WO2001057241A2 - Membranes a diffusion limitee d'analysats deposes au moyen de monomeres hydrophiles photopolymerisables - Google Patents

Membranes a diffusion limitee d'analysats deposes au moyen de monomeres hydrophiles photopolymerisables Download PDF

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Publication number
WO2001057241A2
WO2001057241A2 PCT/US2001/003304 US0103304W WO0157241A2 WO 2001057241 A2 WO2001057241 A2 WO 2001057241A2 US 0103304 W US0103304 W US 0103304W WO 0157241 A2 WO0157241 A2 WO 0157241A2
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WO
WIPO (PCT)
Prior art keywords
layer
membrane system
water
analyte
diffusion
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Application number
PCT/US2001/003304
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English (en)
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WO2001057241A3 (fr
Inventor
Patrick Kelly
Jarad Schiffer
Original Assignee
Spectrx, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Spectrx, Inc. filed Critical Spectrx, Inc.
Priority to CA002398810A priority Critical patent/CA2398810A1/fr
Priority to BR0108042-3A priority patent/BR0108042A/pt
Priority to MXPA02007447A priority patent/MXPA02007447A/es
Priority to EP01908778A priority patent/EP1252509A2/fr
Priority to AU36612/01A priority patent/AU3661201A/en
Priority to JP2001555864A priority patent/JP2003521248A/ja
Publication of WO2001057241A2 publication Critical patent/WO2001057241A2/fr
Publication of WO2001057241A3 publication Critical patent/WO2001057241A3/fr

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Classifications

    • 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
    • C12Q1/002—Electrode membranes
    • 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

