Polylactide containing side hydroxy or side carboxy functional group and preparation method thereof

A technology of polylactide and pendant carboxyl groups, which is applied in the field of polylactide and its preparation, can solve the problems of lack of functional groups, poor water solubility, and single chemical structure, and achieve the effects of good hydrophilicity, low cost, and simple preparation methods

Inactive Publication Date: 2013-09-04
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Aliphatic polyesters represented by polylactide (PLA) are one of the few biomedical materials that have been certified by the US FDA. They have the advantages of good biocompatibility and biodegradability, but they have a single chemical structure and high molecular weight. The main chain lacks functional groups that can further bond with drugs and biologically active substances, and its water solubility is poor. In order to solve these problems, it is necessary to introduce reactive hydrophilic groups on the side chains of polylactide. In order to obtain a polymer drug carrier comparable to polyglutamic acid, that is, a drug carrier with hydrophilicity, degradability and good biocompatibility, while using its reactive functional groups to realize drug Effective bonding of molecules, target molecules and quantum dots, obtaining such a drug carrier polymer has great scientific and economic value

Method used

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  • Polylactide containing side hydroxy or side carboxy functional group and preparation method thereof
  • Polylactide containing side hydroxy or side carboxy functional group and preparation method thereof
  • Polylactide containing side hydroxy or side carboxy functional group and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0040] Preparation of polylactide containing pendant monohydroxy functional groups:

[0041] Under the protection of nitrogen, 0.100 g (double bond: 0.00048 mol) of side norbornene functionalized polylactide (NMR spectrum as shown in figure 1 ,IR image 3 Shown in A) was completely dissolved in 8 mL of tetrahydrofuran (THF), then added 0.187 g (0.0024 mol) of mercaptoethanol, and then dissolved 1-hydroxycyclohexyl phenyl ketone (photoinitiator 184) in 2 mL of THF Add it, under the irradiation of ultraviolet light with a wavelength of about 365nm, and react at room temperature for 1 hour. After the reaction, spin off THF, dissolve in dichloromethane, and precipitate in ether to obtain polylactide containing side monohydroxyl functional groups. Its structural characterization is shown in the NMR spectrum ( figure 2 ), infrared image ( image 3 B), molecular weight distribution see ( Figure 4 ), indicating that the polymer has been successfully synthesized.

Embodiment 2

[0043] Preparation of polylactide containing pendant dihydroxy functional groups:

[0044] Under the protection of nitrogen, 0.100 g (double bond: 0.00048 mol) of norbornene-functionalized polylactide was completely dissolved in 8 mL of THF, and then 0.259 g (0.0024 mol) of 3-mercapto-1 was added, 2-propanediol, and then add 1-hydroxycyclohexyl phenyl ketone dissolved in 2mL THF to it, under the irradiation of ultraviolet light with a wavelength of about 365nm, react at room temperature for 1h, after the reaction, spin off THF, and then Dissolve the crude product with a small amount of DMF, place it in a dialysis bag (3500K) and dialyze in secondary water for 48 hours to obtain polylactide containing pendant dihydroxy functional groups. Its structural characterization is shown in the NMR spectrum ( Figure 5 ), infrared image ( image 3 C), molecular weight distribution (see Figure 6 ), indicating that the polymer has been successfully synthesized.

Embodiment 3

[0046] Preparation of polylactide containing pendant monocarboxyl functional groups:

[0047] Under the protection of nitrogen, 0.100 g (double bond: 0.00048 mol) of side norbornene functionalized polylactide was completely dissolved in 8 mL of THF, then 0.254 g (0.0024 mol) of mercaptoethanol was added, and then the 2mL of THF-dissolved 1-hydroxycyclohexyl phenyl ketone was added to it, under the irradiation of ultraviolet light with a wavelength of about 365nm, the reaction was carried out at room temperature for 1h. A polylactide containing pendant monocarboxyl functional groups is obtained. Its structural characterization is shown in the NMR spectrum ( Figure 7 ), infrared image ( image 3 D), molecular weight distribution (see Figure 8 a), indicating that the polymer has been successfully synthesized.

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Abstract

The invention discloses a polylactide containing a side hydroxy or side carboxy functional group and a preparation method thereof. According to the preparation method, a polylactide with a functionalized norbornene-containing side group and a mercapto compound undergo mercapto-alkene click chemical reaction to form the polylactide containing the side hydroxy or side carboxy functional group. The preparation method for the polylactide is simple, quick and low in cost; a plurality of hydrophilic polar active groups are introduced to the main chain through norbornene, so that the prepared polylactide has multiple structures, high degradability, strong hydrophilic property and many active groups; and when the polylactide serving as a medicament carrier is applied to preparation of a pro-medicament, the prepared pro-medicament is high and controllable in medicament loading rate and good in hydrophilic property, can be completely degraded, contains groups capable of being modified again and has great scientific research and economic value.

Description

technical field [0001] The invention relates to a polylactide containing side hydroxyl or side carboxyl functional groups and a preparation method thereof, belonging to the field of polymer modification. technical background [0002] Aliphatic polyesters represented by polylactide (PLA) are one of the few biomedical materials that have been certified by the US FDA. They have the advantages of good biocompatibility and biodegradability, but they have a single chemical structure and high molecular weight. The main chain lacks functional groups that can further bond with drugs and biologically active substances, and its water solubility is poor. In order to solve these problems, it is necessary to introduce reactive hydrophilic groups on the side chains of polylactide. In order to obtain a polymer drug carrier comparable to polyglutamic acid, that is, a drug carrier with hydrophilicity, degradability and good biocompatibility, while using its reactive functional groups to reali...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/91C08G63/08A61K47/34
Inventor 张雪飞麻戈军
Owner XIANGTAN UNIV
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