US 6,676,816 B2Granted

Transition metal complexes with (pyridyl)imidazole ligands and sensors using said complexes

AssigneeTheraSense, Inc.

InventorsFei Mao, Adam Heller

Life of this patent

Estimating the term…

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.

Claims70

Dependent claims

A transition metal 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;
M is cobalt, iron, osmium, ruthenium, or vanadium;
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;
Ra and Rb 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;
R′3, R′4 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, or a combination of R′3 and R′4 forms a saturated or unsaturated 5- or 6-membered ring;
and
Rc, and Rd 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, or a combination of Rc and Rd forms a saturated or unsaturated 5- or 6-membered ring.

8 more elements

A transition metal complex having the formula:

wherein c is a negative or positive charge represented by −1 to −5 or +1 to +5, inclusive, respectively;
d is a number of counter ions, X, from 1 to 5, inclusive;
X is chloride;
M is cobalt, iron, osmium, ruthenium, or vanadium;
L1 is a substituted or an unsubstituted imidazole 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;
Ra and Rb 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;
R′3, R′4 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, or a combination of R′3 and R′4 forms a saturated or an unsaturated 5- or 6-membered ring;
and
Rc, and Rd 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, or a combination of Rc and Rd forms a saturated or an unsaturated 5- or 6-membered ring.

10 more elements

A sensor comprising:

a working electrode;
a counter electrode;
an enzyme disposed proximate to the working electrode;
a redox mediator disposed proximate to the working electrode, the redox mediator having the formula:
wherein c is a negative, neutral, or positive charge represented by −1 to −5, 0, or +1 to +5, inclusive, respectively;
M is cobalt, iron, osmium, ruthenium, or vanadium;
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;
Ra and Rb 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;
R′3, R′4 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, or a combination of R′3 and R′4 forms a saturated or an unsaturated 5- or 6-membered ring;
and
Rc, and Rd 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, or a combination of Rc and Rd forms a saturated or an unsaturated 5- or 6-membered ring.

12 more elements

Dependencies are inferred from the claim text.

patentgrep

Loading patent…

Abstract