Definitions

  • the present invention relates in general to a diffusion-limiting hydrogel membrane system for use in analyte detection systems. More specifically, the present invention relates to cast analyte diffusion-limiting hydrogel membranes for filtering an analyte from fluids, comprising a water soluble photopolymerizable hydrophilic hydrogel monomer, capable of limiting the amount of analyte that will react with an analyte responsive enzyme and thus, further enabling a detection device to operate on a discrete basis or continually over an extended period of time.
  • the present invention provides a diffusion-limiting hydrogel membrane system for filtering analytes or other desired characteristics from a fluid.
  • the hydrogel membrane system can be employed in a detection device wherein the diffusion-limiting hydrogel membrane operates to regulate the amount of analyte that is present at the sensor electrodes at any given time, thus, allowing the sensor electrodes to operate on a discrete basis or continuously over longer periods of time without substantially depleting the amount of reactant present on the sensor electrodes.
  • Figure 1A illustrates a cross sectional view of an assay device containing one embodiment of a cast analyte diffusion limiting membrane according to the present invention.
  • Figure IB illustrates a front view of an assay device containing one embodiment of a cast analyte diffusion limiting membrane according to the present invention.
  • Figure 2 is a graph indicating the results of example 1.
  • Figure 3 is a graph indicating the results of example 2.
  • Ranges may be expressed herein as from “about” or “approximately” one particular value and/or to “about” or “approximately” another particular value. When such a range is expressed, another embodiment comprises from the one particular value and/or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent "about,” it will be understood that the particular value forms another embodiment.
  • analyte shall mean the component that is being filtered from a liquid or gas and/or detected and/or measured in a detection device.
  • the analyte can include without limitation, glucose, acetoacetate, ammonia, catecholamines, creatine, creatinine, fructose, galactose, ⁇ -hydroxybutyric acid, bilirubin, lactate, lactic acid, amino acids, urea, uric acid, salicylates, pH, magnesium, calcium, lithium, lead, potassium, sodium, chloride, iron, and any other electrolyte, vitamin, protein, nutrient, pharmaceutical compounds, or other such characteristic desired.
  • electrolyte means a chemical compound that ionizes when dissolved to produce an electrically conductive medium.
  • fluid means a liquid or a gas.
  • biological fluid means blood serum, whole blood, interstitial fluid, lymph fluid, spinal fluid, plasma or any combinations of these fluids. "Interstitial fluid” further refers to the clear fluid that occupies the space between the cells in the body.
  • biological membrane means the outer layer of an organism, such as skin or mucous membrane, the structure separating one area of an organism from another, such as a capillary wall, or the outer layer of an organism which separates the organism from its external environment, such as skin, buccal mucosa or other mucous membrane.
  • hydrogel means a polymeric material that can absorb 20% or more of its weight in water while simultaneously maintaining a distinct three- dimensional structure. More specifically, the hydrogels according to the present invention can be comprised of an aerogel that dries without significant collapse of the macroscopic structure and which absorbs water into macropores without substantial macroscopic swelling or, alternatively, xerogels which absorb water by swelling. It is further envisioned by the present invention that suitable hydrogels can include dry polymers that will swell in aqueous environments.
  • suitable hydrogels for use in the present invention include without limitation 2-hydroxyethyl methacrylate, N,N,-dimethacrylamide, N-vinylpyrrolidine, polyethyleneglycol dimethacrylate, and/or copolymers thereof.
  • the term "cast” means a method of forming a coating over an electrode area. Representative examples can include doctor blading, spraying, and/or dipping.
  • diffusion-limiting hydrogel membrane means a hydrogel that limits the flow of analytes from one space to another.
  • the term “detection device” means any assay device suitable for measuring a desired characteristic of a fluid on a continual or discrete basis.
  • An example of such device is that disclosed by International Patent Application No. PCT/US00/09393 which application is incorporated herein by this reference in its entirety.
  • the term “sensor electrode” means an electrode suitable for detecting the concentration of various ions in an aqueous and/or gaseous environment. Examples of suitable sensor electrodes according to the present invention include without limitation platinumized carbon ink or platinum metal held at a given electrical potential to cause the reduction of an analyte.
  • the present invention shows a cross-sectional view of a detection device 10 which operates on a continuous basis.
  • the device 10 contains an inlet port 40 to receive fluid and a chamber 50 in fluid communication with the inlet port 40, and an outlet port 60 in fluid communication with the chamber 50, where the outlet port 60 is designed to allow the discharge of fluid.
  • the chamber 50 further comprises a first working sensor electrode 12, a second working sensor electrode 14, a reference electrode 16 and a counter electrode 18.
  • a first layer of an analyte responsive enzyme 20, such as glucose oxidase, is applied to at least one of the working sensor electrodes 12 or 14.
  • a second layer comprising a composition comprising a diffusion-limiting hydrogel membrane 30 is applied to at least one of the working sensor electrodes 12 or 14, wherein the first layer is in direct contact with at least one sensor electrode and the second layer is in direct contact with the first layer.
  • the device 10 of the present invention may further comprise an external channel 70, wherein one end of the external channel 70 is in fluid communication with the inlet port 40 and the other end is in fluid communication with at least one liquid and/or gas.
  • the analyte responsive enzyme 20 and the composition comprising a diffusion-limiting hydrogel membrane are mixed together and applied to at least one of the working sensor electrodes 12 or 14 as a mono-layer membrane system.
  • Figure IB is a front view of the detection device 10 and is described the same as figure 1 A above.
  • the present invention provides a diffusion limiting membrane system for filtering an analyte from a liquid, comprising: a) a first layer comprising an analyte responsive enzyme; and b) a second layer comprising a water-soluble monomer composition, wherein the first layer is in direct contact with one or more sensor electrodes and the second layer is in direct contact with the first layer.
  • a diffusion-limiting hydrogel membrane system for filtering glucose from fluids comprising a glucose limiting membrane comprising a composition comprising a water soluble monomer, an enzyme, and an initiator, wherein the composition is disposed on one or more sensor electrodes and cured in the presence of sunlight or UV light.
