Chiral DOTA chelators as an improved platform for biomedical imaging and therapy applications
Abstract
Despite established clinical utilisation, there is an increasing need for safer, more inert gadolinium-based contrast agents, and for chelators that react rapidly with radiometals. Here we report the syntheses of a series of chiral DOTA chelators and their corresponding metal complexes and reveal properties that transcend the parent DOTA compound. We incorporated symmetrical chiral substituents around the tetraaza ring, imparting enhanced rigidity to the DOTA cavity, enabling control over the range of stereoisomers of the lanthanide complexes. The Gd chiral DOTA complexes are shown to be orders of magnitude more inert to Gd release than [GdDOTA]¯. These compounds also exhibit very-fast water exchange rates in an optimal range for high field imaging. Radiolabeling studies with (Cu-64/Lu-177) also demonstrate faster labelling properties. These chiral DOTA chelators are alternative general platforms for the development of stable, high relaxivity contrast agents, and for radiometal complexes used for imaging and/or therapy.
- Authors:
-
- The Hong Kong Polytechnic Univ., Hong Kong (China)
- Massachusetts General Hospital and Harvard Medical School, Charlestown, MA (United States)
- Univ. of Pittsburgh, Pittsburgh, PA (United States)
- Publication Date:
- Research Org.:
- Univ. of Pittsburgh, PA (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC)
- OSTI Identifier:
- 1511482
- Grant/Contract Number:
- SC0008833
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Nature Communications
- Additional Journal Information:
- Journal Volume: 9; Journal Issue: 1; Journal ID: ISSN 2041-1723
- Publisher:
- Nature Publishing Group
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 60 APPLIED LIFE SCIENCES
Citation Formats
Dai, Lixiong, Jones, Chloe M., Chan, Wesley Ting Kwok, Pham, Tiffany A., Ling, Xiaoxi, Gale, Eric M., Rotile, Nicholas J., Tai, William Chi-Shing, Anderson, Carolyn J., Caravan, Peter, and Law, Ga -Lai. Chiral DOTA chelators as an improved platform for biomedical imaging and therapy applications. United States: N. p., 2018.
Web. doi:10.1038/s41467-018-03315-8.
Dai, Lixiong, Jones, Chloe M., Chan, Wesley Ting Kwok, Pham, Tiffany A., Ling, Xiaoxi, Gale, Eric M., Rotile, Nicholas J., Tai, William Chi-Shing, Anderson, Carolyn J., Caravan, Peter, & Law, Ga -Lai. Chiral DOTA chelators as an improved platform for biomedical imaging and therapy applications. United States. https://doi.org/10.1038/s41467-018-03315-8
Dai, Lixiong, Jones, Chloe M., Chan, Wesley Ting Kwok, Pham, Tiffany A., Ling, Xiaoxi, Gale, Eric M., Rotile, Nicholas J., Tai, William Chi-Shing, Anderson, Carolyn J., Caravan, Peter, and Law, Ga -Lai. Tue .
"Chiral DOTA chelators as an improved platform for biomedical imaging and therapy applications". United States. https://doi.org/10.1038/s41467-018-03315-8. https://www.osti.gov/servlets/purl/1511482.
@article{osti_1511482,
title = {Chiral DOTA chelators as an improved platform for biomedical imaging and therapy applications},
author = {Dai, Lixiong and Jones, Chloe M. and Chan, Wesley Ting Kwok and Pham, Tiffany A. and Ling, Xiaoxi and Gale, Eric M. and Rotile, Nicholas J. and Tai, William Chi-Shing and Anderson, Carolyn J. and Caravan, Peter and Law, Ga -Lai},
abstractNote = {Despite established clinical utilisation, there is an increasing need for safer, more inert gadolinium-based contrast agents, and for chelators that react rapidly with radiometals. Here we report the syntheses of a series of chiral DOTA chelators and their corresponding metal complexes and reveal properties that transcend the parent DOTA compound. We incorporated symmetrical chiral substituents around the tetraaza ring, imparting enhanced rigidity to the DOTA cavity, enabling control over the range of stereoisomers of the lanthanide complexes. The Gd chiral DOTA complexes are shown to be orders of magnitude more inert to Gd release than [GdDOTA]¯. These compounds also exhibit very-fast water exchange rates in an optimal range for high field imaging. Radiolabeling studies with (Cu-64/Lu-177) also demonstrate faster labelling properties. These chiral DOTA chelators are alternative general platforms for the development of stable, high relaxivity contrast agents, and for radiometal complexes used for imaging and/or therapy.},
doi = {10.1038/s41467-018-03315-8},
journal = {Nature Communications},
number = 1,
volume = 9,
place = {United States},
year = {Tue Feb 27 00:00:00 EST 2018},
month = {Tue Feb 27 00:00:00 EST 2018}
}
Web of Science
Figures / Tables:
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Solution and Solid-State Characterization of Highly Rigid, Eight-Coordinate Lanthanide(III) Complexes of a Macrocyclic Tetrabenzylphosphinate
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Analysis of the Conformational Behavior and Stability of the SAP and TSAP Isomers of Lanthanide(III) NB-DOTA-Type Chelates
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Gd(DOTAlaP): Exploring the Boundaries of Fast Water Exchange in Gadolinium-Based Magnetic Resonance Imaging Contrast Agents
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Aggregation in Amphiphilic Macrocycle-Substituted Gd 3+ DOTA-Type Chelates Is Affected by the Regiochemistry of Substitution
journal, February 2015
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Albumin Binding, Relaxivity, and Water Exchange Kinetics of the Diastereoisomers of MS-325, a Gadolinium(III)-Based Magnetic Resonance Angiography Contrast Agent
journal, August 2007
- Caravan, Peter; Parigi, Giacomo; Chasse, Jaclyn M.
