CA2217053A1 - Method of photochemical immobilization of ligands using quinones - Google Patents

Method of photochemical immobilization of ligands using quinones

Info

Publication number
CA2217053A1
CA2217053A1 CA002217053A CA2217053A CA2217053A1 CA 2217053 A1 CA2217053 A1 CA 2217053A1 CA 002217053 A CA002217053 A CA 002217053A CA 2217053 A CA2217053 A CA 2217053A CA 2217053 A1 CA2217053 A1 CA 2217053A1
Authority
CA
Canada
Prior art keywords
quinone
compound
ligand
conjugate
linking
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002217053A
Other languages
French (fr)
Other versions
CA2217053C (en
Inventor
Mogens Havsteen Jacobsen
Troels Koch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2217053A1 publication Critical patent/CA2217053A1/en
Application granted granted Critical
Publication of CA2217053C publication Critical patent/CA2217053C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • G01N33/54353—Immunoassay; Biospecific binding assay; Materials therefor with an insoluble carrier for immobilising immunochemicals with ligand attached to the carrier via a chemical coupling agent
    • 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
    • C07K1/042—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers characterised by the nature of the carrier
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y10T428/31515—As intermediate layer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y10T428/31515—As intermediate layer
    • Y10T428/31518—Next to glass or quartz

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Biomedical Technology (AREA)
  • Analytical Chemistry (AREA)
  • Urology & Nephrology (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Food Science & Technology (AREA)
  • Cell Biology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Carbon And Carbon Compounds (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)

Abstract

A method of immobilizing a ligand (L) to the surface (P) of a carboncontaining substrate material; said method comprising: a photochemical step of linking of one or more photochemically reactive compounds (Q) to a carboncontaining material surface (P); wherein the photochemically reactive compound (Q) is a quinone compound containing a cyclic hydrocarbon, or from 2 to 10 fused cyclic hydrocarbons, with at least two conjugated carbonyl groups; and wherein the photochemical step comprises irradiation of the photochemically reactive compound (Q) with non-ionizing electromagnetic radiation having a wavelength in the range from UV to visible light.

Claims (23)

1 METHOD OF PHOTOCHEMICAL IMMOBILIZATION OF LIGANDS1. A method of immobilizing a ligand (L) to the surface (P) of a carbon-containing substrate material; said method comprising:
a photochemical step of linking of one or more ligands (L) via one or more photochemically reactive compounds (Q) to a carbon-containing material surface (P);
said carbon-containing material surface (P) being linked to the photochemically reactive compound (Q) either directly or via one or more spacers (S1); and said photochemically reactive compound (Q) being linked to one or more ligands (L) either directly or optionallly via one or more spacers (S) and/or thermochemically reactive compounds (T);
said spacers (S1) and (S) being, equal or different, thermochemically or photochemically reactive or non-reactive spacers;
wherein the photochemically reactive compound (Q) is a quinone compound selected from the group consisting of monomeric quinone compounds, dimeric quinone compounds, and symmetrical or asymmetrical oligomeric quinone compounds;
said quinone compound (Q) containing a cyclic hydrocarbon, or from 2 to 10 fused cyclic hydrocarbons, said
2 quinone compound having at least two conjugated carbonyl groups, the number of which does not exceeding twice the number of fused cyclic hydrocarbons;
said quinone compound (Q) optionally being substituted with substituents (R) which do not result in steric hindrance to the immobilization of the ligand (L) or do not disturb the photochemistry; and wherein the photochemical step comprises irradiation of the photochemically reactive compound (Q) with non-ionizing electromagnetic radiation having a wavelength in the range from UV to visible light, provided that said carbon-containing material does not consist of a nucleic acid probe.
2. A method according to claim 1, wherein the irradiation time is generally shorter than 12 hours, preferably less than 200 minutes, more preferably less than 60 minutes, most preferably less than 30.
3. A method according to claims 1 or 2, wherein the quinone compound comprises 1-4 fused cyclic hydrocarbons according to the general formulas (XXXVII), (XXXVIII), and (XXXIX) below, wherein the letters m, n and o designate 0 or integers from 1-8, the sum of m, n and o being 8 or less; 1 indicates 0 or an integer from 1 to two times n; r and q indicate 0, 1 or 2; k indicates 0 or an integer from 1 to 2 times m; and t indicates 0 or an integer from 1 to 2 times o;

