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

Bond Covalency and Oxidation State of Actinide Ions Complexed with Therapeutic Chelating Agent 3,4,3-LI(1,2-HOPO)

Journal Article · · Inorganic Chemistry
The hydroxypyridinone ligand 3,4,3-LI(1,2-HOPO) is a promising agent for biological decorporation of radionuclides, and allows spectroscopic detection of many lanthanide (Ln) and actinide (An) species via sensitized luminescence. Despite the manifest uses of this ligand, the structural and thermodynamic properties of its complexes across the An series remain understudied. Theoretical investigations of the binding of An(III) and An(IV) ions, from actinium to einsteinium, by the 3,4,3-LI(1,2-HOPO) ligand, as well as experimental extended X-ray absorption fine structure (EXAFS) studies on the trivalent americium, curium, and californium complexes were employed in this paper to address the resulting structures, thermodynamic parameters, redox properties, and corresponding electronic configurations. An(IV) ions were found to form much stronger complexes than An(III) ions, consistent with experimental measurements. Complexation of both An(III) and An(IV) ions generally becomes more favorable for heavier actinides, reflecting increased energy degeneracy driven covalency and concomitant orbital mixing between the 5f orbitals of the An ions and the π orbitals of the ligand. Finally and notably, the ability of this ligand to either accept or donate electron density as needed from its pyridine rings is found to be key to its extraordinary stability across the actinide series.
Research Organization:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States); Los Alamos National Lab. (LANL), Los Alamos, NM (United States); Pacific Northwest National Laboratory (PNNL), Richland, WA (United States); SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
Sponsoring Organization:
USDOE National Nuclear Security Administration (NNSA); USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22). Chemical Sciences, Geosciences & Biosciences Division; USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
Grant/Contract Number:
AC02-05CH11231; AC02-76SF00515; AC52-06NA25396
OSTI ID:
1458511
Alternate ID(s):
OSTI ID: 1463476
Report Number(s):
LA-UR--17-22506; ark:/13030/qt4tc1b0xz
Journal Information:
Inorganic Chemistry, Journal Name: Inorganic Chemistry Journal Issue: 9 Vol. 57; ISSN 0020-1669
Publisher:
American Chemical Society (ACS)Copyright Statement
Country of Publication:
United States
Language:
English

References (89)