  • the present invention further provides a diffusion-limiting hydrogel membrane system for filtering glucose from fluids comprising a composition comprising a water soluble monomer, a cross-linking agent, an enzyme, and an initiator, wherein the composition is disposed on one or more sensor electrodes and cured in the presence of sunlight or UV light.
  • the present invention further provides a diffusion-limiting hydrogel membrane system comprising: a) a first layer comprising an analyte responsive enzyme; and b) a second layer comprising a water-soluble monomer composition, wherein the first layer is in direct contact with one or more sensor electrodes and the second layer is in direct contact with the first layer.
  • the present invention provides a diffusion-limiting hydrogel membrane for filtering an analyte from a fluid, comprising: a) a first layer comprising an analyte responsive enzyme; and b) a second layer comprising a water-soluble monomer composition, wherein the first layer is in direct contact with one or more sensor electrodes and the second layer is in direct contact with the first layer.
  • Suitable analytes for use with the present invention include without limitation glucose, acetoacetate, ammonia, catecholamines, creatine, creatinine, fructose, galactose, ⁇ -hydroxybutyric acid, bilirubin, lactate, lactic acid, amino acids, urea, uric acid, salicylates, pH, magnesium, calcium, lithium, lead, potassium, sodium, chloride, iron, and any other electrolyte, vitamin, protein, nutrient, pharmaceutical compounds, or other such characteristic desired.
  • Suitable analyte responsive enzymes for use in the diffusion-limiting hydrogel membranes of the present invention will be dependent upon the desired use of the invention.
  • the glucose responsive enzyme is glucose oxidase, which is available from Sigma.
  • any appropriate enzyme recognized for use in detecting glucose could be employed.
  • the analyte responsive enzyme is dissolved in deionized water or phosphate buffered de-ionized water.
  • the phosphate buffer system acts to maintain the analyte responsive enzyme at a pH value within the range of normal physiological levels.
  • the analyte responsive enzyme can be dissolved in an amount of from about Img/mL to about lOOmg/mL.
  • the enzyme is dissolved in an amount of from about Img/mL to about 50mg/mL.
  • the enzyme can be dissolved in an amount of from about Img/mL to about lOmg/mL.
  • Suitable water soluble monomers for use in the present include 2-hydroxyethyl methacrylate, N,N,-dimethacrylamide, N-vinylpyrrolidine, polyethyleneglycol dimethacrylate, and/or copolymers thereof.
  • the water- soluble monomers for use in the inventive membranes are highly water permeable hydrogels, such as 2-hydroxyethyl methacrylate (HEMA).
  • HEMA 2-hydroxyethyl methacrylate
  • the water soluble monomer of the present invention is diluted in an aqueous medium.
  • the hydrogel monomers of the present invention can be diluted in the aqueous medium at a range of dilution from about 0.01% to about 50% by volume.
  • the range of dilution is from about 0.05% to about 10% by volume.
  • the range of dilution is from about 0.1% to about 5% by volume.
  • the water soluble monomer of the present invention can further comprise one or more initiators.
  • Any water soluble UV or thermal initiators known in the art can be used with the present invention.
  • suitable initiators for use in the invention include 2,2 dimethoxy-2- phenylacetophenone, Vazo 52®, available from DuPont, and Vazo 64®, also available from DuPont.
  • the initiator is introduced into the water soluble monomer in an amount of from about 1 to about 10% by weight. In another embodiment, the initiator is introduced into the water soluble monomer in an amount of from about 2 to about 5% by weight.
  • the water soluble monomer of the present invention can be cast or cured directly onto an electrode in the presence of sunlight or ultraviolet light without requiring the use of an adhesive or special processing to further protect an enzyme within the system.
  • the water soluble monomer composition further comprises water soluble cross-linking agents.
  • the cross-linking agent can participate in the polymerization of the water soluble monomer and thus facilitate the formation of the desired hydrogel membrane.
  • suitable cross- linking agents include without limitation polytheyleneglycol dimethacryalate and/or gluteraldehyde.
  • any water soluble free radical cross-linking agents can be used in the present invention.
  • the cross-linking agents can be introduced into the water soluble monomer in an amount of from about 1 to about 10% by volume.
  • the cross-linking agent can be introduced into the water soluble monomer in an amount of from about 2 to about 5% by volume.
  • the thickness of the membranes of the present invention is from about 2 to about 50 micrometers. In another embodiment, the thickness of the membrane is from about 2 to about 25 micrometers. In still a further embodiment, the thickness of the membrane is from about 2 to about 20 micrometers.
  • Example 1 relates to a bi-layer diffusion-limiting hydrogel membrane system for filtering glucose from biological fluids.
  • solution 1 was prepared, and consisted of 1000 ⁇ l of 2-hydroxyethyl methacrylate and 4% by weight of a UV initiator, 2,2 Dimethoxy-2-phenylacetophenone .
  • a detection device 10 such as the one shown in figure 1 A, a 0.5 ⁇ l drop of solution 2, comprised of 495 ⁇ l of a phosphate buffer system (PBS), lO ⁇ l of gluteraldehyde, 4 mg of Glucose Oxidase, and 30 mg of bovine serum albumin (BSA), was placed on at least one of the working sensor electrodes 12 or 14.
  • PBS phosphate buffer system
  • BSA bovine serum albumin
  • This drop was allowed to dry for 12hrs after which a l ⁇ l drop of solution 3, which contained 495 ⁇ l of PBS and lO ⁇ l of solution 1, was placed on top of the drop on the at least one working sensor electrode 12 or 14.
  • This second drop was exposed to long wave U V radiation for 0.5 hrs, wherein the radiation value was approximately 415nm tc approximately 430nm.
  • the cured hydrogel membrane was then placed in a solution of de-ionized water and PBS and tested against a series of glucose levels as seen in figure 2.
  • the results for this bi-layer hydrogel membrane system are set forth in said figure 2, wherein it illustrates that the bi-layer diffusion limiting hydrogel membrane system of example 1 was suitable for accurately detecting glucose levels at concentrations of up to approximately 25 to 30mM.
  • Example 2 relates to a single layer diffusion-limiting hydrogel membrane system for filtering glucose from biological fluids.
  • solution 1 was prepared, and consisted of 1000 ⁇ l of 2-hydroxyethyl methacrylate and 4% by weight of 2,2 Dimethoxy-2-phenylacetophenone.
  • a detection device 10 such as the one shown in figure 1A
  • a 0.5 ⁇ l drop of solution 2 which contained 495 ⁇ l of PBS, 4 mg of Glucose Oxidase, and 10 ⁇ l of solution 1
  • This 0.5 ⁇ l drop was exposed to long wave UV radiation for 0.5 hrs, wherein the radiation value was approximately 415nm to approximately 430nm.

