Luminescent macrocyclic lanthanide complexes

Raymond, Kenneth N; Corneillie, Todd M; Xu, Jide

Title: Luminescent macrocyclic lanthanide complexes

Abstract

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.

Inventors:

Raymond, Kenneth N ^[1]; Corneillie, Todd M ^[2]; Xu, Jide ^[1]

Berkeley, CA
Campbell, CA

Publication Date:: Tue May 08 00:00:00 EDT 2012

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

Sponsoring Org.:: USDOE

OSTI Identifier:: 1043899

Patent Number(s):: 8,173,800

Application Number:: 11/839,509

Assignee:: The Regents of the University of California (Oakland, CA)

DOE Contract Number:: AC03-76SF00098

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: 59 BASIC BIOLOGICAL SCIENCES

Citation Formats


                    Raymond, Kenneth N, Corneillie, Todd M, and Xu, Jide. Luminescent macrocyclic lanthanide complexes.  United States: N. p., 2012. 
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                    Raymond, Kenneth N, Corneillie, Todd M, & Xu, Jide. Luminescent macrocyclic lanthanide complexes.  United States.

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                    Raymond, Kenneth N, Corneillie, Todd M, and Xu, Jide. 2012.  
        "Luminescent macrocyclic lanthanide complexes".  United States.  https://www.osti.gov/servlets/purl/1043899.

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@article{osti_1043899,

  title        = {Luminescent macrocyclic lanthanide complexes},

  author       = {Raymond, Kenneth N and Corneillie, Todd M and Xu, Jide},

  abstractNote = {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.},

  doi          = {},

  url          = {https://www.osti.gov/biblio/1043899},
  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {Tue May 08 00:00:00 EDT 2012},

  month        = {Tue May 08 00:00:00 EDT 2012}

}

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Title: Luminescent macrocyclic lanthanide complexes

Abstract

Citation Formats

Allelic discrimination by nick-translation PCR with fluorgenic probes journal, August 1993

Distance distribution in a dye-linked oligonucleotide determined by time-resolved fluorescence energy transfer journal, December 1992

Time-resolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays journal, January 1995

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Multicolor molecular beacons for allele discrimination journal, January 1998

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Luminescence and structure of europium compounds journal, January 2000

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Molecular Beacons: Probes that Fluoresce upon Hybridization journal, March 1996

Design and synthesis of new fluorogenic HIV protease substrates based on resonance energy transfer journal, January 1990

Rapid Sizing of Short Tandem Repeat Alleles Using Capillary Array Electrophoresis and Energy-Transfer Fluorescent Primers journal, April 1995

Homogeneous Time-Resolved Il-2–Il-2rα Assay Using Fluorescence Resonance Energy Transfer journal, July 1998

Molecular Beacons: Spectral Genotyping of Human Alleles journal, February 1998

Simultaneous Amplification and Detection of Specific DNA Sequences journal, April 1992

Fluorescence Energy Transfer as a Spectroscopic Ruler journal, June 1978

Crystal structure of dimeric HIV-1 capsid protein journal, September 1996

Luminescent lanthanide complexes as photochemical supramolecular devices journal, February 1993

Detection of specific polymerase chain reaction product by utilizing the 5'----3' exonuclease activity of Thermus aquaticus DNA polymerase. journal, August 1991

Development of luminescent lanthanide chelate labels for diagnostic assays journal, March 1997

Water-Soluble Neutral Calix[4]arene−Lanthanide Complexes: Synthesis and Luminescence Properties journal, June 1997

Towards materials with planned properties: dinuclear f-f helicates and d-f non-covalent podates based on benzimidazole-pyridine binding units journal, March 1997

Lifetime- and Color-Tailored Fluorophores in the Micro- to Millisecond Time Regime journal, February 2000

A Novel Salicylate-Based Macrobicycle with a “Split Personality” journal, October 1999

Binuclear Metal Complexes. V. Template Synthesis of a Binuclear Copper(II) Complex of a Macrocycle Containing Amido Groups journal, October 1972

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Time-Resolved Fluorescence of Lanthanide Probes and Applications in Biotechnology journal, January 1987

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Complexes of lanthanide perchlorates with N,N,N′,N′-tetramethyl-α-carboxamido-O-anisamide and N,N′-di-t-butyl-α-carboxamido-O-anisamide journal, January 1979

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A Theory of Sensitized Luminescence in Solids journal, May 1953

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[13] Fluorescence resonance energy transfer book, January 1995

Seven-Color, Homogeneous Detection of Six PCR Products journal, August 1999

A closed tube format for amplification and detection of DNA based on energy transfer journal, June 1997

Long-Range Nonradiative Transfer of Electronic Excitation Energy in Proteins and Polypeptides journal, June 1971

Allelic discrimination by nick-translation PCR with fluorgenic probes
journal, August 1993