High-Relaxivity MRI Contrast Agents: Where Coordination Chemistry Meets Medical Imaging journal October 2008
Sequestered Plutonium: [PuIV{5LIO(Me-3,2-HOPO)}2]?The First Structurally Characterized Plutonium Hydroxypyridonate Complex journal April 2005
Highly Luminescent and Stable Hydroxypyridinonate Complexes: A Step Towards New Curium Decontamination Strategies journal July 2014
Diversity of Chemical Bonding and Oxidation States in MS 4 Molecules of Group 8 Elements journal July 2017
Chemistry with ADF journal January 2001
In Vitro Metabolism and Stability of the Actinide Chelating Agent 3,4,3-LI(1,2-HOPO) journal May 2015
Actinides in Animals and Man book January 2007
Complexation of iron by siderophores a review of their solution and structural chemistry and biological function book January 1984
Towards an order- N DFT method
  • Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.
  • Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), Vol. 99, Issue 6 https://doi.org/10.1007/s002140050353
journal November 1998
An implementation of the conductor-like screening model of solvation within the Amsterdam density functional package journal May 1999
The bonding in tris(η5-cyclopentadienyl) actinide complexes IV: Electronic structural effects in AnCl3 and (η5-C5H5)3An (An ≡ Th — Cf) complexes journal April 1989
Luminescence study on determination of the hydration number of Cm(III) journal October 1994
From early prophylaxis to delayed treatment: Establishing the plutonium decorporation activity window of hydroxypyridinonate chelating agents journal April 2017
Covalency in f-element complexes journal January 2013
Recent developments in lanthanide-based luminescent probes journal August 2014
Siderophore inspired tetra- and octadentate antenna ligands for luminescent Eu(III) and Tb(III) complexes journal September 2016
p -SCN-Bn-HOPO: A Superior Bifunctional Chelator for 89 Zr ImmunoPET journal November 2015
Hydroxypyridinonate Complex Stability of Group (IV) Metals and Tetravalent f-Block Elements: The Key to the Next Generation of Chelating Agents for Radiopharmaceuticals journal March 2015
Effects of Ligand Geometry on the Photophysical Properties of Photoluminescent Eu(III) and Sm(III) 1-Hydroxypyridin-2-one Complexes in Aqueous Solution journal December 2015
Structural and Thermodynamic Properties of the Cm III Ion Solvated by Water and Methanol journal April 2016
Ligand-Sensitized Lanthanide Nanocrystals: Merging Solid-State Photophysics and Molecular Solution Chemistry journal June 2016
Engineered Recognition of Tetravalent Zirconium and Thorium by Chelator–Protein Systems: Toward Flexible Radiotherapy and Imaging Platforms journal November 2016
Coordination Chemistry of a Strongly-Donating Hydroxylamine with Early Actinides: An Investigation of Redox Properties and Electronic Structure journal March 2018
Synthesis and Characterization of the Actinium Aquo Ion journal February 2017
Enhanced Ultraviolet Photon Capture in Ligand-Sensitized Nanocrystals journal March 2016
Gd−Hydroxypyridinone (HOPO)-Based High-Relaxivity Magnetic Resonance Imaging (MRI) Contrast Agents journal July 2009
Rational Design of Sequestering Agents for Plutonium and Other Actinides journal November 2003
Applications of Polarizable Continuum Models To Determine Accurate Solution-Phase Thermochemical Values Across a Broad Range of Cation Charge – The Case of U(III–VI) journal December 2014
Plutonium(IV) Sequestration: Structural and Thermodynamic Evaluation of the Extraordinarily Stable Cerium(IV) Hydroxypyridinonate Complexes1 journal September 2000
Specific sequestering agents for the actinides. 9. Synthesis of metal complexes of 1-hydroxy-2-pyridinone and the crystal structure of tetrakis(1-oxy-2-pyridinone)aquathorium(IV) dihydrate journal December 1983
Ferric ion sequestering agents. 13. Synthesis, structures, and thermodynamics of complexation of cobalt(III) and iron(III) tris complexes of several chelating hydroxypyridinones journal March 1985
Gadolinium(III) 1,2-Hydroxypyridonate-Based Complexes: Toward MRI Contrast Agents of High Relaxivity1 journal September 2004
Eu(III) Complexes of Functionalized Octadentate 1-Hydroxypyridin-2-ones: Stability, Bioconjugation, and Luminescence Resonance Energy Transfer Studies journal November 2010
Does Covalency Increase or Decrease across the Actinide Series? Implications for Minor Actinide Partitioning journal June 2012
Bonding Trends Traversing the Tetravalent Actinide Series: Synthesis, Structural, and Computational Analysis of An IV ( Ar acnac) 4 Complexes (An = Th, U, Np, Pu; Ar acnac = Ar N C(Ph)CHC(Ph) O ; Ar = 3,5- t Bu 2 C 6 H 3 ) journal July 2012
Hydration Properties and Ionic Radii of Actinide(III) Ions in Aqueous Solution journal August 2013
Solution Thermodynamic Stability of Complexes Formed with the Octadentate Hydroxypyridinonate Ligand 3,4,3-LI(1,2-HOPO): A Critical Feature for Efficient Chelation of Lanthanide(IV) and Actinide(IV) Ions journal July 2013
Luminescent Lanthanide Cryptates: from the Bench to the Bedside journal December 2013
Highly Luminescent Lanthanide Complexes of 1-Hydroxy-2-pyridinones journal April 2008
Theoretical Studies on the Redox Potentials of Fe Dinuclear Complexes as Models for Hydrogenase journal October 2008
Aryl Bridged 1-Hydroxypyridin-2-one: Effect of the Bridge on the Eu(III) Sensitization Process journal September 2009
Using the Antenna Effect as a Spectroscopic Tool: Photophysics and Solution Thermodynamics of the Model Luminescent Hydroxypyridonate Complex [Eu III (3,4,3-LI(1,2-HOPO))] journal December 2009
Uranyl Sequestering Agents:  Correlation of Properties and Efficacy with Structure for UO 2 2+ Complexes of Linear Tetradentate 1-Methyl-3-hydroxy-2(1 H )-pyridinone Ligands 1 journal January 1999