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  • Chemical & Material Sciences (AREA)
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  • Organic Chemistry (AREA)
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  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Apparatus Associated With Microorganisms And Enzymes (AREA)
  • Measurement Of The Respiration, Hearing Ability, Form, And Blood Characteristics Of Living Organisms (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)

Abstract

La présente invention concerne un système membranaire à diffusion limitée destiné à filtrer un analysat présent dans un fluide et comprenant : a) une première couche constitué par un enzyme réagissant à l'analysat; et b) une seconde couche renfermant une composition monomère hydrosoluble. La première couche est en contact directe avec une ou plusieurs électrodes de détection cependant que la seconde couche est en contact direct avec la première couche.
PCT/US2001/003304 2000-02-01 2001-02-01 Membranes a diffusion limitee d'analysats deposes au moyen de monomeres hydrophiles photopolymerisables WO2001057241A2 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
CA002398810A CA2398810A1 (fr) 2000-02-01 2001-02-01 Membranes a diffusion limitee d'analysats deposes au moyen de monomeres hydrophiles photopolymerisables
BR0108042-3A BR0108042A (pt) 2000-02-01 2001-02-01 Membranas de limitação de difusão de analito fundido usando monÈmeros hidrófilos fotopolimerizáveis
MXPA02007447A MXPA02007447A (es) 2000-02-01 2001-02-01 Membranas moldeadas que limitan la difusion de analitos que usan monomeros hidrofilicos fotopolimerizables.
EP01908778A EP1252509A2 (fr) 2000-02-01 2001-02-01 Membranes a diffusion limitee d'analysats deposes au moyen de monomeres hydrophiles photopolymerisables
AU36612/01A AU3661201A (en) 2000-02-01 2001-02-01 Cast analyte diffusion-limiting membranes using photopolymerizable hydrophylic monomers
JP2001555864A JP2003521248A (ja) 2000-02-01 2001-02-01 光重合可能な親水性モノマーを用いたキャストによる分析物拡散制限膜

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US17971600P 2000-02-01 2000-02-01
US60/179,716 2000-02-01

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WO2001057241A3 WO2001057241A3 (fr) 2002-04-25

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AU (1) AU3661201A (fr)
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CA (1) CA2398810A1 (fr)
MX (1) MXPA02007447A (fr)
WO (1) WO2001057241A2 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1466156A2 (fr) * 2001-05-15 2004-10-13 Therasense, Inc. Membranes de biocapteurs composees de polymeres contenant des groupements d'azote heterocyclique
EP2135064A1 (fr) * 2007-03-21 2009-12-23 Universiti Putra Malaysia Biodétecteur ampérométrique pour la détermination de l'histamine
WO2015081197A1 (fr) * 2013-11-27 2015-06-04 Google Inc. Ajustement de la sensibilité d'un détecteur par la régulation de l'épaisseur d'un film copolymère via une étape de séchage régulée
WO2015084572A1 (fr) * 2013-12-06 2015-06-11 Google Inc. Procédé de stockage et de formulation pour améliorer les stabilités d'enzymes et de détecteurs
US9549697B2 (en) 2004-10-28 2017-01-24 Ascensia Diabetes Care Holdings Ag Hydrogel composition

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Publication number Priority date Publication date Assignee Title
JP5502279B2 (ja) * 2004-10-28 2014-05-28 エコー セラピューティクス， インコーポレイテッド ヒドロゲルを使用した検体のサンプリングおよび分析のためのシステムおよび方法
US9828620B2 (en) * 2013-06-28 2017-11-28 Verily Life Sciences Llc Porous polymeric formulation prepared using monomer
US20220373500A1 (en) 2019-12-11 2022-11-24 Siemens Healthcare Diagnostics Inc. Photocurable reagent(s) for forming chloride ion-selective sensor(s) and methods of production and use thereof