Distance distribution in a dye-linked oligonucleotide determined by time-resolved fluorescence energy transfer
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Time-resolved detection of lanthanide luminescence for ultrasensitive bioanalytical assays
journal, January 1995

Time Gating Improves Sensitivity in Energy Transfer Assays with Terbium Chelate/Dark Quencher Oligonucleotide Probes
journal, December 2004

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Stable Lanthanide Luminescence Agents Highly Emissive in Aqueous Solution: Multidentate 2-Hydroxyisophthalamide Complexes of Sm³⁺, Eu³⁺, Tb³⁺, Dy³⁺
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Time-resolved fluorescence of a new europium-chelate complex: demonstration of highly sensitive detection of protein and DNA samples
journal, November 1993

Time-resolved fluorometry: a sensitive method to quantify DNA-hybrids
journal, January 1986

Crescent Oligoamides: From Acyclic “Macrocycles” to Folding Nanotubes
journal, October 2001

Multicolor molecular beacons for allele discrimination
journal, January 1998

Comparative study of fluorescent ternary terbium complexes. Application in enzyme amplified fluorimetric immunoassay for α-fetoprotein
journal, December 1996

Luminescence and structure of europium compounds
journal, January 2000

Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and β-hydroxyglutaric acid
journal, October 1997

Molecular Beacons: Probes that Fluoresce upon Hybridization
journal, March 1996

Design and synthesis of new fluorogenic HIV protease substrates based on resonance energy transfer
journal, January 1990

Rapid Sizing of Short Tandem Repeat Alleles Using Capillary Array Electrophoresis and Energy-Transfer Fluorescent Primers
journal, April 1995

Homogeneous Time-Resolved Il-2–Il-2rα Assay Using Fluorescence Resonance Energy Transfer
journal, July 1998

Molecular Beacons: Spectral Genotyping of Human Alleles
journal, February 1998

Simultaneous Amplification and Detection of Specific DNA Sequences
journal, April 1992

Fluorescence Energy Transfer as a Spectroscopic Ruler
journal, June 1978

Crystal structure of dimeric HIV-1 capsid protein
journal, September 1996

Luminescent lanthanide complexes as photochemical supramolecular devices
journal, February 1993

Detection of specific polymerase chain reaction product by utilizing the 5'----3' exonuclease activity of Thermus aquaticus DNA polymerase.
journal, August 1991

Development of luminescent lanthanide chelate labels for diagnostic assays
journal, March 1997

Water-Soluble Neutral Calix[4]arene−Lanthanide Complexes: Synthesis and Luminescence Properties
journal, June 1997

Towards materials with planned properties: dinuclear f-f helicates and d-f non-covalent podates based on benzimidazole-pyridine binding units
journal, March 1997

Lifetime- and Color-Tailored Fluorophores in the Micro- to Millisecond Time Regime
journal, February 2000

A Novel Salicylate-Based Macrobicycle with a “Split Personality”
journal, October 1999

Binuclear Metal Complexes. V. Template Synthesis of a Binuclear Copper(II) Complex of a Macrocycle Containing Amido Groups
journal, October 1972

Spectroscopic properties and design of highly luminescent lanthanide coordination complexes
journal, January 2000

Time-Resolved Fluorescence of Lanthanide Probes and Applications in Biotechnology
journal, January 1987

Shape-Persistent Aromatic Amide Oligomers: New Tools for Supramolecular Chemistry
journal, December 2006

Complexes of lanthanide perchlorates with N,N,N′,N′-tetramethyl-α-carboxamido-O-anisamide and N,N′-di-t-butyl-α-carboxamido-O-anisamide
journal, January 1979

Real time quantitative PCR.
journal, October 1996

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

Terbium and Rhodamine as Labels in a Homogeneous Time-resolved Fluorometric Energy Transfer Assay of the β Subunit of Human Chorionic Gonadotropin in Serum
journal, June 1999

A Theory of Sensitized Luminescence in Solids
journal, May 1953

Direct genomic fluorescent on-line sequencing and analysis using in vitro amplification of DNA
journal, April 1989

Detection of nucleic acid hybridization by nonradiative fluorescence resonance energy transfer.
journal, December 1988

Detection of PCR products using self-probing amplicons and fluorescence
journal, August 1999

Mono(di)nuclear Europium(III) Complexes of Macrobi(tri)cyclic Cryptands Derived from Diazatetralactams as Luminophores in Aqueous Solution
journal, April 1999

[13] Fluorescence resonance energy transfer
book, January 1995

Seven-Color, Homogeneous Detection of Six PCR Products
journal, August 1999

A closed tube format for amplification and detection of DNA based on energy transfer
journal, June 1997

Long-Range Nonradiative Transfer of Electronic Excitation Energy in Proteins and Polypeptides
journal, June 1971