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Small molecule prodrugs bridged by redox double-sensitive bonds and their self-assembled nanoparticles

A technology of self-assembling nanoparticles and small molecules, which is applied in the direction of drug combination, effective ingredients of hydroxyl compounds, drug delivery, etc., to achieve high-efficiency entrapment, simple synthesis method, and good stability

Active Publication Date: 2021-06-11
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The selenium bond (single-selenium bond and diselenide bond) of the same group as sulfur also has a certain redox sensitivity, but there are no reports on smart responsive prodrugs and self-assembled nano-drug delivery systems based on selenium bonds.

Method used

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  • Small molecule prodrugs bridged by redox double-sensitive bonds and their self-assembled nanoparticles
  • Small molecule prodrugs bridged by redox double-sensitive bonds and their self-assembled nanoparticles
  • Small molecule prodrugs bridged by redox double-sensitive bonds and their self-assembled nanoparticles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Embodiment 1: the synthesis of monoselenium bridged paclitaxel-citronellol small molecule prodrug (PTX-Se-CIT)

[0054] Add an appropriate amount of selenodipropionic acid into a 50mL round-bottomed flask, and dissolve it with 3mL of acetic anhydride, stir at room temperature for 2 hours, monitor the reaction process by thin-layer chromatography, and then add 20mL of toluene to the system three times, and reduce Distilled to dryness. The obtained product was dissolved in 30 mL of dichloromethane, and an appropriate amount of citronellol and DMAP was added, stirred at room temperature for 1 hour, the reaction process was monitored by thin-layer chromatography, and an intermediate product was obtained by purification by silica gel column chromatography. Finally, the intermediate product, EDCI, HOBt and DMAP were dissolved in 50 mL of anhydrous dichloromethane, ice-bathed for 1 hour, then an appropriate amount of paclitaxel was added, stirred at room temperature for anothe...

Embodiment 2

[0057] Example 2: Synthesis of diselenide bridged paclitaxel-citronellol small molecule prodrug (PTX-SeSe-CIT)

[0058] Add an appropriate amount of 3,3'-diselenodipropionic acid into a 50mL round-bottomed flask, dissolve it with 3mL of acetic anhydride, stir at room temperature for 2 hours, monitor the reaction process by thin-layer chromatography, and then add 20mL of toluene three times system, and evaporated to dryness under reduced pressure. The obtained product was dissolved in 30 mL of dichloromethane, and an appropriate amount of citronellol and DMAP was added, stirred at room temperature for 1 hour, the reaction process was monitored by thin-layer chromatography, and an intermediate product was obtained by purification by silica gel column chromatography. Finally, the intermediate product, EDCI, HOBt and DMAP were dissolved in 50 mL of anhydrous dichloromethane, ice-bathed for 1 hour, then an appropriate amount of paclitaxel was added, stirred at room temperature for ...

Embodiment 3

[0061] Embodiment 3: Synthesis of monosulfide bridged paclitaxel-citronellol small molecule prodrug (PTX-S-CIT)

[0062] Add an appropriate amount of thiodipropionic acid into a 50mL round-bottomed flask, dissolve it with 3mL of acetic anhydride, stir at room temperature for 2 hours, monitor the reaction process by thin-layer chromatography, then add 20mL of toluene to the system three times, and reduce Distilled to dryness. The obtained product was dissolved in 30 mL of dichloromethane, and an appropriate amount of citronellol and DMAP were added, stirred at room temperature for 1 hour, the reaction process was monitored by thin-layer chromatography, and an intermediate product was obtained by purification by silica gel column chromatography. Finally, the intermediate product, EDCI, HOBt and DMAP were dissolved in 50 mL of anhydrous dichloromethane, ice-bathed for 1 hour, then an appropriate amount of paclitaxel was added, stirred at room temperature for another 24 hours, and...

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Abstract

The invention belongs to the technical field of medicine, and relates to a redox double-sensitive bond bridging small molecule prodrug and self-assembled nanoparticle thereof. The oxidation-reduction double-sensitive bond bridging prodrug is used to link antitumor drugs with carbon chains containing unsaturated bonds and active hydroxyl groups through selenium bonds or sulfur bonds. The antitumor drug is an anticancer drug containing active hydroxyl or amino group, selected from taxane compounds, nucleoside compounds, anthracycline compounds or camptothecin compounds; The carbon chain of the hydroxyl group is vitamin E, oleic acid-ethylene glycol ester, citronellol, oleyl alcohol, linoleyl alcohol or linoleyl alcohol. The selenium bond is a monoselenide bond or a disulphide bond, and the sulfur bond is a monosulfide bond or a disulfide bond. The small molecule prodrug of the present invention can be self-assembled into nanoparticles, so as to realize the effects of high drug loading, good stability, low toxicity and side effects, and rapid drug release specific to tumor sites, thereby improving antitumor activity.

Description

technical field [0001] The invention belongs to the field of new excipients and new dosage forms of pharmaceutical preparations, and relates to the construction of self-assembled nanoparticles bridged by redox double-sensitive bonds, in particular to redox double-sensitive small molecule prodrugs bridged by multiple selenium bonds and sulfur bonds. Construction of small molecule prodrug self-assembled nanoparticles and their application in drug delivery. Background technique [0002] Cancer seriously threatens the health of all human beings. According to the statistics of the World Health Organization (WHO), more than 8 million people die of cancer every year in the world. Chemotherapy is one of the most commonly used and effective strategies in cancer treatment, especially for those tumors that cannot be removed by surgery and metastatic spread. However, most chemotherapeutic drugs are cytotoxic drugs, and have disadvantages such as low solubility, poor stability, narrow t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/54A61K47/69A61K31/337A61K31/045A61P35/00
CPCA61K31/045A61K31/337A61K47/542A61K47/6929A61P35/00A61K2300/00
Inventor 孙进何仲贵孙丙军罗聪张轩博左诗意
Owner SHENYANG PHARMA UNIVERSITY
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