Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Luminescent macrocyclic lanthanide complexes

Patent ·
OSTI ID:1132073

The present invention provides a novel class of macrocyclic compounds as well as complexes formed between a metal (e.g., lanthanide) ion and the compounds of the invention. Preferred complexes exhibit high stability as well as high quantum yields of lanthanide ion luminescence in aqueous media without the need for secondary activating agents. Preferred compounds incorporate hydroxy-isophthalamide moieties within their macrocyclic structure and are characterized by surprisingly low, non-specific binding to a variety of polypeptides such as antibodies and proteins as well as high kinetic stability. These characteristics distinguish them from known, open-structured ligands.

Research Organization:
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC03-76SF00098
Assignee:
The Regents of the University of California (Oakland, CA)
Patent Number(s):
8,729,258
Application Number:
13/460,120
OSTI ID:
1132073
Country of Publication:
United States
Language:
English

References (42)

A Novel Salicylate-Based Macrobicycle with a “Split Personality” journal October 1999
Comparative study of fluorescent ternary terbium complexes. Application in enzyme amplified fluorimetric immunoassay for α-fetoprotein journal December 1996
Water-Soluble Neutral Calix[4]arene−Lanthanide Complexes: Synthesis and Luminescence Properties journal June 1997
Luminescence and structure of europium compounds journal January 2000
Simultaneous Amplification and Detection of Specific DNA Sequences journal April 1992
Time-resolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays journal January 1995
Shape-Persistent Aromatic Amide Oligomers: New Tools for Supramolecular Chemistry journal December 2006
Luminescent lanthanide complexes as photochemical supramolecular devices journal February 1993
Molecular Beacons: Probes that Fluoresce upon Hybridization journal March 1996
Crystal structure of dimeric HIV-1 capsid protein journal September 1996
Multicolor molecular beacons for allele discrimination journal January 1998
A Theory of Sensitized Luminescence in Solids journal May 1953
Binuclear Metal Complexes. V. Template Synthesis of a Binuclear Copper(II) Complex of a Macrocycle Containing Amido Groups journal October 1972
Stable Lanthanide Luminescence Agents Highly Emissive in Aqueous Solution: Multidentate 2-Hydroxyisophthalamide Complexes of Sm3+, Eu3+, Tb3+, Dy3+
  • Petoud, Stephane; Cohen, Seth M.; Bünzli, Jean-Claude G.
  • Journal of the American Chemical Society, Vol. 125, Issue 44, p. 13324-13325 https://doi.org/10.1021/ja0379363
journal November 2003
Homogeneous Time-Resolved Il-2–Il-2rα Assay Using Fluorescence Resonance Energy Transfer journal July 1998
Design and synthesis of new fluorogenic HIV protease substrates based on resonance energy transfer journal January 1990
Crescent Oligoamides From Acyclic “Macrocycles” to Folding Nanotubes journal October 2001
Time-Resolved Fluorescence of Lanthanide Probes and Applications in Biotechnology journal January 1987
Mono(di)nuclear Europium(III) Complexes of Macrobi(tri)cyclic Cryptands Derived from Diazatetralactams as Luminophores in Aqueous Solution journal April 1999
Lifetime- and Color-Tailored Fluorophores in the Micro- to Millisecond Time Regime journal February 2000
Spectroscopic properties and design of highly luminescent lanthanide coordination complexes journal January 2000
[13] Fluorescence resonance energy transfer book January 1995
Towards materials with planned properties: dinuclear f-f helicates and d-f non-covalent podates based on benzimidazole-pyridine binding units journal March 1997
Detection of PCR products using self-probing amplicons and fluorescence journal August 1999
Synthesis, Time-Resolved Luminescence, NMR Spectroscopy, Circular Dichroism and Circularly Polarised Luminescence Studies of Enantiopure Macrocyclic Lanthanide Tetraamide Complexes journal March 1999
Allelic discrimination by nick-translation PCR with fluorgenic probes journal August 1993
Time-resolved fluorescence of a new europium-chelate complex: demonstration of highly sensitive detection of protein and DNA samples journal November 1993
Development of luminescent lanthanide chelate labels for diagnostic assays journal March 1997
Real time quantitative PCR. journal October 1996
Molecular Beacons: Spectral Genotyping of Human Alleles journal February 1998
A closed tube format for amplification and detection of DNA based on energy transfer journal June 1997
[2] Fluorimetric assays of proteolytic enzymes book January 1995
Detection of specific polymerase chain reaction product by utilizing the 5'----3' exonuclease activity of Thermus aquaticus DNA polymerase. journal August 1991
Time-resolved fluorometry: a sensitive method to quantify DNA-hybrids journal January 1986
Distance distribution in a dye-linked oligonucleotide determined by time-resolved fluorescence energy transfer journal December 1992
Time Gating Improves Sensitivity in Energy Transfer Assays with Terbium Chelate/Dark Quencher Oligonucleotide Probes
  • Johansson, Mary Katherine; Cook, Ronald M.; Xu, Jide
  • Journal of the American Chemical Society, Vol. 126, Issue 50, p. 16451-16455 https://doi.org/10.1021/ja0452368
journal December 2004
Detection of biotinylated DNA probes by using Eu-labeled streptavidin and time-resolved fluorometry journal July 1987
Rapid Sizing of Short Tandem Repeat Alleles Using Capillary Array Electrophoresis and Energy-Transfer Fluorescent Primers journal April 1995
Detection of nucleic acid hybridization by nonradiative fluorescence resonance energy transfer. journal December 1988
Direct genomic fluorescent on-line sequencing and analysis using in vitro amplification of DNA journal April 1989
Fluorescence Energy Transfer as a Spectroscopic Ruler journal June 1978
Long-Range Nonradiative Transfer of Electronic Excitation Energy in Proteins and Polypeptides journal June 1971

Similar Records

Luminescent macrocyclic lanthanide complexes
Patent · Tue May 08 00:00:00 EDT 2012 · OSTI ID:1043899

Phthalamide lanthanide complexes for use as luminescent markers
Patent · Tue Dec 31 23:00:00 EST 2002 · OSTI ID:875026

Salicylamide-lanthanide complexes for use as luminescent markers
Patent · Tue Jul 29 00:00:00 EDT 2008 · OSTI ID:984449