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Fluorocarbon chain or/and hydrocarbon chain containing phosphatidylcholine blocking agent with hydroxyl or amino at tail end and polyurethane material for blocking same

A technology for hydrocarbon chain phosphatidyl choline and polyurethane materials, which is applied in the field of polyurethane materials and can solve the problems of inability to carry out secondary processing, decreased mechanical properties of materials, poor compatibility and the like

Active Publication Date: 2010-07-28
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the above research reports, we still found that when such phosphatidylcholine-containing diols are used as chain extenders, the molecular weight of the synthesized polyurethane generally decreases significantly, which is the reason for the decline in the mechanical properties of the material compared with ordinary polyurethane. the main reason
[0007] 3) Research on surface phospholipidated polyurethane: grafting 2-methacryloyloxyethyl phosphatidylcholine (MPC) onto the surface of polyurethane [Chem.Mater.1999, 11, 763; Biomaterials, 2002, 23, 263 】It can effectively reduce the adhesion of platelets, and then use an appropriate cross-linking agent to cross-link the MPC grafted on the surface of polyurethane [Chem.Mater.1999, 11, 2155] so that the phosphatidylcholine group has Sequential arrangement has a stronger ability to inhibit platelet adhesion, but it has also been reported that after grafting phospholipids to the surface of polyether polyurethane, it cannot inhibit the adsorption of proteins on the surface, and its biocompatibility has no significant difference with polyether polyurethane. Difference [J. Biomed. Mater. Res., 1998, 40, 195]
However, due to the poor compatibility between MPC polymer and polyurethane, a small amount of MPC copolymer oozes out when the blended material is immersed in water for 10 days [J.Biomed.Mater.Res., 1996, 32:391]
Iwasaki et al [J.Biomed Mater.Res., 2000,52:701.] have prepared a biocomposite material of semi-interpenetrating network of cross-linked phospholipid polymer copolymer and polyurethane, although this material has excellent mechanical properties and Good biocompatibility, but no secondary processing, and Morimoto et al [Biomaterials, 2004, 25, 1098] realized a semi-interpenetrating network between MPC polymer and polyurethane surface layer, the biocompatibility of the material is consistent with Iwasaki's research The results are similar, but only partially overcome the problems encountered by the phospholipidated polyurethane composites prepared by Iwasaki et al.

Method used

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  • Fluorocarbon chain or/and hydrocarbon chain containing phosphatidylcholine blocking agent with hydroxyl or amino at tail end and polyurethane material for blocking same
  • Fluorocarbon chain or/and hydrocarbon chain containing phosphatidylcholine blocking agent with hydroxyl or amino at tail end and polyurethane material for blocking same
  • Fluorocarbon chain or/and hydrocarbon chain containing phosphatidylcholine blocking agent with hydroxyl or amino at tail end and polyurethane material for blocking same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] What this embodiment prepared was HDFOPC, and the codes used in this embodiment are respectively:

[0072] HDFDAC: (10-(1-carboxymethoxy)-2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluorodecane Oxy)acetic acid

[0073] HDFOOL: 2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(2-hydroxyethoxy )decyloxy)ethanol

[0074] ACDFOOL: 2-(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(2-hydroxyethoxy )decyloxy)ethyl acetate

[0075] COP: Ethylene cyclophosphoryl chloride.

[0076] The method and steps for preparing HDFOPC are as follows:

[0077] Step 1: Synthesis of HDFOOL

[0078] Dissolve 2 grams of HDFDAC (3.46mmol) [see patent CN1569917A for the preparation method] in 30ml of anhydrous tetrahydrofuran, lower the temperature to about -15°C, add 0.95ml of N-methylmorpholine (8.65mmol), and then add 0.95ml of chlorine Isobutyl formate (7.3mmol), after reacting for 15 minutes, add excess sodium borohydride, after reacting for 2 hours, add a small amount of water to ...