4 4. A method according to claim 3, wherein the quinone compound (Q) is selected from the group consisting of anthraquinones (V, VI, VII,X,XI,XIII,XXVIII), phenanthrenequinones (VIII, IX,XII), benzoquinones (I,II), naphthoquinones (III, IV,XXVII), and compound (XXVI,XXIX), particularly anthraquinones, phenanthrenequinones, and compound (XXVI).
5
6 5. A method according to any of claims 1-4, wherein the quinone compound (Q) is substitutetd with substituents (R) selected from the group consisting of: functional groups comprising -NO2, -SO3-, -SO2-, -CN, -PO3 2-, -PO2-, - COOH, halogen, i.e. -F, -Cl, -Br, -I, primary amines, secondary amines and tertiary amines, or derivatives thereof; and hydrocarbyls which may be substituted with:
-NO2, -SO3-, -CN, -PO3 2-, -PO2-, -COOH, halogen, i.e -F, -Cl, -Br, -I, epoxide, and -H; said hydrocarbyls preferably being alkyls such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentadecanyl, hexadecanyl, heptadecanyl, octadecanyl, nonadecanyl, eicocanyl, straight or branched, with one or more double or triple bonds, and aryls such as phenyl, naphtyl, biphenyl, tolyl, benzyl, cumenyl, mesityl, xylyl, pentalenyl, indenyl.
6. A method according to claim 1, wherein the polymer is selected from the group consisting of synthetic and natural polymers such as polystyrene, polyethylene, polyvinylacetate, polyvinylchloride, polyvinyl-pyrrolidone, polyacrylonitrile, polymethyl-methacrylate, polytetrafluoroethylene, polycarbonate, poly-4-methyl-
7 pentylene, polyester, polypropylene, cellulose, nitrocellulose, starch, polysaccharides, natural rubber, butyl rubber, styrene butadiene rubber, silicone rubber.
7. A method according to claim 1, wherein the carbon-containing material (P) is selected from the group consisting of premodified materials including silica, glass, controlled pore glass, silica gel, or metal which materials have been premodified to contain carbon;
monolayer or multilayer films; Langmuir-Blodgett-films;
micelles; biological membranes; proteins; natural or synthetic polymers coated with biological or organic material.
8. A method according to claim 1, wherein the ligands (L) is a functional group selected from the group consisting of -COOH (carboxylic acids), sulfonic acid derivatives, -COOR (esters, including active esters), - COX (acid halides, acid fluorids and acid chlorides, acid azides or similar active carboxylic acid derivatives), - CONHNH2 (acid hydrazides), -NHCONHNH2 (semicarbazides), - NHCSNHNH2 (thiosemicarbazides), -CN (nitrites), -CHO
(aldehydes), RR'CO (ketons), -OH (alcohols), -SH
(thioles), -SSR (disulfides), -NH2 (amines, including primary, secondary and tertiary amines), -NHNH2 (hydrazines), -OR (ethers), epoxides, -SR (sulfides), -X
(halides), -NO2, -CH3; or derivatives thereof; a non-functional groups, such as methyl, ethyl, isobutyl, tertbutyl or aromates; or the ligand is selected from the group consisting of: biologically active molecules, such as biotin, toxins, herbicides, pesticides, carbohydrates, antibiotics such as penicillins and other drugs such as cell poisons, steroids, peptides, nucleotides, peptide nucleic acids (PNA) and nucleic acid binding partners, proteins and haptenes.
9. A method according to claim 1, wherein the spacer (S) is distance making group selected from the group consisting of C1-C20 alkyl groups such as poly-methylene, optionally containing aromatic or monopoly-unsaturated hydrocarbons; polyoxyethylene such as poly-ethylene glycol; oligo/polyamides such as poly-b-alanine, poly-glycine, polylysine, peptides; oligosaccharides;
oligo/-polyphosphates such as phospho-mono/diesters, mono/-diamides; and oligo/polysulfonic amides/esters; or combined units of the aforementioned or combined units thereof.
