Thermo-responsive polypeptoid containing oligomeric polyethylene glycol in side chain and preparation method of polypeptoid

A temperature-responsive, oligoethylene glycol technology, which is applied in the field of polymer biomaterials and its preparation, can solve the problems of wide transition range of cloud point of co-polymerization peptides, and achieve simple synthesis methods, wide application prospects, Effects from a wide range of sources

Inactive Publication Date: 2018-04-06
QINGDAO 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 aggregation of the copolymers, the cloud point transition range of the co-aggregated peptides is relatively wide

Method used

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  • Thermo-responsive polypeptoid containing oligomeric polyethylene glycol in side chain and preparation method of polypeptoid
  • Thermo-responsive polypeptoid containing oligomeric polyethylene glycol in side chain and preparation method of polypeptoid
  • Thermo-responsive polypeptoid containing oligomeric polyethylene glycol in side chain and preparation method of polypeptoid

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Experimental program
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Effect test

Embodiment 1

[0038] Preparation of clustering peptides shown in embodiment 1, formula (II)

[0039]

[0040](1) First add glyoxylic acid (16.87g, 227mmol) in a 500ml round bottom flask, add 250mL dichloromethane and stir to make it dissolve, then add propargylamine (5g, 90.8mmol) in this system Propargylamine and glyoxylic acid The molar fraction ratio was 1:2.5, the reaction solution was stirred at room temperature for 24 hours, the solvent was removed by a rotary evaporator, 150 mL of dilute hydrochloric acid (1 mol / L) was added and refluxed at 110°C for 24 hours. Remove the solvent with a rotary evaporator, dissolve in 30mL of methanol, recrystallize in ether, seal it and put it in a -20°C refrigerator for 24 hours, filter and dry in vacuo to obtain a brown solid (9.09g, yield 67%); H NMR 1 H NMR (500MHz,D 2 O): δ3.72(d, 2H), 3.71(t, 2H), 2.71(t, 1H).

[0041] (2) Weigh 9 grams (60.15mmol) of the brown solid obtained in step (1), put it into a clean 500ml single-necked flask, add 1...

Embodiment 2

[0047] Preparation of clustering peptides shown in embodiment 2, formula (III)

[0048] Experimental steps (1)-(4) are the same as in Example 1, (5) the click chemical reaction of this step is carried out in a UV light box: weigh 200mg (0.032mmol) of the white solid obtained in step (4), put it into 10mL In a Shrek bottle, weigh 27 mg (0.102 mmol) of benzoin dimethyl ether (the molar ratio of benzoin dimethyl ether to the alkynyl content in the white solid is 1:20), and add OEG under nitrogen protection 3 -SH1.85mL (10.29mmol) (OEG 3 The mole fraction ratio of -SH to the content of alkynyl groups in the white solid is 5:1), placed in a UV light box for 3 hours of UV light reaction, and dialyzed for 3 days. After dialysis, a brown oil was obtained, which was the clustered peptide shown in (III). H NMR spectrum (such as figure 2 b) 1 H NMR of HEX-PNPG-g-EG 3 (500MHz, CDCl 3 ):δ0.85-0.88(br,3H),1.24-1.27(br,10H),2.68-2.89(br,6H),3.16-3.37(br,6H),3.54(br,21H),3.63(br , 4H)...

Embodiment 3

[0051] Preparation of clustering peptides shown in embodiment 3, formula (IV)

[0052] Experimental steps (1) to (3) are the same as in Example 1, and the polymerization reaction of (4) this step is carried out in a glove box or in a reaction bottle protected by nitrogen or argon: the white crystal 2g obtained in step (3) Transfer to a 200mL Shrek bottle, add 22mL of anhydrous tetrahydrofuran to dissolve it, and make a 100 mg / ml solution, then quickly add 0.81 ml of tetrahydrofuran solution (40 mg / ml) containing hexamethyldisilamine (the system In, the mole fraction ratio of hexamethyldisilazide to the white crystals obtained in step (3) is 1:80) at 55° C. for 48 hours. The solution after the reaction is finished is added dropwise in 200ml of normal hexane for sedimentation, and the settled polymer is put into a centrifuge for centrifugation. The polymer obtained by centrifugation was dissolved in tetrahydrofuran and sedimented again, and after several times of sedimentation ...

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Abstract

The invention discloses a thermo-responsive polypeptoid containing oligomeric polyethylene glycol (OEG) in a side chain and a preparation method of the polypeptoid. A click chemical reaction under ultraviolet light is carried out on a polypeptoid containing acetylenic bonds in a side chain with methoxy oligomeric ethylene glycol mercaptan (OEGX-SH), so that the target thermo-responsive polypeptoidis obtained. The thermo-responsive polypeptoid disclosed by the invention is simple in synthetic route, low in cost, high in purity, high in product yield, stable in property, simple in structure andeasy in regulate and control; the temperature responsiveness is easy to regulate and control; and the thermo-responsive polypeptoid is an excellent thermo-responsive polypeptoid material, and has a wide potential application value and research value.

Description

technical field [0001] The invention relates to a temperature-responsive polymeric peptide containing oligoethylene glycol in its side chain and a preparation method thereof, belonging to the field of high molecular biomaterials and its preparation. Background technique [0002] Biopolymer materials have many unique and excellent properties and are widely used in various fields. Among them, clustering peptide is a kind of polymer material with good biocompatibility and degradability. It has high application value in biomedical fields such as smart coatings, drug delivery and bioseparation, and has attracted more and more attention. , has become a research hotspot in the field of materials worldwide. [0003] The structure of clustered peptides is similar to that of polypeptides, the only difference is that its side chain substituents are located on the main chain nitrogen atoms, so there is no chiral center on the backbone of clustered peptides, and there is no strong hydro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/14C08G69/16C08G69/48
CPCC08G69/14C08G69/16C08G69/48
Inventor 孙静田继亮李志波
Owner QINGDAO UNIV OF SCI & TECH
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