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US5228972A (en) * 1988-05-27 1993-07-20 Daikin Industries, Ltd. Apparatus for measuring concentration of test substance in liquid
DE4426694A1 (de) * 1994-07-28 1996-02-08 Eppendorf Geraetebau Netheler Verfahren und Vorrichtung zur Langzeitbestimmung des Gehaltes von mindestens einer Substanz in Körperflüssigkeiten
WO1998020332A1 (fr) * 1996-11-07 1998-05-14 Sensalyse Holdings Limited Biocapteur contenant un tensioactif

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Cited By (25)

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US9014774B2 (en) 2001-05-15 2015-04-21 Abbott Diabetes Care Inc. Biosensor membranes
US9414778B2 (en) 2001-05-15 2016-08-16 Abbott Diabetes Care Inc. Biosensor membranes
EP1466156A2 (fr) * 2001-05-15 2004-10-13 Therasense, Inc. Membranes de biocapteurs composees de polymeres contenant des groupements d'azote heterocyclique
EP1927602A1 (fr) 2001-05-15 2008-06-04 Abbott Diabetes Care, Inc. Membranes de biocapteur composées de polymères contenant de l'azote hétérocyclique
EP1466156A4 (fr) * 2001-05-15 2006-03-01 Therasense Inc Membranes de biocapteurs composees de polymeres contenant des groupements d'azote heterocyclique
US7670470B2 (en) 2001-05-15 2010-03-02 Abbott Diabetes Care Inc. Biosensor membranes composed of polymers containing heterocyclic nitrogens
EP2292671A1 (fr) 2001-05-15 2011-03-09 Abbott Diabetes Care Inc. Membranes composées de polymères contenant des azotes hétérocycliques.
US9713443B2 (en) 2001-05-15 2017-07-25 Abbott Diabetes Care Inc. Biosensor membranes
US8377271B2 (en) 2001-05-15 2013-02-19 Abbott Diabetes Care Inc. Biosensor membranes composed of polymers containing heterocyclic nitrogens
US8380274B2 (en) 2001-05-15 2013-02-19 Abbott Diabetes Care Inc. Biosensor membranes composed of polymers containing heterocyclic nitrogens
US8437829B2 (en) 2001-05-15 2013-05-07 Abbott Diabetes Care Inc. Biosensor membranes
US9232916B2 (en) 2001-05-15 2016-01-12 Abbott Diabetes Care Inc. Analyte monitoring devices
AU2002367855B2 (en) * 2001-05-15 2006-11-09 Therasense, Inc. Biosensor membranes composed of polymers containing heterocyclic nitrogens
US8147666B2 (en) 2001-05-15 2012-04-03 Abbott Diabetes Care Inc. Biosensor membranes composed of polymers containing heterocyclic nitrogens
US10647846B2 (en) 2004-10-28 2020-05-12 Ascensia Diabetes Care Holdings Ag Electrochemical sensor system
US9549697B2 (en) 2004-10-28 2017-01-24 Ascensia Diabetes Care Holdings Ag Hydrogel composition
US10655004B2 (en) 2004-10-28 2020-05-19 Ascensia Diabetes Care Holdings Ag Electrochemical sensor system
US10988610B2 (en) 2004-10-28 2021-04-27 Ascensia Diabetes Care Holdings Ag Electrochemical sensor system
US10196512B2 (en) 2004-10-28 2019-02-05 Ascensia Diabetes Care Holdings Ag Method of determining an analyte concentration
US10227485B2 (en) 2004-10-28 2019-03-12 Ascensia Diabetics Care Holdings AG Electrochemical sensor system
EP2135064A1 (fr) * 2007-03-21 2009-12-23 Universiti Putra Malaysia Biodétecteur ampérométrique pour la détermination de l'histamine
EP2135064A4 (fr) * 2007-03-21 2014-09-10 Univ Putra Malaysia Biodétecteur ampérométrique pour la détermination de l'histamine
US9763605B2 (en) 2013-11-27 2017-09-19 Verily Life Sciences Llc Adjustment of sensor sensitivity by controlling copolymer film thickness through a controlled drying step
WO2015081197A1 (fr) * 2013-11-27 2015-06-04 Google Inc. Ajustement de la sensibilité d'un détecteur par la régulation de l'épaisseur d'un film copolymère via une étape de séchage régulée
WO2015084572A1 (fr) * 2013-12-06 2015-06-11 Google Inc. Procédé de stockage et de formulation pour améliorer les stabilités d'enzymes et de détecteurs

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AU3661201A (en) 2001-08-14
MXPA02007447A (es) 2004-08-23
EP1252509A2 (fr) 2002-10-30
BR0108042A (pt) 2002-10-29
WO2001057241A3 (fr) 2002-04-25
JP2003521248A (ja) 2003-07-15
CA2398810A1 (fr) 2001-08-09

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