EP0319957A2
Expired / Lapsed
EP
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A method for modifying the surface of a polymer
Assignee: GLUETECH APS
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Filing: 1988-12-07
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Granted: —
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Expires: 2008-12-07
Abstract
Abstract The surface of a polymer may be modified by contacting the polymer with a two or three membered heterocyclic compound I under electromagnetic irradiation. The heterocyclic compound may be substituted and may comprise linking units and/or probes so as to render the combination of polymer and compound I able to bind biomolecules and/or to be identified. Compounds I are preferably substituted psoralens, and the modified polymers can be used in e.g. ELISA methods, bioreactors, chromatography, solid phase chemical synthesis or bio-sensors.
Inventors
- 👤 Henrik Elsner
- 👤 Soren Mouritsen
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 16:26
CPC Classifications
C; C08; C08J; C08J7/00; C08J7/12; C12; C12N; C12N11/00; C12N11/02; C12N11/08; C12N11/082; C12Q; C12Q1/00; C12Q1/001; C12Q1/002; C12Q1/003; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/543; G01N33/54353; G01N33/544; G01N33/545; Y; Y10; Y10S; Y10S530/00; Y10S530/81; Y10S530/812; Y10S530/815; Y10S530/816
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
217 words
A method for modifying the surface of a polymer comprising contacting the polymer surface with a compound of the general formula I in which A is -O-, -S-, -Se-, >NH, >NR¹, -NH-O-, -N=N-, >S⁺R¹, -S-O-, >Se+R¹, CO-O-, -CO-S-, -CS-O-, CSe-O-, -CO-Se-, -CS-NH-, -CO-NH-, -CO-N-(R¹)-, >P=O or -P(=O)(O⁻)-; R¹ is hydrocarbyl or hydrocarbyloxy, any of which may be substituted with NO, NO₂, SO₃, CN, OH, -O, SH, SeH, PO₃⁻⁻, PO₂⁻, COO-, halogen, epoxide, NH₂, NHR¹or NR¹R′¹ (in which R′¹ has the same meaning as defined for R¹); R², R³, R⁴, and R⁵, which may be the same or different, are H, halogen, NO₂, NO, SO₃⁻, CN, OH, O, SH, SeH, PO₃⁻⁻, PO₂⁻, CO-O, epoxide, -NH₂, -NHR¹, -NR¹R′¹ or heterocyclyl, or has the same meaning as defined for R¹; X and Y, which may be the same or different, have the same meaning as defined for R²-R⁵, or X and Y are adjacent to one another and together form a group with the formula -CR⁶=CR⁷-A′- where A′ has the same meaning as defined for A above, and R⁶ and R⁷ which may be the same or different have the same meaning as defined for R²-R⁵; and optionally, one or more of R¹-R⁷ designates a probe; and irradiating the polymer and the compound of the formula I with electromagnetic radiation.
Claim 2
Independent Claim
217 words
A method for modifying the surface of a polymer comprising contacting the polymer surface with a compound of the general formula I in which A is -O-, -S-, -Se-, >NH, >NR¹, -NH-O-, -N=N-, >S⁺R¹, -S-O-, >Se+R¹, CO-O-, -CO-S-, -CS-O-, CSe-O-, -CO-Se-, -CS-NH-, -CO-NH-, -CO-N-(R¹)-, >P=O or -P(=O)(O⁻)-; R¹ is hydrocarbyl or hydrocarbyloxy, any of which may be substituted with NO, NO₂, SO₃, CN, OH, -O, SH, SeH, PO₃⁻⁻, PO₂⁻, COO-, halogen, epoxide, NH₂, NHR¹or NR¹R′¹ (in which R′¹ has the same meaning as defined for R¹); R², R³, R⁴, and R⁵, which may be the same or different, are H, halogen, NO₂, NO, SO₃⁻, CN, OH, O, SH, SeH, PO₃⁻⁻, PO₂⁻, CO-O, epoxide, -NH₂, -NHR¹, -NR¹R′¹ or heterocyclyl, or has the same meaning as defined for R¹; X and Y, which may be the same or different, have the same meaning as defined for R²-R⁵, or X and Y are adjacent to one another and together form a group with the formula -CR⁶=CR⁷-A′- where A′ has the same meaning as defined for A above, and R⁶ and R⁷ which may be the same or different have the same meaning as defined for R²-R⁵; and optionally, one or more of R¹-R⁷ designates a probe; and irradiating the polymer and the compound of the formula I with electromagnetic radiation.
Claim 3
Dependent Claim
24 words
A method as claimed in claim 1 wherein the radiation is performed at a wavelength shorter than 700 nm, preferably shorter than 400 nm.
Claim 4
Dependent Claim
42 words
A method as claimed in claim 1 and b wherein the radiation is performed using ab aqueous solution of compound I preferably having a pH of from about 5 to about 9 and optionally containing an ionic strength modifying compound preferably NaCl.
Claim 5
Dependent Claim
25 words
A method as claimed in anyone of claim 1 and 3 wherein the radiation is performed in the presence of an activator molecule, preferably benzoquinone.
