Examining Interactions of Uranyl(VI) Ions with Amino Acids in the Gas Phase

Lucena, Ana Filipa Folgado de; Maria, Leonor; Gibson, John K.; Marçalo, Joaquim

doi:10.3390/app13063834

Title: Examining Interactions of Uranyl(VI) Ions with Amino Acids in the Gas Phase

Journal Article · 16 March 2023 · Applied Sciences

DOI: https://doi.org/10.3390/app13063834 · OSTI ID:2229664

^[1];

^[2]; Gibson, John K. ^[3];

^[2]

Inst. of Superior Tecnico (IST), Lisbon (Portugal); Univ. of Lisbon (Portugal); European Commission, Geel (Belgium). Joint Research Centre (JRC)
Inst. of Superior Tecnico (IST), Lisbon (Portugal); Univ. of Lisbon (Portugal)
Lawrence Berkeley National Laboratory (LBNL), Berkeley, CA (United States)

Gas-phase experiments, using electrospray ionization quadrupole ion trap mass spectrometry (ESI-QIT/MS), were conducted to probe basic interactions of the uranyl(VI) ion, UO₂²⁺, with selected natural amino acids, namely, L-cysteine (Cys), L-histidine (His), and L-aspartic acid (Asp), which strongly bind to metal ions. The simplest amino acid, glycine (Gly), was also studied for comparison. Cys, His, and Asp have additional potentially coordinating groups beyond the amino and carboxylic acid functional groups, specifically thiol in Cys, imidazole in His, and a second carboxylate in Asp. Gas-phase experiments comprised collision-induced dissociation (CID) of uranyl–amino acid complexes and competitive CID to assess the relative binding strength of different amino acids in the same uranyl complex. Reactivity of selected uranyl–amino acid complexes with water provided further insights into relative stabilities. In positive ion mode, CID and ensuing reactions with water suggested that uranyl–neutral AA binding strength decreased in the order His > Asp > Cys > Gly, which is similar to amino acid proton affinities. In negative ion mode, CID revealed a decreasing dissociation tendency in the order Gly >> His ≈ Cys > Asp, presumably reflecting a reverse enhanced binding to uranyl of the doubly deprotonated amino acids formed in CID.

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

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences & Biosciences Division (CSGB)

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 2229664

Journal Information:: Applied Sciences, Journal Name: Applied Sciences Journal Issue: 6 Vol. 13; ISSN 2076-3417

Publisher:: MDPICopyright Statement

Country of Publication:: United States

Language:: English

References (51)

