certain amount of mother liquor was added to obtain the working solution. After mixing the samples with a pipette, UV absorption spectroscopy and fluorescence emission spectroscopy were performed. At the same time, compound 6 (dissolved in DMF) in Example 1 was used as a control sample and operated in parallel according to the above method.

[0067] from the attached image 3 It can be seen that the UV absorption peak of compound 5 appears at 350 nm under acidic conditions (pH1-6); and with the increase of pH value, under neutral and basic (pH7-14) conditions, UV absorption peaks appear A blue shift of 10 nm means that the absorption peak is at 340 nm. from th...

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Abstract

The present invention relates to a fluorescent probe, particularly to a fluorene small molecule derivative fluorescent probe and applications thereof, wherein the fluorene small molecule derivative is adopted as a fluorescent molecular switch, the fluorescent probe is the DNA-modified fluorene small molecule derivative, and the applications of the fluorene small molecule derivative fluorescent probe in fluorescent molecular switches and logic gate, and cell fluorescence imaging are provided. According to the present invention, the advantages and the characteristics of the crossing integration of material science, organic chemistry, biology and computer science are presented, and the new method for constructing the logical system at the molecular level is provided.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent molecular switch, the fluorescent probe and the application of the fluorescent probe. Background technique [0002] The speed of computer development in recent decades has been astounding. However, the density of integrated circuits based on silicon chips has approached the theoretical limit, which has become a technical problem restricting the further development of modern electronic computers. The realization of artificial intelligence depends on the density and complexity of computer circuits. For this reason, it may be difficult for electronic circuits based on semiconductor technology to generate real cognitive capabilities. The way out to solve the above problems is to completely abandon the traditional silicon semiconductor electronic devices in terms of concept and technology, and then study molecular computers, and then develop biomolecular computers based on biologic...

Claims

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Application Information

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IPC IPC(8): C07C63/49C07C27/02C12N15/11G01N21/64
Inventor 郭静孟晋宇阳仁强王婷
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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