Claim 6
Dependent Claim
38 words
A method as claimed in claim 1 wherein the polymer is selected from polystyrene, polyethylene glycol terephthalate, polyvinyl acetate, polyvinyl chloride, polyvinyl pyrrolidone, polyacrylo nitrile, polymethyl methacrylate, polytetrafluoro ethylene, butyl rubber, styrene-butadiene rubber, natural rubber, polyethylene, and polypropylene.
Claim 7
Independent Claim
29 words
A method as claimed in any of claims 1 to 5 wherein the compound I is selected from the group consisting of optionally substituted coumarins, benzofurans, indols and angelicins.
Claim 8
Dependent Claim
16 words
A method as claimed in claim 6 wherein the optionally substituted coumarins are optionally substituted psoralens.
Claim 9
Dependent Claim
24 words
A method as claimed in claim 7 wherein at least one of the substituent groups in the psoralens is an amino group containing constituent.
Claim 10
Dependent Claim
16 words
A method as claimed in claim 8 wherein the amino group containing constituent is 3-trimethylamino propoxy.
Claim 11
Dependent Claim
22 words
A method as claimed in claim 7 wherein the optionally substituted psoralen is selected from psoralen, 8-methyl-3-carboxypsoralen, 4,5′,8-trimethylpsoralen, 3′-trimethyl-amino-8-propyloxy psoralen or N,N′-dimethylhexanediamine-8-propyloxypsoralen.
Claim 12
Dependent Claim
13 words
A method as claimed claim 6 wherein the optionally substituted coumarin is warfarin.
Claim 13
Dependent Claim
17 words
A method as claimed in claim 6 wherein the optionally substituted indol is 5-hydroxytryptamine or 3-indolacetic acid.
Claim 14
Dependent Claim
26 words
A method as claimed in claim 1 wherein the probe is an organic constituent which is optionally connected to the compound I via a linking unit.
Claim 15
Dependent Claim
33 words
A method as claimed in claim 13 wherein the probe is selected from label moieties which are capable of being identified, compounds comprising reactive chemical groups, non-covalent interacting chemical groups, and other molecules.
Claim 16
Dependent Claim
39 words
A method as claimed in claim 14 wherein the label moieties which are capable of being identified are selected from the group consisting of biotin, radioactive compounds, spin labels, fluorigenic compounds, enzymes, enzyme substrates, pH colourigenic compounds, and haptenes.
Claim 17
Dependent Claim
38 words
A method as claimed in claim 14 wherein the compounds comprising reactive chemical groups are selected from the group consisting of active esters capable of forming covalent bonds with other chemical groups, active halogen-containing compounds, and disulphide-containing compounds.
Claim 18
Dependent Claim
31 words
A method as claimed in claim 14 wherein the non-covalent chemical groups are charged or hydrophobic chemical groups with affinity for compounds carrying an opposite charged group or a hydrophobic group.
Claim 19
Dependent Claim
32 words
A method as claimed in claim 14 wherein the other molecules are selected from the group consisting of proteins, peptides, pharmaceuticals, mono-, oligo- or polysaccharides, or -nucleic acids, and optionally substituted lipids.
Claim 20
Dependent Claim
36 words
A method as claimed in claim 1 wherein the polymer is polystyrene, the compound of formula I is 8-propoxypsoralen which carries a probe, which is biotin connected to the compound I via N,N′-dimethyl hexane diamine linker.
Claim 21
Dependent Claim
38 words
A method as claimed in claim 1 wherein the polymer is polyvinyl chloride, the compound of formula I is 8-propoxypsoralen which carries a probe, which is biotin connected to the compound I via a N,N′-dimethyl hexane diamine linker.
Claim 22
Dependent Claim
40 words
A method as claimed in claim 1 wherein the polymer is polyethylene glycol terephthalate, the compound of formula I is 8-propoxypsoralen which carries a probe, which is biotin connected to the compound I via a N,N′- dimethyl hexane diamine linker.
Claim 23
Dependent Claim
18 words
A method as claimed in claim 1 wherein the polymer is polystyrene and the compound I is 3′-trimethyl-propyloxy-8-psoralen.
Claim 24
Dependent Claim
11 words
A modified polymer as prepared by the method of claim 1.
Claim 25
Dependent Claim
25 words
A modified polymer as claimed in claim 23 and presented in the form of a plate, a particle, a test tube or a test strip.
Claim 26
Dependent Claim
30 words
A method of determining the presence of a molecule in a sample, comprising contacting a sample containing said molecule with a modified polymer as claimed in claim 23 or 24.
Claim 27
Dependent Claim
33 words
A method as claimed in claim 25 wherein the solid surface is selected from a polymeric plate such as a thin layer plate or micro-titre-plate, polymeric beads, strips, dipsticks, test tubes, and (micro)spheres.
Claim 28
Dependent Claim
95 words
A method of immobilizing a molecule on a solid surface comprising the steps of a) reacting the molecule with a compound of the general formula I, optionally by means of a linking unit, contacting the combination with a polymer material and subjecting the polymer and combined molecule and compound I to electromagnetic irradiation or b) modifying the surface of a polymer by contacting it with a compound I as defined in claim 1 by means of electromagnetic irradiation and thereafter reacting the modified polymer surface with the molecule, optionally by means of a linking unit.
References Cited (Backward Citations)
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