EP0314009A2
Expired / Lapsed
EP
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Functionalized conductive polymers and their use in diagnostic devices
Assignee: Bayer Corp
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Filing: 1988-10-21
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Granted: —
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Expires: 2008-10-21
Abstract
Abstract Electrically conducting homo- and/or copolymers and/or tripolymers can be produced from novel monomers, such as a 3-substituted 2,5-di(2-thienyl)pyrrole. The polymers exhibit unexpectedly high stability and conductivities, and can be functionalized, such as with an enzyme, like glucose oxidase, or an ion-specific binding site, like a crown ether, or an antigen, without adversely affecting the conductivity of the polymer. The functionalized, conducting polymer can be used in a diagnostic device to determine the presence and concentration of a specific analyte in a liquid medium. For example, the presence and concentration of glucose is determined by measuring the conductivity change in the polymer caused by the vibrational excitation induced in the enzyme, glucose oxidase, from its reaction with the glucose and/or by measuring a secondary effect of the enzyme/substrate reaction, such as the change in the conductivity of the conducting polymer caused by the generation of hydrogen peroxide during the glucose-glucose oxidase reaction.
Inventors
- 👤 James P. Albarella
- 👤 J. Oakey Noell
- 👤 Paul O. Vogelhut
- 👤 Frederick E. Ward
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 13:44
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08; C07D409/00; C07D409/02; C07D409/04; C07D409/14; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; C12; C12Q; C12Q1/00; C12Q1/001; C12Q1/002; C12Q1/54; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/53; G01N33/531; G01N33/532; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
75 words
A compound having the formula wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, an alkyl group, or a hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to an organic molecule.
Claim 2
Dependent Claim
75 words
A compound having the formula wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, an alkyl group, or a hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to an organic molecule.
Claim 3
Dependent Claim
24 words
The compound of claim 1, wherein B is N-R¹, and R¹ is selected from the group consisting of hydrogen, methyl, ethyl, hydroxymethyl and hydroxyethyl.
Claim 4
Dependent Claim
20 words
The compound of claim 1, wherein R includes an oxygen-containing, sulfur-containing, nitrogen-containing, phosphorous-containing, or silicon-containing moiety; or a combination thereof.
Claim 5
Dependent Claim
25 words
The compound of claim 3, wherein R includes an amino, cyano, sulfhydryl, disulfide, hydroxyl, halogen-substituted alkyl, carbonyl, silyl, or phosphate moiety; or a combination thereof.
Claim 6
Dependent Claim
13 words
The compound of claim 1, wherein R is aminomethyl, aminoethyl, N-trifluoroacetamidomethyl, or 2-trifluoroacetamidoethyl.
Claim 7
Dependent Claim
23 words
The compound of claim 1, wherein A and C are sulfur, and B is N-R¹, wherein N is nitrogen and R¹ is hydrogen.
Claim 8
Dependent Claim
104 words
An electrically-conducting polymer exhibiting sufficient conductivity and stability for use in an analyte sensor having a plurality of monomeric units (I) and/or monomeric units (II) wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, an alkyl group, or hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to a bridging molecule and/or an analyte probe molecule; and a compensating counterion D.
Claim 9
Dependent Claim
104 words
An electrically-conducting polymer exhibiting sufficient conductivity and stability for use in an analyte sensor having a plurality of monomeric units (I) and/or monomeric units (II) wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, an alkyl group, or hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to a bridging molecule and/or an analyte probe molecule; and a compensating counterion D.
Claim 10
Independent Claim
184 words
A method of preparing an electrically-conducting polymer suitable for determining the presence and/or concentration of an analyte in liquid media comprising reacting monomeric unit (I) and/or a monomeric unit (II), to form an electrically conducting polymer, wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, and alkyl group, or a hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to an analyte probe molecule and/or to a bridging molecule that is capable of covalently bonding to the analyte probe molecule; homogeneously incorporating a compensating counterion D into the polymer; and covalently bonding the analyte probe molecule to the polymer by covalently bonding the analyte probe molecule to the reactive R moiety of the polymer, or by covalently bonding the analyte probe molecule to the bridging molecule and by covalently bonding the bridging molecule to the reactive R moiety of the polymer.
Claim 11
Independent Claim
184 words
A method of preparing an electrically-conducting polymer suitable for determining the presence and/or concentration of an analyte in liquid media comprising reacting monomeric unit (I) and/or a monomeric unit (II), to form an electrically conducting polymer, wherein A is selected from the group consisting of sulfur, oxygen, selenium and tellurium; B is selected from the group consisting of sulfur, oxygen, selenium, tellurium and N-R¹, wherein N is nitrogen and R¹ is hydrogen, and alkyl group, or a hydroxyalkyl group; C is selected from the group consisting of sulfur, oxygen, selenium and tellurium; and R is a reactive moiety that can covalently bond to an analyte probe molecule and/or to a bridging molecule that is capable of covalently bonding to the analyte probe molecule; homogeneously incorporating a compensating counterion D into the polymer; and covalently bonding the analyte probe molecule to the polymer by covalently bonding the analyte probe molecule to the reactive R moiety of the polymer, or by covalently bonding the analyte probe molecule to the bridging molecule and by covalently bonding the bridging molecule to the reactive R moiety of the polymer.
Claim 12
Independent Claim
86 words
A method of determining the presence and/or concentration of an analyte in a liquid medium comprising contacting the liquid medium with an electrically-conducting compound having an analyte probe molecule covalently bound to a component of the electrically-conducting compound to interact the liquid medium with the electrically conducting compound thereby producing a detectable signal, and detecting and measuring the presence and/or concentration of the analyte in the liquid medium by transducing the interaction between the analyte and the analyte probe molecule into detectable and measurable electrical signals.
Claim 13
Independent Claim
86 words
A method of determining the presence and/or concentration of an analyte in a liquid medium comprising contacting the liquid medium with an electrically-conducting compound having an analyte probe molecule covalently bound to a component of the electrically-conducting compound to interact the liquid medium with the electrically conducting compound thereby producing a detectable signal, and detecting and measuring the presence and/or concentration of the analyte in the liquid medium by transducing the interaction between the analyte and the analyte probe molecule into detectable and measurable electrical signals.
Claim 14
Dependent Claim
74 words
A diagnostic device for assaying a liquid sample for an analyte comprising a transducer including an analyte probe molecule covalently bound to an electrically-conducting polymer comprising a heterocyclic aromatic compound; metal electrodes in either direct or indirect contact with the transducer for detecting changes in the conductivity of the transducer when the transducer is contacted with the liquid sample; and means connected to the electrodes for measuring changes in the conductivity of the transducer.
Claim 15
Dependent Claim
74 words
A diagnostic device for assaying a liquid sample for an analyte comprising a transducer including an analyte probe molecule covalently bound to an electrically-conducting polymer comprising a heterocyclic aromatic compound; metal electrodes in either direct or indirect contact with the transducer for detecting changes in the conductivity of the transducer when the transducer is contacted with the liquid sample; and means connected to the electrodes for measuring changes in the conductivity of the transducer.
References Cited (Backward Citations)
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