Sensors for determination of uranium: A review Wu, Xumeng; Huang, Qiuxiang; Mao, Yu TrAC Trends in Analytical Chemistry, Vol. 118 https://doi.org/10.1016/j.trac.2019.04.026	journal	September 2019
Can Electrospray Mass Spectrometry Quantitatively Probe Speciation? Hydrolysis of Uranyl Nitrate Studied by Gas-Phase Methods Tsierkezos, Nikos G.; Roithová, Jana; Schröder, Detlef Inorganic Chemistry, Vol. 48, Issue 13 https://doi.org/10.1021/ic900575r	journal	July 2009
Advances in the investigation of dioxouranium(VI) complexes of interest for natural fluids Berto, Silvia; Crea, Francesco; Daniele, Pier Giuseppe Coordination Chemistry Reviews, Vol. 256, Issue 1-2 https://doi.org/10.1016/j.ccr.2011.08.015	journal	January 2012
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 Sturzbecher-Hoehne, M.; Deblonde, G. J. -P.; Abergel, R. J. Radiochimica Acta, Vol. 101, Issue 6 https://doi.org/10.1524/ract.2013.2047	journal	June 2013
Novel drug delivery systems for actinides (uranium and plutonium) decontamination agents Fattal, Elias; Tsapis, Nicolas; Phan, Guillaume Advanced Drug Delivery Reviews, Vol. 90 https://doi.org/10.1016/j.addr.2015.06.009	journal	August 2015
Receptor recognition of transferrin bound to lanthanides and actinides: a discriminating step in cellular acquisition of f-block metals Deblonde, Gauthier J. -P.; Sturzbecher-Hoehne, Manuel; Mason, Anne B. Metallomics, Vol. 5, Issue 6 https://doi.org/10.1039/c3mt20237b	journal	January 2013
Structural features of uranium-protein complexes Carugo, Oliviero Journal of Inorganic Biochemistry, Vol. 189 https://doi.org/10.1016/j.jinorgbio.2018.08.014	journal	December 2018
Optimized Coordination of Uranyl in Engineered Calmodulin Site 1 Provides a Subnanomolar Affinity for Uranyl and a Strong Uranyl versus Calcium Selectivity Pardoux, Romain; Sauge-Merle, Sandrine; Bremond, Nicolas Inorganic Chemistry, Vol. 61, Issue 50 https://doi.org/10.1021/acs.inorgchem.2c03185	journal	December 2022
Coordination chemistry of f-block metal ions with ligands bearing bio-relevant functional groups Götzke, Linda; Schaper, Gerrit; März, Juliane Coordination Chemistry Reviews, Vol. 386 https://doi.org/10.1016/j.ccr.2019.01.006	journal	May 2019
UO ₂ ²⁺ Uptake by Proteins: Understanding the Binding Features of the Super Uranyl Binding Protein and Design of a Protein with Higher Affinity Odoh, Samuel O.; Bondarevsky, Gary D.; Karpus, Jason Journal of the American Chemical Society, Vol. 136, Issue 50 https://doi.org/10.1021/ja5087563	journal	December 2014
Potassium Binding Interactions with Aliphatic Amino Acids: Thermodynamic and Entropic Effects Analyzed via a Guided Ion Beam and Computational Study Jones, Roland M.; Nilsson, Taylor; Walker, Samantha Journal of the American Society for Mass Spectrometry, Vol. 33, Issue 8 https://doi.org/10.1021/jasms.2c00079	journal	May 2022
What do we know about actinides-proteins interactions? Creff, Gaëlle; Zurita, Cyril; Jeanson, Aurélie Radiochimica Acta, Vol. 107, Issue 9-11 https://doi.org/10.1515/ract-2019-3120	journal	July 2019
Mass spectrometric and theoretical study on the formation of uranyl hydride from uranyl carboxylate Xiong, Zhixin; Chen, Xiuting; Gong, Yu Physical Chemistry Chemical Physics, Vol. 23, Issue 36 https://doi.org/10.1039/D1CP03092B	journal	January 2021
A review on the interrogation of peptide–metal interactions using electrospray ionization-mass spectrometry Carlton, Doug D.; Schug, Kevin A. Analytica Chimica Acta, Vol. 686, Issue 1-2 https://doi.org/10.1016/j.aca.2010.11.050	journal	February 2011
Energetics and mechanisms for decomposition of cationized amino acids and peptides explored using guided ion beam tandem mass spectrometry Armentrout, P. B. Mass Spectrometry Reviews https://doi.org/10.1002/mas.21723	journal	August 2021
A Thermodynamic “Vocabulary” for Metal Ion Interactions in Biological Systems Rodgers, M. T.; Armentrout, P. B. Accounts of Chemical Research, Vol. 37, Issue 12 https://doi.org/10.1021/ar0302843	journal	November 2004
High-resolution threshold photodetachment spectroscopy of OH − Smith, Jim R.; Kim, Joseph B.; Lineberger, W. C. Physical Review A, Vol. 55, Issue 3 https://doi.org/10.1103/PhysRevA.55.2036	journal	March 1997
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
