Symmetric pentamethyl cyanine dye and application thereof to molecular imaging

A cyanine dye, symmetrical technology, applied in the field of organic compounds and their preparation, can solve the problems of complex synthetic routes, poor photostability, and many by-products, and achieve strong membrane permeability, simplified synthetic steps, and low toxicity of living cells Effect

Inactive Publication Date: 2013-06-12
XIDIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of pentamethine dyes and their application in cell imaging and optical molecular imaging studies by using sulfhydryl groups to replace the chlorine atoms on the methine chain have not been reported in the literature, and the existing fluorescent probes of cyanine dyes used in molecular imaging It has the disadvantages of complex synthetic route, many by-products, difficult purification, poor photostability, etc.

Method used

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  • Symmetric pentamethyl cyanine dye and application thereof to molecular imaging
  • Symmetric pentamethyl cyanine dye and application thereof to molecular imaging
  • Symmetric pentamethyl cyanine dye and application thereof to molecular imaging

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of Compound B1 and Compound B2:

[0052] (1) Synthesis of iodide N-methyl-2,3,3-trimethyl-5-sulfonic acid group-3H-indole quaternary ammonium salt (compound B1)

[0053] Add 2.8g (10mmol) 2,3,3-trimethyl-5-sulfonic acid-3H-indole A and 2.8g (20mmol) iodomethane into a sealed reaction kettle containing 40mL methanol, and heat to 75°C React for 24 hours; if ethanol is used instead of methanol as the reaction solvent, the reaction temperature is 85°C; if iodomethane is directly used as the reaction solvent, the reaction temperature is 70°C, after cooling, part of the methanol is evaporated in a vacuum rotary until solid appears at the bottom of the bottle, and suction filtered The crude product was washed with ether to obtain 3.3 g of yellow-brown solid quaternary ammonium salt with a yield of 80%.

[0054] (2) Synthesis of iodide N-ethyl-2,3,3-trimethyl-5-sulfonic acid group-3H-indole quaternary ammonium salt (compound B2)

[0055] Add 2.8g (10mmol) 2,3,3-tr...

Embodiment 2

[0057] The preparation of Wujiachuan condensation agent compound C:

[0058] Dissolve 5g (30mmol) of dichlorocrotonin in 15mL of absolute ethanol, add 5.8g (60mmol) of aniline in 20mL of absolute ethanol, heat at 80-85°C for 30min under reflux; or use methanol as the reaction solvent , heated at 70-75° C. to reflux for 30 minutes, an orange solid precipitated out, was filtered by suction, washed with ether, and recrystallized from absolute ethanol to obtain 7.6 g of a bright orange solid with a yield of 86%.

Embodiment 3

[0060] Synthesis of dye CyI-1 and dye CyI-2:

[0061]

[0062] Put 7mmol indole quaternary ammonium salt B1 or B2 and 0.0035mmol pentamethine condensing agent C in 45mL glacial acetic acid and 45mL acetic anhydride, and react under reflux for 1 to 2 hours. The ratio is strictly 2:1. When the molar ratio of feed is less than 2:1, the by-product of pentamethine semicyanine dye will be generated. After the reaction, the crude product was recrystallized with methanol:water=5:1 to obtain a bright dark green solid, and the yield of dye CyI-1 and dye CyI-2 was about 50%. The NMR and mass spectrometry data of product structure identification are as follows:

[0063] CyI-1: 1 H NMR (400 MHz, DMSO-d 6 ) δ (ppm): 1.73 (s, 12H, C (CH 3 ) 2 ), 3.68(s, 6H, NCH 3 ), 6.29 (d, 2H, J=13.6 Hz, -CH=), 7.43 (d, 2H, J=8.0 Hz, ArH), 7.67 (d, 2H, J=8.0 Hz, ArH), 7.88 (s, 2H, ArH), 8.47 (d, 2H, J=13.6 Hz, -CH=). 13 C NMR (400 MHz, DMSO-d 6 )δ (ppm): 26.04, 66.93, 99.72, 110.30, 119.52, 121...

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Abstract

A symmetric pentamethyl cyanine dye with a general formula I and application thereof to molecular imaging belong to the fields of organic compound and optical molecular imaging. In the general formula I, X represents Cl or S (CH2)nCOOH or II; R1 represents C1-6 alkyl, (CH2) pOR3 or (CH2) pC6H5; R2 represents H, methyl, hydroxy, halogen, nitro, benzyloxy, alkoxy or a water-soluble group SO3R4; and R4 represents H, sodium ion or potassium ion; and Y<-> represents halogen ion, PF6<-> or TsO<->. An asymmetric synthesis method is employed to prepare a pentamethyl cyanine dye fluorescence probe with the general formula I, in order to solve the problems of an asymmetric synthesis method, such as tedious steps, by-product and low yield. The dye has advantages of low toxicity, active cell membrane permeability and good light stability, and can be used for labeling live cells and in the field of molecular imaging.

Description

technical field [0001] The present invention relates to the field of organic compounds and preparation methods thereof, and further relates to the application of such organic compounds in the field of optical molecular imaging technology, in particular to a class of symmetrical pentamethine dyes and their preparation methods and the use of symmetrical pentamethine dyes as fluorescent detectors. Needle, in live cell imaging research and its application in optical molecular imaging. Background technique [0002] Molecular imaging technology has the advantages of high sensitivity and no radiation. It can realize real-time, non-invasive and dynamic imaging of physiological and pathological changes of biological organisms at the cellular molecular level. It is an effective method for early diagnosis of diseases, prediction and evaluation of curative effects. Using sensitive optical detection instruments to observe biological processes such as diseases, tumor development, metastas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/16A61K49/00
Inventor 张象涵辛静梁继民田捷詹勇华陈丹王福屈晓超
Owner XIDIAN UNIV
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