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WO2001074968A3 - Saccharide sensing molecules having enhanced fluorescent properties - Google Patents

Saccharide sensing molecules having enhanced fluorescent properties Download PDF

Info

Publication number
WO2001074968A3
WO2001074968A3 PCT/US2001/010541 US0110541W WO0174968A3 WO 2001074968 A3 WO2001074968 A3 WO 2001074968A3 US 0110541 W US0110541 W US 0110541W WO 0174968 A3 WO0174968 A3 WO 0174968A3
Authority
WO
WIPO (PCT)
Prior art keywords
fluorescent
advantageous
wavelengths
compounds
oxazine
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/US2001/010541
Other languages
French (fr)
Other versions
WO2001074968A8 (en
WO2001074968A2 (en
Inventor
Joe H Satcher Jr
Stephen M Lane
Christopher B Darrow
Douglas R Cary
Joe Anh Tran
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Medtronic Minimed Inc
University of California Berkeley
University of California San Diego UCSD
Original Assignee
Medtronic Minimed Inc
University of California Berkeley
University of California San Diego UCSD
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
Priority claimed from US09/663,567 external-priority patent/US6682938B1/en
Application filed by Medtronic Minimed Inc, University of California Berkeley, University of California San Diego UCSD filed Critical Medtronic Minimed Inc
Priority to AU2001251210A priority Critical patent/AU2001251210A1/en
Publication of WO2001074968A2 publication Critical patent/WO2001074968A2/en
Publication of WO2001074968A8 publication Critical patent/WO2001074968A8/en
Publication of WO2001074968A3 publication Critical patent/WO2001074968A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • C09B19/00—Oxazine dyes
    • 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
    • C09B57/08—Naphthalimide dyes; Phthalimide dyes
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)

Abstract

The present invention provides formulae for fluorescent compounds that have a number of properties which make them uniquely suited for use in sensors of analytes such as saccharides. The advantageous fluorescent properties include favorable excitation wavelengths, emission wavelengths, fluorescence lifetimes, and photostability. Additional advantageous properties include enhanced aqueous solubility, as well as temperature and pH sensitivity. The compound comprises an aryl or a substituted phenyl boronic acid that acts as a substrate recognition component, a fluorescent switch component, and a fluorophore. Fluorescent compounds are described that are excited at wavelengths greater than 400 nm and emit at wavelengths greater than 450 nm, which is advantageous for optical transmission through skin. The fluorophore is typically selected from transition metal-ligand complexes and thiazone, oxazine, oxazone, or oxazine-one as well as anthracene compounds. The fluorescent compound can be immobilized in a glucose permeable biocompatible polymer matrix that is implantable below the skin.
PCT/US2001/010541 2000-04-04 2001-03-30 Saccharide sensing molecules having enhanced fluorescent properties Ceased WO2001074968A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001251210A AU2001251210A1 (en) 2000-04-04 2001-03-30 Saccharide sensing molecules having enhanced fluorescent properties

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US19467300P 2000-04-04 2000-04-04
US60/194,673 2000-04-04
US09/663,567 2000-09-15
US09/663,567 US6682938B1 (en) 1999-09-15 2000-09-15 Glucose sensing molecules having selected fluorescent properties

Publications (3)

Publication Number Publication Date
WO2001074968A2 WO2001074968A2 (en) 2001-10-11
WO2001074968A8 WO2001074968A8 (en) 2001-12-20
WO2001074968A3 true WO2001074968A3 (en) 2002-03-28

Family

ID=26890277

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/010541 Ceased WO2001074968A2 (en) 2000-04-04 2001-03-30 Saccharide sensing molecules having enhanced fluorescent properties

Country Status (2)

