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Title: Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89

Journal Article · · ChemComm
DOI: https://doi.org/10.1039/c4cc09256b · OSTI ID:1347094
 [1];  [2];  [3];  [2];  [4]
  1. Wake Forest, Winston-Salem, NC (United States). School of Medicine; DOE Office of Scientific and Technical Information (OSTI)
  2. Lumiphore, Inc., Berkeley, CA (United States)
  3. Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
  4. Wake Forest, Winston-Salem, NC (United States). School of Medicine

The development of bifunctional chelators (BFCs) which can stably chelate zirconium-89 ((89)Zr) while being conjugated to targeting molecules is an area of active research. Herein we report the first octadentate terephthalamide ligands, which are easily radiolabeled with (89)Zr and are highly stable in vitro. Lastly, they represent a novel class of chelators, which are worthy of further development as BFCs for (89)Zr.

Research Organization:
Washington Univ., St. Louis, MO (United States). School of Medicine
Sponsoring Organization:
USDOE Office of Science (SC), Nuclear Physics (NP) (SC-26)
Grant/Contract Number:
SC0008657
OSTI ID:
1347094
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 12 Vol. 51; ISSN CHCOFS; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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A Bidentate Terephthalamide Ligand, TAMmeg, as an Entry into Terephthalamide-Containing Therapeutic Iron Chelating Agents journal February 2006
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Alternative Chelator for 89 Zr Radiopharmaceuticals: Radiolabeling and Evaluation of 3,4,3-(LI-1,2-HOPO) journal December 2013
Annotating MYC status with 89Zr-transferrin imaging journal September 2012
Investigation of Zr( iv ) and 89 Zr( iv ) complexation with hydroxamates: progress towards designing a better chelator than desferrioxamine B for immuno-PET imaging journal January 2013
An octadentate bifunctional chelating agent for the development of stable zirconium-89 based molecular imaging probes journal January 2014
Charting the mechanism and reactivity of zirconium oxalate with hydroxamate ligands using density functional theory: implications in new chelate design journal January 2014
Tripodal tris(hydroxypyridinone) ligands for immunoconjugate PET imaging with 89 Zr 4+ : comparison with desferrioxamine-B journal January 2015
Measuring the Pharmacodynamic Effects of a Novel Hsp90 Inhibitor on HER2/neu Expression in Mice Using 89Zr-DFO-Trastuzumab journal January 2010
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89Zr-DFO-J591 for ImmunoPET of Prostate-Specific Membrane Antigen Expression In Vivo journal July 2010
Magnitude of Enhanced Permeability and Retention Effect in Tumors with Different Phenotypes: 89Zr-Albumin as a Model System journal March 2011
Targeting the Internal Epitope of Prostate-Specific Membrane Antigen with 89Zr-7E11 Immuno-PET journal September 2011
Monitoring Afatinib Treatment in HER2-Positive Gastric Cancer with 18F-FDG and 89Zr-Trastuzumab PET journal April 2013

Cited By (12)

Recent Advances in Zirconium-89 Chelator Development journal March 2018
Evaluation of a 3-hydroxypyridin-2-one (2,3-HOPO) Based Macrocyclic Chelator for 89 Zr 4+ and Its Use for ImmunoPET Imaging of HER2 Positive Model of Ovarian Carcinoma in Mice journal January 2016
Preliminary Therapy Evaluation of 225 Ac-DOTA-c(RGDyK) Demonstrates that Cerenkov Radiation Derived from 225 Ac Daughter Decay Can Be Detected by Optical Imaging for In Vivo Tumor Visualization journal January 2016
Direct comparison of the in vitro and in vivo stability of DFO, DFO* and DFOcyclo* for 89Zr-immunoPET journal June 2019
The study of Zr adsorption on nanodispersed hydroxyapatite: X-ray photoelectron study journal June 2019
Current advances in ligand design for inorganic positron emission tomography tracers 68 Ga, 64 Cu, 89 Zr and 44 Sc journal January 2016
Investigation of the complexation of nat Zr( iv ) and 89 Zr( iv ) by hydroxypyridinones for the development of chelators for PET imaging applications journal January 2017
Zirconium tetraazamacrocycle complexes display extraordinary stability and provide a new strategy for zirconium-89-based radiopharmaceutical development journal January 2017
The chemistry of PET imaging with zirconium-89 journal January 2018
A comprehensively revised strategy that improves the specific activity and long-term stability of clinically relevant 89 Zr-immuno-PET agents journal January 2018
Zirconium tetraazamacrocycle complexes display extraordinary stability and provide a new strategy for zirconium-89-based radiopharmaceutical development text January 2017
Rational Design, Synthesis and Preliminary Evaluation of Novel Fusarinine C-Based Chelators for Radiolabeling with Zirconium-89 journal March 2019

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