WO2013176084A1 - Agent de couplage de type silane contenant un composé silylalkyl phosphoramidate - Google Patents
Agent de couplage de type silane contenant un composé silylalkyl phosphoramidate Download PDFInfo
- Publication number
- WO2013176084A1 WO2013176084A1 PCT/JP2013/063943 JP2013063943W WO2013176084A1 WO 2013176084 A1 WO2013176084 A1 WO 2013176084A1 JP 2013063943 W JP2013063943 W JP 2013063943W WO 2013176084 A1 WO2013176084 A1 WO 2013176084A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silane coupling
- coupling agent
- substrate
- group
- silylalkyl
- Prior art date
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- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 30
- -1 silylalkyl phosphoramidate compound Chemical class 0.000 title abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 239000000758 substrate Substances 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000005353 silylalkyl group Chemical group 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 6
- 239000003495 polar organic solvent Substances 0.000 claims description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims 1
- 239000011521 glass Substances 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 17
- 239000000243 solution Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000004381 surface treatment Methods 0.000 description 6
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 5
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- 238000005481 NMR spectroscopy Methods 0.000 description 4
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 239000002609 medium Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012756 surface treatment agent Substances 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- SBMUNILHNJLMBF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-dioxaphospholane 2-oxide Chemical compound ClP1(=O)OCCO1 SBMUNILHNJLMBF-UHFFFAOYSA-N 0.000 description 1
- GLISOBUNKGBQCL-UHFFFAOYSA-N 3-[ethoxy(dimethyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(C)CCCN GLISOBUNKGBQCL-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- BHWJGSNIXSMRGY-UHFFFAOYSA-N CCO[Si](C)(C)CCCNP1(=O)OCCO1 Chemical compound CCO[Si](C)(C)CCCNP1(=O)OCCO1 BHWJGSNIXSMRGY-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
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- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
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- 102000004142 Trypsin Human genes 0.000 description 1
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- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- YHHSONZFOIEMCP-UHFFFAOYSA-O phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 description 1
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- VSIVTUIKYVGDCX-UHFFFAOYSA-M sodium;4-[2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)tetrazol-2-ium-5-yl]benzene-1,3-disulfonate Chemical compound [Na+].COC1=CC([N+]([O-])=O)=CC=C1[N+]1=NC(C=2C(=CC(=CC=2)S([O-])(=O)=O)S([O-])(=O)=O)=NN1C1=CC=C([N+]([O-])=O)C=C1 VSIVTUIKYVGDCX-UHFFFAOYSA-M 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
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- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
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- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
- A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/424—Anti-adhesion agents
Definitions
- the present invention includes a silylalkyl phosphoramide compound capable of suppressing the adhesion of biological materials such as proteins, cells, and platelets by performing a surface treatment on an inorganic material such as silicon or glass, or a resin such as polyethylene.
- the present invention relates to a silane coupling agent.
- an anticoagulant such as heparin or a drug such as an immunosuppressant must be used in combination.
- MPC polymer poly (2-methacryloyloxyethyl phosphorylcholine) (hereinafter referred to as MPC polymer) having phosphorylcholine, which is the same amphoteric phospholipid as the biological membrane, in the side chain of the polymer chain is used Medical materials that have been proposed have been proposed (see, for example, Patent Document 1 and Patent Document 2).
- CMB polymer N-methacryloyloxyethyl-N, N-dimethylammonium- ⁇ -N-methylcarboxybetaine
- An object of the present invention is a compound that is a non-polymer that is easy to produce, and the compound is directly applied to the surface of a substrate by applying the solution in which the compound is dissolved to the substrate or immersing the substrate in the solution. It is another object of the present invention to provide a compound capable of firmly covering the surface of the body and exhibiting the same biological substance adhesion inhibitory effect as the conventional MPC polymer and CMB polymer.
- silylalkyl phosphoramidade compounds are useful as silane coupling agents, and silane coupling agents containing such compounds are proteins, cells, It has been found that it has an effect of suppressing adhesion of biological substances such as platelets. That is, the present invention 1. Following formula (1):
- a silane coupling agent composition comprising the silylalkyl phosphoramidade compound according to 1 above, 3.
- a silane coupling agent comprising a step of applying and baking the silane coupling agent composition described in 2 or 3 above on a substrate, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
- Immobilization method 5. Immobilization of a silane coupling agent comprising a step of immersing a substrate in the silane coupling agent composition described in 2 or 3 above, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
- Conversion method 6).
- silane coupling agent surface treatment agent
- a base material a resin such as polyethylene
- the surface is coated with a silylalkyl phosphoramidade compound having both stable positive and negative charges in one molecule. Therefore, adhesion of biological substances such as proteins, cells, and platelets to the inorganic substance or resin surface can be suppressed without using a polymer such as MPC polymer or CMB polymer.
- FIG. 1 is a diagram showing the cell adhesion inhibitory action of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate on a glass substrate.
- Cell free represents a glass substrate treated with 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate (30 mg / ml), and the control was controlled with the silane coupling agent of the present invention. Represents the result when no processing is performed.
