WO1996026440A1 - Specific binding materials - Google Patents
Specific binding materials Download PDFInfo
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- WO1996026440A1 WO1996026440A1 PCT/GB1996/000410 GB9600410W WO9626440A1 WO 1996026440 A1 WO1996026440 A1 WO 1996026440A1 GB 9600410 W GB9600410 W GB 9600410W WO 9626440 A1 WO9626440 A1 WO 9626440A1
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- WIPO (PCT)
- Prior art keywords
- target
- specific binding
- materials
- binding material
- shape
- Prior art date
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Classifications
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/543—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3206—Organic carriers, supports or substrates
- B01J20/3208—Polymeric carriers, supports or substrates
- B01J20/3212—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3248—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such
- B01J20/3251—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one type of heteroatom selected from a nitrogen, oxygen or sulfur, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulphur
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3285—Coating or impregnation layers comprising different type of functional groups or interactions, e.g. different ligands in various parts of the sorbent, mixed mode, dual zone, bimodal, multimodal, ionic or hydrophobic, cationic or anionic, hydrophilic or hydrophobic
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/02—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving viable microorganisms
- C12Q1/24—Methods of sampling, or inoculating or spreading a sample; Methods of physically isolating an intact microorganisms
Definitions
- the present invention relates to specific binding materials, to methods for their preparation and methods for their use. Particularly there are provided novel specific binding materials and methods that have application in separation and/or concentration of biological targets such as macromolecules and microorganisms, and particularly those targets found in water supplies, food and food derived materials.
- immobilise biological targets such as DNA, RNA, viruses and viral components, bacteria, antigens and antibodies, using specific binding materials.
- These materials typically comprise immobilised complementary species such as oligonucleotides, antibodies or antigens which have the capability to specifically bind the target.
- the species are immobilised on materials such as microtitre plates or wells, on latex or polymer beads or strips, on column materials such as polysaccharides, or on dipstick structures.
- the present inventors have now provided novel specific binding materials that utilise target shape and/or size, as well as optionally using specific binding species, to enable capture a biological target from a liquid medium in specific fashion.
- a specific binding material adapted to specifically bind with a target material characterised in that the specific binding material has areas upon its surface corresponding to the size and/or shape of the target .
- the target is a biological target, eg. a microorganism such as a virus particle, bacteria, yeast, antibody or antigen, and the areas on the binding material surface are shaped and sized to accommodate a substantial part of the target material.
- a biological target eg. a microorganism such as a virus particle, bacteria, yeast, antibody or antigen
- the areas on the binding material surface are shaped and sized to accommodate a substantial part of the target material.
- size and shape it is intended to refer to more than just a molecular level interaction such as that between two molecules; a physical size and shape of a substantial part of the target being what is being accommodated by the binding material.
- the material comprises a polymeric body on which areas corresponding in size and/or shape to the target have been formed. These areas preferably have a high affinity for binding the target; for example the size and/or shape specific area of the material may have functionalised species such as charge bearing groups or have antibodies or antigens bound to it, eg. by covalent bonding.
- the specificity and affinity of the specific binding material for the target material may be increased by treating the areas of the specific binding material surface that are not sized or shaped to correspond to the target material such as to reduce their ability to bind the target or any other material from a sample from which it is being specifically selected. In this fashion the specificity of the binding is increased as only targets having the correct size or shape can be effectively bound.
- Such treated or 'poisoned' specific binding materials may be used to bind any desired entity; whether a particulate material such as a virus, bacteria or other microorganism, or a specific macromolecule or smaller chemical entity.
- a particulate material such as a virus, bacteria or other microorganism, or a specific macromolecule or smaller chemical entity.
- treatments are those which remove or mask the species on the binding materials surface that cause the target and other materials to become bound.
- hydroxy groups may be esterified or converted to ethers, while carboxyl groups could be esterified or reduced. Still more effectively these groups can be masked by treatment with groups such as silyl or perfluoro groups using entities as will be illustrated in the Examples below.
- a method for preparation of the specific binding materials of the present invention comprising binding a target material to the surface of the specific binding material such that the surface of the specific binding material becomes adapted the size and/or shape of the target material, then removing the target material from that surface.
- the surface of the specific binding material is adapted such as to be capable of conforming or interacting with the shape or size of the target such that non-target materials not having the desired shape or being too large to fit into or onto the conformed area do not become bound or bind with decreased affinity.
- the conformation may be with any part of the target as long as the target can access the binding area so provided.
- the adaptation is such that an imprint of the target is made in or on the surface of the binding material which is located and configured such to allow the target to access the binding surface.
