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Folate-conjugated polyethylene glycol polyalkylcyanoacrylate, preparation method and application thereof

A polyethylene glycol polyalkylcyanoacrylate, polyethylene glycol technology, applied in the field of medicine, can solve the problems of short biological half-life, inactivation, lack of selectivity, etc.

Inactive Publication Date: 2010-03-31
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The currently widely used low-molecular and macromolecular drugs have their own shortcomings: (1) low-molecular drugs are administered orally or by injection, and the drug concentration in the body in a short period of time exceeds the actual demand, and they lack the selectivity to enter the human body; fast metabolism, The half-life is short, and the concentration in the body decreases quickly to affect the curative effect, so large doses of drug administration are required, and excessive drug concentration will enhance the side effects of the drug; (2) biological macromolecular drugs are easily degraded or inactivated by enzymes in the body, biological The half-life is short, and repeated administration is required; it is also restricted by the immune system, tissues, cell membranes, etc., and most of them are not easy to pass through these biological barriers, so the bioavailability of macromolecular drugs is low

Method used

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  • Folate-conjugated polyethylene glycol polyalkylcyanoacrylate, preparation method and application thereof
  • Folate-conjugated polyethylene glycol polyalkylcyanoacrylate, preparation method and application thereof
  • Folate-conjugated polyethylene glycol polyalkylcyanoacrylate, preparation method and application thereof

Examples

Experimental program
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Embodiment 1

[0024] Synthesis of folic acid-polyethylene glycol cyanoacetate: 5000 6 mmol of monoamine polyethylene glycol and 12 mmol of cyanoacetic acid were placed in a 250 ml three-neck flask, 50 ml of dichloromethane was added, and ultrasonically dissolved. Condensing agent DCC 12mmol and a small amount of DMAP were added under stirring, and the mixture was stirred at room temperature for 12h under nitrogen. 30ml of n-hexane was added, filtered, the filter cake was washed with dichloromethane (15ml×3), the filtrate and the washings were combined, concentrated under reduced pressure to a viscous state, solidified at room temperature to obtain a light yellow waxy solid, 6 mmol of folic acid was added, and dichloromethane was added. Chloromethane 50ml. Condensing agent DCC 12mmol and a small amount of DMAP were added under stirring, and the mixture was stirred at room temperature for 12h under nitrogen. 30ml of n-hexane was added, filtered, and the filter cake was washed with dichlorome...

Embodiment 2

[0029] Synthesis of folic acid-polyethylene glycol cyanoacetate: 6mmol of polyethylene glycol 2000 and 12mmol of cyanoacetic acid were placed in a 250ml three-necked bottle, 50ml of dichloromethane was added, and ultrasonically dissolved. Add 12 mmol of condensing agent DCC and a small amount of DMAP under stirring, and stir at room temperature for 12 h under nitrogen gas. Add 30ml of n-hexane, filter, wash the filter cake with dichloromethane (15ml×3), combine the filtrate and lotion, concentrate under reduced pressure until viscous, and solidify at room temperature to give a light yellow waxy solid, add 6mmol of folic acid, add di Chloromethane 50ml. Add 12 mmol of condensing agent DCC and a small amount of DMAP under stirring, and stir at room temperature for 12 h under nitrogen gas. Add 30ml of n-hexane, filter, wash the filter cake with dichloromethane (15ml×3), combine the filtrate and lotion, concentrate under reduced pressure until viscous, and solidify at room temper...

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Abstract

The invention discloses synthesis and application of a type of folate (FA)-conjugated polyethylene glycol polycyanoacrylate (PEG - PHDCA) (FA-PEG-PHDCA for short). The type of polymer is an amphiphilic block copolymer obtained through the Michael addition reaction of folate-polyethylene glycolcyano acetate and alkyl cyanoacetate in the presence of formaldehyde and dimethylamine. The type of polymer can be self-assembled into nano-particles or micelles in water, wherein hydrophobic alkyl segments are aggregated to a core, while hydrophilic polyethylene glycol segments form a hydrophilic shell.Meanwhile, due to excellent surface activity of the polymer and the tumor targeting property of folate, the polymer can also be applied to the modification of solid lipid nano-particles, liposomes, submicroemulsion and other nano-particle preparations. The polymer can be used for intravascular administration, intramuscular injection and oral administration, and is applicable to water-soluble and water-insoluble medicaments. The preparation method has the advantages of mature process and suitability for large-scale continuous production.

Description

technical field [0001] The invention belongs to the technical field of medicine, relates to a preparation method of a medicinal polymer folic acid coupled with polyethylene glycol polyalkyl cyanoacrylate (FA-PEG-PHDCA) and its application, and belongs to a block copolymer. Background technique [0002] Nanoparticles are solid colloidal particles with a particle size of 1 to 1000 nm. They have the characteristics of small size effect, quantum size effect, surface effect, and macroscopic quantum tunneling effect, and can be absorbed by tissues and cells, making them possible excellent drug delivery. system. Currently widely used low-molecular-weight and macromolecular drugs have their own shortcomings: (1) Low-molecular-weight drugs are administered orally or by injection, the drug concentration in the body far exceeds the actual demand in a short period of time, and the selectivity of entering the human body is lacking; The half-life is short, and the concentration in the bo...

Claims

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Application Information

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IPC IPC(8): C08G65/48A61K47/34A61K47/54A61K47/69
Inventor 王东凯李翔潘卫三邱立朋
Owner SHENYANG PHARMA UNIVERSITY
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