Uridylated heptamethine indocyanine dye as well as preparation method and application

A kind of technology of indole heptamethanine and uracil, applied in the field of medicine

Active Publication Date: 2017-06-23
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, according to literature research, this type of dye is used for cell mitochondria Hg 2+ detection has not yet been reported

Method used

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  • Uridylated heptamethine indocyanine dye as well as preparation method and application
  • Uridylated heptamethine indocyanine dye as well as preparation method and application
  • Uridylated heptamethine indocyanine dye as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] The preparation of embodiment 1 dialdehyde chlorocyclohexene (2-chloro-3-hydroxymethane-1-formyl cyclohexene)

[0040]

[0041] In the reactor containing 60ml of anhydrous DMF, slowly drop 20ml of POCl under stirring 3 , and control the internal temperature not higher than 5°C. Add 5ml of cyclohexanone after dropping, and control the internal temperature not to exceed 10°C. After dropping, the oil was heated to raise the internal temperature to 80°C, and the reaction was stirred for 3.5 hours. Stop the reaction, pour the reaction solution into water, and stir for 3 hours. A large number of yellow solids precipitated, filtered with suction, and the filter cake was washed with cold water until neutral. The crude product was refined with ethyl acetate to obtain 5.2 g of yellow granular crystals, with a yield of 65.3%. Store away from light and low temperature (4°C). Melting point: 130-131°C (literature melting point: 130-131°C) TLC detection: cyclohexane: ethyl acet...

Embodiment 2

[0043] Example 2 Preparation of 1-(3-bromopropyl)pyrimidine-2,4(1H,3H)-dione (Compound 1)

[0044]

[0045] Add 12.0 mmol of uracil or fluorouracil to a 50 mL reaction flask, add hexamethyldisilamine (HMDS, 48.0 mmol) and 0.25 mL of trimethylchlorosilane under nitrogen protection, and then heat and stir at 126°C for reaction. After 5h, directly concentrate under reduced pressure to remove the solvent. The residue was added with 10mL of 1,3-dibromopropane, heated and stirred at 105°C to react. After 5h, it was directly concentrated under reduced pressure, the residue was dissolved in dichloromethane, washed with water, washed with saturated brine, separated, the organic layer was dried over anhydrous sodium sulfate, filtered with suction, concentrated, and purified by column separation (elution condition: CH 2 Cl 2 / CH 3 OH=50 / 1) to obtain compound 1a or 1b.

[0046] 1a (82%): 1 H NMR (400MHz, CDCl 3 ):δ11.352(s,1H),7.47-7.45(d,J=8Hz,1H),7.27-7.26(d,J=8Hz,1H),7.04-6.98...

Embodiment 3

[0048] The preparation of embodiment 3N-thymine indole quaternary ammonium bromide salt (2a, 2b)

[0049]

[0050] Take a 25mL reaction flask (with condensing reflux device), add compound 1a or 1b (1.83mmol), indole (3.66mmol). Under nitrogen protection, anhydrous acetonitrile (6 mL) was added to dissolve, and the reaction was heated and stirred at 81°C. After 22 hours, the reaction was stopped, and after the reaction solution was cooled to room temperature, the pressure was reduced directly to obtain a dark red viscous substance. The viscous material was washed with isopropyl ether and dried to obtain the crude product of the target compound (2a, 2b). The next reaction was carried out without further purification.

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Abstract

The invention relates to uridylated heptamethine indocyanine dye as well as a preparation method and application. The uridylated heptamethine indocyanine dye can be used for preparing a fluorescent probe in a kit for detecting the concentration of Hg2+ in chondriosome in a cell; the probe has the characteristics of mitochondrial targeting, near-infrared absorption, fluorescent development and the specific binding with the Hg2+.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a uracilized indole heptamethine cyanine dye and a preparation method thereof. The indole heptamethine cyanine dye can be used for cell mitochondrial Hg 2+ detection. Background technique [0002] Mercury is an environmental pollutant that is highly toxic to humans. Among them, divalent mercury ions (Hg 2+ ) is the main form of its toxicity, it can accumulate in some aquatic organisms, and enter the food chain with the consumption of other carnivores. Hg 2+ Once ingested by the human body, it is quickly distributed to various tissues and organs, among which the mitochondria in the cells are Hg 2+ main accumulation site. Hg 2+ Reduces mitochondrial membrane potential, binds to various proteins, and leads to cell death. In recent years, various high-sensitivity and high-selectivity Hg 2+ Detection methods, such as ultraviolet absorption photometry, infrared analysis, electrochemical...

Claims

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Application Information

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IPC IPC(8): C09B23/08C09K11/06G01N21/64
CPCC09B23/0016C09B23/0066C09B23/086C09K11/06C09K2211/1044G01N21/6486
Inventor 罗圣霖隆磊谭旭周君娥史春梦
Owner ARMY MEDICAL UNIV
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