- the specific binding material is adapted to the shape and size of a target by forming a body of the specific binding material in the presence of the target material. It is known to imprint polymers with templates (see Wulff (1986) 'Polymeric Reagents and Catalysis' (ACS SympSer 308) Ed W T Ford. pl86 American Chemical Society) but not with labile materials such as the preferred biological targets of the present invention.
- the condition for formation of the specific binding material body eg. polymeric bodies, in the presence of biological target materials must meet several criteria if the specificity of the interaction for living or otherwise high temperature and chemically labile materials is to be maintained.
- the formation preferably takes place at target physiological pH and temperature, with low toxicity conditions, and preferably with short reaction time and appropriate functionality for the purposes of binding the target.
- the formation must result in a mirroring of target surface features, eg. for bacteria preferably being on a 0.1 to 5 ⁇ m scale and more preferably on a 0.5 to 2 ⁇ m scale.
- the material produced should preferably be durable and have easy and safe handling characteristics.
- the specific binding material is functionalised at its binding surface by functional groups, eg. such as amino and/or hydroxy and/or carboxyl and/or amide groups; these allowing for direct binding and/or functionalising of the surface once formed.
- functional groups eg. such as amino and/or hydroxy and/or carboxyl and/or amide groups; these allowing for direct binding and/or functionalising of the surface once formed.
- Dynabeads will bind bacteria or viruses in non-specific fashion to their surfaces to various extents. Dynabeads as such are too small to be of use in binding bacteria by shape and size interaction, but can be used to bind smaller entities such as viral targets. Other larger commercial beads will of course be usable with bacteria and larger entities such as yeasts and protozoans. These commercially available beads are ideal starting materials for the surface poisoning aspect of the present invention, but other custom made materials may of course be used.
- Preparation of polymer bodies at physiological/biological pH can be carried out by interfacial reactions using dispersed organic phase.
- One preferred method uses radiation cross-linking of monomer components to provide polymerisation.
- the target material Once formed about the target material, the latter may be removed by a variety of means, eg. by subjecting the materials to a high vortex and/or use of acids or alkalis.
- a method for production of preferred materials of the invention wherein the specific binding materials of the invention are preformed in the absence of target material; the preformed material exposed to target material, particularly in the absence of non- arget materials, to allow surface interaction, ie. binding; the two materials in bound form exposed to a further treatment whereby the surface of the specific binding material which is not covered by target material becomes wholly or partially inactivated with respect to its ability to bind target and non-target materials.
- the form of the specific binding material is not limited to any specific type; convenient forms will include beads, capsules, strips, films and membranes, ie. semi-permeable films through which samples may be passed while retaining particulates.
- Figure 1 Shows a diagrammatic representation of the formation of a specific binding material body at the interface between an aqueous layer and an organic layer at which a bacteria is located.
- Figure 2 Shows a diagrammatic representation of the four stages of formation areas of size and shape specific to target bacteria on polymeric beads as they form at a liquid interface.
- Figure 3 Shows a diagrammatic representation of a variation of the method shown in Figure 2 wherein the beads formed from the second step, or preformed solid Deads that have had bacteria bound to them, are treated such as to 'poison' unbound surfaces such as to reduce or destroy their ability to bind the target and other materials.
- Plates la, lb Confocal Laser Scanning Micrographs (Zeiss LSM ID). of ethidium bromide-stained Listeria monocvtogenes . and Staphylococcus aureus. respectively, attached to polyamide microcapsules. Plate la depicts the upper surface of a mircocapsule with Listeria monocytogenes showing clearly in fluorescence, indicating the density of cell coverage.
- Plat lb is an optical slice through the middle of a polymer microcapsule: the fluorescent Staphylococcus aureus cells delineate the outer surface of the polymer membrane.
- Plates 2a, 2b Scanning Electron Micrographs (Hitachi S570) showing polymer beads after cross-linking of the diacrylate-containing organic core. The microorganisms can be seen partially embedded in the surface. The retention of the rod and coccoid shapes indicates that the gross physical morphology of the cells was unaffected by the polymerization process.
- Plates 3a. 3b Scanning Electron Micrographs depicting the "lithographic prints" of the respective bacteria. The size and shape of the "prints” can be seen to correspond exactly to those of the microorganisms. In addition to the shape anisotropy, these sites were rendered distinct chemically by reaction of the beads with a diisocyanato-tipped perfluoropolyether, thus blocking the areas of the polymer surface not covered by the microorganisms. Following the hydrolysis step to remove the cells, the original functionality at the sites was exposed, allowing for further derivitization ("development" of the lithographic prints).