Conductor-like Screening Model for Real Solvents: A New Approach to the Quantitative Calculation of Solvation Phenomena journal February 1995
A Highly Stable Gadolinium Complex with a Fast, Associative Mechanism of Water Exchange journal November 2003
Cymothoe sangaris”:  An Extremely Stable and Highly Luminescent 1,2-Hydroxypyridinonate Chelate of Eu(III) July 2006
Characterization of a Mixed Salt of 1-Hydroxypyridin-2-one Pu(IV) Complexes 1 journal May 2007
Experimental and Theoretical Comparison of the O K-Edge Nonresonant Inelastic X-ray Scattering and X-ray Absorption Spectra of NaReO 4 journal October 2010
Determining Relative f and d Orbital Contributions to M–Cl Covalency in MCl 6 2– (M = Ti, Zr, Hf, U) and UOCl 5 Using Cl K-Edge X-ray Absorption Spectroscopy and Time-Dependent Density Functional Theory journal March 2012
New Insights into Structure and Luminescence of Eu III and Sm III Complexes of the 3,4,3-LI(1,2-HOPO) Ligand journal February 2015
On the Origin of Covalent Bonding in Heavy Actinides journal July 2017
Specific Sequestering Agents for the Actinides. 28. Synthesis and Initial Evaluation of Multidentate 4-Carbamoyl-3-hydroxy-1-methyl-2(1H)-pyridinone Ligands for in Vivo Plutonium(IV) Chelation journal July 1995
Specific sequestering agents for the actinides. 16. Synthesis and initial biological testing of polydentate oxohydroxypyridinecarboxylate ligands journal January 1988
Alternative Chelator for 89 Zr Radiopharmaceuticals: Radiolabeling and Evaluation of 3,4,3-(LI-1,2-HOPO) journal December 2013
Predicting the Energy of the Water Exchange Reaction and Free Energy of Solvation for the Uranyl Ion in Aqueous Solution journal July 2006
Hydration Shell Structure and Dynamics of Curium(III) in Aqueous Solution: First Principles and Empirical Studies journal May 2011
Importance of Counteranions on the Hydration Structure of the Curium Ion journal June 2013
Chelation and stabilization of berkelium in oxidation state +IV journal April 2017
Spectroscopic and computational investigation of actinium coordination chemistry journal August 2016
Approaching actinide(+III) hydration from first principles journal January 2007
Anion binding in water at lanthanide centres: from structure and selectivity to signalling and sensing journal January 2013
New evidence for 5f covalency in actinocenes determined from carbon K-edge XAS and electronic structure theory journal January 2014
First structural characterization of Pa( iv ) in aqueous solution and quantum chemical investigations of the tetravalent actinides up to Bk( iv ): the evidence of a curium break journal January 2016
Intramolecular sensitization of americium luminescence in solution: shining light on short-lived forbidden 5f transitions journal January 2016
Bonding trends across the series of tricarbonato-actinyl anions [(AnO 2 )(CO 3 ) 3 ] 4− (An = U–Cm): the plutonium turn journal January 2017
Toxic heavy metal – Pb, Cd, Sn – complexation by the octadentate hydroxypyridinonate ligand archetype 3,4,3-LI(1,2-HOPO) journal January 2018
COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient journal January 1993
Parameter-free calculations of X-ray spectra with FEFF9 journal January 2010
Covalency in AnCp4 (An = Th–Cm): a comparison of molecular orbital, natural population and atoms-in-molecules analyses journal January 2010
3,4,3-LI(1,2-HOPO): In vitro formation of highly stable lanthanide complexes translates into efficacious in vivo europium decorporation journal January 2011
Intriguing aspects of lanthanide luminescence journal January 2013
Valence basis sets for relativistic energy-consistent small-core actinide pseudopotentials journal January 2003
A Variation of the F-Test for Determining Statistical Relevance of Particular Parameters in EXAFS Fits
  • Downward, L.; Booth, C. H.; Lukens, W. W.
  • X-RAY ABSORPTION FINE STRUCTURE - XAFS13: 13th International Conference, AIP Conference Proceedings https://doi.org/10.1063/1.2644450
conference January 2007
Energy‐adjusted pseudopotentials for the actinides. Parameter sets and test calculations for thorium and thorium monoxide journal May 1994
Treatment of the outlying charge in continuum solvation models journal December 1996
Siderocalin-mediated recognition, sensitization, and cellular uptake of actinides journal August 2015
Lanthanide Complexes for Luminescence Imaging Applications journal January 2005
Confirmation of standard error analysis techniques applied to EXAFS using simulations journal November 2009
Development of Decorporation Agents for the Actinides journal October 1998
In Vivo Chelation of Am(III), Pu(IV), Np(V), and U(VI) in Mice by TREN-(Me-3,2-HOPO) journal May 1994
A Public Health Perspective on the U.S. Response to the Fukushima Radiological Emergency journal January 2015
Biomimetic Actinide Chelators: an Update on the Preclinical Development of the Orally Active Hydroxypyridonate Decorporation Agents 3,4,3-Li(1,2-Hopo) and 5-Lio(Me-3,2-Hopo) journal January 2010
X-ray-absorption fine-structure standards: A comparison of experiment and theory journal September 1995
Covalency in the actinide dioxides: Systematic study of the electronic properties using screened hybrid density functional theory journal July 2007
Generalized Gradient Approximation Made Simple journal October 1996
Revised effective ionic radii and systematic studies of interatomic distances in halides and chalcogenides journal September 1976
Actinide Environmental Chemistry journal December 1995
Solution thermodynamic evaluation of hydroxypyridinonate chelators 3,4,3-LI(1,2-HOPO) and 5-LIO(Me-3,2-HOPO) for UO 2 (VI) and Th(IV) decorporation journal June 2013
238 Pu elimination profiles after delayed treatment with 3,4,3LI(1,2HOPO) in female and male Swiss-Webster mice journal August 2014

