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Synthesis and application of indole hemicyanine dye

A technology for indole and cyanine dyes, applied in the synthesis and application of indole semicyanine dyes, can solve problems such as hindering application, increasing the water solubility of dyes, reducing cell membrane permeability, etc. Fluorescence background interference, the effect of wide emission wavelength range

Inactive Publication Date: 2013-03-13
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although dual dyes connected by flexible chains (charged or uncharged) have appeared in the first three types of semi-cyanine dyes, there are very few indole-based bis-semicyanine dyes for biomolecular detection, while those for protein detection Indole bis-semicyanine dyes have not been reported
It is worth noting that among all the above-mentioned biscyanine dyes, there are few reports on the structure with living cell permeability, which may be because most of the reported biscyanine dyes use positively charged carbon chains as linking groups, which increase the water solubility of the dyes. , which reduces the cell membrane permeability and hinders the application of these dyes with superior properties in the visualization of living cell organelles

Method used

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  • Synthesis and application of indole hemicyanine dye
  • Synthesis and application of indole hemicyanine dye
  • Synthesis and application of indole hemicyanine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0094] Synthesis of dye intermediate 1-methyl-5-nitro-2,3,3-trimethyl-3H indole quaternary ammonium salt:

[0095] Add 20mmol of 5-nitro-2,3,3-trimethyl-3Hindole and 40mmol of iodomethane into a 100ml round-bottomed flask containing 20ml of toluene under argon protection. The reaction was heated to reflux for 20 h and then stopped. After the mixture was cooled, the precipitate was filtered and the filter cake was washed with ether. After drying, a light yellow solid powder was obtained with a crude yield of 85%.

Embodiment 2

[0097] Preparation of Compound A:

[0098]

[0099] Add 5mmol of 1-methyl-5-nitro-2,3,3-trimethyl-3H indole quaternary ammonium salt and 6mmol of p-hydroxybenzaldehyde into a 25ml round-bottomed flask containing 10ml of ethanol, nitrogen protection, stirring at room temperature After 24 h, the reaction solution was placed at -20 °C overnight. The precipitated solid was collected by filtration, rinsed with ethyl acetate, and then dried in vacuo to obtain an orange-yellow solid powder with a yield of 85%.

[0100] 1H NMR (400 MHz, DMSO-d6, ppm): 1.87 (s, 6H, C(CH3)2), 4.12 (s, 3H, CH3-N+), 7.00 (d, 2H, J = 8.4, Ar-H ), 7.52 (d, 1H, J = 16, CH=CH), 8.06 (d, 1H, J = 8.8, Ar-H), 8.23 ​​(d, 2H, J = 8.4, Ar-H), 8.50 (d , 1H, J = 8.8, Ar-H), 8.56 (d, 1H, J = 16, CH=CH), 8.83(s, 1H, Ar-H), 11.09(s, 1H, OH). 13C NMR ( 100 MHz, DMSO-D6, PPM): 25.45, 34.44, 52.02, 109.29, 115.36, 116.67, 118.63, 126.09, 134.65, 146.59, 147.00, 156.89, 184.64. for C19H19N2O3 [M-I-]+ 323.1390, found ...

Embodiment 3

[0102] Preparation of Compound B:

[0103]

[0104] 5mmol 1-propargyl-2,3,3-trimethyl-3H indole quaternary ammonium salt and 5mmol 3-Br-4-hydroxybenzaldehyde were added to a 25ml round-bottomed flask containing 10ml methanol, nitrogen protection, After heating to reflux for 4 h, the reaction solution was placed at -20 °C overnight. The precipitated solid was collected by filtration, rinsed with ethyl acetate, and then dried in vacuo to obtain an orange solid powder with a yield of 88%.

[0105]1H NMR (400 MHz, CDCl3, ppm): 1.73 (s, 6H, C(CH3)2), 3.31 (t, 1H, J = 2.38, Alkyne-H) 5.41 (s, 2H, CH2-N+), 6.82 (d, 2H, J = 8.8, Ar-H), 7.19 (d, 1H, J = 15.6, CH=CH), 7.46 (t, 1H, J = 7.2, Ar-H), 7.54 (t, 1H, J = 7.6, Ar-H), 7.67 (d, 1H, J = 8.0, Ar-H), 7.75 (d, 1H, J = 7.2, Ar-H), 7.99 (d, 1H, J = 8.8, Ar -H), 8.19 (d, 1H, J = 15.6, CH=CH), 8.45 (s, 1H, Ar-H). 13C NMR (100 MHz, DMSO-d6, ppm): 26.09, 33.92, 51.16, 72.24 , 81.35, 113.8, 114.68, 119.45, 123.05, 125.24, 127.79, 129....

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Abstract

Belong to synthesis of functional dyes and their application as fluorescent dyes in the field of fine chemicals, the invention relates to synthesis and application of an indole hemicyanine dye. The compound is formed by condensation of an indole quaternary ammonium salt and corresponding aldehyde, and has the advantages of large molar extinction coefficient, good light stability, and easy synthesis, etc. According to different substituent groups and anions, the molecule involved in the invention can have pH probe properties, solid-state fluorescence properties and the performance to combine with biomacromolecules. When serving as a pH probe, the compound can adjust probe pKa according to different substituent groups, and can be used for bi-color living cell imaging; when serving as a solid-state emission dye, the compound can adjust its solid-state emission wavelength according to different substituent groups and anions; and when serving as a biomolecular probe, the compound has good response to biological molecules and live cell membrane permeability, and can be used for cell staining. Due to its long absorption and emission wavelength, the compound can avoid the interference of biomass autofluorescence, and also reduce the damage of excitation light on cells or biological tissues.

Description

technical field [0001] The invention relates to the synthesis and application of a class of indole semicyanine dyes, belonging to the synthesis of a class of functional dyes in the fine chemical industry and their application as fluorescent dyes. Background technique [0002] Intracellular protons play an important role in many cellular processes, such as: cell growth, calcium regulation, endocytosis, cell adhesion, etc. Studying the dynamics of intracellular pH is crucial to understanding the regulatory mechanisms of many intracellular physiological functions. There are many methods for detecting intracellular pH, such as microelectrodes, nuclear magnetic resonance, etc., but fluorescence microscopy is more sensitive and convenient than these methods. Therefore, fluorescent pH probes have been widely used to monitor intracellular pH changes in recent years. In general, there are two broad pH ranges inside cells: one around 6.8–7.4, such as the cytoplasm, and the other arou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/14G01N21/64
Inventor 彭孝军王炳帅樊江莉王静云吴彤
Owner DALIAN UNIV OF TECH
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