10. A method according to claim 1, wherein the thermochemical reactive compound (T) is a compound containing a thermochemical reactive group selected from the group consisting of: -COOH (carboxylic acids), sulfonic acid derivatives, -COOR (esters, comprising active esters), -COX (acid halides, acid azides and similar carboxylic acid derivatives), -CONHNH2 (acid hydrazides), -NHCONHNH2 (semicarbazides), -NHCSNHNH2 (thiosemicarbazides), -CHO (aldehydes), RR'CO (ketones), -OH (alcohols), -X (halides: chloride, bromide, iodide), -SH (thioles), -SSR (disulfides), -NH2 (amines, comprising primary, secondary and tertiary amines), -NHNH2 (hydrazines), epoxides, maleimides.
11. A method according to claim 1, comprising the steps of linking a quinone compound (Q) as defined in claim 1 to a ligand (L) to obtain a quinone-ligand conjugate (Q-L), and photoimmobilizing the quinone-ligand conjugate (Q-L) onto the substrate material surface (P) to obtain the substrate material (P-Q-L).
12. A method according to claim 1, comprising the steps of linking a ligand (L) to a spacer molecule (S) by use of a photochemical or a thermochemical compound, linking the spacer-ligand conjugate (S-L) to a quinone compound (Q) as defined in claim 1 to obtain a quinone-ligand conjugate (Q-S-L) having an intermediate spacer molecule, and photoimmobilizing the quinone-ligand conjugate (Q-S-L) on the substrate surface (P) to obtain the substrate material (P-Q-S-L).
13. A method according to claim 1, comprising the steps of linking at least one quinone compound (Q) as defined in claim 1 to a spacer molecule (S), linking the spacer-quinone conjugate (Q-S) to a ligand (L) to obtain a quinone-ligand conjugate (Q-S-L) having an intermediate spacer molecule, and then photoimmobilizing the quinone-ligand conjugate on the substrate surface (P) to obtain the substrate material (P-Q-S-L).
14. A method according to claim 1, comprising the steps of linking a quinone compound (Q) as defined in claim 1 to a substrate surface (P) to obtain a quinone-substrate surface conjugate (P-Q), photoimmobilizing a ligand (L) to a quinone-substrate surface conjugate (P-Q) to obtain the substrate material (P-Q-L).
15. A method according to claim 1, comprising the steps of linking a spacer molecule (S1) by use of a photochemical or a thermochemical compound to a substrate surface (P), linking a quinone compound (Q) as defined in claim 1 to the spacer-substrate surface conjugate (P-S1) to obtain a quinone-substrate surface conjugate (P-S1-Q) having an intermediate spacer molecule, and photoimmobilizing a ligand (L) to a quinone-polymer surface conjugate.
16. A method according to claim 1, comprising the steps of linking a quinone compound (Q) as defined in claim 1 to a spacer molecule (S), linking the spacer-quinone conjugate (Q-S) to a substrate surface to obtain a quinone-substrate surface conjugate (P-Q-S) having an intermediate spacer molecule.
17. A method according to claim 1, wherein the photo-reaction takes place in an aqueous medium.
18. Use of a quinone (Q) as defined in claim 1 for immobilizing a ligand to a carbon-containing substrate material surface (P) according to the method as claimed in claim 1.
19. A carbon-containg material having a ligand (L) immobilized to its surface (P) prepared according to the method as claimed in claim 1.
20. Use of a carbon-containing substrate material as prepared according to the method as claimed in claim 1 in a detection system.
21. Use of a carbon-containing substrate material as prepared in claim 1 as a carrier for solid phase immunoassays.
22. Use as claimed in claim 21, wherein the carrier is selected from the group consisting of well plates, test particles such as beads and micro spheres, test tubes, test sticks, and test strips.
23. Use of a carbon-containing substrate material as prepared in claim 1 as a carrier for solid phase synthesis of peptides, oligonucleotides, carbohydrates and small organic molecules.
CA2217053A 1995-04-07 1996-04-03 Method of photochemical immobilization of ligands using quinones Expired - Lifetime CA2217053C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DK0425/95 1995-04-07
DK42595 1995-04-07
PCT/DK1996/000167 WO1996031557A1 (en) 1995-04-07 1996-04-03 Method of photochemical immobilization of ligands using quinones

