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Two/three cluster glycosyl rhodamine derivatives and its preparation method and application

A derivative and reaction technology, applied in the field of two/three-cluster glycosyl rhodamine derivatives and their preparation, can solve the problems of poor water solubility and limitation of rhodamine, achieve good water solubility, strong hydrophilicity, and simple synthesis method Effect

Active Publication Date: 2019-06-21
GUANGXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to the poor water solubility of rhodamine after ring closure, its application in monitoring the pH changes of cells and environments is severely limited.

Method used

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  • Two/three cluster glycosyl rhodamine derivatives and its preparation method and application
  • Two/three cluster glycosyl rhodamine derivatives and its preparation method and application
  • Two/three cluster glycosyl rhodamine derivatives and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Add acetic anhydride (30mL) in a 100mL three-necked flask, add 3 drops of 70% perchloric acid dropwise under ice-water bath, stir for ten minutes, add D-galactose (5.00g) in batches, control the reaction temperature at 30- 40°C, after reacting for 1.5h, add red phosphorus (3.75g) when the reaction solution was cooled to 15°C, and stir for 10 minutes, then slowly add liquid bromine (2.8 mL) dropwise, and control the temperature below 20°C, dropwise After completion, stir at 15-20°C for 0.5h, continue to control the temperature below 20°C and slowly add deionized water (4.5mL), react at 15-20°C for about 0.5h, leave it at room temperature for 2h, add CH 2 Cl 2 (40mL), filter with suction, pour the filtrate into 200mL ice water, separate the organic layer, and wash the water layer with CH 2 Cl 2 Extract (4×30 mL), combine the organic layers, and wash the organic phase with saturated NaHCO 3 The solution was washed to neutrality, then washed with saturated br...

Embodiment 2

[0053]

[0054] Dissolve 5g of trishydroxymethylaminomethane in a mixed solution composed of 30mL of methanol and 30mL of tert-butanol, add BOC anhydride (11.75g) tert-butanol (50mL) solution under stirring, react overnight at room temperature, spin off the solvent, add ethyl acetate The ester was refrigerated overnight and filtered to give 8 (8.5 g, 93%) as a white solid. 1 H NMR (600MHz, DMSO-d6) δ4.49(s, 3H), 3.52(s, 6H), 1.37(s, 9H).

[0055]

[0056] A suspension of powdered KOH (2.3 g) and dry DMF (10 mL) was cooled to 0° C. under Ar protection. After compound 8 (1.5g) was dissolved in anhydrous THF (10mL), it was added dropwise to the reaction solution. After the addition was completed, it was reacted at 0°C for 10min, and 3.3mL of propyne bromide was added dropwise, and the temperature was raised to 35°C after 5min at 0°C. ℃ to react overnight, add deionized water (100 mL), CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 It was dried, fi...

Embodiment 3

[0066]

[0067] Dissolve compound 6 (0.5g) and compound 14 (1.0g) in 10mL THF, Ar protection, add 10mL sodium ascorbate (0.115g) and CuSO 4 ·5H 2 O (0.07g) deionized aqueous solution, and react overnight at room temperature. Add deionized water, CH 2 Cl 2 Extraction, washed with saturated brine, anhydrous Na 2 SO 4 Drying, filtration, concentration, column separation (CH 2 Cl 2 :CH 3 OH = 40:1-20:1), to give 15 as a light red solid (1.14 g, 78%). 1 H NMR (600MHz, CDCl 3 )67.90 -7.83(m, 3H), 7.46(dd, J=8.9, 5.5Hz, 2H), 7.11(dd, J=5.2, 2.6Hz, 1H), 6.45(dt, J=8.9, 4.6Hz, 2H ), 6.39(d, J=2.4Hz, 2H), 6.30 -6.25(m, 2H), 5.91(d, J=9.2Hz, 2H), 5.51(td, J=9.4, 4.4Hz, 2H), 5.44 (t, J=9.1Hz, 2H), 5.38(d, J=3.3Hz, 2H), 5.15(dd, J=10.3, 8.0Hz, 2H), 5.00(dd, J=10.4, 3.4Hz, 2H) , 4.61(dd, J=12.5, 4.9Hz, 4H), 4.57(d, J=7.9Hz, 2H), 4.51(d, J=11.1Hz, 2H), 4.29(dd, J=10.5, 5.2Hz, 1H), 4.19-4.11(m, 6H), 4.04(td, J=9.4, 5.0Hz, 2H), 4.01-3.96(m, 2H), 3.93(t, J=6.7Hz, 2H), 3.65-3.58 ...

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Abstract

The invention discloses a two / three-cluster glycosyl rhodamine derivative with general formulas I and II. Researches show that the obtained two / three-cluster glycosyl rhodamine derivative is good in water solubility, sensitive to pH and capable of being used as a fluorescent probe for monitoring pH changes so as to be directly used for monitoring pH changes in solutions, and has important scientific significance in research and application for monitoring on pH changes in cells and environments. Meanwhile, it is found that within the pH range between 4.35 and 7.5, the higher the acidity is, the higher the fluorescence intensity of the two types of compounds is, and the two / three-cluster glycosyl rhodamine derivative can be lightened in liver cancer cells (HepG2) under the slightly-acid condition to release strong red fluorescence and can be positioned in lysosome in a targeted manner. Meanwhile, the inventor established a preparation method of the corresponding compounds, the click chemistry reaction technology is used for the method, and synthesis is easy and scientific.

Description

technical field [0001] The invention belongs to the field of biomedicine and environmental monitoring, and in particular relates to two / three-cluster glycosyl rhodamine derivatives and a preparation method and application thereof. Background technique [0002] Rhodamine compounds have many advantages such as high quantum yield, high extinction coefficient, excellent photostability, long excitation wavelength, high detection sensitivity, cheap price, etc., and show fluorescence "on-off" under different pH conditions Effect (the fluorescence is quenched after the ring is closed under alkaline conditions, and the fluorescence is emitted after the ring is opened under acidic conditions). [0003] The structure and fluorescent switch mechanism of rhodamine B are as follows: [0004] [0005] Due to the poor water solubility of rhodamine after ring closure, its application in monitoring the pH changes of cells and environments is severely limited. Therefore, it is of great sc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/02C07H1/00C09K11/06G01N21/64
CPCC07H1/00C07H17/02C09K11/06C09K2211/1029C09K2211/1059C09K2211/1088G01N21/6428G01N2021/6432
Inventor 王勉王坚毅陈政君
Owner GUANGXI UNIV
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