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NZ774001B2 - Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same - Google Patents
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NZ774001B2 - Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same - Google Patents

Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same Download PDF

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Publication number
NZ774001B2
NZ774001B2 NZ774001A NZ77400119A NZ774001B2 NZ 774001 B2 NZ774001 B2 NZ 774001B2 NZ 774001 A NZ774001 A NZ 774001A NZ 77400119 A NZ77400119 A NZ 77400119A NZ 774001 B2 NZ774001 B2 NZ 774001B2
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NZ
New Zealand
Prior art keywords
group
carbon atoms
unsubstituted
chemical formula
oxidation
Prior art date
Application number
NZ774001A
Other versions
NZ774001A (en
Inventor
Sumin Gwak
In Seok Jeong
Young Jea Kang
Jinseon Lee
Hyunseo Shin
Bona Yang
Hyunhee Yang
Original Assignee
I Sens Inc
Filing date
Publication date
Application filed by I Sens Inc filed Critical I Sens Inc
Priority claimed from PCT/KR2019/006000 external-priority patent/WO2020059997A1/en
Publication of NZ774001A publication Critical patent/NZ774001A/en
Publication of NZ774001B2 publication Critical patent/NZ774001B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C07F15/0026—Osmium compounds without a metal-carbon linkage
    • 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
    • C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F226/06—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • 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
    • 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
    • C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
    • 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
    • C08F8/42—Introducing metal atoms or metal-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
    • C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/338—Polymers modified by chemical after-treatment with inorganic and organic compounds
    • 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
    • C12Q1/001—Enzyme electrodes
    • 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
    • C12Q1/001—Enzyme electrodes
    • C12Q1/004—Enzyme electrodes mediator-assisted
    • 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
    • C12Q1/001—Enzyme electrodes
    • C12Q1/005—Enzyme electrodes involving specific analytes or enzymes
    • C12Q1/006—Enzyme electrodes involving specific analytes or enzymes for glucose
    • 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
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • 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
    • C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
    • C12Q1/32—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving dehydrogenase
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/28—Electrolytic cell components
    • G01N27/30—Electrodes, e.g. test electrodes; Half-cells
    • G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
    • G01N27/3271—Amperometric enzyme electrodes for analytes in body fluids, e.g. glucose in blood
    • G01N27/3272—Test elements therefor, i.e. disposable laminated substrates with electrodes, reagent and channels
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
    • G01N27/28—Electrolytic cell components
    • G01N27/30—Electrodes, e.g. test electrodes; Half-cells
    • G01N27/327—Biochemical electrodes, e.g. electrical or mechanical details for in vitro measurements
    • G01N27/3275—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction
    • G01N27/3277—Sensing specific biomolecules, e.g. nucleic acid strands, based on an electrode surface reaction being a redox reaction, e.g. detection by cyclic voltammetry
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B13/00—Apparatus or processes specially adapted for manufacturing conductors or cables

Abstract

The present invention relates to an oxidation-reduction polymer which has a unique structure so as to be prepared in a simple step compared to a conventional art, and includes a transition metal complex in which the immobilization rate of the transition metal complex is increased and a functional group or linker can be easily introduced; a method for preparing same; and an electrochemical biosensor comprising the oxidation-reduction polymer.

Claims (1)

