CA2391425A1 - Transition metal complexes with bidentate ligand having an imidazole ring - Google Patents

Transition metal complexes with bidentate ligand having an imidazole ring Download PDF

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Publication number
CA2391425A1
CA2391425A1 CA002391425A CA2391425A CA2391425A1 CA 2391425 A1 CA2391425 A1 CA 2391425A1 CA 002391425 A CA002391425 A CA 002391425A CA 2391425 A CA2391425 A CA 2391425A CA 2391425 A1 CA2391425 A1 CA 2391425A1
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transition metal
metal complex
alkyl
unsubstituted
substituted
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CA002391425A
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French (fr)
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CA2391425C (en
Inventor
Fei Mao
Adam Heller
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Therasense Inc
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Therasense, Inc.
Fei Mao
Adam Heller
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B5/00—Measuring for diagnostic purposes; Identification of persons
    • A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
    • A61B5/1486—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using enzyme electrodes, e.g. with immobilised oxidase
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/005—Compounds of elements of Group 5 of the Periodic System without metal-carbon linkages
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B5/00—Measuring for diagnostic purposes; Identification of persons
    • A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
    • A61B5/14532—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue for measuring glucose, e.g. by tissue impedance measurement
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61B—DIAGNOSIS; SURGERY; IDENTIFICATION
    • A61B5/00—Measuring for diagnostic purposes; Identification of persons
    • A61B5/145—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue
    • A61B5/1468—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using chemical or electrochemical methods, e.g. by polarographic means
    • A61B5/1477—Measuring characteristics of blood in vivo, e.g. gas concentration, pH value; Measuring characteristics of body fluids or tissues, e.g. interstitial fluid, cerebral tissue using chemical or electrochemical methods, e.g. by polarographic means non-invasive
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/002—Osmium compounds
    • C07F15/0026—Osmium compounds without a metal-carbon linkage
    • 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 System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0046—Ruthenium compounds
    • C07F15/0053—Ruthenium compounds without a metal-carbon linkage
    • 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 System
    • C07F15/02—Iron compounds
    • C07F15/025—Iron compounds without a metal-carbon linkage
    • 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 System
    • C07F15/06—Cobalt compounds
    • C07F15/065—Cobalt 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
    • 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
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
    • 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

Abstract

Novel transition metal complexes of iron, cobalt, ruthenium, osmium, and vanadium are described. The transition metal complexes can be used as redox mediators in enzyme based electrochemical sensors. In such instances, transition metal complexes accept electrons form, or transfer electrons to, enzymes at a high rate and also exchange electrons rapidly with the sensor. The transition metal complexes include at least one substituted or unsubstituted biimidazole ligand and may further include a second substitute d or unsubstituted biimidazole ligand or a substituted or unsubstituted bipyridine or pyridylimidazole ligand. Transition metal complexes attached t o polymeric backbones are also described.

Claims (28)

1. A transition metal complex having the formula:

wherein M is cobalt, iron, ruthenium, osmium, or vanadium;
L is selected from the group consisting of:

R1, R2, and R'1 are independently substituted or unsubstituted alkyl, alkenyl, or aryl groups;
R3, R4, R5, R6, R'3, R'4, R a, R b, R c, and R d are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl;

c is an integer selected from -1 to -5 or +1 to +5 indicating a positive or negative charge;

X represents at least one counter ion;
d is an integer from 1 to 5 representing the number of counter ions, X; and L1, L2, L3 and L4 are ligands.
2. The transition metal complex of claim 1, wherein both R1, R1', and R2 are unsubstituted C1 to C12 alkyl.
3. The transition metal complex of claim l, wherein R3, R4, R5 and R6 are -H.
4. The transition metal complex of claim 1, wherein L1 is a monodentate ligand.
5. The transition metal complex of claim 1, wherein L1 comprises a heterocyclic compound containing at least one nitrogen atom.
6. The transition metal complex of claim 1, wherein L1 comprises a heterocyclic compound coupled to a polymeric backbone.
7. The transition metal complex of claim 6, wherein L1 and L2 in combination form a bidentate ligand.
8. The transition metal complex of claim 1, wherein L1 and L2 in combination form a bidentate ligand.
9. The transition metal complex of claim 8, wherein the bidentate ligand comprises a 2,2'-bipyridine having the following formula:

wherein R16, R17, R18, R19, R20, R21, R22 and R23 are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl.
10. The transition metal complex of claim 1, wherein L1 and L2 in combination form a first bidentate ligand and L3 and L4 in combination form a second bidentate ligand.
11. The transition metal complex of claim 10, wherein at least one of the first and second bidentate ligands is selected from the group consisting of substituted and unsubstituted 2,2'-bipyridines, 2,2'-biimidazoles, and 2-(2-pyridyl)imidazoles.
12. The transition metal complex of claim 1, wherein M is osmium and the transition complex has the following formula:

wherein R3, R4, R5, R6, R16, R17, R19, R20, R22 and R23 are -H;
R1 and R2 are independently substituted or unsubstituted C1 to C12 alkyls;
and R18 and R21, are independently -H or substituted or unsubstituted C1-C12 alkoxy, C1-12 alkylthio, C1-C12 alkylamino, C2-C24 dialkylamino, or C1-C12 alkyl.
13. The transition metal complex of claim 12, wherein at least one of R"
R2, R18 and R21, comprises a reactive group selected from the group consisting of carboxy, activated ester, sulfonyl halide, sulfonate ester, isocyanate, isothiocyanate, epoxide, aziridine, halide, aldehyde, ketone, amine, acrylamide, thiol, acyl azide, acyl halide, hydrazine, hydroxylamine, alkyl halide, imidazole, pyridine, phenol, alkyl sulfonate, halotriazine, imido ester, maleimide, hydrazide, hydroxy, and photo-reactive azido aryl groups.
14. The transition metal complex of claim 12, wherein at least one of R1, R2, R18, and R21 is coupled to a polymeric backbone.
15. The transition metal complex of claim 1, wherein M is osmium and the transition complex has the following formula:

