Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides

Raymond, Kenneth N.; Xu, Jide; Moore, Evan G.; Werner, Eric J.

Title: Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides

Abstract

The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.

Inventors:: Raymond, Kenneth N.; Xu, Jide; Moore, Evan G.; Werner, Eric J.

Issue Date:: 2017-01-31

Research Org.:: Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1342102

Patent Number(s):: 9556122

Application Number:: 14/048,475

Assignee:: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE

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C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D213/89 - with hetero atoms directly attached to the ring nitrogen atom
C07D217/26 - Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C09K11/06 - containing organic luminescent materials
C09K2211/1022 - bridged by heteroatoms, e.g. N, P, Si or B
C09K2211/1029 - containing one nitrogen atom as the heteroatom
C09K2211/1044 - containing two nitrogen atoms as heteroatoms
C09K2211/1088 - containing oxygen as the only heteroatom
C09K2211/185 - of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

H - ELECTRICITY H05 - ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR H05B - ELECTRIC HEATING
H05B33/14 - characterised by the chemical or physical composition or the arrangement of the electroluminescent material {, or by the simultaneous addition of the electroluminescent material in or onto the light source}

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DOE Contract Number:: AC03-76SF00098

Resource Type:: Patent

Resource Relation:: Patent File Date: 2013 Oct 08

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

Citation Formats


                    Raymond, Kenneth N., Xu, Jide, Moore, Evan G., and Werner, Eric J. Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides.  United States: N. p., 2017. 
        Web.

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                    Raymond, Kenneth N., Xu, Jide, Moore, Evan G., & Werner, Eric J. Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides.  United States.

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                    Raymond, Kenneth N., Xu, Jide, Moore, Evan G., and Werner, Eric J. Tue .  
        "Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides".  United States.  https://www.osti.gov/servlets/purl/1342102.

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@article{osti_1342102,

  title        = {Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides},

  author       = {Raymond, Kenneth N. and Xu, Jide and Moore, Evan G. and Werner, Eric J.},

  abstractNote = {The present invention provides luminescent complexes between a lanthanide ion and an organic ligand which contains 1,2-hydroxypyridinone units. The complexes of the invention are stable in aqueous solutions and are useful as molecular probes, for example in medical diagnostics and bioanalytical assay systems. The invention also provides methods of using the complexes of the invention.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2017},

  month        = {1}

}

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Title: Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides

Abstract

Citation Formats

2,3-Dihydroxybenzoic acid amides of tetraazaalkanes and tetaaza cycloalkanes patent, January 1980

In vitro removal of actinide (IV) ions patent, January 1982

Polycatecholamide chelating agents patent, April 1984

Process for preparing 2,3-dihydroxybenzoic acid amides of tetraazaalkanes and cycloalkanes patent, September 1985

Pharmaceutical compositions of hydroxypyridones patent, May 1987

Hydroxypyridonate chelating agents patent, October 1987

Aryl substituted aminomethyl benzene derivatives having antiarrhythmic utility patent, May 1988

Method of detecting electrophoretically separated oligonucleotides patent, August 1989

Analyte detection by means of energy transfer patent, September 1989

Template synthesis of macrocyclic catecholamide complexes patent, July 1990

Method of detecting a substance using enzymatically-induced decomposition of dioxetanes patent, December 1990

Imaging agents for in vivo magnetic resonance and scintigraphic imaging patent, April 1991

Alkynylamino-nucleotides patent, September 1991

2,3-dihydroxyterephthalamides as highly effective metal ion sequestering compounds patent, September 1991

Enzyme activity determinations method characterized by the using of substrates whose fluorescent properties differs those of the converted products patent, October 1993

Macrocyclic congugates and their use as diagnostic and therapeutic agents patent, July 1995

Storage-stable solutions of accelerator systems patent, November 1995

Antibodies to the HRPII protein of plasmodium falciparum patent, December 1995

Detection and therapy of lesions with biotin/avidin polymer conjugates patent, January 1996

New multifunctional ligands for potential use in the design therapeutic or diagnostic radiopharmaceutical imaging agents patent, February 1997

3-hydroxy-2(1H)-pyridinone chelating agents patent, April 1997

Cascade polymer complexes, process for their production and pharamceutical agents containing said complexes patent, October 1998

3-hydroxy-2(1H)-pyridinone chelating agents patent, April 1999

Homogeneous detection of a target through nucleic acid ligand-ligand beacon interaction patent, November 1999

Homogeneous luminescence assay method based on energy transfer patent, December 1999

Polymeric membranes functionalized with polyhydroxypyridinone ligands patent, April 2001

Salicylamide-lanthanide complexes for use as luminescent markers patent, June 2002

Phthalamide lanthanide complexes for use as luminescent markers patent, February 2003

