CA2413885A1 - Polymers for binding of phenols - Google Patents

Polymers for binding of phenols Download PDF

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Publication number
CA2413885A1
CA2413885A1 CA002413885A CA2413885A CA2413885A1 CA 2413885 A1 CA2413885 A1 CA 2413885A1 CA 002413885 A CA002413885 A CA 002413885A CA 2413885 A CA2413885 A CA 2413885A CA 2413885 A1 CA2413885 A1 CA 2413885A1
Authority
CA
Canada
Prior art keywords
phenol
polymer
group
substituted
imprinted polymer
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
CA002413885A
Other languages
French (fr)
Other versions
CA2413885C (en
Inventor
Miruna Petcu
Janine Cooney
Christian Cook
Denis Lauren
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.)
New Zealand Insitiute for Plant and Food Research Ltd
Original Assignee
The Horticulture And Food Research Institute Of New Zealand Limited
Miruna Petcu
Janine Cooney
Christian Cook
Denis Lauren
The New Zealand Institute For Plant And Food Research Limited
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 The Horticulture And Food Research Institute Of New Zealand Limited, Miruna Petcu, Janine Cooney, Christian Cook, Denis Lauren, The New Zealand Institute For Plant And Food Research Limited filed Critical The Horticulture And Food Research Institute Of New Zealand Limited
Publication of CA2413885A1 publication Critical patent/CA2413885A1/en
Application granted granted Critical
Publication of CA2413885C publication Critical patent/CA2413885C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • G01N33/94—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving narcotics or drugs or pharmaceuticals, neurotransmitters or associated receptors
    • G01N33/9406—Neurotransmitters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/12—Hydrolysis
    • 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
    • G01N33/5308—Immunoassay; Biospecific binding assay; Materials therefor for analytes not provided for elsewhere, e.g. nucleic acids, uric acid, worms, mites
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2810/00—Chemical modification of a polymer
    • C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2600/00—Assays involving molecular imprinted polymers/polymers created around a molecular template
    • 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
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/20—Oxygen containing
    • 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
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/20—Oxygen containing
    • Y10T436/203332—Hydroxyl containing

Abstract

The invention relates to a method for the detection and/or measurement of a phenol comprising: (a) contacting the sample to be tested with a polymer imprinted with the phenol or an analogue thereof; and (b) measuring binding of the phenol to the polymer. The polymer may be prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis. Propofol is a preferred phenol for use in the invention.

Claims (29)

1. A method for the detection and/or measurement of a phenol comprising:

(a) contacting the sample to be tested with a polymer imprinted with the phenol or an analogue thereof;

(b) measuring binding of the phenol to the polymer.
2. A method as claimed in claim 1 wherein said imprinted polymer was prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis.
3. A method as claimed in claim 2 wherein said monomer has the formula MXP
wherein;

P is a (substituted) phenoxy group;

M is a polymerisable group containing an alkenyl group;

X is a bond or a linker group susceptible to hydrolysis under conditions which do not result in destruction of the polymer backbone.
4. A method as claimed in claim 3 wherein X or X together with M and/or P
contains an -O-CO-O- group.
5. A method as claimed in claim 4 wherein M is a vinylphenyl group, and X and the oxy group of P form an -O-CO-O- group.
6. A method as claimed in claim 1 wherein said imprinted polymer was prepared by preparing or crosslinking a polymer in the presence of the phenol, with subsequent removal of phenol.
7. A method as claimed in claim 6 wherein the polymer is a crosslinked polyacrylate or polymethacrylate.
8. A method as claimed in claim 7 wherein the polymer is a polymethacrylate crosslinked with ethylenedimethacrylate.
9. A method as claimed in any preceding claim wherein the particle size of at least 50% (by weight) of the polymer is in the range 0.5-5 microns.
10. A method according to any preceding claim wherein the imprinted polymer is formed by placing the polymerisation mixture on a porous polymer membrane and allowing the mixture to polymerise.
11. A method as claimed in claim 10 wherein the porous polymer membrane is a PTFE
membrane.
12. A method as claimed in any one of the preceding claims wherein the phenol is phenol or is a mono- di- or tri-substituted phenol.
13. A method as claimed in claim 12 where the phenol is substituted with 1 to 3 substituents selected from C1-C6 alkyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, amino, C1-alkylamino, di(C1-C3 alkyl) amino, -CONH2, -CN, carboxy, hydroxy, C1-C6 alkylsulfonyl, nitro, and substituted C1-C6 alkyl or alkoxy wherein the substituent is selected from halogen, hydroxy, C1-C3 alkoxy, amino, -CONH2, -CN and carboxy.
14. A method as claimed in claim 13 wherein the phenol is substituted with 1 to 3 C1-C3 alkyl groups.
15. A method as claimed in claim 14 wherein the phenol is propofol or a cresol.
16. A method as claimed in claim 15 wherein the phenol is propofol.
17. A sensor for detecting/measure propofol, comprising a probe having an imprinted polymer as defined in any previous claim.
18. An imprinted polymer prepared by polymerising a polymerisable monomer, to which a phenol is covalently bound by a hydrolysable linker, and subsequently removing the phenol by hydrolysis.
19. An imprinted polymer as claimed in claim 18 wherein said monomer has the formula MXP and wherein;