- FIG. 2 is a diagram showing the results of measurement of living cells attached to a glass substrate of a silylalkyl phosphoramidade compound. Control represents the result when the treatment with the silane coupling agent of the present invention is not performed.
- silylalkyl phosphoramidade compound of the present invention represented by the formula (1) is 0.8 to 1.2 equivalents, preferably 1 equivalent of the formula (II) to the aminoalkylsilane represented by the formula (I). ) Is reacted at 20 to 80 ° C. in the presence of a base to obtain a compound represented by the formula (III). It can be obtained by reacting 8 to 1.2 equivalents, preferably 1 equivalent of a tertiary amine represented by the formula (IV) at 0 to 50 ° C.
- an organic base such as triethylamine is preferable.
- R 1 , R 2 and R 3 are methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl.
- Group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group, and methyl group and ethyl group are particularly preferable.
- R 4 is methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s -Butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group can be mentioned, and methyl group and ethyl group are particularly preferable.
- R 5 represents methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s -Butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group can be mentioned, and methyl group and ethyl group are particularly preferable.
- n may be an integer of 1 to 5, and 2 or 3 is particularly preferable.
- p may be an integer of 1 to 5, but 2 or 3 is particularly preferable.
- q is an integer of 1 to 3.
- the silylalkyl phosphoramariae compound of the present invention is used for surface treatment of an inorganic substance as a base material
- the inorganic substance is not particularly limited.
- silicon, copper, iron, aluminum, zinc or an alloy thereof, glass, silica, aluminum oxide, aluminum hydroxide, and magnesium oxide can be given.
- the resin is not particularly limited.
- examples include poly (meth) acrylamide, poly (meth) acrylamide derivatives, polysulfone, polycarbonate, cellulose, and cellulose derivatives.
- the silylalkyl phosphoramidade compound of the present invention can be used for surface treatment of pharmaceuticals, quasi drugs, medical instruments and the like.
- medical devices include drug delivery system materials, molding aids, packaging materials, artificial blood vessels, hemodialysis membranes, catheters, guard wires, contact lenses, blood filters, blood storage packs, endoscopes, artificial organs, biotechnology A chip, a cell culture sheet, and a sugar chain synthesizer can be mentioned, but there are no particular limitations on the medical instrument.
- the silane coupling agent (surface treatment agent) composition containing the silylalkyl phosphoramidade compound of the present invention includes, for example, water and a polar organic solvent such as methanol, ethanol, propylene glycol monomethyl ether and the like on the silylalkylphosphoramidade compound. In addition, it is prepared by diluting to 0.001 to 20% by mass.
- a polar organic solvent such as methanol, ethanol, propylene glycol monomethyl ether and the like on the silylalkylphosphoramidade compound.
- an organic acid may be further added. Examples of the organic acid include acetic acid, formic acid, lactic acid, and oxalic acid.
- the surface treatment of the substrate with the silane coupling agent composition of the present invention is not particularly limited, and for example, the substrate can be treated by dipping, coating (spin coating, spray coating, etc.) or vapor deposition.
- silane coupling is performed through a step of applying and baking the silane coupling agent composition of the present invention on a substrate, a step of washing the substrate with a polar solvent, and a step of drying the substrate. Immobilize the agent.
- the silane coupling agent is immobilized through a step of immersing the substrate in the silane coupling agent composition, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
- the polar solvent used in the washing step for example, water or a polar organic solvent contained in the silane coupling agent composition can be used.
- 2-Chloro-2-oxo-1,3,2-dioxaphospholane (3.37 g) was dissolved in tetrahydrofuran (20 mL), cooled to 0 ° C., triethylamine (2.88 g, 1.2 molar equivalent) was added, and the mixture was stirred. . 3.82 g (1.0 molar equivalent) of (3-aminopropyl) dimethylethoxysilane was added dropwise, and the temperature was gradually raised to 25 ° C. After stirring overnight, the insoluble material was filtered under reduced pressure.
- Example 4 Treatment of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate on a glass substrate
- 2- (Trimethylammonio) ethyl (3- (ethoxy) synthesized in Example 2 10 mg of dimethylsilyl) propyl) phosphoramidate is dissolved in 1 mL of 70% ethanol aqueous solution, and 0.1 mL is dropped on a glass substrate (a square with a side of 2 cm) attached to a spin coater, and 300 rpm for 5 seconds, followed by 2500 rpm, 25 Spin coating was performed for 2 seconds. Then, it heat-processed for 60 second with a 100 degreeC hotplate, and was fixed.
- a similar treatment was performed on a solution of 30 mg of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate in 1 mL of 70% ethanol aqueous
- Example 5 Treatment of 2- (trimethylammonio) ethyl (3- (triethoxysilyl) propyl) phosphoramidate on a glass substrate
- 2- (trimethylammonio) ethyl (3- (tri 30 mg of ethoxysilyl) propyl) phosphoramidate is dissolved in 1 mL of 70% ethanol aqueous solution, and 0.1 mL is dropped on a glass substrate (a square with a side of 2 cm) mounted on a spin coater, and 300 rpm for 5 seconds, followed by 2500 rpm, 25 Spin coating was performed for 2 seconds. Furthermore, it was fixed by heat treatment for 60 seconds on a 100 ° C. hot plate.
