Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89
Abstract
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.
- Authors:
-
- Wake Forest, Winston-Salem, NC (United States). School of Medicine
- Lumiphore, Inc., Berkeley, CA (United States)
- Univ. of California, Berkeley, CA (United States). Dept. of Chemistry
- Publication Date:
- Research Org.:
- Washington Univ., St. Louis, MO (United States). School of Medicine
- Sponsoring Org.:
- USDOE Office of Science (SC), Nuclear Physics (NP)
- OSTI Identifier:
- 1347094
- Grant/Contract Number:
- SC0008657; IIP-1215462
- Resource Type:
- Accepted Manuscript
- Journal Name:
- ChemComm
- Additional Journal Information:
- Journal Volume: 51; Journal Issue: 12; Journal ID: ISSN 1359-7345
- Publisher:
- Royal Society of Chemistry
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Pandya, Darpan N., Pailloux, Sylvie, Tatum, David, Magda, Darren, and Wadas, Thaddeus J. Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89. United States: N. p., 2014.
Web. doi:10.1039/c4cc09256b.
Pandya, Darpan N., Pailloux, Sylvie, Tatum, David, Magda, Darren, & Wadas, Thaddeus J. Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89. United States. https://doi.org/10.1039/c4cc09256b
Pandya, Darpan N., Pailloux, Sylvie, Tatum, David, Magda, Darren, and Wadas, Thaddeus J. Thu .
"Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89". United States. https://doi.org/10.1039/c4cc09256b. https://www.osti.gov/servlets/purl/1347094.
@article{osti_1347094,
title = {Di-macrocyclic terephthalamide ligands as chelators for the PET radionuclide zirconium-89},
author = {Pandya, Darpan N. and Pailloux, Sylvie and Tatum, David and Magda, Darren and Wadas, Thaddeus J.},
abstractNote = {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.},
doi = {10.1039/c4cc09256b},
journal = {ChemComm},
number = 12,
volume = 51,
place = {United States},
year = {Thu Dec 18 00:00:00 EST 2014},
month = {Thu Dec 18 00:00:00 EST 2014}
}
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Works referenced in this record:
Coordinating Radiometals of Copper, Gallium, Indium, Yttrium, and Zirconium for PET and SPECT Imaging of Disease
journal, May 2010
- Wadas, Thaddeus J.; Wong, Edward H.; Weisman, Gary R.
- Chemical Reviews, Vol. 110, Issue 5
89Zr-huJ591 immuno-PET imaging in patients with advanced metastatic prostate cancer
journal, August 2014
- Pandit-Taskar, Neeta; O’Donoghue, Joseph A.; Beylergil, Volkan
- European Journal of Nuclear Medicine and Molecular Imaging, Vol. 41, Issue 11
Monitoring Afatinib Treatment in HER2-Positive Gastric Cancer with 18F-FDG and 89Zr-Trastuzumab PET
journal, April 2013
- Janjigian, Y. Y.; Viola-Villegas, N.; Holland, J. P.
- Journal of Nuclear Medicine, Vol. 54, Issue 6
Annotating MYC status with 89Zr-transferrin imaging
journal, September 2012
- Holland, Jason P.; Evans, Michael J.; Rice, Samuel L.
- Nature Medicine, Vol. 18, Issue 10
Targeting the Internal Epitope of Prostate-Specific Membrane Antigen with 89Zr-7E11 Immuno-PET
journal, September 2011
- Ruggiero, A.; Holland, J. P.; Hudolin, T.
- Journal of Nuclear Medicine, Vol. 52, Issue 10
Magnitude of Enhanced Permeability and Retention Effect in Tumors with Different Phenotypes: 89Zr-Albumin as a Model System
journal, March 2011
- Heneweer, C.; Holland, J. P.; Divilov, V.
- Journal of Nuclear Medicine, Vol. 52, Issue 4
89Zr-DFO-J591 for ImmunoPET of Prostate-Specific Membrane Antigen Expression In Vivo
journal, July 2010
- Holland, J. P.; Divilov, V.; Bander, N. H.
- Journal of Nuclear Medicine, Vol. 51, Issue 8
Measuring the Pharmacodynamic Effects of a Novel Hsp90 Inhibitor on HER2/neu Expression in Mice Using 89Zr-DFO-Trastuzumab
journal, January 2010
- Holland, Jason P.; Caldas-Lopes, Eloisi; Divilov, Vadim
- PLoS ONE, Vol. 5, Issue 1
Standardized methods for the production of high specific-activity zirconium-89
journal, October 2009
- Holland, Jason P.; Sheh, Yiauchung; Lewis, Jason S.
- Nuclear Medicine and Biology, Vol. 36, Issue 7
Evaluation of desferal as a bifunctional chelating agent for labeling antibodies with Zr-89
journal, December 1992
- Meijs, Wilma E.; Herscheid, Jacobus D. M.; Haisma, Hidde J.
