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Drug carrier with end group modified by hydrogen sulfide fluorescent probe as well as preparation and application thereof

A fluorescent probe, hydrogen sulfide technology, used in drug combinations, preparations for in vivo tests, medical preparations with inactive ingredients, etc.

Inactive Publication Date: 2016-05-04
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the detection of hydrogen sulfide produced by tumor cells and the targeting of positively charged nanoparticles have been extensively studied, the use of azidohydrogen sulfide fluorescent probes to modify drug-loaded nanoparticles achieves the reversal of the surface charge of drug-loaded nanoparticles, thereby The study of positively charged targeting of tumor cells has not been reported

Method used

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  • Drug carrier with end group modified by hydrogen sulfide fluorescent probe as well as preparation and application thereof
  • Drug carrier with end group modified by hydrogen sulfide fluorescent probe as well as preparation and application thereof
  • Drug carrier with end group modified by hydrogen sulfide fluorescent probe as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of the initiator 1 of atom transfer radical polymerization:

[0049] Dissolve 0.64g (2.0mmol) of 4-bromo-N-hydroxyethyl-1,8-naphthalimide in dimethylformamide, cool to 0°C, and then add 0.052g (2.4mmol) of bromoisobutyryl Bromine was added dropwise to the above solution, and reacted at room temperature for 12 hours after the dropwise addition. Use a TCL plate to detect the disappearance of the raw material 4-bromo-N-hydroxyethyl-1,8-naphthalimide point, and stop the reaction. Precipitate the reaction solution in deionized water, dissolve the precipitate with dichloromethane, extract and wash 3 times with deionized water, dry over sodium sulfate without deionized water, spin dry, and separate with a silica gel column. The particle size is 200-300 mesh, the eluent ratio is ethyl acetate / petroleum ether=1:10, and the yield is 86%. figure 1 for initiator 1 1 HNMR diagram, 1 H-NMR (400MHz, CDCl 3 )δ8.64(d,J=7.2Hz,1H,Ar-H),8.61(d,J=8.4Hz,1H,Ar...

Embodiment 2

[0050] Embodiment 2: the synthesis of macromolecular atom transfer radical polymerization initiator 2:

[0051] Dissolve 0.469g (1.0mmol) of initiator 1, 5.2g (40mmol) of hydroxyethyl methacrylate and 0.173g (1.0mmol) of pentamethyldiethylenetriamine in 8ml of dimethylformamide and place in a reaction flask ; Use nitrogen bubbling method to remove oxygen for 30 minutes at room temperature, add 0.144 g (1.0 mmol) cuprous bromide under nitrogen protection, and then pass nitrogen for 15 minutes, seal the reaction bottle, and react at room temperature for 6 hours. The reaction was terminated by exposing the reaction solution to air. After diluting the reaction liquid with 30ml of tetrahydrofuran, the copper ions were removed through a neutral aluminum oxide column, and the eluent ratio was absolute ethanol / tetrahydrofuran=1:40. After concentration, it was precipitated in ether. After dissolving with absolute ethanol, it was repeatedly dissolved and precipitated in ether for 3 ti...

Embodiment 3

[0052] Embodiment 3: the synthesis of polyhydroxyethyl methacrylate-polymethyl methacrylate amphiphilic block polymer 3:

[0053] Dissolve 0.56g (0.1mmol) of initiator 2, 0.4g (4mmol) of methyl methacrylate and 0.0173g (0.1mmol) of pentamethyldiethylenetriamine in 2ml of dimethylformamide and place in a reaction flask; Nitrogen bubbling method was used to remove oxygen at room temperature for 30 minutes, and 0.0144 g (0.1 mmol) of cuprous bromide was added under the protection of nitrogen, and after nitrogen was passed for 15 minutes, the reaction bottle was sealed and reacted at room temperature for 6 hours. The reaction was terminated by exposing the reaction solution to air. Add 10ml of tetrahydrofuran to dilute the reaction solution, remove copper ions through a neutral aluminum oxide column, the eluent ratio is absolute ethanol / tetrahydrofuran = 1:30, concentrate, precipitate in ether, dissolve with absolute ethanol Repeated dissolution and precipitation in ether for 3 t...

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Abstract

The invention relates to a drug carrier with an end group modified by a hydrogen sulfide fluorescent probe as well as preparation and an application thereof and belongs to the field of preparation of drug carriers. The drug carrier provided by the invention and an antitumor drug are self-assembled into a nano-drug co-transporter. The hydrogen sulfide fluorescent probe containing an azide group is on the surface of the nano-drug co-transporter, so that the surface of the nano-drug co-transporter is negatively charged. After the nano-drug co-transporter reaches a tumor part, the azide group in the fluorescent probe is reduced by hydrogen sulfide generated by tumor cells into an amino group, and the change of fluorescence color can be observed under ultraviolet light, so that the selective rapid detection of the hydrogen sulfide is realized; meanwhile, the amino group enables charges on the surface of the nano-drug co-transporter to overturn, a large amount of positive charges generates a positive charge attraction effect with negative charges on the surfaces of the tumor cells, and by means of an active targeting effect of the positive charges, the antitumor drug on the nano-drug co-transporter is quickly transported into the tumor cells; therefore, the targeted drug delivery is realized.

Description

technical field [0001] The invention relates to a drug carrier whose end group is modified by a hydrogen sulfide fluorescent probe and its preparation and application, belonging to the field of drug carrier preparation. Background technique [0002] Nowadays, active targeting of drug carriers has become an indispensable means in the diagnosis and treatment of cancer. Active targeting refers to the targeting of receptors, antibodies or specific gene fragments on the cell surface. The body binds to the surface of the carrier, so that the drug carrier can accurately interact with the target on the cell surface, and deliver the drug into the cell to achieve targeted therapy. Commonly used ligands include antibodies, polypeptides, glycosyl groups, and folic acid. The difficulty of ligand targeting is how to maintain the activity of the ligand during the modification process, and the price of the ligand is generally relatively expensive, so exploring new targeting mechanisms is a...

Claims

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Application Information

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IPC IPC(8): A61K47/32A61K49/00A61K9/107A61K31/704A61P35/00
CPCA61K47/32A61K9/107A61K31/704A61K49/0019A61K49/0054
Inventor 林伟英张海涛孔秀琪
Owner UNIV OF JINAN
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