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:
- Issue Date:
- Research Org.:
- Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1176518
- Patent Number(s):
- 8557601
- Application Number:
- 12/373,275
- Assignee:
- The Regents of the University of California (Oakland, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C09 - DYES C09K - MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- AC03-76SF00098
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2007 Jul 10
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
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., 2013.
Web.
Raymond, Kenneth N., Xu, Jide, Moore, Evan G., & Werner, Eric J. Luminescent 1-hydroxy-2-pyridinone chelates of lanthanides. United States.
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/1176518.
@article{osti_1176518,
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 = {2013},
month = {10}
}
Works referenced in this record:
Gadolinium(III) 1,2-Hydroxypyridonate-Based Complexes: Toward MRI Contrast Agents of High Relaxivity1
journal, September 2004
- Xu, Jide; Churchill, David G.; Botta, Mauro
- Inorganic Chemistry, Vol. 43, Issue 18, p. 5492-5494
Syntheses and Relaxation Properties of Mixed Gadolinium Hydroxypyridinonate MRI Contrast Agents
journal, December 2000
- Cohen, Seth M.; Xu, Jide; Radkov, Emil
- Inorganic Chemistry, Vol. 39, Issue 25, p. 5747-5756
In Vivo Chelation of Am(III), Pu(IV), Np(V), and U(VI) in Mice by TREN-(Me-3,2-HOPO)
journal, May 1994
- Durbin, P. W.; Kullgren, B.; Xu, J.
- Radiation Protection Dosimetry, Vol. 53, Issue 1-4
Specific sequestering agents for the actinides. 16. Synthesis and initial biological testing of polydentate oxohydroxypyridinecarboxylate ligands
journal, January 1988
- White, David L.; Durbin, Patricia W.; Jeung, Nylan
- Journal of Medicinal Chemistry, Vol. 31, Issue 1, p. 11-18
Time-resolved fluorometry: a sensitive method to quantify DNA-hybrids
journal, January 1986
- Syvanen, Ann-Christine; Tchen, Paul; Ranki, Marjut
- Nucleic Acids Research, Vol. 14, Issue 2, p. 1017-1028
Force Field Parametrization for Gadolinium Complexes Based on ab Initio Potential Energy Surface Calculations
journal, April 2000
- Villa, Alessandra; Cosentino, Ugo; Pitea, Demetrio
- The Journal of Physical Chemistry A, Vol. 104, Issue 15, p. 3421-3429
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
- Hajela, Sharad P.; Johnson, Adam R.; Xu, Jide
- Inorganic Chemistry, Vol. 40, Issue 13, p. 3208-3216
Highly Soluble Tris-hydroxypyridonate Gd(III) Complexes with Increased Hydration Number, Fast Water Exchange, Slow Electronic Relaxation, and High Relaxivity1
journal, February 2007
- Werner, Eric J.; Avedano, Stefano; Botta, Mauro
- Journal of the American Chemical Society, Vol. 129, Issue 7, p. 1870-1871
Stereospecific binding of MRI contrast agents to human serum albumin: the case of Gd-(S)-EOB-DTPA (Eovist) and its (R) isomer
journal, February 2001
- Vander Elst, Luce; Chapelle, Florence; Laurent, Sophie
- JBIC Journal of Biological Inorganic Chemistry, Vol. 6, Issue 2, p. 196-200
6-Carboxamido-5,4-Hydroxypyrimidinones: A New Class of Heterocyclic Ligands and Their Evaluation as Gadolinium Chelating Agents
journal, December 2001
- Sunderland, Christopher J.; Botta, Mauro; Aime, Silvio
- Inorganic Chemistry, Vol. 40, Issue 26, p. 6746-6756
In vivo diagnosis and therapy of human tumors with monoclonal antibodies: Overview of the symposium
journal, January 1989
- Larson, Steven M.; Britton, Keith E.; Porta, E.
- International Journal of Radiation Applications and Instrumentation. Part B. Nuclear Medicine and Biology, Vol. 16, Issue 2
Study of metal complexes of a tripodal hydroxypyridinone ligand by electrospray tandem mass spectrometry
journal, June 2005
- Budimir, Natali; Fournier, Françoise; Bailly, Théodorine
- Rapid Communications in Mass Spectrometry, Vol. 19, Issue 13, p. 1822-1828
Synthesis of 3,4,3 LI 1,2 HOPO labelled with 14C: Synthesis of 3,4,3
journal, February 2001
- Burgada, R.; Bailly, T.; Noël, J. P.
- Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 44, Issue 1, p. 13-19
Next Generation, High Relaxivity Gadolinium MRI Agents†
journal, December 2004
- Raymond, Kenneth N.; Pierre, Valérie C.
