Adenine-based cyanine probe, and preparation method and application thereof

An adenine and probe technology, which is applied in the field of adenine-based cyanine probe and its preparation, can solve the problems of high toxicity, low selectivity and low sensitivity, and achieves high sensitivity, easy control of reaction conditions and simple synthesis method. Effect

Active Publication Date: 2021-12-24
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, many fluorescent sensors currently use metal complexes, SQDs

Method used

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  • Adenine-based cyanine probe, and preparation method and application thereof
  • Adenine-based cyanine probe, and preparation method and application thereof
  • Adenine-based cyanine probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) Material 1 (0.5000g, 2.57mmol) and material 2 (0.2214g, 2.57mmol) were refluxed at 120°C for 2.5 hours under acetic acid (8ml) and nitrogen protection conditions. Ethyl ester developer (volume ratio 4:1) was passed through a silica gel column to obtain intermediate 3 (0.5100 g, 2.44 mmol, yield 94.94%).

[0025] (2) Intermediate 3 (0.5100g, 2.44mmol) and raw material 4 (2.2700g, 11.6mmol) were refluxed at 110°C for 36 hours under acetonitrile (8ml) and nitrogen protection conditions, and dissolved with 3ml of dichloromethane after removing the solvent. After adding 3 ml of diethyl ether to precipitate a solid, the solid 5 (0.6610 g, 2.04 mmol, yield 83.61%) was collected by filtration.

[0026] (3) Dissolve Intermediate 5 (0.6610g, 2.04mmol) and Intermediate 6 (0.4986g, 2.24mmol) in a mixed solution of 8mL acetic acid and 8mL acetic anhydride, reflux at 120°C for 4 hours under nitrogen, and remove solvent to obtain the crude solid intermediate 7 (1.0105g, 2.04mmol,...

Embodiment 2

[0034] (1) Material 1 (0.2500g, 1.29mmol) and material 2 (0.1107g, 1.29mmol) were refluxed at 115°C for 2 hours under the conditions of acetic acid (4ml) and nitrogen protection, and the solvent was removed after the reaction, and the mixture was washed with petroleum ether and acetic acid Ethyl ester developer (volume ratio 4:1) was passed through a silica gel column to obtain intermediate 3 (0.2318 g, 1.11 mmol, yield 86.05%).

[0035] (2) Intermediate 3 (0.2318g, 1.11mmol) and raw material 4 (1.0293g, 5.3mmol) were refluxed at 105°C for 30 hours under acetonitrile (4ml) and nitrogen protection, and dissolved in 1.5ml of dichloromethane after removing the solvent Subsequently, 1.5 ml of diethyl ether was added to precipitate a solid, and the solid 5 (0.3305 g, 1.02 mmol, yield 91.89%) was collected by filtration.

[0036] (3) Intermediate 5 (0.3305g, 1.02mmol) and Intermediate 6 (0.2493, 1.12mmol) were dissolved in a mixed solution of 4mL acetic acid and 4mL acetic anhydride...

Embodiment 3

[0040] (1) Material 1 (0.1250g, 0.645mmol) and material 2 (0.0554g, 0.645mmol) were refluxed at 110°C for 2 hours under acetic acid (2ml) and nitrogen protection conditions. Ethyl ester developer (volume ratio 4:1) was passed through a silica gel column to obtain intermediate 3 (0.1172 g, 0.56 mmol, yield 86.82%).

[0041] (2) Intermediate 3 (0.1172g, 0.56mmol) and raw material 4 (0.5071g, 2.6mmol) were refluxed at 100°C for 24 hours under acetonitrile (2ml) and nitrogen protection, and dissolved in 1.0ml of dichloromethane after removing the solvent Subsequently, 1.0 ml of diethyl ether was added to precipitate a solid, and the solid 5 (0.1653 g, 0.51 mmol, yield 91.07%) was collected by filtration.

[0042] (3) Intermediate 5 (0.1653g, 0.51mmol) and Intermediate 6 (0.1247, 0.56mmol) were dissolved in a mixed solution of 2mL acetic acid and 2mL acetic anhydride, and refluxed at 110°C for 3 hours under nitrogen to obtain a crude solid intermediate 7 (0.2527 g, 0.51 mmol, 99.9...

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Abstract

The invention belongs to the field of chemical analysis and testing, and particularly relates to an adenine-based cyanine probe, and a preparation method and application thereof. The method comprises the following steps: synthesizing a CY5.5 dye through a four-step reactionl and reacting the CY5.5 dye with adenine under the conditions of N, N'-dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP), and separating an obtained crude product through thin layer chromatography to obtain the final product. The cyanine probe obtained by the invention has excellent optical performance and hemoglobin recognition effect, and is beneficial to detection of hemoglobin.

Description

technical field [0001] The invention belongs to the field of chemical analysis and testing, and in particular relates to an adenine-based cyanine probe and a preparation method and application thereof. Background technique [0002] Hemoglobin (Hb), a metalloprotein found in red blood cells, is essential for transporting oxygen from the lungs to various parts of the body and carbon dioxide from various parts to the lungs. The level of hemoglobin in the blood is associated with many clinical diseases such as leukemia, anemia, and heart disease. Many people around the world are affected each year, mostly women and children, due to insufficient levels of hemoglobin in the blood. Therefore, accurate determination of Hb content in blood is of great significance to control some clinical diseases. [0003] The design and synthesis of chemical sensors with selective recognition function for hemoglobin has attracted much attention in recent years, and has become a research hotspot i...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06G01N21/6428
Inventor 刘晓骞秦军
Owner CHANGZHOU UNIV
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