Hydroxypyridonate and hydroxypyrimidinone chelating agents patent, January 2005

Phthalamide-lanthanide complexes for use as luminescent markers patent, March 2005

Salicylamide-lanthanide complexes for use as luminescent markers patent, March 2006

Salicylamide-lanthanide complexes for use as luminescent markers patent, July 2008

Phthalamide-lanthanide complexes for use as luminescent markers patent, October 2008

Hydroxypyridonate and hydroxypyrimidinone chelating agents patent, May 2010

Radionuclides for medical use patent, September 2010

Luminescent macrocyclic lanthanide complexes patent, May 2012

Multi-color time resolved fluorophores based on macrocyclic lanthanide complexes patent, August 2013

Aromatic triamide-lanthanide complexes patent, October 2013

Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides patent, October 2013

Luminescent macrocyclic lanthanide complexes patent, May 2014

Phthalamide-lanthanide complexes for use as luminescent markers patent-application, September 2002

Phthalamide lanthanide complexes for use as luminescent markers patent-application, December 2002

Macrocyclic module compositions patent-application, October 2003

Hydroxypyridonate and hydroxypyrimidinone chelating agents patent-application, January 2005

Phthalamide-lanthanide complexes for use as luminescent markers patent-application, March 2005

Reagent system and method for modifying the luminescence of lanthanide(III) macrocyclic complexes patent-application, June 2007

Multi-Color Time Resolved Fluorophores Based on Macrocyclic Lanthanide Complexes patent-application, September 2008

Luminescent Macrocyclic Lanthanide Complexes patent-application, September 2008

Phthalamide-Lanthanide Complexes for Use as Luminescent Markers patent-application, January 2009

Aromatic Triamide-Lanthanide Complexes patent-application, February 2009

Luminescent 1-Hydroxy-2-Pyridinone Chelates of Lanthanides patent-application, January 2010

Rapid Homogeneous Diagnostic Testing Platform Based on Lanthanide Fluorescent Resonance Energy Transfer patent-application, June 2010

Multi-color Time Resolved Fluorophores Based on Macrocyclic Lanthanide Complexes patent-application, July 2010

Radiopharmaceutical Complexes patent-application, August 2011

Combination Treatment of Hydroxpyridonate Actinide/Lanthanide Decorporation Agents patent-application, August 2012

Determination of the Prototropic Exchange Rate at the Water Molecule Coordinated to an Anionic Paramagnetic GdIII Chelate journal, September 1998

Nouvelle méthode de synthèse du 3,4,3 LI 1,2 HOPO (1,5,10,14-tétra (1-hydroxy-2-pyridone-6 oyl) 1,5,10,14 tétraazatétradécane) [A new synthesis of 3,4,3 LI 1,2 HOPO] journal, April 1998

Synthesis and relaxometry of high-generation (G = 5, 7, 9, and 10) PAMAM dendrimer-DOTA-gadolinium chelates journal, February 1999

Study of metal complexes of a tripodal hydroxypyridinone ligand by electrospray tandem mass spectrometry journal, June 2005

Synthesis of 3,4,3 LI 1,2 HOPO labelled with 14C: Synthesis of 3,4,3 journal, February 2001

New compounds of tetradentate Schiff bases with vanadium(IV) and vanadium(V) † journal, January 1999

Syntheses and Relaxation Properties of Mixed Gadolinium Hydroxypyridinonate MRI Contrast Agents journal, December 2000

Detection of biotinylated DNA probes by using Eu-labeled streptavidin and time-resolved fluorometry journal, July 1987

Detection of pulmonary emboli by using MR angiography with MPEG-PL-GdDTPA: an experimental study in rabbits. journal, May 1994

Synthesis of Homochiral Tris(2-alkyl-2-aminoethyl)amine Derivatives from Chiral α-Amino Aldehydes and Their Application in the Synthesis of Water Soluble Chelators journal, June 2001

Synthesis of a Ligand Based upon a New Entry into the 3-Hydroxy-N-alkyl-2(1H)-pyridinone Ring System and Thermodynamic Evaluation of Its Gadolinium Complex journal, June 2000

Tris(pyrone) Chelates of Gd(III) as High Solubility MRI-CA journal, February 2006

Next Generation, High Relaxivity Gadolinium MRI Agents† journal, December 2004

Oxygen‐17 NMR and EPR studies of water exchange from the first coordination sphere of gadolinium(III) aquoion and gadolinium(III) propylenediaminetetra‐acetate journal, December 1980

Rational reduction of the conformational space of a siderophore analog through nonbonded interactions: the role of entropy in enterobactin journal, July 1993

A solid-state study of eight-coordinate lanthanide(iii) complexes (Ln = Eu, Gd, Tb, Dy) with 1-hydroxy-2-pyridinone journal, March 2003

Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands journal, February 1993

Gadolinium-containing copolymeric chelates—a new potential MR contrast agent journal, August 1999

Force Field Parametrization for Gadolinium Complexes Based on ab Initio Potential Energy Surface Calculations journal, April 2000

Highly Soluble Tris-hydroxypyridonate Gd(III) Complexes with Increased Hydration Number, Fast Water Exchange, Slow Electronic Relaxation, and High Relaxivity1 journal, February 2007

Specific sequestering agents for the actinides. 16. Synthesis and initial biological testing of polydentate oxohydroxypyridinecarboxylate ligands journal, January 1988

Gadolinium complex of tris[(3-hydroxy-1-methyl- 2-oxo-1,2-didehydropyridine-4-carboxamido)ethyl]-amine: A New Class of gadolinium magnetic resonance relaxation agents journal, July 1995

2,3-Dihydroxybenzoic acid amides of tetraazaalkanes and tetaaza cycloalkanes
patent, January 1980

In vitro removal of actinide (IV) ions
patent, January 1982

Polycatecholamide chelating agents
patent, April 1984

Process for preparing 2,3-dihydroxybenzoic acid amides of tetraazaalkanes and cycloalkanes
patent, September 1985

Pharmaceutical compositions of hydroxypyridones
patent, May 1987

Hydroxypyridonate chelating agents
patent, October 1987

Aryl substituted aminomethyl benzene derivatives having antiarrhythmic utility
patent, May 1988

Method of detecting electrophoretically separated oligonucleotides
patent, August 1989

Analyte detection by means of energy transfer
patent, September 1989

Template synthesis of macrocyclic catecholamide complexes
patent, July 1990

Method of detecting a substance using enzymatically-induced decomposition of dioxetanes
patent, December 1990

Imaging agents for in vivo magnetic resonance and scintigraphic imaging
patent, April 1991

Alkynylamino-nucleotides
patent, September 1991

2,3-dihydroxyterephthalamides as highly effective metal ion sequestering compounds
patent, September 1991

Enzyme activity determinations method characterized by the using of substrates whose fluorescent properties differs those of the converted products
patent, October 1993

Macrocyclic congugates and their use as diagnostic and therapeutic agents
patent, July 1995

Storage-stable solutions of accelerator systems
patent, November 1995

Antibodies to the HRPII protein of plasmodium falciparum
patent, December 1995

Detection and therapy of lesions with biotin/avidin polymer conjugates
patent, January 1996

New multifunctional ligands for potential use in the design therapeutic or diagnostic radiopharmaceutical imaging agents
patent, February 1997

3-hydroxy-2(1H)-pyridinone chelating agents
patent, April 1997

Cascade polymer complexes, process for their production and pharamceutical agents containing said complexes
patent, October 1998

3-hydroxy-2(1H)-pyridinone chelating agents
patent, April 1999

Homogeneous detection of a target through nucleic acid ligand-ligand beacon interaction
patent, November 1999

Homogeneous luminescence assay method based on energy transfer
patent, December 1999

Polymeric membranes functionalized with polyhydroxypyridinone ligands
patent, April 2001

Salicylamide-lanthanide complexes for use as luminescent markers
patent, June 2002

Phthalamide lanthanide complexes for use as luminescent markers
patent, February 2003

Hydroxypyridonate and hydroxypyrimidinone chelating agents
patent, January 2005

Phthalamide-lanthanide complexes for use as luminescent markers
patent, March 2005

Salicylamide-lanthanide complexes for use as luminescent markers
patent, March 2006

Salicylamide-lanthanide complexes for use as luminescent markers
patent, July 2008

Phthalamide-lanthanide complexes for use as luminescent markers
patent, October 2008

Hydroxypyridonate and hydroxypyrimidinone chelating agents
patent, May 2010

Radionuclides for medical use
patent, September 2010

Luminescent macrocyclic lanthanide complexes
patent, May 2012

Multi-color time resolved fluorophores based on macrocyclic lanthanide complexes
patent, August 2013

Aromatic triamide-lanthanide complexes
patent, October 2013

Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides
patent, October 2013

Luminescent macrocyclic lanthanide complexes
patent, May 2014

Phthalamide-lanthanide complexes for use as luminescent markers
patent-application, September 2002

Phthalamide lanthanide complexes for use as luminescent markers
patent-application, December 2002

Macrocyclic module compositions
patent-application, October 2003

Hydroxypyridonate and hydroxypyrimidinone chelating agents
patent-application, January 2005

Phthalamide-lanthanide complexes for use as luminescent markers
patent-application, March 2005

Reagent system and method for modifying the luminescence of lanthanide(III) macrocyclic complexes
patent-application, June 2007

