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Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof

A carbazole bridge, fluorescent cyanine technology, applied in the field of fluorescent dyes, can solve the problems of small Stocks shift, small maximum fluorescence emission wavelength, weak fluorescence intensity, etc., and achieves increased Stocks shift, large molar extinction coefficient, and increased fluorescence intensity. big effect

Active Publication Date: 2011-08-17
TIANJIN URBAN CONSTR COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak fluorescence intensity of thiazole orange (TO) and oxazole yellow (YO), the shortcomings of the maximum fluorescence emission wavelength and the small Stocks shift restrict the application of these two fluorescent dyes in biomarkers.

Method used

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  • Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof
  • Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof
  • Novel carbazole-bridge-based fluorescent cyanine dye probe and preparation method thereof

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preparation example Construction

[0024] The preparation method of the carbazole bridging fluorescent cyanine dye probe of the present invention comprises the following steps:

[0025] 1) 3-benzothiazolyl-6-formyl-N-ethylcarbazole, 3-benzoxazolyl-6-formyl-N-ethylcarbazole, 3-benzoxazolyl-6 Preparation of -formyl-N-benzylcarbazole, 3-benzothiazolyl-6-formyl-N-benzylcarbazole

[0026] Add N,N-dimethylformamide (DMF) and phosphorus oxychloride at a ratio of 1:1 to four 100mL round-bottomed flasks respectively, after dropping, stir at room temperature until the reaction system turns reddish. , the amount of substance added dropwise is 3-benzothiazolyl-N-ethylcarbazole, 3-benzoxazolyl-N-ethylcarbazole, 3-benzothiazolyl-N-ethylcarbazole, 3-benzoxazolyl- N-benzylcarbazole, 3-benzothiazolyl-N-benzylcarbazole in 1,2-dichloroethane solution, the total volume is 40-70mL, reflux and stir at the temperature of 79-85°C for 6h -12h, cooled to room temperature, poured into ice water, extracted with dichloromethane, separate...

Embodiment 1

[0035] The preparation of embodiment 1N-ethylcarbazole bridging thiazole orange dye probe comprises the following steps:

[0036] 1.3-Benzothiazolyl-6-formyl-N-ethylcarbazole

[0037] Add 7.7mL (100mmol) of DMF to a 100mL round-bottomed flask, dropwise add 9.5mL (15.2g, 100mmol) of phosphorus oxychloride in an ice-water bath, dropwise, stir at room temperature until the reaction system is reddish, slowly add 3- A solution of 2 g (6 mmol) of benzothiazolyl-N-ethylcarbazole in 30 mL of 1,2-dichloroethane was added and reacted under reflux at 83° C. for 6 h. After cooling to room temperature, it was poured into ice water, extracted with dichloromethane, and separated by column chromatography to obtain 3-benzothiazolyl-6-formyl-N-ethylcarbazole.

[0038] 2. Preparation of N-ethylcarbazole bridging thiazole orange dye probe a

[0039] Dissolve 0.1g (0.28mmol) of 3-benzothiazolyl-6-formyl-N-ethylcarbazole in 30mL of ethanol, then dissolve 0.13g (0.42mmol) of carboxyquinoline salt ...

Embodiment 2

[0041] The preparation of embodiment 2N-benzylcarbazole bridge thiazole orange dye probe comprises the following steps:

[0042] 1. Preparation of 3-benzothiazolyl-6-formyl-N-benzylcarbazole

[0043] Add DMF 7.7mL (100mmol) to the flask, add phosphorus oxychloride 9.5mL (15.2g, 100mmol) dropwise under ice-water bath, after dropping, stir at room temperature until the solution is reddish, slowly add 3-benzothiazolyl - A solution of 2.34g (6mmol) of N-benzylcarbazole in 30mL of 1,2-dichloroethane, after dropping, reflux at 83°C for 16h. After cooling to room temperature, it was poured into ice water, extracted with dichloromethane, and separated by column chromatography to obtain 3-benzothiazolyl-6-formyl-N-benzylcarbazole.

[0044] 2. Preparation of N-benzylcarbazole bridging thiazole orange dye probe k

[0045] Dissolve 0.1g (0.28mmol) of 3-benzothiazolyl-6-formyl-N-benzylcarbazole in 30mL of ethanol, then dissolve 0.13g (0.42mmol) of carboxyquinoline salt in 20mL of ethanol...

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Abstract

The invention provides a carbazole-bridge-based fluorescent cyanine dye probe. The structure of the cyanine dye probe comprises a cyanine dye probe which is formed by respectively bonding carbazole bridge bases between enzoxazol and 4-methyl quinoline salt of thiazole orange and thiazole yellow; one end of a 3-site side chain of a carbazole ring is connected with the 2-C of the enzoxazol, and the other end of the 6-formoxy is connected with 4-vinyl quinoline salt compound. The invention simultaneously provides a preparation method of the carbazole-bridge-based fluorescent cyanine dye probe. According to the invention, the preparation method of the fluorescent dye biological probe is simple, and a raw material is available; by the preparation method, the maximum emission wavelength of the newly synthesized fluorescent dye probe generates red shift, fluorescence strength is enlarged, Stocks displacement is enlarged, fluorescence quantum yield is improved, and light stability is enhanced. In the probe provided by the invention, the advantages of hiazole orange and thiazole yellow embedded fluorescent dye are maintained, thereby being beneficial to further improvement of sensitivity and reduction of dosage as well as improvement of stability. The probe provided by the invention has the characteristics of wide spectral range, large molar extinction coefficient, high capitalization rate, high sensitivity and the like.

Description

technical field [0001] The invention relates to a fluorescent dye technology starting from the chemical field and applied to the biological field, in particular to a novel fluorescent cyanine dye probe based on a carbazole bridge and a preparation method thereof. Background technique [0002] As we all know, cancer has become the number one killer that threatens human health, and how to effectively control its occurrence and development has become a top priority. Most scholars believe that in the prevention and treatment of tumors, secondary prevention of tumors, that is, early detection, early diagnosis, and early treatment will be the direction for greatly improving the curative effect of solid tumors for a long period of time in the future. Molecular biomarkers have attracted more and more attention in medical early diagnosis due to their advantages of cheapness, safety and accuracy. At present, this technology has been well applied in the identification of cancer and AI...

Claims

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Application Information

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IPC IPC(8): C09K11/06G01N21/64
Inventor 费学宁谷迎春李超杨旭
Owner TIANJIN URBAN CONSTR COLLEGE
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