Publications (2)

Publication Number Publication Date
CA2217053A1 true CA2217053A1 (en) 1996-10-10
CA2217053C CA2217053C (en) 2010-11-30

Family

ID=8093384

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2217053A Expired - Lifetime CA2217053C (en) 1995-04-07 1996-04-03 Method of photochemical immobilization of ligands using quinones

Country Status (12)

Country Link
US (1) US6033784A (en)
EP (1) EP0820483B1 (en)
JP (1) JP3124037B2 (en)
AT (1) ATE198079T1 (en)
AU (1) AU699321B2 (en)
CA (1) CA2217053C (en)
DE (1) DE69611235T2 (en)
DK (1) DK0820483T3 (en)
ES (1) ES2153097T3 (en)
GR (1) GR3035079T3 (en)
PT (1) PT820483E (en)
WO (1) WO1996031557A1 (en)

Families Citing this family (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL135000A0 (en) 1997-09-12 2001-05-20 Exiqon As Bi- and tri-cyclic nucleoside, nucleotide and oligonucleotide analogues
US6465178B2 (en) * 1997-09-30 2002-10-15 Surmodics, Inc. Target molecule attachment to surfaces
US6762019B2 (en) * 1997-09-30 2004-07-13 Surmodics, Inc. Epoxide polymer surfaces
US6132561A (en) * 1997-10-13 2000-10-17 Mincher; Bruce J. Process for the solvent extraction for the radiolysis and dehalogenation of halogenated organic compounds in soils, sludges, sediments and slurries
DE19818360C2 (en) * 1998-04-24 2000-05-31 Suisse Electronique Microtech Dextran coated surface
US6436653B1 (en) 1998-12-15 2002-08-20 Exiqon A/S Method for introduction of reporter groups into bacterial lipopolysaccharide-derived carbohydrates and the subsequent coupling of such derivatives onto solid surfaces
EP1141718B1 (en) * 1998-12-15 2005-07-20 Exiqon A/S Coupling of lipopolysaccharide-derived carbohydrates onto solid surfaces
AUPP856399A0 (en) * 1999-02-08 1999-03-04 Australian Membrane And Biotechnology Research Institute Improved compounds for protein binding
EP1152009B2 (en) 1999-02-12 2017-09-06 Daiichi Sankyo Company, Limited Novel nucleosides and oligonucleotide analogues
CN1361829A (en) 1999-03-18 2002-07-31 埃克西库恩公司 Detection of mutations in genes by specific LNA primers
US6780980B1 (en) * 1999-06-30 2004-08-24 Centre Suisse D'electronique Et De Microtechnique S.A. Process for the modification of surface
US6531591B1 (en) 1999-07-07 2003-03-11 Exiqon A/S Synthesis of stable quinone and photoreactive ketone phosphoramidite reagents for solid phase synthesis of photoreactive-oligomer conjugates
JP4151751B2 (en) 1999-07-22 2008-09-17 第一三共株式会社 New bicyclonucleoside analogues
AU2001277635A1 (en) * 2000-03-14 2001-10-08 Exiqon A/S New methods for separation and isolation of subpopulations of cells in biological samples
DE10041809A1 (en) * 2000-08-25 2002-03-07 Giesing Michael Arrays of immobilized biomolecules, their manufacture and use
DE10105079A1 (en) * 2001-02-05 2002-08-08 Febit Ferrarius Biotech Gmbh Photolabile protecting groups for the synthesis of biopolymers
US20030108585A1 (en) * 2001-05-04 2003-06-12 Roe R. Michael Polymer conjugates of insecticidal peptides or nucleic acids or insecticides and methods of use thereof
EP1392339A4 (en) * 2001-05-04 2009-05-27 Univ North Carolina State Polymer conjugates of insecticidal peptides or nucleic acids and methods of use thereof
EP1446412B1 (en) 2001-09-04 2012-03-07 Exiqon A/S Novel lna compositions and uses thereof
US20040023413A1 (en) * 2001-11-26 2004-02-05 Molecular Reflections, Inc. Microscale immobilization of molecules using a hydrogel and methods of use thereof
JP3888947B2 (en) * 2002-02-01 2007-03-07 日清紡績株式会社 Immobilization of biomolecules on a carrier
US20030198967A1 (en) * 2002-04-23 2003-10-23 Matson Robert S. Multi-functional microarrays and methods