- Comparative Example 1 Treatment of MPC polymer on glass substrate 15 mg of MPC (2-methacryloyloxyphosphorylcholine) polymer (PUREBRIGHT MB, registered by NOF Corporation) was dissolved in 0.5 mL of 70% aqueous ethanol solution, and 0.1 mL was spinned. It was dropped on a glass substrate (a square having a side of 2 cm) mounted on the coater, and spin coating was performed at 300 rpm for 5 seconds followed by 2500 rpm for 25 seconds. Furthermore, it was fixed by heat treatment for 60 seconds on a 100 ° C. hot plate.
- MPC (2-methacryloyloxyphosphorylcholine) polymer PUREBRIGHT MB, registered by NOF Corporation
- Example 6 Confirmation of Cell Adhesion Inhibition Action on Glass Substrate Treated with 2- (Trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) Phosphoramidate HEK293 cells (human kidney-derived cell line Human Embryonic Kidney ( 2 ⁇ 10 6 cells / ml) was pre-cultured in a Dulbecco's Modified Eagle Medium (D-MEM) medium at 37 ° C. for 2 days, and 3 mL seeded in a 12-well plate containing a glass substrate treated by the method of Example 4 Then, 0.8 mL of D-MEM was added and cultured for 1 day at 37 ° C.
- D-MEM Dulbecco's Modified Eagle Medium
- the glass substrate was then transferred to another 12-well plate and 1 mL phosphate buffer (Dulbecco phosphate buffered saline, Dulbecco's Phosphate Buffered Sali
- phosphate buffer Dulbecco phosphate buffered saline, Dulbecco's Phosphate Buffered Sali
- the cells were detached from the glass substrate by adding 0.3 mL of a 0.1% trypsin solution (manufactured by SIGMA), to which 3 mL of D-MEM was added, and WST was further added.
- 0.3 mL of -8 Korean (registered trademark) was added to each well and incubated at 37 ° C. for 4 hours, and then 0.11 mL was transferred to a 96-well plate and the absorbance was measured.
- 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate is obtained by treating 0.1 mL of 10 mg / mL and 30 mg / mL solutions on a glass substrate. The adhesion of HEK cells to the glass substrate was suppressed.
- Example 7 Measurement of living cells attached to a treated glass substrate.
- HEK293 cells human kidney-derived cell line Human Embroidic Kidney (2 ⁇ 10 6 cells / ml) pre-cultured in Dulbecco's Modified Eagle Medium (D-MEM) medium at 37 ° C. for 2 days were treated in Example 4.
- D-MEM Dulbecco's Modified Eagle Medium
- these glass substrates were transferred to another 6-well plate and washed with 1 mL of phosphate buffer (Dulbecco's phosphate buffered saline, Dulbecco's Phosphate Buffered Saline), respectively, and 1 mL of D-MEM was then removed.
- phosphate buffer Dulbecco's phosphate buffered saline, Dulbecco's Phosphate Buffered Saline
- WST-8 Wooda Chemical
- 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate and 2- (trimethylammonio) ethyl (3- (triethoxysilyl) propyl) phosphoramidate are By treating 0.1 mL of a 30 mg / mL solution on a glass substrate, HEK cell adhesion to the glass substrate was suppressed. This inhibitory effect was equivalent to or better than that of MPC polymer.
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Abstract
L'invention a pour but de proposer un nouvel agent de couplage de type silane. A cet effet, l'invention concerne un composé silylalkyl phosphoramidate représenté par la formule (1), et une composition d'agent de couplage de type silane qui contient le composé. (Dans la formule, chacun parmi R1, R2 et R3 représente indépendamment un groupe alkyle ayant 1-5 atomes de carbone ; chacun parmi R4 et R5 représente indépendamment un groupe alkyle ayant 1-5 atomes de carbone ; chacun de n et p représente indépendamment un entier de 1-5 ; et q représente un entier de 1-3).
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EP2957563A1 (fr) * | 2014-06-19 | 2015-12-23 | Pentracor GmbH | Matériau de séparation comprenant des dérivés de la phosphorylcholine |
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JPH08507293A (ja) * | 1993-01-28 | 1996-08-06 | バイオコンパテイブルズ・リミテツド | 新規な材料 |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2957563A1 (fr) * | 2014-06-19 | 2015-12-23 | Pentracor GmbH | Matériau de séparation comprenant des dérivés de la phosphorylcholine |
WO2015193504A1 (fr) * | 2014-06-19 | 2015-12-23 | Pentracor Gmbh | Matériau de séparation comprenant des dérivés phosphorylcholine |
CN106459108A (zh) * | 2014-06-19 | 2017-02-22 | 彭特科尔有限公司 | 包含磷酰胆碱衍生物的分离材料 |
RU2666357C2 (ru) * | 2014-06-19 | 2018-09-07 | Пентракор Гмбх | Сепарационный материал, включающий производные фосфорилхолина |
CN106459108B (zh) * | 2014-06-19 | 2019-10-15 | 彭特科尔有限公司 | 包含磷酰胆碱衍生物的分离材料 |
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