- Plates 4a, 4b show the "chemically-amplified" prints of the bacteria.
- the beads were reached with a fluorescent-labelled lectin, FITC-Concanavalin A.
- Confocal Laser Scanning Microscopy has been used to define an optical section across the upper surface of the polymer beads, with the bright regions corresponding to areas reactive towards FITC-Concanavalin A.
- the anisotropic functionality of the surfaces can be seen to match exactly the dimensions of the bacteria in Plates 1 and 2, and the sites in Plate 3. thus establishing the lithographic prints of the bacteria both topologically and chemically.
- 1,6-hexanedioldiacrylate (Aldrich) and divinylbenzene (80% tech. grade, Aldrich) were washed with dilute aqueous NaHCO , passed through activated neutral alumina and stored over dried 4A molecular sieves.
- Adipoyl chloride (Aldrich) was double -distilled in vacuo and stored under nitrogen in a Schlenk flask.
- Azobis(isobutyronitrile) (AIBN) was purchased from Fluka and recrystallised from methanol before use.
- 6-aminohexylmethacrylamide was prepared by reaction of methacrylic anhydride (1.0 equivalent) with 1,6-diaminohexane under Schotten-Baumann conditions followed by repeated extraction from chloroform with dilute aqueous acid.
- Example 1 Preparation of polvamide-surf ce beads (Polvamide 1). A solution of MOPS buffer (0.6N, pH7.8, 250ml) was placed in a reaction vessel equipped with a magnetic bar and stirred at setting 5 over a IKA-MINI-MR stirrer plate whilst nitrogen was bubbled through for 10 minutes.
- MOPS buffer 0.N, pH7.8, 250ml
- the capsules formed were irradiated (Blak-Ray B-100A lamp) with stirring for 12hrs and the resultant polymer beads filtered, washed with water (3 x 100ml) and methanol (3 x 100ml) and dried in air.
- Example 2 Preparation of polva ide surface beads with optimise.. physical properties (Pnlvfltmde 2).
- a solution of sodium carbonate buffer (0.5N, pH11.5. 400ml) was placed in a reaction vessel equipped with a magnetic bar and stirred at setting 5 over a IKA-MINI-MR stirrer plate whilst nitrogen was bubbled through for 10 minutes.
- a solution of adipoyl chloride (2.0ml) in a mixed organic phase containing chloroform (25ml).
- Example 1 Preparation of 'Imprinted' polymeric adsorbents (Imprinted Polvmer 1).
- a solution of MOPS buffer (0.6N, pH7.8. 250ml) was placed in a reaction vessel equipped with a magnetic stirrer bar and stirred at setting 5 over a IKA-MINI-MR stirrer plate whilst nitrogen was bubbled through for 10 minutes.
- polyallylamine solution M w 100,000, 0.2N in 0.6N MOPS, 45ml
- the capsules formed were assessed for bacterial binding by Confocal Laser Scanning Microscopy (CLSM) and irradiated (Blak-Ray B-100A lamp) with stirring for 12 hours.
- CLSM Confocal Laser Scanning Microscopy
- Blak-Ray B-100A lamp irradiated (Blak-Ray B-100A lamp) with stirring for 12 hours.
- the resultant polymer beads were filtered, washed with water (3 x 100ml) and methanol (3 x 100ml) and dried in air.
- 6-aminohexylmethacrylate (l.Og) in chloroform/1,6-hexanedioldiacrylate (50:50 v/v, 10ml) was added.
- Example 5 Preparation of 'Imprinted' polymeric adsorbents (Imprinted Polvmer Film ) .
- a suspension of Listeria monocvtogenes (5.0ml of 10 8 cfu/ml) was stirred in MOPS buffer (0.6N, 100ml) as nitrogen was bubbled through for 10 minutes.
- the suspension was then poured carefully onto a solution of AIBN (lOOmg), 6-aminohexylmethacrylate (l.Og) in chloroform/1,6-hexandioldiacrylate (50:50 v/v, 10ml) in a beaker. Irradiation of the two-phase system was carried out until film solidification occurred.
- the resultant film was washed with methanol prior to examination by Scanning Electron Microscopy. Samples were then washed with either 6M HCl/MeOH or 50% ammonia 880/MeOH solution to remove bacteria.
