WO2000053625A2 - Micro-reseaux de sondes d'affinite peptidique et techniques destines a l'analyse de produits geniques - Google Patents

Micro-reseaux de sondes d'affinite peptidique et techniques destines a l'analyse de produits geniques Download PDF

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Publication number
WO2000053625A2
WO2000053625A2 PCT/US2000/006676 US0006676W WO0053625A2 WO 2000053625 A2 WO2000053625 A2 WO 2000053625A2 US 0006676 W US0006676 W US 0006676W WO 0053625 A2 WO0053625 A2 WO 0053625A2
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WO
WIPO (PCT)
Prior art keywords
array
peptide
electrode
chemical functional
amino acid
Prior art date
Application number
PCT/US2000/006676
Other languages
English (en)
Other versions
WO2000053625A3 (fr
WO2000053625A9 (fr
Inventor
Francis M. Rossi
Donald D. Montgomery
Original Assignee
Combimatrix Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Combimatrix Corporation filed Critical Combimatrix Corporation
Priority to AU38833/00A priority Critical patent/AU3883300A/en
Publication of WO2000053625A2 publication Critical patent/WO2000053625A2/fr
Publication of WO2000053625A3 publication Critical patent/WO2000053625A3/fr
Publication of WO2000053625A9 publication Critical patent/WO2000053625A9/fr

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Classifications

    • 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
    • G01N33/551—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals the carrier being inorganic
    • 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
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/0046—Sequential or parallel reactions, e.g. for the synthesis of polypeptides or polynucleotides; Apparatus and devices for combinatorial chemistry or for making molecular arrays
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C07K1/047—Simultaneous synthesis of different peptide species; Peptide libraries
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00277—Apparatus
    • B01J2219/0054—Means for coding or tagging the apparatus or the reagents
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00585—Parallel processes
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00596—Solid-phase processes
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
    • B01J2219/00614—Delimitation of the attachment areas
    • B01J2219/00617—Delimitation of the attachment areas by chemical means
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
    • B01J2219/00623—Immobilisation or binding
    • B01J2219/00626—Covalent
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00605—Making arrays on substantially continuous surfaces the compounds being directly bound or immobilised to solid supports
    • B01J2219/00632—Introduction of reactive groups to the surface
    • B01J2219/00637—Introduction of reactive groups to the surface by coating it with another layer
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00639—Making arrays on substantially continuous surfaces the compounds being trapped in or bound to a porous medium
    • B01J2219/00641—Making arrays on substantially continuous surfaces the compounds being trapped in or bound to a porous medium the porous medium being continuous, e.g. porous oxide substrates
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00653—Making arrays on substantially continuous surfaces the compounds being bound to electrodes embedded in or on the solid supports
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00583—Features relative to the processes being carried out
    • B01J2219/00603—Making arrays on substantially continuous surfaces
    • B01J2219/00659—Two-dimensional arrays
    • 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
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/00274—Sequential or parallel reactions; Apparatus and devices for combinatorial chemistry or for making arrays; Chemical library technology
    • B01J2219/00718—Type of compounds synthesised
    • B01J2219/0072—Organic compounds
    • B01J2219/00725—Peptides
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B40/00—Libraries per se, e.g. arrays, mixtures
    • C40B40/04—Libraries containing only organic compounds
    • C40B40/10—Libraries containing peptides or polypeptides, or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C40—COMBINATORIAL TECHNOLOGY
    • C40B—COMBINATORIAL CHEMISTRY; LIBRARIES, e.g. CHEMICAL LIBRARIES
    • C40B70/00—Tags or labels specially adapted for combinatorial chemistry or libraries, e.g. fluorescent tags or bar codes
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2333/00—Assays involving biological materials from specific organisms or of a specific nature
    • G01N2333/435—Assays involving biological materials from specific organisms or of a specific nature from animals; from humans
    • G01N2333/665—Assays involving proteins derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • G01N2333/70—Enkephalins