P is a (substituted) phenoxy group;

M is a polymerisable group containing an alkenyl group;

X is a bond or a linker group susceptible to hydrolysis under conditions which do not result in destruction of the polymer backbone.
20. An imprinted polymer claimed in claim 19 wherein X or X together with M
and/or P
contains an -O-CO-O- group.
21. An imprinted polymer as claimed in claim 20 wherein M is a vinylphenyl group, and X
and the oxy group of P form an -O-CO-O- group.
22. An imprinted polymer prepared by preparing or crosslinking a polymer in the presence of the phenol, and subsequently removing the phenol.
23. A method as claimed in claim 22 wherein the polymer is a crosslinked polyacrylate or polymethacrylate.
24. A method as claimed in claim 23 wherein the polymer is a polymethacrylate crosslinked with ethylenedimethacrylate.
25. An imprinted polymer as claimed in any one of claims 18-24 wherein the phenol is phenol or is mono- di- or tri-substituted phenol.
26. An imprinted polymer as claimed in claim 25 where the phenol is substituted with 1 to 3 substituents selected from C1-C6 alkyl, halogen, C1-C6 alkoxy, C1-C6 alkylthio, amino, C1-C6 alkylamino, di(C1-C3 alkyl) amino, -CONH2, -CN, carboxy, hydroxy, C1-C6 alkylsulfonyl, nitro, and substituted C1-C6 alkyl or alkoxy wherein the substituent is selected from halogen, hydroxy, C1-C3 alkoxy, amino, -CONH2, -CN and carboxy.
27. An imprinted polymer as claimed in claim 26 wherein the phenol is substituted with 1 to 3 C1-C3 alkyl groups.
28. An imprinted polymer as claimed in claim 27 wherein the phenol is propofol or a cresol.
29. An imprinted polymer as claimed in claim 28 wherein the phenol is propofol.
CA2413885A 2000-06-30 2001-06-29 Polymers for binding of phenols Expired - Fee Related CA2413885C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NZ505525 2000-06-30
NZ505525A NZ505525A (en) 2000-06-30 2000-06-30 Polymers imprinted with phenols for the binding of phenols, and a method and sensor for the detection and/or measurement of a phenol by measuring the binding of phenol to the polymer
PCT/NZ2001/000128 WO2002000737A1 (en) 2000-06-30 2001-06-29 Polymers for binding of phenols

Publications (2)

Publication Number Publication Date
CA2413885A1 true CA2413885A1 (en) 2002-01-03
CA2413885C CA2413885C (en) 2010-06-15

Family

ID=19927976

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2413885A Expired - Fee Related CA2413885C (en) 2000-06-30 2001-06-29 Polymers for binding of phenols

Country Status (7)

Country Link
US (1) US7229836B2 (en)
EP (1) EP1297026A4 (en)
JP (1) JP2004502149A (en)
AU (2) AU2001280298B2 (en)
CA (1) CA2413885C (en)
NZ (1) NZ505525A (en)
WO (1) WO2002000737A1 (en)

