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Lysosome targeting rhodamine B hydrazide fluorescent probe as well as preparation method and application thereof

A fluorescent probe and targeting technology, applied in the field of probes, can solve the problem of less fluorescent probes, and achieve the effects of simple synthesis method, high selectivity, and obvious changes in fluorescence intensity.

Pending Publication Date: 2022-06-24
JINZHONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

lysosome-targeted Al 3+ Very few fluorescent probes

Method used

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  • Lysosome targeting rhodamine B hydrazide fluorescent probe as well as preparation method and application thereof
  • Lysosome targeting rhodamine B hydrazide fluorescent probe as well as preparation method and application thereof
  • Lysosome targeting rhodamine B hydrazide fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of Rhodamine B Hydrazide

[0039] In a 250 mL round bottom flask, 3.832 g of rhodamine B (8 mmol), 8 mL of hydrazine hydrate (132 mmol) and 100 mL of anhydrous methanol were added, and the mixture was stirred. The mixture was heated to reflux, maintained at 65°C for 3 hours, cooled to room temperature of 25°C, and the methanol solvent was removed by rotary evaporation under reduced pressure. The residue was dissolved in 30 mL of hydrochloric acid (1 M), and NaOH solution (1 M) adjust the pH to 9, generate a large amount of light pink solids, suction filter, wash the filter cake with ice water several times, and vacuum dry to obtain 3.3642 g of light pink powdery solids with a yield of 92.1%. m.p. 215-217ºC.

[0040] Synthesis and characterization of lysosome-targeted rhodamine B hydrazide fluorescent probe RM

[0041] In a 50 mL round-bottom flask, 0.23 g (0.50 mmol) of rhodamine B hydrazide, 0.14 g (0.50 mmol) of 4-morpholinyl benzaldehyde, and 10 mL of...

Embodiment 2

[0044] Synthesis of Rhodamine B Hydrazide

[0045] In a 250 mL round bottom flask, 3.832 g of rhodamine B (8 mmol), 8 mL of hydrazine hydrate (132 mmol) and 100 mL of anhydrous methanol were added, and the mixture was stirred. The mixture was heated to reflux and kept at 50 °C for 4 hours. After cooling to 20 °C, the methanol solvent was removed by rotary evaporation under reduced pressure. The residue was dissolved in 30 mL of hydrochloric acid (1 M) and adjusted with NaOH solution (1 M). pH=9.0, a large amount of light pink solids were formed, suction filtration, the filter cake was washed several times with ice water, and dried in vacuo to obtain 3.3642 g of light pink powdery solids with a yield of 92.1%. m.p. 215-217ºC.

[0046] Synthesis and characterization of lysosome-targeted rhodamine B hydrazide fluorescent probe RM

[0047] In a 50 mL round-bottom flask, 0.23 g (0.50 mmol) of rhodamine B hydrazide, 0.14 g (0.50 mmol) of 4-morpholinyl benzaldehyde, and 10 mL o...

Embodiment 3

[0049] Synthesis of Rhodamine B Hydrazide

[0050] In a 250 mL round bottom flask, 3.832 g of rhodamine B (8 mmol), 8 mL of hydrazine hydrate (132 mmol) and 100 mL of anhydrous methanol were added, and the mixture was stirred. The mixture was heated to reflux, kept at 70 °C for 2 hours, cooled to 30 °C, the methanol solvent was removed by rotary evaporation under reduced pressure, the residue was dissolved in 30 mL of hydrochloric acid (1 M), and adjusted with NaOH solution (1 M) pH=9.0, a large amount of light pink solids were formed, suction filtration, the filter cake was washed several times with ice water, and dried in vacuo to obtain 3.3642 g of light pink powdery solids with a yield of 92.1%. m.p. 215-217ºC.

[0051] Synthesis and characterization of lysosome-targeted rhodamine B hydrazide fluorescent probe RM

[0052] In a 50 mL round-bottom flask, 0.23 g (0.50 mmol) of rhodamine B hydrazide, 0.14 g (0.50 mmol) of 4-morpholinyl benzaldehyde, and 10 mL of absolute...

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Abstract

The invention relates to a lysosome targeting rhodamine B hydrazide fluorescent probe as well as a preparation method and application thereof. According to the probe, rhodamine B hydrazide and 4-morpholinyl benzaldehyde are subjected to condensation reaction to obtain the fluorescent probe with good chemical and optical stability, the probe compound has specific fluorescent response to aluminum ions in the presence of various metal ions, and when the concentration of the aluminum ions is within the range of 40-100 [mu] M, the probe compound can be used for detecting the aluminum ions. The fluorescence intensity of the probe and the concentration of aluminum ions are in a good linear relationship, and the detection limit is 4.79 * 10 <-7 > M. Compared with a commercial lysosome selective dye, the probe has a lysosome targeting capability, and can successfully realize visual imaging of aluminum ions in the cell lysosome.

Description

technical field [0001] The invention belongs to the technical field of probes, and relates to an aluminum ion fluorescent probe RM with lysosome targeting, a preparation method thereof, and an application of the probe. Background technique [0002] The metal aluminum element ranks third in reserves on the earth (about 8.3% of the weight of the earth). This metal element is closely related to our life and is widely used in food additives, clinical drugs, kitchenware, furniture, water treatment, etc. aspect. Since it is an amphoteric metal element, aluminum ions are easily released into the environment. In modern life, due to excessive use or improper use of aluminum products, the environment is polluted and human health is threatened. In particular, the large accumulation of aluminum ions in the environment will eventually form the accumulation in the human body through the food chain. This result can easily lead to a variety of diseases. For example, the excessive presen...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06G01N21/6428G01N21/6456C09K2211/1033
Inventor 马玲
Owner JINZHONG UNIV
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