Two-Electron Three-Centered Bond in Side-On (η ² ) Uranyl(V) Superoxo Complexes Bryantsev, Vyacheslav S.; Jong, Wibe A. de; Cossel, Kevin C. The Journal of Physical Chemistry A, Vol. 112, Issue 26 https://doi.org/10.1021/jp804202q	journal	July 2008
Gas-Phase Deconstruction of UO₂²⁺: Mass Spectrometry Evidence for Generation of [OU^VICH]⁺ by Collision-Induced Dissociation of [U^VIO₂(C≡CH)]⁺ van Stipdonk, Michael J.; Tatosian, Irena J.; Iacovino, Anna C. Journal of the American Society for Mass Spectrometry, Vol. 30, Issue 5 https://doi.org/10.1007/s13361-019-02179-6	journal	March 2019
Thermodynamic and Structural Investigation of Synthetic Actinide–Peptide Scaffolds Safi, Samir; Jeanson, Aurélie; Roques, Jérome Inorganic Chemistry, Vol. 55, Issue 2 https://doi.org/10.1021/acs.inorgchem.5b02379	journal	January 2016
Infrared Multiphoton Dissociation Spectroscopy with Free-Electron Lasers: On the Road from Small Molecules to Biomolecules Jašíková, Lucie; Roithová, Jana Chemistry - A European Journal, Vol. 24, Issue 14 https://doi.org/10.1002/chem.201705692	journal	February 2018
Engineering Short Peptide Sequences for Uranyl Binding Lebrun, Colette; Starck, Matthieu; Gathu, Vicky Chemistry – A European Journal, Vol. 20, Issue 50 https://doi.org/10.1002/chem.201404546	journal	October 2014
Revisiting Fragmentation Reactions of Protonated α-Amino Acids by High-Resolution Electrospray Ionization Tandem Mass Spectrometry with Collision-Induced Dissociation Zhang, Pengwei; Chan, Wan; Ang, Irene L. Scientific Reports, Vol. 9, Issue 1 https://doi.org/10.1038/s41598-019-42777-8	journal	April 2019
A protein engineered to bind uranyl selectively and with femtomolar affinity Zhou, Lu; Bosscher, Mike; Zhang, Changsheng Nature Chemistry, Vol. 6, Issue 3 https://doi.org/10.1038/nchem.1856	journal	January 2014
Characterization of UO ₂ ²⁺ binding to osteopontin, a highly phosphorylated protein: insights into potential mechanisms of uranyl accumulation in bones Qi, Lei; Basset, Christian; Averseng, Olivier Metallomics, Vol. 6, Issue 1 https://doi.org/10.1039/C3MT00269A	journal	January 2014
Cyclic Phosphopeptides to Rationalize the Role of Phosphoamino Acids in Uranyl Binding to Biological Targets Starck, Matthieu; Laporte, Fanny A.; Oros, Stephane Chemistry – A European Journal, Vol. 23, Issue 22 https://doi.org/10.1002/chem.201605481	journal	March 2017
CRC Handbook of Chemistry and Physics Haynes, W. M.; Lide, David R.; Bruno, Thomas J. CRC press https://doi.org/10.1201/9781315380476	book	June 2016
A review of recent trends in electrospray ionisation–mass spectrometry for the analysis of metal–organic ligand complexes Keith-Roach, Miranda J. Analytica Chimica Acta, Vol. 678, Issue 2 https://doi.org/10.1016/j.aca.2010.08.023	journal	September 2010
Synthesis and Hydrolysis of Uranyl, Neptunyl, and Plutonyl Gas-Phase Complexes Exhibiting Discrete Actinide–Carbon Bonds Dau, Phuong D.; Rios, Daniel; Gong, Yu Organometallics, Vol. 35, Issue 9 https://doi.org/10.1021/acs.organomet.6b00079	journal	April 2016
Recent advances in uranyl binding in proteins thanks to biomimetic peptides Garai, Aditya; Delangle, Pascale Journal of Inorganic Biochemistry, Vol. 203 https://doi.org/10.1016/j.jinorgbio.2019.110936	journal	February 2020
Gas Phase Studies of the Pesci Decarboxylation Reaction: Synthesis, Structure, and Unimolecular and Bimolecular Reactivity of Organometallic Ions O’Hair, Richard A. J.; Rijs, Nicole J. Accounts of Chemical Research, Vol. 48, Issue 2 https://doi.org/10.1021/ar500377u	journal	January 2015
Recent Approaches for Chemical Speciation and Analysis by Electrospray Ionization (ESI) Mass Spectrometry Indelicato, Serena; Bongiorno, David; Ceraulo, Leopoldo Frontiers in Chemistry, Vol. 8 https://doi.org/10.3389/fchem.2020.625945	journal	January 2021
A novel fluorescence sensor for uranyl ion detection based on a dansyl-modified peptide Zhang, Lianshun; Jia, Mengqing; Wang, Xi Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, Vol. 292 https://doi.org/10.1016/j.saa.2023.122403	journal	May 2023
Fragmentation Reactions of Protonated α-Amino Acids Dookeran, Nyla N.; Yalcin, Talat; Harrison, Alex. G. Journal of Mass Spectrometry, Vol. 31, Issue 5 https://doi.org/10.1002/(SICI)1096-9888(199605)31:5<500::AID-JMS327>3.0.CO;2-Q	journal	May 1996