- International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 43, Issue 12
Charting the mechanism and reactivity of zirconium oxalate with hydroxamate ligands using density functional theory: implications in new chelate design
journal, January 2014
- Holland, Jason P.; Vasdev, Neil
- Dalton Trans., Vol. 43, Issue 26
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
- Guérard, François; Lee, Yong-Sok; Tripier, Raphaël
- Chem. Commun., Vol. 49, Issue 10
An octadentate bifunctional chelating agent for the development of stable zirconium-89 based molecular imaging probes
journal, January 2014
- Patra, Malay; Bauman, Andreas; Mari, Cristina
- Chem. Commun., Vol. 50, Issue 78
Alternative Chelator for 89 Zr Radiopharmaceuticals: Radiolabeling and Evaluation of 3,4,3-(LI-1,2-HOPO)
journal, December 2013
- Deri, Melissa A.; Ponnala, Shashikanth; Zeglis, Brian M.
- Journal of Medicinal Chemistry, Vol. 57, Issue 11
Tripodal tris(hydroxypyridinone) ligands for immunoconjugate PET imaging with 89 Zr 4+ : comparison with desferrioxamine-B
journal, January 2015
- Ma, Michelle T.; Meszaros, Levente K.; Paterson, Brett M.
- Dalton Transactions, Vol. 44, Issue 11
Synthesis and Thermodynamic Evaluation of Mixed Hexadentate Linear Iron Chelators Containing Hydroxypyridinone and Terephthalamide Units 1
journal, May 2006
- Abergel, Rebecca J.; Raymond, Kenneth N.
- Inorganic Chemistry, Vol. 45, Issue 9
Terephthalamide-containing ligands: fast removal of iron from transferrin
journal, November 2007
- Abergel, Rebecca J.; Raymond, Kenneth N.
- JBIC Journal of Biological Inorganic Chemistry, Vol. 13, Issue 2
A Bidentate Terephthalamide Ligand, TAMmeg, as an Entry into Terephthalamide-Containing Therapeutic Iron Chelating Agents
journal, February 2006
- Jurchen, Kristy M. Clarke; Raymond, Kenneth N.
- Inorganic Chemistry, Vol. 45, Issue 6
Physicochemical Profiling (Solubility, Permeability and Charge State)
journal, September 2001
- Avdeef, Alex
- Current Topics in Medicinal Chemistry, Vol. 1, Issue 4
Physicochemical profiling in drug research: a brief survey of the state-of-the-art of experimental techniques
journal, October 2002
- Avdeef, A.; Testa, B.
- Cellular and Molecular Life Sciences, Vol. 59, Issue 10
Determination of lipophilicity and its use as a predictor of blood–brain barrier penetration of molecular imaging agents
journal, December 2003
- Waterhouse, R.
- Molecular Imaging & Biology, Vol. 5, Issue 6
Works referencing / citing this record:
Direct comparison of the in vitro and in vivo stability of DFO, DFO* and DFOcyclo* for 89Zr-immunoPET
journal, June 2019
- Raavé, René; Sandker, Gerwin; Adumeau, Pierre
- European Journal of Nuclear Medicine and Molecular Imaging, Vol. 46, Issue 9
The study of Zr adsorption on nanodispersed hydroxyapatite: X-ray photoelectron study
journal, June 2019
- Teterin, Yuri A.; Kazakov, Andrey G.; Teterin, Anton Yu
- Journal of Radioanalytical and Nuclear Chemistry, Vol. 321, Issue 1
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
- Guérard, F.; Beyler, M.; Lee, Y. -S.
- Dalton Transactions, Vol. 46, Issue 14
Zirconium tetraazamacrocycle complexes display extraordinary stability and provide a new strategy for zirconium-89-based radiopharmaceutical development
journal, January 2017
- Pandya, Darpan N.; Bhatt, Nikunj; Yuan, Hong
- Chemical Science, Vol. 8, Issue 3
A comprehensively revised strategy that improves the specific activity and long-term stability of clinically relevant 89 Zr-immuno-PET agents
journal, January 2018
- Bhatt, Nikunj B.; Pandya, Darpan N.; Rideout-Danner, Stephanie
- Dalton Transactions, Vol. 47, Issue 37
Rational Design, Synthesis and Preliminary Evaluation of Novel Fusarinine C-Based Chelators for Radiolabeling with Zirconium-89
journal, March 2019
- Zhai, Chuangyan; He, Shanzhen; Ye, Yunjie
- Biomolecules, Vol. 9, Issue 3
Zirconium tetraazamacrocycle complexes display extraordinary stability and provide a new strategy for zirconium-89-based radiopharmaceutical development
text, January 2017
- Hong, Yuan,; Ulrich, Bierbach,; J., Wadas, Thaddeus
- The University of North Carolina at Chapel Hill University Libraries
Recent Advances in Zirconium-89 Chelator Development
journal, March 2018
- Bhatt, Nikunj; Pandya, Darpan; Wadas, Thaddeus
- Molecules, Vol. 23, Issue 3
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
- N. Tinianow, Jeff; Pandya, Darpan N.; Pailloux, Sylvie L.
- Theranostics, Vol. 6, Issue 4
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
- Pandya, Darpan N.; Hantgan, Roy; Budzevich, Mikalai M.
- Theranostics, Vol. 6, Issue 5