Combinatorial design of multimeric chelating peptoids for selective metal coordination

Ricano, Abel; Captain, Ilya; Carter, Korey P.; Nell, Bryan P.; Deblonde, Gauthier J. -P.; Abergel, Rebecca J.

doi:10.1039/c9sc01068h

Title: Combinatorial design of multimeric chelating peptoids for selective metal coordination

Journal Article · 12 June 2019 · Chemical Science

DOI: https://doi.org/10.1039/c9sc01068h · OSTI ID:1525901

Ricano, Abel ^[1]; Captain, Ilya ^[1];

^[1];

^[2]

Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States); Univ. of California, Berkeley, CA (United States)

Current methods for metal chelation are generally based on multidentate organic ligands, which are generated through cumbersome multistep synthetic processes that lack flexibility for systematically varying metal-binding motifs. Octadentate ligands incorporating hydroxypyridinone or catecholamide binding moieties onto a spermine scaffold are known to display some of the highest affinities towards f-elements. Enhancing binding affinity for specific lanthanide or actinide ions however, necessitates ligand architectures that allow for modular and high throughput synthesis. Here we introduce a high-throughput combinatorial library of 16 tetrameric N-substituted glycine oligomers (peptoids) containing hydroxypyridinone or catecholamide chelating units linked via an ethylenediamine bridge and, for comparison, we also synthesized the corresponding mixed ligands derived from the spermine scaffold: 3,4,3-LI(1,2-HOPO)₂(CAM)₂ and 3,4,3-LI(CAM)₂(1,2-HOPO)₂. Coordination-based luminescence studies were carried out with Eu³⁺ and Tb³⁺ to begin probing the properties of the new ligand architecture and revealed higher sensitization efficiency with the spermine scaffold as well as different spectroscopic features among the structural peptoid isomers. Solution thermodynamic properties of selected ligands revealed different coordination properties between the spermine and peptoid analogues with Eu³⁺ stability constants log β₁₁₀ ranging from 28.88 ± 3.45 to 43.97 ± 0.49. The general synthetic strategy presented here paves the way for precision design of new specific and versatile ligands, with a variety of applications tailored towards the use of f-elements, including separations, optical device optimization, and pharmaceutical development.

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

Sponsoring Organization:: USDOE Office of Nuclear Energy (NE)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1525901

Alternate ID(s):: OSTI ID: 1560603

Journal Information:: Chemical Science, Vol. 10, Issue 28; ISSN 2041-6520

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

References (52)