Embodiment 2

[0090] What this embodiment prepared was ADDPC, and the codes used in this embodiment were respectively:

[0091] (BOC) 2 O: tert-butoxycarbonic anhydride

[0092] BOC-Serine: 2-(tert-butoxycarbonylamino)-3-(hydroxy)propionic acid

[0093] BDPA: 2-(tert-butoxycarbonylamino)-3-(decyloxy)propionic acid

[0094] BDOHP: 2-(tert-butoxycarbonylamino)-3-(decyloxy)propanol

[0095] ACDOHPC: 2-Amino-3(decyloxy)propylphosphatidylcholine

[0096] HOSu: N-Hydroxysuccinimide

[0097] BSA: 10-(2-(tert-butoxycarbonylamino)ethylamino)-10-oxodecanoic acid

[0098] BSSI: Succinimidyl 10-(2-(tert-butoxycarbonylamino)ethylamino)-10-oxodecanoate

[0099] BDDPC: 2-(10-(2-(tert-butoxycarbonylamino)ethylamino)-10-oxodecanylamido)-3-decyloxypropylphosphatidylcholine

[0100] ADDPC: 2-(10-(2-aminoethylamino)-10-oxydecylamino)-3-decyloxypropylphosphatidylcholine The method and steps for preparing ADDPC are as follows:

[0101] Step -: Synthesis of BOC-Serine

[0102] Dissolve 30 grams (0.2857mo...

Embodiment 3

[0133] What this embodiment prepared was ADFPC, and the codes used in this embodiment were respectively:

[0134]BAEFAC: 2-(10-(2-(2-(tert-butoxycarbonylamino)ethylamino)-2-oxyethoxy)-2,2,3,3,4,4,5,5, 6,6,7,7,8,8,9,9-hexadecafluorodecyloxy)acetic acid

[0135] ACDFOPC: ACDOHPC: 2-Amino-3(decyloxy)propylphosphatidylcholine

[0136] ADFPC: 2-(2-(10-(2-(2-aminoethylamino)-2-oxyethoxy)-2,2,3,3,4,4,5,5,6,6, 7,7,8,8,9,9-Hexadecafluorodecyloxy)acetamido)-3-(decyloxy)propylphosphatidylcholine

[0137] DCC: Cyclohexylcarbodiimide DCU: N,N-Dicyclohexylurea

[0138] The method and steps for preparing ADFPC are as follows:

[0139] Step 1: Synthesis of BAEFAC

[0140] Dissolve 5 grams (8.65 mmol) of HDFDAC [see patent CN1569917A for the preparation method] in 100 ml of anhydrous tetrahydrofuran, lower the temperature to about -10°C, add 1.14 ml (10.4 mmol) of N-methylmorpholine and 1.13 ml ( 8.65mmol) of isobutyl chloroformate, after 10 minutes of reaction, 1.38 grams (8.65mmol) of ...

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Abstract

The invention discloses fluorocarbon chain or / and hydrocarbon chain containing phosphatidylcholine blocking agent with hydroxyl or amino at the tail end, fluorocarbon single-chain containing phosphatidylcholine with hydroxyl or amino at the tail end, fluorocarbon double-chain containing phosphatidylcholine with hydroxyl or amino at the tail end, fluorocarbon and hydrocarbon mixed double-chain containing phosphatidylcholine with hydroxyl or amino at the tail end, or hydrocarbon double-chain containing phosphatidylcholine with hydroxyl or amino at the tail end. The invention also discloses a polyurethane material for blocking the blocking agents respectively. Because the blocking agent provided by the invention enables a phosphatidylcholine group to be positioned at the polyurethane tail end with high activity, the phosphatidylcholine group easily moves to the surface of the material so as to obtain phosphatide surface polyurethane; therefore, the blocking agent can endow the material with good biocompatibility and keep excellent physical and mechanical properties of the material, and the material has low cost and can be secondarily processed conveniently for manufacturing artificial blood vessels, artificial cardiac pacemaker leads, artificial heart valves, interposed catheters and the like.

Description

technical field [0001] The invention belongs to the technical field of phosphatidylcholine end-capping agents containing fluorocarbon chains or / and hydrocarbon chains and polyurethane materials capped therewith, in particular to phospholipids containing fluorocarbon chains or / and hydrocarbon chains with hydroxyl or amine groups at the end Acylcholine blocking agent and polyurethane material blocked by it. Background technique [0002] Polyurethane is widely used in biomedical fields (implanted medical devices and artificial organs) due to its excellent mechanical strength, high elasticity, wear resistance, lubricity, fatigue resistance, good biocompatibility, and processability. Such as cardiac pacemaker insulated wires, artificial blood vessels, interventional catheters, etc. Although polyurethane has good biocompatibility, it still cannot avoid the formation of thrombus after contact with blood during long-term use. Therefore, polyurethane cannot be used to prepare small...

Claims

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Application Information

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IPC IPC(8): C07F9/09C08G18/38
Inventor 谭鸿傅强张笑晴谭东升周立娟李洁华
Owner SICHUAN UNIV
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