Cationic Noncovalent Interactions: Energetics and Periodic Trends Rodgers, M. T.; Armentrout, P. B. Chemical Reviews, Vol. 116, Issue 9 https://doi.org/10.1021/acs.chemrev.5b00688	journal	March 2016
Radionuclide speciation: A key point in the field of nuclear toxicology studies Bresson, Carole; Ansoborlo, Eric; Vidaud, Claude Journal of Analytical Atomic Spectrometry, Vol. 26, Issue 3 https://doi.org/10.1039/c0ja00223b	journal	January 2011
Gas-Phase Reactions of Molecular Oxygen with Uranyl(V) Anionic Complexes—Synthesis and Characterization of New Superoxides of Uranyl(VI) Lucena, Ana F.; Carretas, José M.; Marçalo, Joaquim The Journal of Physical Chemistry A, Vol. 119, Issue 15 https://doi.org/10.1021/acs.jpca.5b01445	journal	April 2015
Evaluated Gas Phase Basicities and Proton Affinities of Molecules: An Update Hunter, Edward P. L.; Lias, Sharon G. Journal of Physical and Chemical Reference Data, Vol. 27, Issue 3 https://doi.org/10.1063/1.556018	journal	May 1998
Emerging health risks and underlying toxicological mechanisms of uranium contamination: Lessons from the past two decades Ma, Minghao; Wang, Ruixia; Xu, Lining Environment International, Vol. 145 https://doi.org/10.1016/j.envint.2020.106107	journal	December 2020
Gas-phase acidities of the 20 protein amino acids Jones, Christopher M.; Bernier, Matthew; Carson, Erin International Journal of Mass Spectrometry, Vol. 267, Issue 1-3 https://doi.org/10.1016/j.ijms.2007.02.018	journal	November 2007
Addition of H ₂ O and O ₂ to Acetone and Dimethylsulfoxide Ligated Uranyl(V) Dioxocations Leavitt, Christopher M.; Bryantsev, Vyacheslav S.; Jong, Wibe A. de The Journal of Physical Chemistry A, Vol. 113, Issue 11 https://doi.org/10.1021/jp807651c	journal	March 2009
Fragmentation mechanisms of α-amino acids protonated under electrospray ionization: a collisional activation and ab initio theoretical study Rogalewicz, Françoise; Hoppilliard, Yannik; Ohanessian, Gilles International Journal of Mass Spectrometry, Vol. 195-196 https://doi.org/10.1016/S1387-3806(99)00225-0	journal	January 2000
Variable denticity in carboxylate binding to the uranyl coordination complexes Groenewold, Gary S.; Jong, Wibe A.; Oomens, Jos Journal of the American Society for Mass Spectrometry, Vol. 21, Issue 5 https://doi.org/10.1016/j.jasms.2010.01.021	journal	May 2010
Vibrational spectroscopy of bare and solvated ionic complexes of biological relevance Polfer, Nick C.; Oomens, Jos Mass Spectrometry Reviews, Vol. 28, Issue 3 https://doi.org/10.1002/mas.20215	journal	February 2009
Gas-Phase Uranyl, Neptunyl, and Plutonyl: Hydration and Oxidation Studied by Experiment and Theory Rios, Daniel; Michelini, Maria C.; Lucena, Ana F. Inorganic Chemistry, Vol. 51, Issue 12 https://doi.org/10.1021/ic3001625	journal	June 2012
Uranium(VI) bio-coordination chemistry from biochemical, solution and protein structural data Vanhorn, J.; Huang, H. Coordination Chemistry Reviews, Vol. 250, Issue 7-8 https://doi.org/10.1016/j.ccr.2005.09.010	journal	April 2006
Uranyl Binding to Proteins and Structural-Functional Impacts Lin, Ying-Wu Biomolecules, Vol. 10, Issue 3 https://doi.org/10.3390/biom10030457	journal	March 2020
Lauriston s. Taylor Lecture: the Quest for Therapeutic Actinide Chelators Durbin, Patricia W. Health Physics, Vol. 95, Issue 5 https://doi.org/10.1097/01.HP.0000326345.41816.c2	journal	January 2008
Electrospray mass spectrometry (ESI-MS) in the study of metal–ligand solution equilibria Di Marco, Valerio B.; Bombi, G. Giorgio Mass Spectrometry Reviews, Vol. 25, Issue 3 https://doi.org/10.1002/mas.20070	journal	January 2006
Binding of Molecular O ₂ to Di- and Triligated [UO ₂ ] ⁺ Groenewold, Gary S.; Cossel, Kevin C.; Gresham, Garold L. Journal of the American Chemical Society, Vol. 128, Issue 9 https://doi.org/10.1021/ja0573209	journal	March 2006

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38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
uranyl ions
amino acids
gas-phase ion chemistry
electrospray ionization mass spectrometry

Title: Examining Interactions of Uranyl(VI) Ions with Amino Acids in the Gas Phase

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References (51)

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