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Oral multi-sensitive micelle prodrug based on beta-sitosterol and 5-ASA and used for treating inflammatory bowel diseases

A 5-ASA, inflammatory bowel disease technology, applied in the direction of drug combination, pharmaceutical formula, organic active ingredients, etc., to achieve the effect of not easy to retain, high stability, and good effect

Active Publication Date: 2020-04-24
JIANGSU PROVINCIAL HOSPITAL OF TCM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to solve the problem of an existing drug for treating inflammatory bowel disease, the present invention provides an oral polysensitive micellar prodrug based on β-sitosterol and 5-ASA for treating inflammatory bowel disease

Method used

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  • Oral multi-sensitive micelle prodrug based on beta-sitosterol and 5-ASA and used for treating inflammatory bowel diseases
  • Oral multi-sensitive micelle prodrug based on beta-sitosterol and 5-ASA and used for treating inflammatory bowel diseases
  • Oral multi-sensitive micelle prodrug based on beta-sitosterol and 5-ASA and used for treating inflammatory bowel diseases

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Experimental program
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Effect test

Embodiment

[0027] A kind of oral polysensitivity micellar prodrug based on β-sitosterol and 5-ASA for the treatment of inflammatory bowel disease, comprising the steps of:

[0028] S1. Synthesis of BSMA: Dissolve β-sitosterol in DCM, add triethylamine to balance the reaction, add methacryloyl chloride dropwise at 0°C, after the reaction is stable, stir at room temperature for 12h, and saturate with NaHCO 3 The reaction product was extracted three times with anhydrous Na 2 SO 4 Dehydration, after the solvent evaporates, use DCM to dissolve the solid to form an emulsion, use methanol to reprecipitate the emulsion, and dry the white solid obtained by a rotary evaporator is BSMA;

[0029] S2. Synthesis of ASAPPDMA: dissolve N-boc-p-phenylenediamine with THF, add triethylamine to balance the reaction, add methacryloyl chloride dropwise at 0°C under nitrogen protection and reflux for 4h, saturate Na 2 CO 3 Extract the reaction product, remove excess methacryloyl chloride and use anhydrous N...

experiment example

[0035] The chemical structures of the polymers and their precursors were characterized by nuclear magnetic resonance (1hnmr), as shown in image 3 Shown, in Fig. (3, A), the characteristic peak of CH2=C(CH3)-(A, b) of BSMA appears in 5.8-6.2ppm and 2.0ppm respectively, and the characteristic peak of the tertiary hydrocarbon that is connected with hydroxyl Peak (c) occurs at 4.7ppm, and the tetracyclic triterpenoids of β-sitosterol appear a large number of proton peaks at 0.7-2.0ppm, wherein methyl (e) is the characteristic peak of β-sitosterol at 0.7ppm; In figure (3, B), the characteristic peaks of CH2=C(CH3)-(B, d) and-NH(a) of ASAPPDMA appear in 5.6-5.8ppm, 2.0ppm and 10.2ppm respectively, and the characteristic peaks of benzene ring The characteristic peak moves to 7.8ppm (C) due to the influence of azo bond; Figure (3, C) shows the NMR figure of PMMA polymer, and 0.75-1.2ppm and 1.72-1.9ppm correspond to -CCH on the main chain respectively 3 (d) and -CH2–(c), while -OCH ...

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Abstract

The invention provides an oral multi-sensitive micelle prodrug based on beta-sitosterol and used for treating inflammatory bowel diseases, belonging to the technical field of drug synthesis. A preparation method for the oral multi-sensitive micelle prodrug comprises the following steps: synthesis of BSMA: dissolving beta-sitosterol with dichloromethane, and dissolving a solid with dichloromethaneto form an emulsion, wherein a formed white solid is BSMA; synthesis of ASAPPDMA: dissolving N-boc-p-phenylenediamine by using tetrahydrofuran so as to obtain a white solid, namely Boc-PPDMA; synthesis of PPDMA: dissolving Boc-PPDMA with dichloromethane, and adding trifluoroacetic acid to obtain a solid, namely PPDMA; synthesis of ASAPPDMA: dissolving PPDMA in hydrochloric acid and adding NaNO2 into the formed solution to form an intermediate product, wherein the obtained solid is named as ASAPPDMA; synthesis of a PMMA-PEGMA polymer: dissolving methyl methacrylate in 10 mL of N,N-dimethylformamide and carrying out mixing in a flask to obtain a solid, namely the PMMA-PEGMA polymer; and assembling of the polymer: dissolving the PMMA-PEGMA polymer into N,N-dimethylformamide, pumping a formedsolution into water to form a blank micelle P(MMA-BSMA-ASAPPDMA)-PEGMA polymer, and pumping the blank micelle P(MMA-BSMA-ASAPPDMA)-PEGMA polymer into water to form a fluorescent micelle. The fluorescent micelle prepared in the invention has the advantages of good effect and high stability.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and relates to an oral polysensitivity micellar prodrug based on β-sitosterol and 5-ASA for treating inflammatory bowel disease. Background technique [0002] Inflammatory bowel disease (IBD) is a global disease whose incidence has shown a steady upward trend in Western countries and is emerging and developing worldwide. Crohn's disease (CD) and ulcerative colitis (UC) are two common forms of IBD. There is no cure for IBD, and current treatment strategies aim to achieve and maintain remission of inflammatory episodes. As a result, patients can only be treated with drugs designed to block or suppress various levels of immune inflammation. [0003] Sulfapyridine salicylate (SASP) and 5-ASA are effective in mild to moderate IBD, whereas steroids are more effective in severe acute IBD. SASP is a compound formed by the azo bond between sulfadiazine (SP) and 5-ASA. After oral administration o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K31/606A61K31/575A61K47/32A61P1/00C08F220/14C08F220/28
CPCA61K9/1075A61K31/575A61K31/606A61K47/32A61P1/00C08F220/14C08F220/28A61K2300/00
Inventor 朱磊沈洪
Owner JIANGSU PROVINCIAL HOSPITAL OF TCM