WO2003104792A2 (en) * 2002-06-07 2003-12-18 Picosep A/S A method of separating biocomponents contained in a liquid, a separating system and a separating unit
US7629016B2 (en) * 2002-06-10 2009-12-08 Council of Industrial and Scientific Research Process for photochemical activation of polymer surface and immobilization of biomolecules onto the activated surface
WO2004024314A2 (en) * 2002-09-11 2004-03-25 Exiqon A/S A population of nucleic acids including a subpopulation of lna oligomers
US20040219565A1 (en) * 2002-10-21 2004-11-04 Sakari Kauppinen Oligonucleotides useful for detecting and analyzing nucleic acids of interest
WO2004073843A1 (en) * 2003-02-19 2004-09-02 Mcmaster University Composite materials comprising supported porous gels
DE10323685A1 (en) * 2003-05-22 2004-12-09 Rühe, Jürgen, Prof. Dr. Process for the covalent immobilization of probe biomolecules on organic surfaces
CA2558271A1 (en) * 2004-03-05 2005-09-15 Nisshinbo Industries, Inc. Immobilized biomolecule and method of detecting substance capable of interacting with biomolecule
EP1758671B9 (en) 2004-04-08 2014-02-19 Natrix Separations Inc. Membrane stacks
US7026851B2 (en) * 2004-05-12 2006-04-11 System General Corp. PWM controller having frequency jitter for power supplies
WO2005120701A1 (en) * 2004-06-07 2005-12-22 Mcmaster University Stable composite material comprising supported porous gels
US20060154894A1 (en) * 2004-09-15 2006-07-13 Massachusetts Institute Of Technology Biologically active surfaces and methods of their use
GB0424560D0 (en) 2004-11-08 2004-12-08 Leuven K U Res & Dev Heart valve tissue engineering
US20060199207A1 (en) * 2005-02-24 2006-09-07 Matysiak Stefan M Self-assembly of molecules using combinatorial hybridization
JP5217973B2 (en) * 2007-12-05 2013-06-19 大日本印刷株式会社 Method for producing substance immobilization carrier
AU2009288234B2 (en) 2008-09-02 2014-08-21 Merck Millipore Ltd. Chromatography membranes, devices containing them, and methods of use thereof
WO2011058439A1 (en) * 2009-11-13 2011-05-19 Natrix Separations, Inc. Hydrophobic interaction chromatography membranes, and methods of use thereof
US9770515B2 (en) 2010-06-01 2017-09-26 Advanced Proteome Therapeutics Inc. Crosslinking of proteins and other entities via conjugates of α-haloacetophenones, benzyl halides, quinones, and their derivatives
JP6272755B2 (en) 2011-05-17 2018-01-31 ナトリックス セパレイションズ インコーポレーテッド Layered tubular membrane for chromatography and method of use thereof
IN2015DN03105A (en) 2012-09-26 2015-10-02 Harvard College
US10847829B2 (en) 2013-09-26 2020-11-24 President And Fellows Of Harvard College Quinone and hydroquinone based flow battery
WO2018032003A1 (en) 2016-08-12 2018-02-15 President And Fellows Of Harvard College Aqueous redox flow battery electrolytes with high chemical and electrochemical stability, high water solubility, low membrane permeability
US10840532B2 (en) 2017-01-27 2020-11-17 President And Fellows Of Harvard College Flow battery with electrolyte rebalancing system
WO2019157437A1 (en) 2018-02-09 2019-08-15 President And Fellows Of Harvard College Quinones having high capacity retention for use as electrolytes in aqueous redox flow batteries
WO2020072406A2 (en) 2018-10-01 2020-04-09 President And Fellows Of Harvard College Extending the lifetime of organic flow batteries via redox state management
CN112390739B (en) * 2020-11-06 2022-06-17 南京航空航天大学 Catalyst for preparing hydrogen peroxide by electrocatalysis and preparation method thereof
CN114716289B (en) * 2022-03-30 2024-03-01 华中师范大学 Preparation method of chiral benzyl alcohol derivative