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JP5183841B2 (en) * 2001-09-07 2013-04-17 日鉄住金環境株式会社 Method for producing polymer specifically binding to phenolic compound having endocrine disrupting action or structural analogue thereof, and method for separating phenolic compound having endocrine disrupting action or structural analogue thereof
DE10335236B3 (en) * 2003-08-01 2005-02-24 Drägerwerk AG Measuring system for the determination of the concentration of propofol (2,6-diisopropylphenol) in the respiratory flow
CN100547583C (en) 2003-08-14 2009-10-07 甲骨文国际公司 Database automatically and the method that dynamically provides
US7552171B2 (en) 2003-08-14 2009-06-23 Oracle International Corporation Incremental run-time session balancing in a multi-node system
WO2005075995A1 (en) * 2004-02-03 2005-08-18 Sphere Medical Ltd Sensor
NZ533818A (en) * 2004-06-29 2007-06-29 Horticulture & Food Res Inst Polymer for binding of organic molecules or metal ions
US9176772B2 (en) 2005-02-11 2015-11-03 Oracle International Corporation Suspending and resuming of sessions
GB0509276D0 (en) * 2005-05-06 2005-06-15 Univ Cranfield Synthetic receptor
GB0509275D0 (en) * 2005-05-06 2005-06-15 Univ Cranfield Synthetic receptor
EP2004783B1 (en) * 2006-04-10 2009-10-21 R.J.Reynolds Tobacco Company A method to selectively remove safrole from nutmeg oil
JP4724188B2 (en) * 2008-01-24 2011-07-13 株式会社東芝 Molecular recognition sensor
US20100328411A1 (en) * 2009-06-30 2010-12-30 Sivapackia Ganapathiappan Printing on vinyl print media
CN102735711B (en) * 2011-04-15 2015-02-04 洪健中 Method for measuring concentration of microscale substance to be measured in solution and anesthetic sensing wafer
US9192193B2 (en) 2011-05-19 2015-11-24 R.J. Reynolds Tobacco Company Molecularly imprinted polymers for treating tobacco material and filtering smoke from smoking articles
US20160157515A1 (en) 2014-12-05 2016-06-09 R.J. Reynolds Tobacco Company Smokeless tobacco pouch

Family Cites Families (11)

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US4069105A (en) * 1977-03-03 1978-01-17 Syva Company Lidocaine antigens and antibodies
US4650771A (en) * 1983-11-04 1987-03-17 Miles Laboratories, Inc. Immunogens, antibodies, labeled conjugates, and related derivatives for lidocaine and analogs thereof
SE8900130D0 (en) * 1989-01-16 1989-01-16 Klaus Mosback THE CONCEPT OF USING THE MOLECULE PRINTING METHOD FOR MANUFACTURED ARTIFICIAL ANTIBODIES THROUGH IMPRINTING EX ANTIGENES AND MANUFACTURING ARTIFICIAL ENTYZYMS THROUGH IMPRINTING WITH TRANSITION STATE
US5630978A (en) * 1995-06-07 1997-05-20 Yissum Research Development Co. Of The Hebrew University Of Jerusalem Preparation of biologically active molecules by molecular imprinting
US6063637A (en) * 1995-12-13 2000-05-16 California Institute Of Technology Sensors for sugars and other metal binding analytes
DE19736366A1 (en) * 1997-08-21 1999-02-25 Ernst Prof Dr Bayer Isolating anionic substances e.g. protein, nucleic acids, from aqueous systems
SG77209A1 (en) * 1997-12-16 2000-12-19 Givaudan Roure Int Polymer
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US6057377A (en) * 1998-10-30 2000-05-02 Sandia Corporation Molecular receptors in metal oxide sol-gel materials prepared via molecular imprinting

Also Published As

Publication number Publication date
US7229836B2 (en) 2007-06-12
CA2413885C (en) 2010-06-15
NZ505525A (en) 2003-03-28
EP1297026A4 (en) 2006-11-22
US20040096979A1 (en) 2004-05-20
AU2001280298B2 (en) 2005-09-15
AU8029801A (en) 2002-01-08
JP2004502149A (en) 2004-01-22
EP1297026A1 (en) 2003-04-02
WO2002000737A1 (en) 2002-01-03

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