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
Application number
PCT/US2001/010541
Other languages
French (fr)
Other versions
WO2001074968A2 (en
WO2001074968A8 (en
Inventor
Joe H Satcher Jr
Stephen M Lane
Christopher B Darrow
Douglas R Cary
Joe Anh Tran
Original Assignee
Univ California
Medtronic Minimed 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
Priority claimed from US09/663,567 external-priority patent/US6682938B1/en
Application filed by Univ California, Medtronic Minimed Inc filed Critical Univ California
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

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 System
    • 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

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 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 US6682938B1 (en) 1999-09-15 2000-09-15 Glucose sensing molecules having selected fluorescent properties
US09/663,567 2000-09-15

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 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
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
US6653141B2 (en) 2000-12-05 2003-11-25 The Regents Of The University Of California Polyhydroxyl-substituted organic molecule sensing method and device
US7470420B2 (en) 2000-12-05 2008-12-30 The Regents Of The University Of California Optical determination of glucose utilizing boronic acid adducts
ATE520661T1 (en) 2003-06-27 2011-09-15 Univ Maryland HETEROCYCLIC COMPOUNDS WITH QUATERNARY NITROGEN FOR THE DETECTION OF AQUEOUS MONOSACHARIDES IN PHYSIOLOGICAL LIQUIDS
WO2009105709A1 (en) 2008-02-21 2009-08-27 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
AU2001251210A1 (en) 2001-10-15
WO2001074968A2 (en) 2001-10-11
WO2001074968A8 (en) 2001-12-20

Similar Documents

Publication Publication Date Title
Ma et al. Dual-emissive nanoarchitecture of lanthanide-complex-modified silica particles for in vivo ratiometric time-gated luminescence imaging of hypochlorous acid
Park et al. A ratiometric fluorescent probe based on a BODIPY–DCDHF conjugate for the detection of hypochlorous acid in living cells
WO2000016810A8 (en) Near infrared fluorescent contrast agent and fluorescence imaging
Mishra et al. Fluorescence spectroscopic studies on binding of a flavonoid antioxidant quercetin to serum albumins
EP1671118B1 (en) Cyanide sensing compounds and uses thereof
CA2394539A1 (en) Near infrared fluorescent contrast agent and fluorescence imaging
WO2001020334A1 (en) Glucose sensing molecules having selected fluorescent properties
US5308581A (en) Substance of an optical fluorescence measuring arrangement for measuring the pH of a sample and optical sensor with such an indicator substance
Meier et al. A FRET based pH probe with a broad working range applicable to referenced ratiometric dual wavelength and luminescence lifetime read out
WO2009146157A2 (en) Methods of generating florescence resonance energy transfer (fret) between semiconductor quantum dots and fluorescent dyes/proteins via multi-photon excitation, achieving zero background or direct excitation contributions to the fret signature
Ma et al. Insight into fluorescence imaging and bioorthogonal reactions in biological analysis
WO2001074968A3 (en) Saccharide sensing molecules having enhanced fluorescent properties
Harvey et al. Ratiometric detection of enzyme turnover and flavin reduction using rare-earth upconverting phosphors
Gonzàlez-Rosell et al. DNA Stabilizes Eight-Electron Superatom Silver Nanoclusters with Broadband Downconversion and Microsecond-Lived Luminescence
Strömberg et al. A fluorescence ratiometric detection scheme for ammonium ions based on the solvent sensitive dye MC 540
US7378282B2 (en) Method for measuring hypochlorite ion
Vázquez et al. dsDNA-triggered energy transfer and lanthanide sensitization processes. Luminescent probing of specific A/T sequences
WO2000042418A1 (en) Method and material for ratiometric fluorescent determination of analyte concentration
Rim Kim et al. A Two‐Photon Ratiometric Sensing Platform Based on Solid‐State Luminescent Benzocoumarin: Application to Prolonged Bioimaging of Hydrogen Peroxide
US8759381B1 (en) Two-photon absorbing water soluble fluorescent probe as a near-neutral pH indicator
Boltersdorf et al. Long-lived lanthanide emission via a pH-sensitive and switchable LRET complex
EP0705897B1 (en) Luminescent dyes, active elements on their basis and method for measuring oxygen concentration using said luminescent dyes
Lakowicz et al. Polarization-based sensing of glucose using an oriented reference film
Parker et al. Luminescent lanthanide complexes as sensors and imaging probes
Van Antwerp et al. Detection of biological molecules using chemical amplification and optical sensors

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
AK Designated states

Kind code of ref document: C1

Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: C1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

CFP Corrected version of a pamphlet front page
CR1 Correction of entry in section i
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
AK Designated states

Kind code of ref document: A3

Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A3

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP