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Fluorescent probe for quantitatively detecting heparin, and synthesis method and application thereof

A technology of fluorescent probes and synthesis methods, which is applied in the fields of biological analysis and chemical analysis, and can solve problems such as low sensitivity, large errors, and short fluorescence emission wavelengths

Inactive Publication Date: 2012-11-28
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] At present, there are few heparin chemical sensors reported in the literature, and these sensors have poor selectivity, low sensitivity, short fluorescence emission wavelength or only a single wavelength detection, resulting in unreliable detection results, large errors, and it is difficult to avoid the interference of other fluorescent substances in blood. , there are almost no practical applications

Method used

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  • Fluorescent probe for quantitatively detecting heparin, and synthesis method and application thereof
  • Fluorescent probe for quantitatively detecting heparin, and synthesis method and application thereof
  • Fluorescent probe for quantitatively detecting heparin, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The preparation of monoquaternary ammonium salt diamine includes the following steps:

[0069] Dissolve tetramethylethylenediamine in methanol, then add 0.8 times the molar amount of tetramethylethylenediamine to tetradecyl bromide, and react at 60°C for 10 hours. After concentrating the reaction solution, add water and use organic Solvent extraction and separation and separation by column chromatography, dichloromethane / methanol mixed solvent (volume ratio 8 / 1) as eluent, white solid compound: N, N, N', N'-tetramethyl-N -Tetradecyl ethylene diamine a.

[0070] 1 H NMR (400MHz, DMSO): δ 0.85 (t, 3H), 1.25 (m, 22H), 1.73 (m, 2H), 2.27 (s, 6H), 2.80 (t, 2H), 3.24 (t, 2H) ), 3.30(s, 6H), 3.34(t, 2H);

[0071] 13 C NMR(100MHz, CDCl 3 ): δ 14.2, 20.7, 22.7, 28.1, 29.3, 29.6, 31.8, 45.6, 51.7, 52.2, 60.8, 64.4. ESI-MS m / z=313.39M + , Calcd for C 20 H 45 N 2 + 313.36.

Embodiment 2

[0073] The preparation of monoquaternary ammonium salt diamine includes the following steps:

[0074] Dissolve tetramethylpropanediamine in N,N-dimethylformamide, add 0.8 times the molar amount of tetramethylpropanediamine to tetradecyl bromide, react at 50°C for 10 hours, and concentrate the reaction solution Then, water was added, the layers were extracted with organic solvent, and separated by column chromatography. The mixed solvent of dichloromethane / methanol (volume ratio 9 / 1) was used as eluent to obtain a white solid compound: N, N, N', N '-Tetramethyl-N-tetradecylpropanediamine b.

[0075] 1 H NMR (400MHz, DMSO): δ 0.85 (t, 3H), 1.26 (m, 22H), 1.73 (m, 2H), 1.83 (m, 2H), 2.27 (s, 6H), 2.36 (t, 2H) ), 3.24(t, 4H), 3.30(s, 6H);

[0076] 13 C NMR(100MHz, CDCl 3 ): δ14.1, 20.1, 20.7, 22.7, 28.1, 29.3, 29.6, 31.8, 45.9, 52.5, 57.6, 62.4, 64.7. ESI-MS m / z=327.39M + , Calcd for C 21 H 47 N 2 + 327.37.

Embodiment 3

[0078] The preparation of monoquaternary ammonium salt diamine includes the following steps:

[0079] Dissolve tetramethylhexamethylenediamine in a mixed solvent of dichloromethane and anhydrous methanol (the volume ratio of dichloromethane and anhydrous methanol is 6:1), add 0.8 times the molar amount of tetramethylhexamethylenediamine Methyl bromotetradecyl carboxylate was reacted at 30°C for 6 hours. After the reaction solution was concentrated, it was obtained by silica gel column chromatography using a dichloromethane / methanol mixed solvent (volume ratio 15 / 1) as the eluent White solid c.

[0080] 1 H NMR (400MHz, DMSO): δ, 1.26 (m, 6H), 1.29 (m, 10H), 1.30 (m, 2H), 1.68 (m, 2H), 1.73 (m, 2H), 1.83 (m, 2H) ), 2.25(t, 2H), 2.27(t, 6H), 2.36(t, 2H), 3.24(t, 4H), 3.30(s, 6H), 3.58(s, 3H).

[0081] 13 C NMR(100MHz, CDCl 3 ): δ20.1, 20.7, 25.0, 28.1, 29.0, 29.3, 29.6, 33.6, 45.4, 51.9, 52.5, 57.6, 62.4, 64.7, 173.1. ESI-MS m / z=371.36M + , Calcd for C 22 H 47 N 2 O 2 + 371.36.

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Abstract

The invention discloses a fluorescent probe which has the following structural formula, wherein R1, R2, R3, R4 and R5 are selected from C1-C18 alkyl group, aryl group, ester group or ether group; n and m are selected from 0-8; Ar is selected from naphthalene, anthracene or pyrene; and X<-> is selected from F<->, Cl<->, Br<-> or I<->. The invention also discloses a synthesis method and application of the fluorescent probe. The fluorescent probe can be used for detecting heparin in blood, and has the advantages of simple molecular structure, short response time, high detection sensitivity and simple synthesis method.

Description

Technical field [0001] The invention relates to the fields of chemical analysis and biological analysis, in particular to a fluorescent probe and its synthesis method and application. Background technique [0002] As we all know, heparin is the drug of choice that can quickly achieve anticoagulant effects. It can be used for surgical prevention of thrombus formation and anticoagulation treatment for pregnant women. For patients with acute myocardial infarction, heparin can be used to prevent venous thrombosis, and to prevent arterial embolism in patients with large anterior wall transmural myocardial infarction. Another important clinical application of heparin is to maintain unblocked blood circulation during heart, surgery and kidney dialysis. In addition, heparin can be used to treat diffuse intravascular coagulation (DIC) caused by various reasons, and it can also be used to treat glomerulonephritis, nephrotic syndrome, rheumatoid arthritis, etc. [0003] The main adverse re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07C211/63C07C209/68C07C229/16C07C227/18C07C217/58C07C213/02C07D487/08G01N33/52G01N21/64
Inventor 汪鹏飞代青刘卫敏赵文文庄晓青
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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