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US31712A (en) * 1861-03-19 Improvement in plows
US32991A (en) * 1861-08-06 Improvement in locomotives and steam-carriages for common roads
US3891327A (en) * 1973-11-01 1975-06-24 Grace W R & Co Mounted slides and method of securing a cover glass to a glass slide having a specimen thereon
US4016306A (en) * 1974-07-15 1977-04-05 Mitsubishi Rayon Co., Ltd. Process for forming a coated film in water
USRE31712E (en) 1980-01-24 1984-10-23 Biochemical avidin-biotin multiple-layer system
US4737544A (en) * 1982-08-12 1988-04-12 Biospecific Technologies, Inc. Biospecific polymers
US5002582A (en) * 1982-09-29 1991-03-26 Bio-Metric Systems, Inc. Preparation of polymeric surfaces via covalently attaching polymers
US4973493A (en) * 1982-09-29 1990-11-27 Bio-Metric Systems, Inc. Method of improving the biocompatibility of solid surfaces
US4722906A (en) * 1982-09-29 1988-02-02 Bio-Metric Systems, Inc. Binding reagents and methods
SE8401437D0 (en) * 1984-03-14 1984-03-14 Sven Gothe SURFACE MODIFIED PLASTIC SURFACES AND ITS APPLICATIONS FOR IMMUNOASSAYS (IA)
USRE32991E (en) 1984-11-13 1989-07-18 Thermedics, Inc. Drug dispensing wound dressing
DE3624898A1 (en) * 1986-07-23 1988-01-28 Merck Patent Gmbh ORIENTED POLYMER MATERIALS
JP2551580B2 (en) * 1987-04-30 1996-11-06 ホ−ヤ株式会社 How to make contact lenses hydrophilic
DK641487A (en) * 1987-12-07 1989-06-08 Gluetech Aps PROCEDURE FOR MODIFYING POLYMER SURFACES
JPH01153776A (en) * 1987-12-10 1989-06-15 Fuji Kagakushi Kogyo Co Ltd Liquid ink for printing
CA1335721C (en) * 1987-12-24 1995-05-30 Patrick E. Guire Biomolecule attached to a solid surface by means of a spacer and methods of attaching biomolecules to surfaces
DE69031655T2 (en) * 1989-08-21 1998-05-14 Mag Georg Mayrhofer & Co Ohg IMMOBILIZATION OF MOLECULES BY USING RADIODERIVATIZED POLYMERS
US5252743A (en) * 1989-11-13 1993-10-12 Affymax Technologies N.V. Spatially-addressable immobilization of anti-ligands on surfaces
US5292873A (en) * 1989-11-29 1994-03-08 The Research Foundation Of State University Of New York Nucleic acids labeled with naphthoquinone probe
IT1251576B (en) * 1991-10-02 1995-05-17 Donegani Guido Ist PROCEDURE FOR SEALING TO FORMED BODIES HAVING POLYMER SURFACES HYDROPHILE MONOMERS CONTAINING DOUBLE BONDS.
US5378502A (en) * 1992-09-09 1995-01-03 U.S. Philips Corporation Method of chemically modifying a surface in accordance with a pattern
US5288514A (en) * 1992-09-14 1994-02-22 The Regents Of The University Of California Solid phase and combinatorial synthesis of benzodiazepine compounds on a solid support
US5409731A (en) * 1992-10-08 1995-04-25 Tomei Sangyo Kabushiki Kaisha Method for imparting a hydrophilic nature to a contact lens
DE4331086A1 (en) * 1993-09-11 1995-03-16 Herberts Gmbh Process for the fixation of wound goods with radically polymerizable masses
US5391438A (en) * 1993-10-01 1995-02-21 Texaco Inc. Polymer treating process