- Example 6 Preparation of imprinted polvmer beads with 'poisoner-' surface. (Imprinted Pnlvmer 4). A suspension of imprinted polymer beads (l.Og) was stirred in 1,1,2 -trichlorotrifluoroethane (250ml) was stirred rapidly as a solution of F0MBLIN DIS0C (1.5g perfluoropolyether, diisocyanato terminated) in
- 1,1,2-trifluorotrichloroethane (20ml) was added dropwise via a funnel equipped with a drying tube. Stirring was continued for 3 hours before addition of the suspension to methanol (250ml) and the solvent was removed by decanting before washing the beads with further methanol (5 x 100ml).
- Example 7 Removal of bacteria from 'Imprinted' polvmer beads. (Imprinted polvmer 5) . A suspension of imprinted polymer beads (250mg) was refluxed in 6M HCl/methanol (150ml) for _ ⁇ hours with regular monitoring of the extent of cell removal by Scanning Electron Microscope. The beads were then repeatedly washed in methanol and dried in air.
- Example 8 Preparation of 'Fnotprinted' polvmer beads having size and shape adaptation 'on' bead surface.
- Preformed polymer polyamide beads (l.Og) were added to 50ml of 1/4 strength Ringer's solution in the presence of bacteria serially diluted in 0.1/. peptone to give a final concentration of 10 8 cfu/ml.
- the beads were incubated for 2 hours at 4°C with rolling.
- Example Q Preparation of 'Footprinted' beads with 'poisoned' surface (Footprinted Polvmer 1).
- Polymer beads with adsorbed bacteria (l.Og) were stirred in 1 ,1,2-trichlorofluoroethane (250ml) was stirred rapidly as a solution of F0MBLIN DIS0C (1.5g perfluorpolyether, diidocyanato terminated) in 1.1,2-trichloroethane (20ml) was added dropwise via a funnel equipped with a drying tube. Stirring was continued for 3 hours before addition of the suspension to methanol (250ml), the solvent was removed by decanting and the beads were washed with further methanol (5 x 100ml).
- Example 10 Removal of bacteria from 'Footprinted' beads with 'poisoned' surface (Footprinted polvmer 2).
- a suspension of imprinted polymer beads (250mg) was refluxed in 1M HC1 /methanol (150ml) for 4 hours with regular monitoring of the extent of cell removal by Scanning Electron Microscopy. The beads were then repeatedly washed in methanol and dried in air.
- Example 11 Use of Specific binding material beads of the invention. Specificity of beads of the invention was determined (see Table 1). Plate count: Serial dilutions of Escherichia coli. Staphylococcus aureus. Listeria monocvtogenes and Salmonella enteritidis in 0.1 peptone were plated using Yeast-Dextrose Agar (Unipath Ltd. Basingstoke UK) Colonies were counted after 24 to 48 hours incubation at 30°C.
- DEFT Bacterial Count The DEFT was performed according to British Standard Methods BS 4285- The pre-filtration step using 5-0 micron nylon mesh to remove particulate matter from suspension was ommitted.
- Samples of imprinted beads were dual stained in ethidium bromide and acridine orange, prior to examination by confocal microscopy. Samples were initially stained for 2 minutes by immersion in 0.1. ethidium bromide prepared in 0.05% benzalkonium chloride and were rinsed three times with deionised water before staining in acridine orange (0.025% in 0.1M citrate/NaOH buffer, pH6.6). After 2 minutes samples were washed twice in 0.1M citrate/NaOH at pH3-0. Stained preparations were mounted onto a microscope slide and covered with a coverslip.
- Bacterial species Cone Bacteria %Bacteria added added cfu/assay extracted
- Salmonella Salmonella 10 21 Footprinted enteritidis Polymer 2 Samples contained 5ml buffer (lOmM MOPS pH7.0), 50mg polymer beads, 100ml bacteria (l ⁇ " cfu/ml). Rotation was carried out for 2 hours followed by settling of beads. Samples of supernatant (100ml) were drawn and plated for bacterial counting.
- This material can be used to form the beads of the invention by substitution for the polyallylamine reactants in each case.
- “Development" of the exposed lithographic prints was effected by stirring the beads (lOOmg) in pH 4.75 sodium acetate buffer (5ml, 50mM, containing 5mM MnCl 2 , 5mM CaCl 2 , and ethanol (500ml)) with fluorescein isothiocyanate-labelled Concanavalin A (lmg, ⁇ O.OOOlmmol) and l-ethyl-3-(3-dimethylaminopropyl) carbodiimide (5mg, 0.025mmol).
