TRANSITION METAL COMPLEXES WITH (PYRIDYL)IMIDAZOLE LIGANDS
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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. The transition metal complexes include substituted or unsubstituted (pyridyl)imidazole ligands. Transition metal complexes attached to polymeric backbones are also described.
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Citations
76 Claims
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1-48. -48. (canceled)
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49. A test strip comprising:
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a working electrode; a counter electrode; wherein the working electrode comprises an analyte-responsive enzyme and a mediator complex, the mediator complex having the formula; wherein c is a negative, neutral, or positive charge represented by −
1 to −
5, 0, or +1 to +5, inclusive, respectively;d is a number of counter ions, X, from 1 to 5, inclusive; M is osmium or ruthenium; L1 is a substituted or an unsubstituted heterocyclic nitrogen-containing ligand; L2 is a negatively charged ligand; and L and L′
are independently;wherein R′
1 is a substituted or an unsubstituted alkyl, alkenyl or aryl;each of Ra and Rb is 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;each of Re and Rd is 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, or a combination of Re and Rd forms a saturated or an unsaturated 5- or 6-membered ring; andeach of R′
3 and R′
4 is 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, or a combination of R′
3 and R′
4 forms a saturated or an unsaturated 5- or 6-membered ring.- View Dependent Claims (50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66)
L2 is a halide; and L and L′
are independently;wherein R′
1 is a substituted or an unsubstituted C1-C6 alkyl;R′
3 and R′
4 are independently —
H;Ra, Rb, Rc, and Rd are independently —
H or C1 alkyl;c is a negative, neutral, or positive charge represented by −
1 to −
5, 0, or +1 to +5, inclusive, respectively.
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51. The test strip of claim 50, wherein L1 is a substituted or unsubstituted pyridine.
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52. The test strip of claim 50, wherein L1 has the formula:
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wherein R11, R12, R13, R14 and R15 are independently —
H, —
F, —
Cl, —
Br, —
I, —
NO2, —
CN, —
CO2H, —
OH, —
NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl.
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53. The test strip of claim 52, wherein R11 and R15 are independently —
- H;
R12 and R14 are the same and —
H or methyl; and
R13 is —
H, C1 to C12 alkoxy, —
NH2, C1 to C12 alkylamino, C2 to C24 dialkylamino, hydrazino, C1 to C12 alkylhydrazino, hydroxylamino, C1 to C12 alkoxyamino, C1 to C12 alkylthio, or C1 to C12 alkyl.
- H;
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54. The test strip complex of claim 50, wherein L1 has the formula:
wherein R11, R12, R13, R14 and R15 are independently —
H, methyl, C1-C2 alkoxy, C1-C2 alkylamino, C2-C4 dialkylamino, or a C1-C6 lower alkyl substituted with a reactive group.
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55. The test strip of claim 50, wherein L2 is —
- F, —
Cl, or —
Br.
- F, —
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56. The test strip of claim 50, wherein L2 is —
- Cl.
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57. The test strip of claim 50, wherein R′
- 1 is a C1-C2 alkyl.
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58. The test strip of claim 50, wherein R′
- 1 is a C1 alkyl.
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59. The test strip of claim 50, wherein each of Ra and Rc is —
- H.
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60. The test strip of claim 50, wherein each of Ra, Rb, and Rc is —
- H.
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61. The test strip of claim 50, wherein each of Ra, Rb, Rc, and Rd is —
- H.
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62. The test strip of claim 50, wherein X is a halide.
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63. The test strip of claim 50, wherein X is chloride.
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64. The test strip of claim 49, wherein the analyte-responsive enzyme is glucose dehydrogenase (GDH).
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65. The test strip of claim 49, wherein the analyte-responsive enzyme further comprises an enzyme cofactor.
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66. The test strip of claim 64, wherein the enzyme cofactor is flavin adenine dinucleotide (FAD).
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67. A test strip comprising:
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a working electrode; a counter electrode; wherein the working electrode comprises an analyte-responsive enzyme and a mediator complex, the mediator complex having the formula; wherein M is cobalt, iron, osmium, ruthenium, or vanadium; L1 has the formula; wherein R11, R12, R13, R14 and R15 are independently —
H, —
F, —
Cl, —
Br, —
I, —
NO2, —
CN, —
CO2H, —
OH, —
NH2, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkoxy, alkylamino, dialkylamino, alkanoylamino, arylcarboxamido, hydrazino, alkylhydrazino, hydroxylamino, alkoxyamino, alkylthio, alkenyl, aryl, or alkyl;L2 is chloride; L and L′
are independently;wherein R′
1 is methyl; and
R′
3, R′
4, Ra, Rb, Rc, and Rd are independently —
H;c is a negative, neutral, or positive charge represented by −
1 to −
5, 0, or +1 to +5, inclusive, respectively;d is a number of X sufficient to balance the charge c; and X is an anion. - View Dependent Claims (68, 69, 70, 71, 72, 74, 75, 76)
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73. A test strip comprising:
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a working electrode; a counter electrode; wherein the working electrode comprises an analyte-responsive enzyme and a mediator complex, the mediator complex having the formula; wherein M is osmium; L1 has the formula; wherein R11, R12, R14 and R15 are —
H;R13 is C1-C2 alkylamino; L2 is chloride; L and L′
are independently;wherein R′
1 is methyl; and
R′
3, R′
4, Ra, Rb, Rc, and Rd are independently —
H;c is +2; d is 2; and X is chloride.
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Specification