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Application of compounds based on rhodamine B and thiobisethylamine in live cell imaging

An aminoethyl sulfide and compound technology, applied in the field of live cell imaging, can solve the problems of less live cell imaging, difficult synthesis, complex structure, etc., and achieve the effects of low toxicity, high sensitivity, high sensitivity and accuracy

Active Publication Date: 2016-10-12
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported rhodamine-based fluorescent probes have rare raw materials, complex structures, and difficult synthesis, and some can only detect Hg in pure organic solvents (such as absolute ethanol). 2+ , especially for active cell imaging (see: Xu L, Wang S, Lv YN, Son YA, CaoDR. A highly selective and sensitive photo switchable fluorescent probe for Hg 2+ based on bisthienylethene-rhodamine 6G dyad and for live cells imaging. Spectrochim. Acta Part A 2014; 128: 567-574; Bhalla V, Tejpal R, Kumar M.Rhodamine appended terphenyl: A reversible “off-on” fluorescent chemosensor for mercu . Sens. Actuators B 2010; 151: 180-185; Zhang X, Zhu YY. A new fluorescent chemodosimeter for Hg 2+ -selective detection in aqueous solution based on Hg 2+ -promoted hydrolysis of rhodamine-glyoxylic acid conjugate. Sens. Actuators B 2014; 202: 609-614)

Method used

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  • Application of compounds based on rhodamine B and thiobisethylamine in live cell imaging
  • Application of compounds based on rhodamine B and thiobisethylamine in live cell imaging
  • Application of compounds based on rhodamine B and thiobisethylamine in live cell imaging

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment one: Hg 2+ Preparation of probe RMTE

[0030] The molar ratio of rhodamine B and aminoethyl sulfide is 1:3, with dichloromethane as solvent, N,N-diisopropylethylamine as additive, and the molar ratio of rhodamine B is 7:1, in N 2 Under protection, the reaction was stirred at 30 °C for 20 h, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain the crude product as a yellow solid powder with a yield of 49.8%. Carry out column chromatography separation, eluent is methanol / chloroform / petroleum ether, 1 / 12 / 2 (v / v / v), dry, obtain yellow solid powder target product RMTE, yield rate is 35.1%.

[0031] NMR, 1 H NMR (400 MHz, CDCl 3 ), δ / ppm: 1.16 ( t , 12H, J=6.8 Hz), 2.23( t , 2H, J=8 Hz), 2.50 ( t , 2H, J=6.4 Hz), 2.77 ( t , 2H, J=6.4 Hz), 3.27–2.37 ( m , 10H), 3.66 (s, 2H), 6.27 ( d , 2H, J=6.4 Hz), 6.37 ( d , 2H, J=2.4Hz), 6.44 ( s , 2H), 7.08–7.10 ( m , 1H), 7.43–7.46 ( m , 2H), 7.89–7.91( m , 1H), 13 C NMR (300 ...

Embodiment 2

[0032] Embodiment two: Hg 2+ Preparation of probe RMTE

[0033] The molar ratio of rhodamine B and aminoethyl sulfide is 1:7, with ethanol as solvent, N,N-diisopropylethylamine as additive, and the molar ratio of rhodamine B is 7:1, in N 2 Under protection, the reaction was stirred at 40 °C for 24 h, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain a crude yellow solid powder with a yield of 63.2%. Carry out column chromatography separation, eluent is methanol / chloroform / petroleum ether, 1 / 12 / 2 (v / v / v), dry, obtain yellow solid powder target product RMTE, yield rate is 42.8%.

Embodiment 3

[0034] Embodiment three: Hg 2+ Preparation of probe RMTE

[0035] The molar ratio of rhodamine B and aminoethyl sulfide is 1:5, acetonitrile is used as solvent, N,N-diisopropylethylamine is used as additive, and the molar ratio of rhodamine B is 7:1. 2 Under protection, the reaction was stirred at 20 °C for 18 h, cooled to room temperature, and the solvent was removed by rotary evaporation to obtain the crude product as a yellow solid powder with a yield of 49.8%. Carry out column chromatography separation, eluent is methanol / chloroform / petroleum ether, 1 / 12 / 2 (v / v / v), dry, obtain yellow solid powder target product RMTE, yield rate is 36.3%.

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PUM

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Abstract

The invention discloses application of compounds based on rhodamine B and thiobisethylamine in live cell imaging. Materials for the compounds are easy to obtain, and the compounds are simple to synthesize and simple in molecular structure; the compounds are good in Hg2+ selectivity and high in sensitivity; the compounds are useful for detecting Hg2+ in nearly neutral and almost pure water buffer solution; the compounds are useful for detecting Hg2+ in HgCl2; particularly, the compounds are slightly toxic to living cells and are useful for living cell imaging to detect Hg2+ concentration in living cells.

Description

technical field [0001] The invention belongs to the technical field of living cell imaging, and in particular relates to the application of a compound based on rhodamine B and aminoethyl sulfide in living cell imaging. Background technique [0002] Hg 2+ It is a highly physiologically toxic chemical substance. Its harm to the human body is mainly concentrated in the central nervous system, digestive system and internal organs, and it also has certain effects on the respiratory system, skin, blood and eyes. Hg 2+ The mechanism of poisoning is not yet fully understood, and the widely accepted Hg 2+ The basis of toxicity is the Hg-S reaction. Hg 2+ It has a high affinity for sulfhydryl groups in proteins and enzymes in organisms. Once combined with sulfhydryl groups in proteins, many metabolisms in cells (such as energy generation, protein and nucleic acid synthesis, etc.) will be affected, thereby affecting cell functions and grow. and Hg 2+ It is persistent, easy to mi...

Claims

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Application Information

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IPC IPC(8): C12Q1/02G01N21/64C07D491/107C09K11/06
CPCC07D491/107C09K11/06C09K2211/1088G01N21/6486
Inventor 徐冬梅洪苗苗
Owner SUZHOU UNIV
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