Lanthanides: Applications in Cancer Diagnosis and Therapy: Miniperspective Teo, Ruijie D.; Termini, John; Gray, Harry B. Journal of Medicinal Chemistry, Vol. 59, Issue 13 https://doi.org/10.1021/acs.jmedchem.5b01975	journal	February 2016
Synthesis and luminescence properties of lanthanide complexes with a new tripodal ligand featuring N -thenylsalicylamide arms : Luminescent lanthanide coordination polymer Song, Xue-Qin; Zheng, Qing-Fang; Wang, Li Luminescence, Vol. 27, Issue 6 https://doi.org/10.1002/bio.1375	journal	January 2012
A rationally designed metal-binding helical peptoid for selective recognition processes Baskin, Maria; Maayan, Galia Chemical Science, Vol. 7, Issue 4 https://doi.org/10.1039/C5SC04358A	journal	January 2016
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 Deblonde, Gauthier J-P.; Sturzbecher-Hoehne, Manuel; Abergel, Rebecca J. Inorganic Chemistry, Vol. 52, Issue 15 https://doi.org/10.1021/ic4010246	journal	July 2013
New Insights into Structure and Luminescence of Eu ^III and Sm ^III Complexes of the 3,4,3-LI(1,2-HOPO) Ligand Daumann, Lena J.; Tatum, David S.; Snyder, Benjamin E. R. Journal of the American Chemical Society, Vol. 137, Issue 8 https://doi.org/10.1021/ja5116524	journal	February 2015
A Peptoid-Based Combinatorial and Computational Approach to Developing Ligands for Uranyl Sequestration from Seawater Parker, Bernard F.; Knight, Abigail S.; Vukovic, Sinisa Industrial & Engineering Chemistry Research, Vol. 55, Issue 15 https://doi.org/10.1021/acs.iecr.5b03500	journal	December 2015
Engineered Recognition of Tetravalent Zirconium and Thorium by Chelator–Protein Systems: Toward Flexible Radiotherapy and Imaging Platforms Captain, Ilya; Deblonde, Gauthier J. -P.; Rupert, Peter B. Inorganic Chemistry, Vol. 55, Issue 22 https://doi.org/10.1021/acs.inorgchem.6b02041	journal	November 2016
Rational Design of Sequestering Agents for Plutonium and Other Actinides Gorden, Anne E. V.; Xu, Jide; Raymond, Kenneth N. Chemical Reviews, Vol. 103, Issue 11 https://doi.org/10.1021/cr990114x	journal	November 2003
A modular platform to develop peptoid-based selective fluorescent metal sensors Knight, Abigail S.; Kulkarni, Rishikesh U.; Zhou, Effie Y. Chemical Communications, Vol. 53, Issue 24 https://doi.org/10.1039/C7CC00931C	journal	January 2017
Photoluminescence of lanthanide aromatic carboxylates Utochnikova, V. V.; Kuzmina, N. P. Russian Journal of Coordination Chemistry, Vol. 42, Issue 10 https://doi.org/10.1134/S1070328416090074	journal	October 2016
Spectroscopic and Computational Characterization of Diethylenetriaminepentaacetic Acid/Transplutonium Chelates: Evidencing Heterogeneity in the Heavy Actinide(III) Series Deblonde, Gauthier J. -P.; Kelley, Morgan P.; Su, Jing Angewandte Chemie International Edition, Vol. 57, Issue 17 https://doi.org/10.1002/anie.201709183	journal	March 2018
A Macrocyclic Chelator That Selectively Binds Ln ⁴⁺ over Ln ³⁺ by a Factor of 10 ²⁹ Pham, Tiffany A.; Altman, Alison B.; Stieber, S. Chantal E. Inorganic Chemistry, Vol. 55, Issue 20 https://doi.org/10.1021/acs.inorgchem.6b00684	journal	June 2016
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) Abergel, Rebecca J.; Durbin, Patricia W.; Kullgren, Birgitta Health Physics, Vol. 99, Issue 3 https://doi.org/10.1097/HP.0b013e3181c21273	journal	January 2010
Relative and absolute determination of fluorescence quantum yields of transparent samples Würth, Christian; Grabolle, Markus; Pauli, Jutta Nature Protocols, Vol. 8, Issue 8 https://doi.org/10.1038/nprot.2013.087	journal	July 2013
3,4,3-LI(1,2-HOPO): In vitro formation of highly stable lanthanide complexes translates into efficacious in vivo europium decorporation Sturzbecher-Hoehne, Manuel; Ng Pak Leung, Clara; D'Aléo, Anthony Dalton Transactions, Vol. 40, Issue 33 https://doi.org/10.1039/c1dt10840a	journal	January 2011
Correlation between the lowest triplet state energy level of the ligand and lanthanide(III) luminescence quantum yield Latva, Martti; Takalo, Harri; Mukkala, Veli-Matti Journal of Luminescence, Vol. 75, Issue 2 https://doi.org/10.1016/S0022-2313(97)00113-0	journal	September 1997
Relations between Intramolecular Energy Transfer Efficiencies and Triplet State Energies in Rare Earth β-diketone Chelates Sato, Susumu; Wada, Masanobu Bulletin of the Chemical Society of Japan, Vol. 43, Issue 7 https://doi.org/10.1246/bcsj.43.1955	journal	July 1970
