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Compound containing double-rhodamine B and preparation method and application of compound

A compound and target compound technology, applied in biochemical equipment and methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as easy decomposition, low selectivity of biomarkers, and weak cell penetration ability of probes. To achieve the effect of optimizing performance

Inactive Publication Date: 2012-08-15
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the development of environmental, medical, biological and other disciplines, it has gradually become apparent that rhodamine-based dye probe molecules are insufficient in the application of biological fluorescent recognition tags, for example: the selectivity for specific biomarkers is not high; Sensitive, poor chemical stability, easy to decompose under strong light detection; poor solubility in solvents under physiological conditions; weak probe penetration into cells, etc.

Method used

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  • Compound containing double-rhodamine B and preparation method and application of compound
  • Compound containing double-rhodamine B and preparation method and application of compound
  • Compound containing double-rhodamine B and preparation method and application of compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Synthesis of compound I 2,5-bis[rhodamine B-9'-(2''-benzoyl)yl]-1,3,4 oxadiazole:

[0062] (1) Synthesis of rhodamine hydrazide

[0063] Dissolve 5 g (10.4 mmol) of rhodamine B in 100 mL of ethanol and put it into a 250 mL flask, then add 0.9 mL of 85% (15.6 mmol) hydrazine hydrate dropwise to the mixed system at room temperature After the dropwise addition, the mixture was heated under strong reflux for 3 hours. When the solution changed from dark purple to clear bright orange, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. 1M HCl was added to the evaporated mixture, and then 1M Adjust the pH of the mixture to 9 with NaOH, filter with suction, and wash the product 3 times with 15 mL of distilled water. 3.33 g of the product was obtained, yield: 70%.

[0064] (2) Preparation of rhodamine B acid chloride

[0065] Add 10.00 g (20.9 mmol) of Rhodamine B and 3 mL of phosphorus oxychloride into a 100 mL flask, r...

Embodiment 2

[0068] Synthesis of Compound I 2,5-bis[rhodamine B-9'-(2''-benzoyl)yl]-1,3,4-oxadiazole:

[0069] (1) Synthesis of rhodamine hydrazide

[0070] Dissolve 5 g (10.4 mmol) of Rhodamine B in 100 mL of ethanol and put it into a 250 mL flask, then add 8 mL of 85% (138.6 mmol) hydrazine hydrate dropwise to the mixed system at room temperature After the dropwise addition, the mixture was heated under strong reflux for 10 hours. When the solution changed from dark purple to clear bright orange, the reaction was complete, cooled to room temperature, and the solvent was removed under reduced pressure. 1M HCl was added to the evaporated mixture, and then 1M The pH of the mixture was adjusted to 9 with NaOH, suction filtered, and the product was washed 5 times with 15 mL of distilled water. Obtain product 4.1 g, yield: 87%

[0071] (2) Preparation of rhodamine B acid chloride

[0072] Add 10.00 g (20.9 mmol) of Rhodamine B and 35 mL of phosphorus oxychloride into a 100 mL flask, reflux ...

Embodiment 3

[0075] Intermediate compound II N , N’ -Synthesis of [rhodamine B-9'-(2-benzoyl) base]hydrazine:

[0076] (1) Synthesis of rhodamine hydrazide

[0077] Dissolve 5 g (10.4 mmol) of rhodamine B in 100 mL of ethanol and put it into a 250 mL flask, then add 0.6 mL of 85% (10.4 mmol) hydrazine hydrate dropwise to the mixed system at room temperature After the dropwise addition, the mixture was heated under strong reflux for 3 hours. When the solution changed from dark purple to clear bright orange, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. 1M HCl was added to the evaporated mixture, and then 1M Adjust the pH of the mixture to 9 with NaOH, filter with suction, and wash the product 3 times with 15 mL of distilled water. 3.27 g of the product was obtained, yield: 69%.

[0078] (2) Preparation of rhodamine B acid chloride

[0079] Add 10.00 g (20.9 mmol) of Rhodamine B and 20 mL of phosphorus oxychloride into a 100 ...

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Abstract

The invention discloses 2, 5-di (rhodamine B-9'-(2''-benzoyl) radical)-1, 3, 4-diazole fluorescent stain compound I and a preparation method and application thereof. The compound I has excellent dissolubility in water, emits strong fluorescent light and can be applied to being biological stain, namely cell stain, and water solution of the compound I cannot suddenly extinct in fluorescence spectrum in a range of the pH (potential of hydrogen) value from 2 to 10. The compound I can be prepared from rhodamine B and phosphorus oxychloride directly or can be prepared through intermediate compound IIN and N'-double-rhodamine B hydrazine. The invention further discloses the application of the structural formula I serving as biological stain, namely cell stain.

Description

[0001] The invention was conducted with the funding of the Tianjin Normal University Development Fund (fund number 52XK1102). Technical field [0002] Ben Mingfa belongs to the field of chemical sensing technology, involving compounds I 2,5-2 [Rodin Ming B-9 '-(2' '-zide) base]Sports compound II N ,, N’ -Drinodama B -based 物 compounds, and their preparation methods, the use of compound I is used as a biological staining agent for cell dyes. Background technique [0003] The development and application of fluorescent dye probe molecules is a cross -area of chemistry and biological science.The fluorescent probe technology is based on the molecular physics and photochemical characteristics, and the fluorescent analysis method of researching objects at the molecular scale is determined by the fluorescent peak wavelength or fluorescent microscopic imaging of the fluorescent probe marker.Essence [0004] The use of fluorescent probes for chemical lighting imaging is a means to achieve h...

Claims

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Application Information

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IPC IPC(8): C07D413/14C07D519/00C09K11/06C09B57/00G01N21/64C12Q1/02
CPCC09B11/24G01N33/582
Inventor 史学芳马媛柴璐郭萍胡灵敏
Owner TIANJIN NORMAL UNIVERSITY
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