- Photomicrographs of polymeric beads obtained after irradiation of the respective capsules are presented in Plates 2a and 2b. Examination of the surface by SEM showed a certain degree of variation with regard to position of the bacteria at the surface, with some cells almost completely buried in the outer layer of the polyamide and the majority only slightly embedded in the surface. After removal of the template microorganisms, the presence of deep indentations (100-200nm) was readily apparent in SEM micrographs (Plates 3a and 3b) . These "sites” exhibited exact size and shape complementarity to the bacteria. However, to demonstrate the success of our lithographic procedure it was necessary to "develop” the difference in chemical functionality between the now exposed sites and the perfluoropolymer modified surfaces.
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Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9713952A GB2312045A (en) | 1995-02-21 | 1996-02-21 | Specific binding materials |
JP8525502A JPH11500824A (en) | 1995-02-21 | 1996-02-21 | Specific binding material |
EP96903137A EP0811161A1 (en) | 1995-02-21 | 1996-02-21 | Specific binding materials |
AU47281/96A AU4728196A (en) | 1995-02-21 | 1996-02-21 | Specific binding materials |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9503429.4A GB9503429D0 (en) | 1995-02-21 | 1995-02-21 | Specific binding materials |
GB9503429.4 | 1995-02-21 | ||
GB9519427A GB2298274A (en) | 1995-02-21 | 1995-09-22 | Specific binders for target materials in which the binder comprises surface areas corresponding to said target material |
GB9519427.0 | 1995-09-22 |
Publications (1)
Publication Number | Publication Date |
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WO1996026440A1 true WO1996026440A1 (en) | 1996-08-29 |
Family
ID=26306551
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1996/000410 WO1996026440A1 (en) | 1995-02-21 | 1996-02-21 | Specific binding materials |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0811161A1 (en) |
JP (1) | JPH11500824A (en) |
AU (1) | AU4728196A (en) |
CA (1) | CA2211174A1 (en) |
WO (1) | WO1996026440A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1385988A2 (en) * | 2001-04-16 | 2004-02-04 | Semorex Inc. | Selective covalent-binding compounds having therapeutic diagnostic and analytical applications |
Citations (4)
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EP0089425A1 (en) * | 1982-03-19 | 1983-09-28 | Uop Inc. | Method for the preparation of integral shaped replications of shaped, porous and dissolvable materials for use as adsorbents in fixed bed adsorption processes |
US4748042A (en) * | 1987-03-31 | 1988-05-31 | V-Tech, Inc. | Method and apparatus for imprinting membranes with patterns of antibody |
WO1992013447A1 (en) * | 1991-02-01 | 1992-08-20 | California Institute Of Technology | Template polymerization using metal chelates and fluid imprint matrices |
WO1993005068A1 (en) * | 1991-09-06 | 1993-03-18 | Magnus Glad | Selective affinity material, preparation thereof by molecular imprinting, and use of the same |
-
1996
- 1996-02-21 CA CA002211174A patent/CA2211174A1/en not_active Abandoned
- 1996-02-21 AU AU47281/96A patent/AU4728196A/en not_active Abandoned
- 1996-02-21 WO PCT/GB1996/000410 patent/WO1996026440A1/en not_active Application Discontinuation
- 1996-02-21 JP JP8525502A patent/JPH11500824A/en active Pending
- 1996-02-21 EP EP96903137A patent/EP0811161A1/en not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0089425A1 (en) * | 1982-03-19 | 1983-09-28 | Uop Inc. | Method for the preparation of integral shaped replications of shaped, porous and dissolvable materials for use as adsorbents in fixed bed adsorption processes |
US4748042A (en) * | 1987-03-31 | 1988-05-31 | V-Tech, Inc. | Method and apparatus for imprinting membranes with patterns of antibody |
WO1992013447A1 (en) * | 1991-02-01 | 1992-08-20 | California Institute Of Technology | Template polymerization using metal chelates and fluid imprint matrices |
WO1993005068A1 (en) * | 1991-09-06 | 1993-03-18 | Magnus Glad | Selective affinity material, preparation thereof by molecular imprinting, and use of the same |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1385988A2 (en) * | 2001-04-16 | 2004-02-04 | Semorex Inc. | Selective covalent-binding compounds having therapeutic diagnostic and analytical applications |
EP1385988A4 (en) * | 2001-04-16 | 2008-04-09 | Semorex Inc | Selective covalent-binding compounds having therapeutic diagnostic and analytical applications |
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Publication number | Publication date |
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JPH11500824A (en) | 1999-01-19 |
EP0811161A1 (en) | 1997-12-10 |
CA2211174A1 (en) | 1996-08-29 |
AU4728196A (en) | 1996-09-11 |
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