- Bioconjugate Chemistry, Vol. 16, Issue 1, p. 3-8
Selective Inhibition of Fe-versus Cu/Zn-Superoxide Dismutases by 2,3-Dihydroxybenzoic Acid Derivatives
journal, January 2002
- Soulere, Laurent; Viode, Cecile; Perie, Jacques
- Chemical and Pharmaceutical Bulletin, Vol. 50, Issue 5, p. 578-582
Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties and biological activity
journal, June 1990
- Streater, Michael; Taylor, Paul D.; Hider, Robert C.
- Journal of Medicinal Chemistry, Vol. 33, Issue 6, p. 1749-1755
A solid-state study of eight-coordinate lanthanide(iii) complexes (Ln = Eu, Gd, Tb, Dy) with 1-hydroxy-2-pyridinone
journal, March 2003
- Tedeschi, Christine; Azema, Joelle; Gornitzka, Heinz
- Dalton Transactions, Issue 9, p. 1738-1745
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
- Xu, Jide; Franklin, Sonya J.; Whisenhunt, Donald W.
- Journal of the American Chemical Society, Vol. 117, Issue 27, p. 7245-7246
Rational reduction of the conformational space of a siderophore analog through nonbonded interactions: the role of entropy in enterobactin
journal, July 1993
- Stack, T. D. P.; Hou, Zhiguo; Raymond, Kenneth N.
- Journal of the American Chemical Society, Vol. 115, Issue 14, p. 6466-6467
Gadolinium-containing copolymeric chelates—a new potential MR contrast agent
journal, August 1999
- Unger, E.
- Magnetic Resonance Materials in Biology, Physics, and Medicine, Vol. 8, Issue 3
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
- Southwood‐Jones, Rosalind V.; Earl, William L.; Newman, Kenneth E.
- The Journal of Chemical Physics, Vol. 73, Issue 12, p. 5909-5918
Ferric ion sequestering agents. 14. 1-Hydroxy-2(1H)-pyridinone complexes: properties and structure of a novel iron-iron dimer
journal, November 1985
- Scarrow, Robert C.; White, David L.; Raymond, Kenneth N.
- Journal of the American Chemical Society, Vol. 107, Issue 23, p. 6540-6546
Detection of pulmonary emboli by using MR angiography with MPEG-PL-GdDTPA: an experimental study in rabbits.
journal, May 1994
- Frank, H.; Weissleder, R.; Bogdanov, A. A.
- American Journal of Roentgenology, Vol. 162, Issue 5, p. 1041-1046
Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands
journal, February 1993
- Uhlir, Linda C.; Durbin, Patricia W.; Jeung, Nylan
- Journal of Medicinal Chemistry, Vol. 36, Issue 4, p. 504-509
Stereoselectivity in chiral iron(III) and gallium(III) tris(catecholate) complexes effected by nonbonded weakly polar interactions
journal, July 1993
- Karpishin, Timothy B.; Stack, T. D. P.; Raymond, Kenneth N.
- Journal of the American Chemical Society, Vol. 115, Issue 14, p. 6115-6125
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
- Bailly, Théodorine; Burgada, Ramon
- Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry, Vol. 1, Issue 4, p. 241-245
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
- Johnson, Adam R.; O'Sulliva, Brendon; Raymond, Kenneth N.
- Inorganic Chemistry, Vol. 39, Issue 12, p. 2652-2660
Detection of biotinylated DNA probes by using Eu-labeled streptavidin and time-resolved fluorometry
journal, July 1987
- Dahlén, Patrik
- Analytical Biochemistry, Vol. 164, Issue 1, p. 78-83
Tris(pyrone) Chelates of Gd(III) as High Solubility MRI-CA
journal, February 2006
- Puerta, David T.; Botta, Mauro; Jocher, Christoph J.
- Journal of the American Chemical Society, Vol. 128, Issue 7, p. 2222-2223
A Tris-hydroxymethyl-Substituted Derivative of Gd-TREN-Me-3,2-HOPO: An MRI Relaxation Agent with Improved Efficiency
journal, November 2000
- Hajela, Sharad; Botta, Mauro; Giraudo, Sabrina
- Journal of the American Chemical Society, Vol. 122, Issue 45, p. 11228-11229
Specific Sequestering Agents for the Actinides. 28. Synthesis and Initial Evaluation of Multidentate 4-Carbamoyl-3-hydroxy-1-methyl-2(1H)-pyridinone Ligands for in Vivo Plutonium(IV) Chelation
journal, July 1995
- Xu, Jide; Kullgren, Birgitta; Durbin, Patricia W.
- Journal of Medicinal Chemistry, Vol. 38, Issue 14