Definitions

  • Pirrung method Another drawback of the Pirrung method is that the photolabile protecting groups used cannot be removed as effectively as conventional acid or base labile protecting groups can be removed and are plagued by contamination due to undesired side reactions. Consequently, using Pirrung's method, the purity of the chemical array is often compromised due to incomplete removal of the protecting groups and subsequent failure of the underlying functional groups to react with the desired monomer, as well as contamination from undesired side reactions.
  • FIG. 1 describes how an array according to the present invention may be used to synthesize a pattern of molecules.
  • the array may be coated with a biocompatible porous membrane that allows molecules to flow freely between a bulk solvent and an electrode.
  • the array may then be immersed in a solution containing a precursor to an electrochemically- generated (ECG) reagent of interest.
  • ECG electrochemically-generated
  • a computer may then interface with the array to turn on the desired electrode pattern, and the precursor may be electrochemically converted into an active species.
  • the electrochemically-generated (ECG) reagent reacts with molecules immobilized to the membrane overlying the electrode.
  • an array of electrodes can be poised to perform electrochemistry whenever they are illuminated.
  • the whole array can be flood illuminated or each electrode can be illuminated separately.
  • This technique is useful for very rapid pulsing of the electrochemistry without the need for fast switching electronics.
  • Direct connection from an electrode to a bond pad on the perimeter of the semiconductor chip is another possibility, although this method of connection could limit the density of the array.
  • the target gene products are not themselves labeled. Rather, the peptide probes are labeled or are attached directly or indirectly to a signal resposive moiety.
  • Methods for detecting labeled target gene products bound to the probes of a high density microarray are known to those of skill in the art.
  • a colorimetric label or a radioactive labeled probe may be used.
  • the methods of the present invention are preferably performed using a computer.
  • the computer runs a software program that includes computer code incorporating the invention for analyzing binding intensities measured from a substrate and monitoring and/or quantifying the expression of one or more target gene products.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Immunology (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Analytical Chemistry (AREA)
  • Urology & Nephrology (AREA)
  • Hematology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biomedical Technology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Microbiology (AREA)
  • Cell Biology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Food Science & Technology (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Peptides Or Proteins (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

La présente invention concerne un réseau de sondes peptidiques destiné à l'analyse de produits géniques. Ce réseau de sondes peptidiques est constitué de préférence sur une membrane poreuse, proche d'au moins une électrode. L'invention concerne également une technique permettant de déterminer la présence d'un produit génique dans un échantillon. Cette technique consiste à mettre en contact un échantillon biologique avec un réseau peptidique. Ce réseau peptidique comprend de préférence au moins environ 100 sondes peptidiques et idéalement au moins environ 1000.
PCT/US2000/006676 1999-03-11 2000-03-10 Micro-reseaux de sondes d'affinite peptidique et techniques destines a l'analyse de produits geniques WO2000053625A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38833/00A AU3883300A (en) 1999-03-11 2000-03-10 Microarrays of peptide affinity probes for analyzing gene products and methods for analyzing gene products

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US12387799P 1999-03-11 1999-03-11
US12379199P 1999-03-11 1999-03-11
US60/123,791 1999-03-11
US60/123,877 1999-03-11

Publications (3)

Publication Number Publication Date
WO2000053625A2 true WO2000053625A2 (fr) 2000-09-14
WO2000053625A3 WO2000053625A3 (fr) 2001-04-05
WO2000053625A9 WO2000053625A9 (fr) 2002-07-04

Family

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Country Link
AU (1) AU3883300A (fr)
WO (1) WO2000053625A2 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6406921B1 (en) 1998-07-14 2002-06-18 Zyomyx, Incorporated Protein arrays for high-throughput screening
WO2002081413A2 (fr) * 2001-04-09 2002-10-17 Carlsberg A/S Protection unichemo (ucp) unidimensionnelle en synthese organique
US6576478B1 (en) 1998-07-14 2003-06-10 Zyomyx, Inc. Microdevices for high-throughput screening of biomolecules
US6682942B1 (en) 1998-07-14 2004-01-27 Zyomyx, Inc. Microdevices for screening biomolecules
US6780582B1 (en) 1998-07-14 2004-08-24 Zyomyx, Inc. Arrays of protein-capture agents and methods of use thereof
WO2005012558A1 (fr) * 2003-07-29 2005-02-10 University Court Of The University Of Edinburgh Analyse des proteases
US6977138B2 (en) 2001-07-24 2005-12-20 Massachusetts Institute Of Technology Reactive polymer coatings
US7909928B2 (en) 2006-03-24 2011-03-22 The Regents Of The University Of Michigan Reactive coatings for regioselective surface modification
US7947148B2 (en) 2006-06-01 2011-05-24 The Regents Of The University Of Michigan Dry adhesion bonding
US8399047B2 (en) 2007-03-22 2013-03-19 The Regents Of The Univeristy Of Michigan Multifunctional CVD coatings

