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Epsilon-caprolactone polymer featuring key joint by folic acid

A technology of polymer and caprolactone, which is applied in the directions of non-active ingredients, such as medical preparations and pharmaceutical formulations, can solve problems such as difficulty in increasing polymer chains.

Inactive Publication Date: 2009-11-18
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the lack of reactive side functional groups on the main chain, it is difficult to modify the polymer chain (such as targeting factors, etc.)

Method used

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  • Epsilon-caprolactone polymer featuring key joint by folic acid
  • Epsilon-caprolactone polymer featuring key joint by folic acid
  • Epsilon-caprolactone polymer featuring key joint by folic acid

Examples

Experimental program
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Effect test

preparation example Construction

[0018] (1) Preparation of aminofolate:

[0019] Put the compound shown in formula E, the compound shown in formula F, dehydrating agent, catalyst and anhydrous polar aprotic organic solvent in a reactor, and react for 10 hours to 20 hours at 15°C to 30°C in the presence of an inert gas hours, the obtained product was dissolved in TFA, and kept at 15°C to 30°C for 1 hour to 2 hours to obtain aminofolate;

[0020] The molar ratio of the compound represented by formula E to the compound represented by formula F is (1-5):1.

[0021] (2) Preparation of ε-caprolactone polymers with side functional groups:

[0022] (2-1) Preparation of ε-caprolactone copolymer

[0023] 4-carbonyl-ε-caprolactone (compound represented by formula A) and ε-caprolactone (compound represented by formula B) are mixed in a molar ratio of 1: (1-10) and then added to the polymerization reactor to completely 0.05% (mole percent) to 1.0% (mole percent) of the number of moles of the monomer is stannous octanoa...

Embodiment 1

[0035] (1) Preparation of aminofolate:

[0036] 0.600 g of folic acid, 0.879 g of Boc monoprotected 1,6-hexanediamine, and 1.88 g of dehydrating agent DCC were dissolved in 32 mL of anhydrous DMSO, and 4 mL of catalyst pyridine was added. in N 2 Under protection, react at 25°C for 18 hours. The obtained compound was dissolved in 5 mL of TFA, and reacted at 25° C. for 2 hours to obtain aminofolate. 1 H-NMR (CDCl 3 , δppm) characteristic peak: 8.48 (1H, H a ), 7.52 (2H, H b，b′ ), 6.59 (2H,H cc′ ), 1.91 (2H,H d ).

[0037]

[0038] (3) Preparation of ε-caprolactone polymers with side functional groups:

[0039] (2-1) Preparation of ε-caprolactone polymer

[0040] 4-carbonyl-ε-caprolactone and ε-caprolactone are mixed in a molar ratio of 1:4 and then added to the polymerization reactor, with 0.5% stannous isooctanoate as the catalyst of the total monomer moles, dried toluene As a solvent, a copolymer was obtained after reacting at 80°C for 24 hours. 4-carbonyl-ε-capr...

Embodiment 2-3

[0054] Embodiment 2-3 concrete steps and operation are substantially the same as embodiment, only change 4-carbonyl-ε-caprolactone (OPD) and caprolactone mol ratio in embodiment 1 step (2-1) be 1: 2 and 1:9, polymers with different molecular weights can be obtained. The obtained copolymer was analyzed by gel permeation chromatography, and the results are shown in Table 1.

[0055] Table 1

[0056]

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Abstract

The invention relates to an epsilon-caprolactone polymer featuring key joint by folic acid which can serve as targeted drug carrier; wherein, the epsilon-caprolactone polymer are obtained by the following steps: first, 4-carbonyl group-epsilon-caprolactone and epsilon-caprolactone are copolymerized to obtain copolymer with number-average molecular weight ranging from 5,000 to 100,000; then, reduction reaction, esterification reaction with carboxyanhydride and graft reaction with amination folic acid are carried out on the copolymer sequentially, thus obtaining the polymer. The superiority of the invention lies in that targeted compound with controllable folic acid content is obtained by the method of graft key joint, thus realizing the aim of regulating targeting of the epsilon-caprolactone polymer and further carrying out functionalized modification.

Description

technical field [0001] The invention relates to an ε-caprolactone polymer, in particular to a folic acid-linked ε-caprolactone polymer which can be used as a targeted drug carrier. Background technique [0002] ε-caprolactone polymer (PCL), because of its good biocompatibility and biodegradability, is a good drug release carrier. However, due to the lack of reactive side group functional groups on its main chain, it increases the difficulty of modifying the polymer chain (such as targeting factors, etc.). Therefore, the functional modification and modification of PCL is imperative. [0003] In order to meet different needs, different functionalization methods can be used. Such as Mikael T. (Macromolecules.2000, 33: 4619-46), Lang M D (J Polym Sci Polym Chem. 2001, 39: 4214-4226), etc. synthesized monocaprolactone containing protected functional substituents Body, ring-opening polymerization and deprotection to obtain side group reactive functional groups; Rieger J et al. ...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K47/22A61K47/34
Inventor 郎美东李家诗张琰
Owner EAST CHINA UNIV OF SCI & TECH
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