wherein R3, R4, R5, R6, R'3, R'4, Ra, and Rc are -H;
Rd is -H or methyl;
Rb is -H or substituted or unsubstituted C1-C12 alkoxy, C1-12 alkylthio, C1-C12 alkylamino, C2-C24 dialkylamino, or C1-C12 alkyl; and R1, R'1, and R2 are independently substituted or unsubstituted C1 to C12 alkyl.
16. The transition metal complex of claim 15, wherein at least one of R1, R2, and R'1 comprises a reactive group selected from the group consisting of carboxy, activated ester, sulfonyl halide, sulfonate ester, isocyanate, isothiocyanate, epoxide, aziridine, halide, aldehyde, ketone, amine, acrylamide, thiol, acyl azide, acyl halide, hydrazine, hydroxyamine, alkyl halide, imidazole, pyridine, phenol, alkyl sulfonate, halotriazine, imido ester, maleimide, hydrazide, hydroxy, and photo-reactive azido aryl groups.
17. The transition metal complex of claim 15, wherein at least one of R1, R2, and R'1, is coupled to a polymeric backbone.
18. A redox mediator having the formula:
wherein M is iron, cobalt, ruthenium, osmium, or vanadium;
L is a bidentate ligand comprising at least one imidazole ring;
c is an integer selected from -1 to -5 or +1 to +5 indicating a positive or negative charge;
X represents at least one counter ion;
d is an integer from 1 to 5 representing the number of counter ions, X; and L1, L2, L3, and L4 are ligands.
19. The redox mediator of claim 18, wherein L is selected from the group consisting of:

wherein R1, R2, and R'1 are independently -H or substituted or unsubstituted alkyl, alkenyl, or aryl; and R3, R4, R5, R6, R'3, R'4, R a, R b, R c, and R d are independently -H, -F, -Cl, -Br, -I, -NO2, -CN, -CO2H, -SO3H, -NHNH2, -SH, -OH, -NH2, or substituted or unsubstituted alkoxylcarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxylamino, alkylthio, alkenyl, aryl, or alkyl.
20. The redox mediator of claim 18, wherein L1 comprises a heterocyclic compound containing at least one nitrogen atom.
21. The redox mediator of claim 18, wherein L1 comprises a heterocyclic compound coupled to a polymeric backbone.
22. The redox mediator of claim 18, wherein at least one of L, L1, L2, L3 and L4 is coupled to a polymeric backbone.
23 A polymer comprising:
a polymeric backbone; and a transition metal complex having the following formula:
wherein M is iron, cobalt, ruthenium, osmium, or vanadium;
L is a bidentate ligand comprising at least one imidazole ring;
c is an integer selected from -1 to -5 or +1 to +5 indicating a positive or negative charge;
X represents at least one counter ion;
d is an integer from 1 to 5 representing the number of counter ions, X; and L1, L2, L3 and L4 are ligands.
wherein at least one of L, L1, L2, L3 and L4 is coupled to the polymeric backbone.
24. The polymer of claim 23, wherein the polymer backbone is selected from the group consisting of styrene/maleic anhydride copolymer, methylvinylether/maleic anhydride copolymer, poly(4-vinylbenzylchloride) copolymer, poly(allylamine) copolymer, poly(4-vinylpyridine) copolymer, poly(4-vinylpyridine), poly(N-vinylimidazole), and poly(4-styrene sulfonate).
25. A sensor comprising:
a working electrode;
a counter electrode; and a redox mediator disposed proximate to the working electrode, the redox mediator having the formula:
wherein M is iron, cobalt, ruthenium, osmium, or vanadium;
L is a bidentate ligand comprising at least one imidazole ring;
c is an integer selected from -1 to -5 or +1 to +5 indicating a positive or negative charge;
X represents at least one counter ion;
d is an integer from 1 to 5 representing the number of counter ions, X; and L1, L2, L3 and L4 are ligands.
26. The sensor of claim 25, further comprising an enzyme disposed proximate to the working electrode.
27. The sensor of claim 25, wherein at least one of L, L1, L2, L3 and L4 is coupled to a polymeric backbone.
28. The sensor of claim 25, wherein the redox mediator is non-leachably disposed on the working electrode.
CA2391425A 1999-11-15 2000-11-14 Transition metal complexes with bidentate ligand having an imidazole ring Expired - Lifetime CA2391425C (en)

Applications Claiming Priority (3)

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US16556599P 1999-11-15 1999-11-15
US60/165,565 1999-11-15
PCT/US2000/031268 WO2001036430A1 (en) 1999-11-15 2000-11-14 Transition metal complexes with bidentate ligand having an imidazole ring

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CA2391425A1 true CA2391425A1 (en) 2001-05-25
CA2391425C CA2391425C (en) 2010-07-06

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CA002391423A Abandoned CA2391423A1 (en) 1999-11-15 2000-11-14 Polymeric transition metal complexes and uses thereof
CA2391425A Expired - Lifetime CA2391425C (en) 1999-11-15 2000-11-14 Transition metal complexes with bidentate ligand having an imidazole ring

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EP (2) EP1230249B1 (en)
JP (2) JP5308609B2 (en)
AT (2) ATE268336T1 (en)
AU (2) AU1602601A (en)
CA (2) CA2391423A1 (en)
DE (2) DE60011286T2 (en)
DK (1) DK1230249T3 (en)
ES (1) ES2222252T3 (en)
TR (1) TR200401326T4 (en)
WO (2) WO2001036430A1 (en)

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