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022678A2 (fr) * 1992-04-23 1993-11-11 Massachusetts Institute Of Technology Procedes et appareil optiques et electriques de detection de molecules
WO1994022889A1 (fr) * 1993-03-31 1994-10-13 Cis Bio International Copolymere nucleotide(s)/polymere conducteur electronique, son procede de preparation et son utilisation
WO1995012808A1 (fr) * 1993-11-01 1995-05-11 Nanogen, Inc. Dispositifs et systemes microelectroniques autoadressables a autoassemblage pour diagnostics et analyses biologiques moleculaires
WO1996007917A1 (fr) * 1994-09-09 1996-03-14 Nanogen, Inc. Systeme de diagnostic automatise de biologie moleculaire
WO1997049718A2 (fr) * 1996-06-25 1997-12-31 Cis Bio International Conjugues d'un oligonucleotide/polymere conducteur electronique avec une molecule d'interet, et leurs utilisations
WO1998001221A1 (fr) * 1996-07-05 1998-01-15 Combimatrix Corporation Synthese electrochimique de polymeres en phase solide
WO1999024645A1 (fr) * 1997-11-10 1999-05-20 Ben Gurion University Of The Negev, Research And Development Authority Reseau de microelectrodes fonctionnalisees

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993022678A2 (fr) * 1992-04-23 1993-11-11 Massachusetts Institute Of Technology Procedes et appareil optiques et electriques de detection de molecules
WO1994022889A1 (fr) * 1993-03-31 1994-10-13 Cis Bio International Copolymere nucleotide(s)/polymere conducteur electronique, son procede de preparation et son utilisation
WO1995012808A1 (fr) * 1993-11-01 1995-05-11 Nanogen, Inc. Dispositifs et systemes microelectroniques autoadressables a autoassemblage pour diagnostics et analyses biologiques moleculaires
WO1996007917A1 (fr) * 1994-09-09 1996-03-14 Nanogen, Inc. Systeme de diagnostic automatise de biologie moleculaire
WO1997049718A2 (fr) * 1996-06-25 1997-12-31 Cis Bio International Conjugues d'un oligonucleotide/polymere conducteur electronique avec une molecule d'interet, et leurs utilisations
WO1998001221A1 (fr) * 1996-07-05 1998-01-15 Combimatrix Corporation Synthese electrochimique de polymeres en phase solide
WO1999024645A1 (fr) * 1997-11-10 1999-05-20 Ben Gurion University Of The Negev, Research And Development Authority Reseau de microelectrodes fonctionnalisees

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6682942B1 (en) 1998-07-14 2004-01-27 Zyomyx, Inc. Microdevices for screening biomolecules
US6596545B1 (en) 1998-07-14 2003-07-22 Zyomyx, Inc. Microdevices for screening biomolecules
US6475808B1 (en) 1998-07-14 2002-11-05 Zyomyx, Incorporated Arrays of proteins and methods of use thereof
US6475809B1 (en) 1998-07-14 2002-11-05 Zyomyx, Incorporated Protein arrays for high-throughput screening
US6406921B1 (en) 1998-07-14 2002-06-18 Zyomyx, Incorporated Protein arrays for high-throughput screening
US6582969B1 (en) 1998-07-14 2003-06-24 Zyomyx, Inc. Microdevices for high-throughput screening of biomolecules
US6780582B1 (en) 1998-07-14 2004-08-24 Zyomyx, Inc. Arrays of protein-capture agents and methods of use thereof
US6630358B1 (en) 1998-07-14 2003-10-07 Zyomyx, Incorporated Arrays of proteins and methods of use thereof
US6576478B1 (en) 1998-07-14 2003-06-10 Zyomyx, Inc. Microdevices for high-throughput screening of biomolecules
WO2002081413A3 (fr) * 2001-04-09 2004-05-27 Carlsberg As Protection unichemo (ucp) unidimensionnelle en synthese organique
WO2002081413A2 (fr) * 2001-04-09 2002-10-17 Carlsberg A/S Protection unichemo (ucp) unidimensionnelle en synthese organique
US6977138B2 (en) 2001-07-24 2005-12-20 Massachusetts Institute Of Technology Reactive polymer coatings
WO2005012558A1 (fr) * 2003-07-29 2005-02-10 University Court Of The University Of Edinburgh Analyse des proteases
US7909928B2 (en) 2006-03-24 2011-03-22 The Regents Of The University Of Michigan Reactive coatings for regioselective surface modification
US7947148B2 (en) 2006-06-01 2011-05-24 The Regents Of The University Of Michigan Dry adhesion bonding
US8399047B2 (en) 2007-03-22 2013-03-19 The Regents Of The Univeristy Of Michigan Multifunctional CVD coatings

Also Published As

Publication number Publication date
WO2000053625A3 (fr) 2001-04-05
AU3883300A (en) 2000-09-28
WO2000053625A9 (fr) 2002-07-04

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AL Designated countries for regional patents

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COP Corrected version of pamphlet

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122 Ep: pct application non-entry in european phase