Cited By (9)

Spontaneous Chelation‐Driven Reduction of the Neptunyl Cation in Aqueous Solution journal February 2020
Ultra-selective ligand-driven separation of strategic actinides journal June 2019
Revisiting complexation thermodynamics of transplutonium elements up to einsteinium journal January 2018
Reductive activation of neptunyl and plutonyl oxo species with a hydroxypyridinone chelating ligand journal January 2018
Soft-donor dipicolinamide derivatives for selective actinide( iii )/lanthanide( iii ) separation: the role of S- vs. O-donor sites journal January 2019
The coordination chemistry of lanthanide and actinide metal ions with hydroxypyridinone-based decorporation agents: orbital and density based analyses journal January 2018
Is hydroxypyridonate 3,4,3-LI(1,2-HOPO) a good competitor of fetuin for uranyl metabolism? journal January 2019
Lanthanide and actinide doped B 12 H 12 2− and Al 12 H 12 2− clusters: new magnetic superatoms with f-block elements journal January 2019
Inducing selectivity and chirality in group IV metal coordination with high-denticity hydroxypyridinones journal January 2019

Similar Records

3,4,3-LI(1,2-HOPO): In Vitro Formation of Highly Stable Lanthanide Complexes Translates into Efficacious In Vivo Europium Decorporation
Journal Article · Wed Jul 13 00:00:00 EDT 2011 · Dalton Transactions · OSTI ID:1051843

Toxic heavy metal – Pb, Cd, Sn – complexation by the octadentate hydroxypyridinonate ligand archetype 3,4,3-LI(1,2-HOPO)
Journal Article · Thu Feb 01 19:00:00 EST 2018 · New Journal of Chemistry · OSTI ID:1458507