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Light-operated dual-channel fluorescent dye and preparation method and application thereof

A fluorescent dye, dual-channel technology, applied in the field of light-controlled dual-channel fluorescent dyes and their preparation, can solve the problems of poor photochemical stability, low fluorescence quantum yield and the like, achieve improved fluorescence intensity, avoid low fluorescence quantum yield, Effect of increasing photochemical stability

Active Publication Date: 2020-09-04
CHIFENG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the deficiencies in the prior art, the present invention provides a kind of light control dual-channel fluorescent dye and its preparation method and application, the new compound provided by the present invention The molecule has a 1,8-naphthalimide skeleton that can emit green fluorescence and two spiropyran units that can emit red fluorescence after illumination. The result of the two spiropyran units’ cooperative ring opening will make it open The fluorescence intensity of the body is increased, which in turn increases the efficiency of fluorescence resonance energy transfer, and the ring-closing isomerization will not quench the fluorescence after the light is stopped, avoiding the low fluorescence quantum yield and photochemical stability of general near-infrared fluorescent labeling dyes. Poor disadvantages; the N-hydroxysuccinimide ester introduced in the molecule can be used to stably bond with the amino groups in biomolecules, and emit green fluorescence before illumination, emit red fluorescence after illumination, and reduce the fluorescence intensity in the green light area It can realize the function of dual-channel co-localization fluorescent labeling of biomolecules

Method used

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  • Light-operated dual-channel fluorescent dye and preparation method and application thereof
  • Light-operated dual-channel fluorescent dye and preparation method and application thereof
  • Light-operated dual-channel fluorescent dye and preparation method and application thereof

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preparation example Construction

[0036] The preparation method of the above-mentioned light-controlled dual-channel fluorescent dye comprises the following steps:

[0037] S1, using absolute ethanol as a solvent, 4-bromo-1,8-naphthalene dicarboxylic anhydride and glycine tert-butyrate as raw materials, stirring and reflux temperature, to prepare intermediate 1 through condensation reaction;

[0038] S2, dissolving the intermediate 1 prepared in S1 in ethylene glycol monomethyl ether, adding diethanolamine, stirring, and preparing intermediate 2 through a nucleophilic substitution reaction at reflux temperature;

[0039]S3. Mix the intermediate 2, 1-carboxyethylspiropyran, dicyclohexylcarbodiimide, 4-dimethylaminopyridine and dichloromethane prepared in S2, and carry out esterification under room temperature and dark conditions. Reaction makes intermediate 3;

[0040] S4. The intermediate 3 prepared in S3 is first subjected to a deprotection reaction, and then mixed with N-hydroxysuccinimide, dicyclohexylcarb...

Embodiment 1

[0045] A method for preparing a light-controlled dual-channel fluorescent dye, comprising the following steps:

[0046] (1) Synthesis of intermediate 1

[0047] The amount of 4-bromo-1,8-naphthalene dicarboxylic anhydride and glycine tert-butyrate in absolute ethanol was stirred and refluxed for 4 hours, the consumption of 4-bromo-1,8-naphthalene dicarboxylic anhydride and absolute ethanol The ratio is 1mmol: 30mL, after cooling to room temperature, pour it into deionized water, add ethyl acetate for extraction, dry the organic layer with anhydrous magnesium sulfate, filter out the desiccant, add activated carbon for decolorization, evaporate most of the solvent, and cool Set, and filtered to obtain a light yellow solid, which is intermediate 1.

[0048] 1 H NMR [CDC1 3 ,300MHz]δ=1.49(s,9H),4.83(s,2H),7.85(t,1H),7.04(d,1H),8.42(d,1H),8.58(d,1H),8.66(d ,1H).

[0049] (2) Synthesis of intermediate 2

[0050] Dissolve 1.65g (4mmol) of intermediate 1 in 50mL of ethylene glyc...

Embodiment 2

[0062] A method for preparing a light-controlled dual-channel fluorescent dye, comprising the following steps:

[0063] Step is with embodiment 1, and difference is:

[0064] In step (1), the molar ratio of 4-bromo-1,8-naphthalene dicarboxylic anhydride and glycine tert-butyrate is 1:1.5, the amount of 4-bromo-1,8-naphthalene dicarboxylic anhydride and absolute ethanol The ratio is 1mol: 20L, and the reaction time is 3.5h;

[0065] In step (2), the dosage ratio of intermediate 1 and diethanolamine is 1mol:1L, the volume ratio of ethylene glycol monomethyl ether and diethanolamine is 40:3, and the reaction time is 9.5h;

[0066] In step (3), the ratio of intermediate 2: 1-carboxyethylspiropyran: dicyclohexylcarbodiimide: dichloromethane is 1mmol: 2.2mmol: 2.4mmol: 75mL; intermediate 2: 4 -The molar ratio of dimethylaminopyridine is 10:1, and the reaction time is 11.5h;

[0067] In step (4), the mol ratio of intermediate 3: N-hydroxysuccinimide: dicyclohexylcarbodiimide is 1:...

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Abstract

The invention discloses a light-operated dual-channel fluorescent dye and a preparation method and application thereof, and belongs to the technical field of organic optical functional materials. Thestructural formula of the light-operated dual-channel fluorescent dye is shown as a formula (I), molecules of the new compound obtained by the invention have a 1, 8-naphthalimide skeleton capable of emitting green fluorescence and two spiropyrane units capable of emitting red fluorescence after illumination so that the fluorescent dye is enabled to have obvious photochromic and light-regulated double-color fluorescence properties, and succinimide active ester groups enable the fluorescent dye to be stably bonded with amino groups, and thus the fluorescent dye can be used as a fluorescence labeling dye for double-channel co-localization of biomolecules.

Description

technical field [0001] The invention belongs to the technical field of organic optical functional materials, and in particular relates to a light-controlled dual-channel fluorescent dye, a preparation method and application thereof. Background technique [0002] In recent years, the technology of fluorescent labeling of biomacromolecules has achieved relatively rapid development. After fluorescent labeling of biomolecules, sensitive and accurate fluorescence methods can be applied, such as live cell imaging using fluorescent confocal microscopy, intracellular and intracellular The detection of substances and nucleic acids, etc., so fluorescent labeling technology plays an important role in the fields of biological and medical research. [0003] Fluorescent dye-labeled protein or peptide technology is a common in vitro labeling technology for biological macromolecules. Since amino groups are very common in proteins and peptides, and N-hydroxysuccinimide ester (NHS ester) can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D519/00C09B57/08G01N1/30G01N21/64
CPCC09K11/06C07D519/00C09B57/08G01N1/30G01N21/6486C09K2211/1029C09K2211/1033G01N2001/302Y02E10/542
Inventor 杨素华刘箫音段永平莫显红卢晓会吕杰
Owner CHIFENG UNIV
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