- Inorganic Chemistry, Vol. 46, Issue 16
Optimization of the Relaxivity of MRI Contrast Agents: Effect of Poly(ethylene glycol) Chains on the Water-Exchange Rates of Gd III Complexes
journal, October 2001
- Doble, Dan M. J.; Botta, Mauro; Wang, Jay
- Journal of the American Chemical Society, Vol. 123, Issue 43
The Interaction of MS-325 with Human Serum Albumin and Its Effect on Proton Relaxation Rates
journal, March 2002
- Caravan, Peter; Cloutier, Normand J.; Greenfield, Matthew T.
- Journal of the American Chemical Society, Vol. 124, Issue 12
Circularly Polarized Luminescence of Curium: A New Characterization of the 5f Actinide Complexes
journal, September 2012
- Law, Ga-Lai; Andolina, Christopher M.; Xu, Jide
- Journal of the American Chemical Society, Vol. 134, Issue 37
Direct Measurement of the Mn(II) Hydration State in Metal Complexes and Metalloproteins through 17 O NMR Line Widths
journal, October 2013
- Gale, Eric M.; Zhu, Jiang; Caravan, Peter
- Journal of the American Chemical Society, Vol. 135, Issue 49
Lanthanide(III) Complexes with a Reinforced Cyclam Ligand Show Unprecedented Kinetic Inertness
journal, December 2014
- Rodríguez-Rodríguez, Aurora; Esteban-Gómez, David; Tripier, Raphaël
- Journal of the American Chemical Society, Vol. 136, Issue 52
Structural and Dynamic Parameters Obtained from 17 O NMR, EPR, and NMRD Studies of Monomeric and Dimeric Gd 3+ Complexes of Interest in Magnetic Resonance Imaging: An Integrated and Theoretically Self-Consistent Approach 1
journal, January 1996
- Powell, D. Hugh; Dhubhghaill, Orla M. Ni; Pubanz, Dirk
- Journal of the American Chemical Society, Vol. 118, Issue 39
Chiral Tetraazamacrocycles Having Four Pendant-Arms
journal, June 2009
- Kamioka, Seiji; Takahashi, Takashi; Kawauchi, Susumu
- Organic Letters, Vol. 11, Issue 11
Lanthanide( III ) chelates for NMR biomedical applications
journal, January 1998
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Strategies for increasing the sensitivity of gadolinium based MRI contrast agents
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Analysis of the isomer ratios of polymethylated-DOTA complexes and the implications on protein structural studies
journal, January 2016
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Gadolinium—a specific trigger for the development of nephrogenic fibrosing dermopathy and nephrogenic systemic fibrosis?
journal, June 2006
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Commentary on T1-Weighted Hypersignal in the Deep Cerebellar Nuclei After Repeated Administrations of Gadolinium-Based Contrast Agents in Healthy Rats
journal, August 2015
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A Sterically Overcrowded, Isopropyl‐Substituted, Lanthanide‐Chelating Tag for Protein Pseudocontact Shift NMR Spectroscopy: Synthesis of its Macrocyclic Scaffold and Benchmarking on Ubiquitin S57 C and hCA II S166 C
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Effect of Ligand Chirality and Hyperconjugation on the Thermodynamic Stability of a Tris(aquated) Gd III Complex: Synthesis, Characterization, and T 1 -Weighted Phantom MR Image Study: Effect of Ligand Chirality and Hyperconjugation on the Thermodynamic Stability of a Tris(aquated) GdIII Complex: Synthesis, Characterization, and T1-W
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Synthesis of chiral nine and twelve-membered cyclic polyamines from natural building blocks
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A Sterically Overcrowded, Isopropyl-Substituted, Lanthanide-Chelating Tag for Protein Pseudocontact Shift NMR Spectroscopy: Synthesis of its Macrocyclic Scaffold and Benchmarking on Ubiquitin S57 C and hCA II S166 C
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