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Cell membrane carbonic anhydrase IX fluorescent probe with high brightness and high stability

A high stability, carbonic anhydrase technology, applied in the field of fluorescent probes, can solve the problems of inability to provide powerful tools for hypoxic tumor diagnosis, lack of fluorescent probes, etc., and achieve convenient synthesis, simple structure, and high cell membrane impermeability. Effect

Active Publication Date: 2020-06-26
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the scarcity of commercially available fluorescent probes for carbonic anhydrase IX cannot provide a powerful tool for the diagnosis of hypoxic tumors

Method used

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  • Cell membrane carbonic anhydrase IX fluorescent probe with high brightness and high stability
  • Cell membrane carbonic anhydrase IX fluorescent probe with high brightness and high stability
  • Cell membrane carbonic anhydrase IX fluorescent probe with high brightness and high stability

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Small molecule fluorescent probe Rho6G-SO for human carbonic anhydrase Ⅸ in cell membrane 2 NH 2 Synthetic method.

[0035] Synthesis of intermediate rhodamine 6G-carboxylic acid:

[0036]

[0037] 1 g of rhodamine 6G was dissolved in 30 mL of ethanol, and 300 mg of sodium hydroxide was dissolved in 5 mL of water, then slowly added to the reaction mixture, and heated with stirring to reflux. After 6h, click the panel to monitor, and stop the reaction after the reaction of the raw materials is complete. The solvent was removed by rotary evaporation and separated on a silica gel column. Dichloromethane: methanol = 5:1 (volume ratio) was used as the eluent, and the solvent was removed under reduced pressure to obtain 700 mg of a purple solid with a yield of 80%. The hydrogen spectrum data of the NMR spectrum are as follows:

[0038] 1 H NMR (400MHz, CD 3 OD)δ8.22(d,J=6.4Hz,1H), 7.80(m,2H), 7.36(d,J=6.8Hz,1H), 6.89(d,J=10.4Hz,4H), 3.50(q ,J=7.2Hz,4H),2.15(s,6H),1.35(t,J=6.8Hz,6...

Embodiment 2

[0056] Small molecule fluorescent probe Rho6G-SO for human carbonic anhydrase Ⅸ in cell membrane 2 NH 2 Synthetic method.

[0057] Synthesis of intermediate rhodamine 6G-carboxylic acid:

[0058]

[0059] 1 g of rhodamine 6G was dissolved in 20 mL of ethanol, and 200 mg of sodium hydroxide was dissolved in 5 mL of water, then slowly added to the reaction mixture, and heated under stirring to reflux. After 5h, click the panel to monitor, and stop the reaction after the reaction of the raw materials is complete. The solvent was removed by rotary evaporation, and separated on a silica gel column. Dichloromethane:methanol=5:1 (volume ratio) was used as the eluent, and the solvent was removed under reduced pressure to obtain 600 mg of purple solid with a yield of 69%.

[0060] Synthesis of intermediate rhodamine 6G-succinimide carboxylate:

[0061]

[0062] Weigh 500mg of rhodamine 6G-carboxylic acid and 300mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 20mL of dichl...

Embodiment 3

[0072] Small molecule fluorescent probe Rho6G-SO for human carbonic anhydrase Ⅸ in cell membrane 2 NH 2 Synthetic method.

[0073] Synthesis of intermediate rhodamine 6G-carboxylic acid:

[0074]

[0075] 1 g of rhodamine 6G was dissolved in 40 mL of ethanol, 400 mg of sodium hydroxide was dissolved in 5 mL of water, and then slowly added to the reaction mixture, heated and stirred to reflux. After 6h, click the panel to monitor, and stop the reaction after the reaction of the raw materials is complete. The solvent was removed by rotary evaporation and separated on a silica gel column. Dichloromethane:methanol=5:1 (volume ratio) was used as the eluent, and the solvent was removed under reduced pressure to obtain 672 mg of a purple solid with a yield of 77%.

[0076] Synthesis of intermediate rhodamine 6G-succinimide carboxylate:

[0077]

[0078] Weigh 500mg of rhodamine 6G-carboxylic acid and 400mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 30mL of dichloromet...

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Abstract

The invention provides a cell membrane carbonic anhydrase IX fluorescent probe with high brightness and high stability. The probe is based on a rhodamine 6G fluorescent parent, is connected with a benzenesulfonamide targeting group, has a structural formula shown in (1), has high cell membrane impermeability, and realizes no-clean imaging of the cell membrane carbonic anhydrase IX by utilizing rapid coordination combination of benzenesulfonamide and zinc atoms in the human carbonic anhydrase IX. The probe is simple in structure, cheap and easily available in raw materials and convenient to synthesize, and has a wide prospect in research in the field of cell membrane carbonic anhydrase IX.

Description

Technical field [0001] The invention belongs to the field of fluorescent probes, and specifically relates to a fluorescent probe of cell membrane carbonic anhydrase IX with high brightness and high stability. Background technique [0002] Carbonic anhydrase is a zinc-containing metal enzyme that catalyzes CO 2 The hydration reaction and the hydration reaction of certain lipids and aldehydes participate in various ion exchanges to maintain the steady state of the body's environment and play a key role in the process of human life activities. Carbonic anhydrase IX is an important subtype in its family. It is overexpressed in tumors directly caused by hypoxia. It is related to tumor cell proliferation, cell adhesion, and tumor progression. It has been confirmed by many scientific researchers that it can be used as a deficiency. Oxygen tumor markers. At present, the detection of carbonic anhydrase is mainly through immunoblotting and mass spectrometry, both of which require cell lys...

Claims

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Application Information

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IPC IPC(8): C07D311/82C09K11/06G01N21/64
CPCC07D311/82C09K11/06G01N21/6486C09K2211/1007C09K2211/1088
Inventor 徐兆超周伟乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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