Also Published As

Publication number Publication date
EP0820483A1 (en) 1998-01-28
WO1996031557A1 (en) 1996-10-10
EP0820483B1 (en) 2000-12-13
PT820483E (en) 2001-03-30
DK0820483T3 (en) 2001-01-02
ATE198079T1 (en) 2000-12-15
AU699321B2 (en) 1998-12-03
AU5332996A (en) 1996-10-23
JPH11505554A (en) 1999-05-21
DE69611235T2 (en) 2001-04-05
US6033784A (en) 2000-03-07
GR3035079T3 (en) 2001-03-30
ES2153097T3 (en) 2001-02-16
CA2217053C (en) 2010-11-30
DE69611235D1 (en) 2001-01-18
JP3124037B2 (en) 2001-01-15

Similar Documents

Publication Publication Date Title
CA2217053A1 (en) Method of photochemical immobilization of ligands using quinones
Elbert et al. Hydrophilic spacer groups in polymerizable lipids: formation of biomembrane models from bulk polymerized lipids
Mathew et al. (η3-Allyl) palladium (II) and palladium (II) nitrile catalysts for the addition polymerization of norbornene derivatives with functional groups
Albagli et al. Surface attachment of well-defined redox-active polymers and block polymers via terminal functional groups
DE69128918D1 (en) METHOD, TEST SETS AND REACTIVE CARRIERS FOR 3 'LABELING OF OLIGONUCLEOTIDES
US6271315B1 (en) Methods for making multivalent arrays
Jung et al. Enantiomeric separation by GC on Chirasil‐Dex: systematic study of cyclodextrin concentration, polarity, immobilization, and column stability
Regen et al. Ghost vesicles
Pau et al. Proof of Concept Studies Directed Towards Designed Molecular Wires: Property‐Driven Synthesis of Air and Moisture‐Stable Polystannanes
Allcock et al. Thin-layer grafts of poly [bis ((methoxyethoxy) ethoxy) phosphazene] on organic polymer surfaces
Gross et al. Synthesis and characterization of osmium (II) compounds of stoichiometry (C5Me5) OsL2Br,(C5Me5) OsL2H, and (C5Me5) Os (NO) Br2
CN106866900B (en) A kind of photoresponse molecularly imprinted material on surface and its preparation method and application
CA1328786C (en) Layer elements and their production
EP0733216A1 (en) A method and material for the detection of ionising radiation
Morawetz Some recent studies of polymer reactivity
Ferritto et al. Photoregulation of the binding of a synthetic polyelectrolyte to phosphatidylcholine bilayer membranes
EP0369398A2 (en) Polyphosphazene derivatives containing carbonyl groups suitable for photoreticulation processes
TW448200B (en) Hydrogenation products of copolymers prepared by ring-opening metathetical polymerisation, their preparation processes and their use
Machell et al. Synthesis and structural characterization of [Sn (1, 2− O2C6H3NO2− 4)(C4H8O) n A Tin (II) catechol complex
Boileau et al. Cyclization of poly (bisphenol A-diethylene glycol carbonate)—Intramolecular pyrene excimer formation
JPH05148163A (en) Separating agent
JPH0368429A (en) Formation of thin organic film and its use
JP4185978B2 (en) Macrocycles and molecular assemblies
JPS6085448A (en) Optical recordidng medium
JPS60239743A (en) Recording medium

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20160404