Multi-Color Time Resolved Fluorophores Based on Macrocyclic Lanthanide Complexes
patent-application, September 2008

Luminescent Macrocyclic Lanthanide Complexes
patent-application, September 2008

Phthalamide-Lanthanide Complexes for Use as Luminescent Markers
patent-application, January 2009

Aromatic Triamide-Lanthanide Complexes
patent-application, February 2009

Luminescent 1-Hydroxy-2-Pyridinone Chelates of Lanthanides
patent-application, January 2010

Rapid Homogeneous Diagnostic Testing Platform Based on Lanthanide Fluorescent Resonance Energy Transfer
patent-application, June 2010

Multi-color Time Resolved Fluorophores Based on Macrocyclic Lanthanide Complexes
patent-application, July 2010

Radiopharmaceutical Complexes
patent-application, August 2011

Combination Treatment of Hydroxpyridonate Actinide/Lanthanide Decorporation Agents
patent-application, August 2012

Determination of the Prototropic Exchange Rate at the Water Molecule Coordinated to an Anionic Paramagnetic Gd^III Chelate
journal, September 1998

Nouvelle méthode de synthèse du 3,4,3 LI 1,2 HOPO (1,5,10,14-tétra (1-hydroxy-2-pyridone-6 oyl) 1,5,10,14 tétraazatétradécane) [A new synthesis of 3,4,3 LI 1,2 HOPO]
journal, April 1998

Synthesis and relaxometry of high-generation (G = 5, 7, 9, and 10) PAMAM dendrimer-DOTA-gadolinium chelates
journal, February 1999

Study of metal complexes of a tripodal hydroxypyridinone ligand by electrospray tandem mass spectrometry
journal, June 2005

Synthesis of 3,4,3 LI 1,2 HOPO labelled with ¹⁴C: Synthesis of 3,4,3
journal, February 2001

New compounds of tetradentate Schiff bases with vanadium(IV) and vanadium(V) †
journal, January 1999

Syntheses and Relaxation Properties of Mixed Gadolinium Hydroxypyridinonate MRI Contrast Agents
journal, December 2000

Detection of biotinylated DNA probes by using Eu-labeled streptavidin and time-resolved fluorometry
journal, July 1987

Detection of pulmonary emboli by using MR angiography with MPEG-PL-GdDTPA: an experimental study in rabbits.
journal, May 1994

Synthesis of Homochiral Tris(2-alkyl-2-aminoethyl)amine Derivatives from Chiral α-Amino Aldehydes and Their Application in the Synthesis of Water Soluble Chelators
journal, June 2001

Synthesis of a Ligand Based upon a New Entry into the 3-Hydroxy-N-alkyl-2(1H)-pyridinone Ring System and Thermodynamic Evaluation of Its Gadolinium Complex
journal, June 2000

Tris(pyrone) Chelates of Gd(III) as High Solubility MRI-CA
journal, February 2006

Next Generation, High Relaxivity Gadolinium MRI Agents^†
journal, December 2004

Oxygen‐17 NMR and EPR studies of water exchange from the first coordination sphere of gadolinium(III) aquoion and gadolinium(III) propylenediaminetetra‐acetate
journal, December 1980

Rational reduction of the conformational space of a siderophore analog through nonbonded interactions: the role of entropy in enterobactin
journal, July 1993

A solid-state study of eight-coordinate lanthanide(iii) complexes (Ln = Eu, Gd, Tb, Dy) with 1-hydroxy-2-pyridinone
journal, March 2003

Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands
journal, February 1993

Gadolinium-containing copolymeric chelates—a new potential MR contrast agent
journal, August 1999

Force Field Parametrization for Gadolinium Complexes Based on ab Initio Potential Energy Surface Calculations
journal, April 2000

Highly Soluble Tris-hydroxypyridonate Gd(III) Complexes with Increased Hydration Number, Fast Water Exchange, Slow Electronic Relaxation, and High Relaxivity¹
journal, February 2007

Specific sequestering agents for the actinides. 16. Synthesis and initial biological testing of polydentate oxohydroxypyridinecarboxylate ligands
journal, January 1988

Gadolinium complex of tris[(3-hydroxy-1-methyl- 2-oxo-1,2-didehydropyridine-4-carboxamido)ethyl]-amine: A New Class of gadolinium magnetic resonance relaxation agents
journal, July 1995

Gadolinium(III) 1,2-Hydroxypyridonate-Based Complexes: Toward MRI Contrast Agents of High Relaxivity¹
journal, September 2004

Paramagnetic Gd^IIIFe^III heterobimetallic complexes of DTPA-bis-salicylamide
journal, August 1993

A family of novel DNA sequencing instruments based on single-photon detection
journal, August 2002