Country Link
AU (1) AU2001251210A1 (en)
WO (1) WO2001074968A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6465644B1 (en) 2000-05-02 2002-10-15 Applera Corporation Sulfonated [8,9] benzophenoxazine dyes and the use of their labelled conjugates
US6653141B2 (en) 2000-12-05 2003-11-25 The Regents Of The University Of California Polyhydroxyl-substituted organic molecule sensing method and device
US6627177B2 (en) 2000-12-05 2003-09-30 The Regents Of The University Of California Polyhydroxyl-substituted organic molecule sensing optical in vivo method utilizing a boronic acid adduct and the device thereof
US7470420B2 (en) 2000-12-05 2008-12-30 The Regents Of The University Of California Optical determination of glucose utilizing boronic acid adducts
WO2005000109A2 (en) 2003-06-27 2005-01-06 University Of Maryland Biotechnology Institute Quaternary nitrogen heterocyclic compounds for detecting aqueous monosaccharides in physiological fluids
US9143569B2 (en) 2008-02-21 2015-09-22 Dexcom, Inc. Systems and methods for processing, transmitting and displaying sensor data

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2253794A1 (en) * 1973-12-06 1975-07-04 Hoechst Ag
WO1991018912A1 (en) * 1990-06-01 1991-12-12 Univ Texas Derivatization and identification of saccharides
US5235045A (en) * 1992-03-19 1993-08-10 Microbiomed Corporation Non-azo naphthalimide dyes
US5308773A (en) * 1992-11-16 1994-05-03 Microbiomed Corp. Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium
US5503770A (en) * 1993-11-07 1996-04-02 Research Development Corporation Of Japan Fluorescent compound suitable for use in the detection of saccharides
EP0729962A1 (en) * 1995-03-03 1996-09-04 Research Development Corporation Of Japan A boronic acid compound having a binaphthyl group
WO1997029154A1 (en) * 1996-02-05 1997-08-14 Amersham Pharmacia Biotech Uk Limited Benzophenoxazine dyes
US6002954A (en) * 1995-11-22 1999-12-14 The Regents Of The University Of California Detection of biological molecules using boronate-based chemical amplification and optical sensors

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2253794A1 (en) * 1973-12-06 1975-07-04 Hoechst Ag
WO1991018912A1 (en) * 1990-06-01 1991-12-12 Univ Texas Derivatization and identification of saccharides
US5235045A (en) * 1992-03-19 1993-08-10 Microbiomed Corporation Non-azo naphthalimide dyes
US5308773A (en) * 1992-11-16 1994-05-03 Microbiomed Corp. Non-azo 1,8-naphthalimide dyes for the detection and quantitation of a paramagnetic metal cation in a non-aqueous medium
US5503770A (en) * 1993-11-07 1996-04-02 Research Development Corporation Of Japan Fluorescent compound suitable for use in the detection of saccharides
EP0729962A1 (en) * 1995-03-03 1996-09-04 Research Development Corporation Of Japan A boronic acid compound having a binaphthyl group
US5763238A (en) * 1995-03-03 1998-06-09 Research Development Corporation Of Japan Boronic acid compound having a binaphthyl group
US6002954A (en) * 1995-11-22 1999-12-14 The Regents Of The University Of California Detection of biological molecules using boronate-based chemical amplification and optical sensors
WO1997029154A1 (en) * 1996-02-05 1997-08-14 Amersham Pharmacia Biotech Uk Limited Benzophenoxazine dyes

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
OKAFOR C O: "Synthesis, Properties and Uses of Angular Phenoxazines", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, GB, vol. 7, no. 2, 1986, pages 103 - 131, XP002122264, ISSN: 0143-7208 *
XUHONG Q ET AL: "THE SYNTHESIS, APPLICATION AND PREDICTION OF STOKES SHIFT IN FLUORESCENT DYES DERIVED FROM 1,8-NAPHTHALIC ANHYDRIDE", DYES AND PIGMENTS, ELSEVIER APPLIED SCIENCE PUBLISHERS. BARKING, GB, vol. 11, no. 1, 1989, pages 13 - 20, XP000026521, ISSN: 0143-7208 *

Also Published As

Publication number Publication date
WO2001074968A8 (en) 2001-12-20
AU2001251210A1 (en) 2001-10-15
WO2001074968A2 (en) 2001-10-11

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