?CLAIMS? ?Claim 1? 20 An oxidation-reduction polymer for an electron transport medium of an electrochemical biosensor, having any one structure of the following Chemical Formulas 1 to 4: [Chemical Formula 1] 37 20930975_1 (GHMatters) P114803.NZ [Chemical Formula 2] [Chemical Formula 3] 38 20930975_1 (GHMatters) P114803.NZ [Chemical Formula 4] wherein, 5 M is a transition metal selected from the group consisting of Os, Rh, Ru, Ir, Fe and Co; L1 and L2 are combined with each other to form a bidentate ligand selected from the following Chemical Formulas 5 to 7; L3 and L4 are combined with each other to form a bidentate ligand 39 20930975_1 (GHMatters) P114803.NZ selected from the following Chemical Formulas 5 to 7; L5 and L6 are each combined with each other to form a bidentate ligand selected from the following Chemical Formulas 5 to 7; [Chemical Formula 5] 5 [Chemical Formula 6] [Chemical Formula 7] 10 the R1, R2 and R'1 are each independently selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group 15 having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, 40 20930975_1 (GHMatters) P114803.NZ an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen, the R3 to R20 are each independently selected from the group consisting of an unsubstituted alkyl group having 1 to 10 carbon atoms, an 5 unsubstituted cycloalkyl group having 3 to 40 carbon atoms, an unsubstituted aryl group having 6 to 50 carbon atoms, an unsubstituted heteroaryl group having 3 to 50 carbon atoms, an unsubstituted alkoxy group having 1 to 20 carbon atoms, an unsubstituted alcohol group having 1 to 20 carbon atoms, an unsubstituted alkylhalogen group having 1 to 20 carbon 10 atoms, an unsubstituted thiol group having 1 to 20 carbon atoms, an unsubstituted alkyl azide group having 3 to 20 carbon atoms, an unsubstituted aryl azide group having 7 to 30 carbon atoms, an unsubstituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted alkylamino group having 1 to 20 carbon atoms, an unsubstituted arylamino group having 15 6 to 30 carbon atoms, an unsubstituted alkylsilyl group having 1 to 20 carbon atoms, an unsubstituted arylsilyl group having 6 to 30 carbon atoms, an unsubstituted arylalkylamino group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 40 carbon atoms, an unsubstituted alkynyl group having 2 to 40 carbon atoms, a cyano group, a halogen group, 20 deuterium and hydrogen; the Ad is selected from the group consisting of a primary and secondary amine group, an ammonium group, a halogen group, an epoxy group, an azide group, an acrylate group, an alkenyl group, an alkynyl group, a thiol group, isocyanate, an alcohol group, and a silane group; 25 the X is a counter ion; 41 20930975_1 (GHMatters) P114803.NZ the a is an integer of 1 to 15; the b is an integer of 1 to 15; the c is an integer of 1 to 15; the m is an integer of 10 to 600; 5 the n is an integer of 10 to 600; and the o is an integer of 0 to 600. ?Claim 2? The oxidation-reduction polymer for an electron transport medium 10 according to claim 1, wherein the compound of Chemical Formula 1 has a structure represented by the following Chemical Formula 8 or 9 [Chemical Formula 8] [Chemical Formula 9] 42 20930975_1 (GHMatters) P114803.NZ . ?Claim 3? A method for preparing an oxidation-reduction polymer as set forth in claim 1, the method comprising the steps of: 5 (i) functionalizing polyvinylpyridine or polyimidazole to produce a polyvinylpyridine precursor or a polyimidazole precursor; (ii) functionalizing the transition metal complex; and (iii) reacting the polyvinylpyridine precursor or polyimidazole precursor produced in step (i) and the functionalized transition metal 10 complex produced in step (ii) by a click reaction to prepare the oxidationreduction polymer as set forth in claim 1. ?Claim 4? The method according to claim 3, wherein the click reaction of step 15 (iii) is azide-alkyne Huisgen cycloaddition or thiol-ene reaction. 43 20930975_1 (GHMatters) P114803.NZ ?Claim 5? A composition for an electrochemical biosensor comprising : an enzyme capable of subjecting a liquid biological sample to an 5 oxidation-reduction reaction; and the oxidation-reduction polymer as set forth in claim 1. ?Claim 6? The composition according to claim 5, wherein the enzyme comp rises: 10 at least one oxidoreductase selected from the group consisting of dehydrogenase, oxidase, and esterase; or at least one oxidoreductase selected from the group consisting of dehydrogenase, oxidase, and esterase, and at least one cofactor selected from the group consisting of flavin adenine dinucleotide (FAD), nicotinamide 15 adenine dinucleotide (NAD), and pyrroloquinoline quinone (PQQ). ?Claim 7? The composition according to claim 5, wherein the enzyme is at least one selected from the group consisting of flavin adenine dinucleotide20 glucose dehydrogenase (FAD-GDH) and nicotinamide adenine dinucleotideglucose dehydrogenase. ?Claim 8? The composition according to claim 5, further comprising one or 25 more additives selected from the group consisting of surfactants, water- 44 20930975_1 (GHMatters) P114803.NZ soluble polymers, and thickeners, and a crosslinking agent. ?Claim 9? An electrochemical biosensor comprising the oxidation-reduction 5 polymer according to claim 1. ?Claim 10? The electrochemical biosensor according to claim 9, further comprising a sensing layer, a diffusion layer, a protection layer, two or more 10 electrodes, an insulator and a substrate, comprising the oxidation-reduction polymer as set forth in claim
1. ?Claim 11? The electrochemical biosensor according to claim 10, wherein the 15 electrode is a 2-electrode consisting of an working electrode and a counter electrode, or a 3-electrode consisting of an working electrode, a counter electrode and a reference electrode. ?Claim 12? 20 The electrochemical biosensor according to claim 9, wherein the electrochemical biosensor is a blood glucose sensor.
NZ774001A 2019-05-09 Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same NZ774001B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20180111633 2018-09-18
PCT/KR2019/006000 WO2020059997A1 (en) 2018-09-18 2019-05-09 Oxidation-reduction polymer including transition metal complex, and electrochemical biosensor using same

Publications (2)

Publication Number Publication Date
NZ774001A NZ774001A (en) 2024-07-26
NZ774001B2 true NZ774001B2 (en) 2024-10-30

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