Development of peptoid-based ligands for the removal of cadmium from biological media Knight, Abigail S.; Zhou, Effie Y.; Francis, Matthew B. Chemical Science, Vol. 6, Issue 7 https://doi.org/10.1039/C5SC00676G	journal	January 2015
p -SCN-Bn-HOPO: A Superior Bifunctional Chelator for ⁸⁹ Zr ImmunoPET Deri, Melissa A.; Ponnala, Shashikanth; Kozlowski, Paul Bioconjugate Chemistry, Vol. 26, Issue 12 https://doi.org/10.1021/acs.bioconjchem.5b00572	journal	November 2015
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))] ⁻ Abergel, Rebecca J.; D’Aléo, Anthony; Ng Pak Leung, Clara Inorganic Chemistry, Vol. 48, Issue 23 https://doi.org/10.1021/ic9013703	journal	December 2009
Preparation and photophysical studies of [Ln(hfac)3DPEPO], Ln = Eu, Tb, Yb, Nd, Gd; interpretation of total photoluminescence quantum yields Congiu, Martina; Alamiry, Mohamed; Moudam, Omar Dalton Transactions, Vol. 42, Issue 37 https://doi.org/10.1039/c3dt51380g	journal	January 2013
Hydroxypyridinonate Complex Stability of Group (IV) Metals and Tetravalent f-Block Elements: The Key to the Next Generation of Chelating Agents for Radiopharmaceuticals Sturzbecher-Hoehne, Manuel; Choi, Taylor A.; Abergel, Rebecca J. Inorganic Chemistry, Vol. 54, Issue 7 https://doi.org/10.1021/acs.inorgchem.5b00033	journal	March 2015
Chelating agents for radiolanthanides: Applications to imaging and therapy Amoroso, Angelo J.; Fallis, Ian A.; Pope, Simon J. A. Coordination Chemistry Reviews, Vol. 340 https://doi.org/10.1016/j.ccr.2017.01.010	journal	June 2017
On the design of highly luminescent lanthanide complexes Bünzli, Jean-Claude G. Coordination Chemistry Reviews, Vol. 293-294 https://doi.org/10.1016/j.ccr.2014.10.013	journal	June 2015
Restricted Speciation and Supramolecular Assembly in the 5f Block Carter, Korey P.; Surbella, Robert G.; Kalaj, Mark Chemistry - A European Journal, Vol. 24, Issue 49 https://doi.org/10.1002/chem.201801044	journal	July 2018
Chiral Cu( ii ), Co( ii ) and Ni( ii ) complexes based on 2,2′-bipyridine modified peptoids Baskin, Maria; Maayan, Galia Dalton Transactions, Vol. 47, Issue 31 https://doi.org/10.1039/C8DT01308J	journal	January 2018
Interpretation of europium(III) spectra Binnemans, Koen Coordination Chemistry Reviews, Vol. 295 https://doi.org/10.1016/j.ccr.2015.02.015	journal	July 2015
Redox and environmentally relevant aspects of actinide(IV) coordination chemistry Natrajan, Louise S.; Swinburne, Adam N.; Andrews, Michael B. Coordination Chemistry Reviews, Vol. 266-267 https://doi.org/10.1016/j.ccr.2013.12.021	journal	May 2014
Radiometals for Combined Imaging and Therapy Cutler, Cathy S.; Hennkens, Heather M.; Sisay, Nebiat Chemical Reviews, Vol. 113, Issue 2, p. 858-883 https://doi.org/10.1021/cr3003104	journal	October 2012
Selective Chromium(VI) Ligands Identified Using Combinatorial Peptoid Libraries Knight, Abigail S.; Zhou, Effie Y.; Pelton, Jeffrey G. Journal of the American Chemical Society, Vol. 135, Issue 46 https://doi.org/10.1021/ja408788t	journal	November 2013
Electronic Energy Levels in the Trivalent Lanthanide Aquo Ions. I. Pr ³⁺ , Nd ³⁺ , Pm ³⁺ , Sm ³⁺ , Dy ³⁺ , Ho ³⁺ , Er ³⁺ , and Tm ³⁺ Carnall, W. T.; Fields, P. R.; Rajnak, K. The Journal of Chemical Physics, Vol. 49, Issue 10 https://doi.org/10.1063/1.1669893	journal	November 1968
Synthesis, Characterization, and Luminescence of Europium(III) Schiff Base Complexes ¹ ^a Archer, Ronald D.; Chen, Huiyong; Thompson, Larry C. Inorganic Chemistry, Vol. 37, Issue 8 https://doi.org/10.1021/ic960244d	journal	April 1998
Evaluating the potential of chelation therapy to prevent and treat gadolinium deposition from MRI contrast agents Rees, Julian A.; Deblonde, Gauthier J. -P.; An, Dahlia D. Scientific Reports, Vol. 8, Issue 1 https://doi.org/10.1038/s41598-018-22511-6	journal	March 2018
Luminescence study on preferential solvation of Europium(III) in water/non-aqueous solvent mixtures Kimura, Takaumi; Nagaishi, Ryuji; Kato, Yoshiharu Journal of Alloys and Compounds, Vol. 323-324 https://doi.org/10.1016/S0925-8388(01)01121-5	journal	July 2001
Chelation and stabilization of berkelium in oxidation state +IV Deblonde, Gauthier J. -P.; Sturzbecher-Hoehne, Manuel; Rupert, Peter B. Nature Chemistry, Vol. 9, Issue 9 https://doi.org/10.1038/nchem.2759	journal	April 2017
Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands Uhlir, Linda C.; Durbin, Patricia W.; Jeung, Nylan Journal of Medicinal Chemistry, Vol. 36, Issue 4, p. 504-509 https://doi.org/10.1021/jm00056a011	journal	February 1993
Rational Design of Sequestering Agents for Plutonium and Other Actinides Gorden, Anne E. V.; Xu, Jide; Raymond, Kenneth N. ChemInform, Vol. 35, Issue 5 https://doi.org/10.1002/chin.200405275	journal	February 2004
Direct solid-phase synthesis of molecular heterooligonuclear lanthanoid-complexes Kreidt, Elisabeth; Leis, Wolfgang; Seitz, Michael Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-020-15199-8	journal	March 2020
Spectroscopic and Computational Characterization of Diethylenetriaminepentaacetic Acid/Transplutonium Chelates: Evidencing Heterogeneity in the Heavy Actinide(III) Series Deblonde, Gauthier J. -P.; Kelley, Morgan P.; Su, Jing Angewandte Chemie, Vol. 130, Issue 17 https://doi.org/10.1002/ange.201709183	journal	March 2018
Restricted Speciation and Supramolecular Assembly in the 5f Block Carter, Korey P.; Surbella, Robert G.; Kalaj, Mark Chemistry - A European Journal, Vol. 24, Issue 49 https://doi.org/10.1002/chem.201801044	journal	July 2018
Hydroxypyridinonate Complex Stability of Group (IV) Metals and Tetravalent f-Block Elements: The Key to the Next Generation of Chelating Agents for Radiopharmaceuticals Sturzbecher-Hoehne, Manuel; Choi, Taylor A.; Abergel, Rebecca J. Inorganic Chemistry, Vol. 54, Issue 7 https://doi.org/10.1021/acs.inorgchem.5b00033	journal	March 2015
Radiometals for Combined Imaging and Therapy Cutler, Cathy S.; Hennkens, Heather M.; Sisay, Nebiat Chemical Reviews, Vol. 113, Issue 2, p. 858-883 https://doi.org/10.1021/cr3003104	journal	October 2012
Rational Design of Sequestering Agents for Plutonium and Other Actinides Gorden, Anne E. V.; Xu, Jide; Raymond, Kenneth N. Chemical Reviews, Vol. 103, Issue 11 https://doi.org/10.1021/cr990114x	journal	November 2003
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 Deblonde, Gauthier J-P.; Sturzbecher-Hoehne, Manuel; Abergel, Rebecca J. Inorganic Chemistry, Vol. 52, Issue 15 https://doi.org/10.1021/ic4010246	journal	July 2013
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))] ⁻ Abergel, Rebecca J.; D’Aléo, Anthony; Ng Pak Leung, Clara Inorganic Chemistry, Vol. 48, Issue 23 https://doi.org/10.1021/ic9013703	journal	December 2009
Selective Chromium(VI) Ligands Identified Using Combinatorial Peptoid Libraries Knight, Abigail S.; Zhou, Effie Y.; Pelton, Jeffrey G. Journal of the American Chemical Society, Vol. 135, Issue 46 https://doi.org/10.1021/ja408788t	journal	November 2013
New Insights into Structure and Luminescence of Eu ^III and Sm ^III Complexes of the 3,4,3-LI(1,2-HOPO) Ligand Daumann, Lena J.; Tatum, David S.; Snyder, Benjamin E. R. Journal of the American Chemical Society, Vol. 137, Issue 8 https://doi.org/10.1021/ja5116524	journal	February 2015
Specific sequestering agents for the actinides. 21. Synthesis and initial biological testing of octadentate mixed catecholate-hydroxypyridinonate ligands Uhlir, Linda C.; Durbin, Patricia W.; Jeung, Nylan Journal of Medicinal Chemistry, Vol. 36, Issue 4, p. 504-509 https://doi.org/10.1021/jm00056a011	journal	February 1993
Chelation and stabilization of berkelium in oxidation state +IV Deblonde, Gauthier J. -P.; Sturzbecher-Hoehne, Manuel; Rupert, Peter B. Nature Chemistry, Vol. 9, Issue 9 https://doi.org/10.1038/nchem.2759	journal	April 2017
Relative and absolute determination of fluorescence quantum yields of transparent samples Würth, Christian; Grabolle, Markus; Pauli, Jutta Nature Protocols, Vol. 8, Issue 8 https://doi.org/10.1038/nprot.2013.087	journal	July 2013
3,4,3-LI(1,2-HOPO): In vitro formation of highly stable lanthanide complexes translates into efficacious in vivo europium decorporation Sturzbecher-Hoehne, Manuel; Ng Pak Leung, Clara; D'Aléo, Anthony Dalton Transactions, Vol. 40, Issue 33 https://doi.org/10.1039/c1dt10840a	journal	January 2011
Preparation and photophysical studies of [Ln(hfac)3DPEPO], Ln = Eu, Tb, Yb, Nd, Gd; interpretation of total photoluminescence quantum yields Congiu, Martina; Alamiry, Mohamed; Moudam, Omar Dalton Transactions, Vol. 42, Issue 37 https://doi.org/10.1039/c3dt51380g	journal	January 2013

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