Analytical Chemistry, volume 93, issue 44, pages 14869-14877
Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?
Davide Corinti
1
,
Barbara Chiavarino
1
,
M Spano
1
,
Aura Tintaru
2
,
Simonetta Fornarini
1
,
Maria Elisa Crestoni
1
Publication type: Journal Article
Publication date: 2021-10-29
Journal:
Analytical Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 7.4
ISSN: 00032700, 15206882, 21542686
Analytical Chemistry
Abstract
Thyroid hormones are biologically active small molecules responsible for growth and development regulation, basal metabolic rate, and lipid and carbohydrate metabolism. Liquid chromatography mass spectrometry (LC-MS) can be used to quantify thyroid hormones blood level with high speed and selectivity, aiming to improve the diagnosis and treatment of the severe pathological conditions in which they are implicated, i.e., hypo- and hyperthyroidism. In this work, the gas-phase behavior of the isomeric thyroid hormones triiodothyronine (T3) and reverse triiodothyronine (rT3) in their deprotonated form was studied at a molecular level using MS-based techniques. Previously reported collision-induced dissociation experiments yielded distinct spectra despite the high structural similarity of the two compounds, suggesting different charge sites to be responsible. Infrared multiple photon dissociation spectroscopy on [T3-H]- and [rT3-H]- was performed, and the results were interpreted using DFT and MP2 calculations, assessing the prevalence of T3 in the carboxylate form and rT3 as a phenolate isomer. The different deprotonation sites of the two isomers were also found to drive their ion-mobility behavior. In fact, [T3-H]- and [rT3-H]- were successfully separated. Drift times were correlated with collisional cross section values of 209 and 215 Å2 for [T3-H]- and [rT3-H]-, respectively. Calculations suggested the charge site to be the main parameter involved in the different mobilities of the two anions. Finally, bare [T3-H]- and [rT3-H]- were made to react with neutral acetylacetone and trifluoroacetic acid, confirming rT3 to be more acidic than T3 in agreement with the calculated gas-phase acidities of T3 and rT3 equal to 1345 and 1326 kJ mol-1, respectively.
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Citations by publishers
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4 publications, 44.44%
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2 publications, 22.22%
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1 publication, 11.11%
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1 publication, 11.11%
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- We do not take into account publications without a DOI.
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Corinti D. et al. Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination? // Analytical Chemistry. 2021. Vol. 93. No. 44. pp. 14869-14877.
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Corinti D., Chiavarino B., Spano M., Tintaru A., Fornarini S., Crestoni M. E. Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination? // Analytical Chemistry. 2021. Vol. 93. No. 44. pp. 14869-14877.
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TY - JOUR
DO - 10.1021/acs.analchem.1c03892
UR - https://doi.org/10.1021/acs.analchem.1c03892
TI - Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?
T2 - Analytical Chemistry
AU - Corinti, Davide
AU - Chiavarino, Barbara
AU - Tintaru, Aura
AU - Fornarini, Simonetta
AU - Crestoni, Maria Elisa
AU - Spano, M
PY - 2021
DA - 2021/10/29 00:00:00
PB - American Chemical Society (ACS)
SP - 14869-14877
IS - 44
VL - 93
SN - 0003-2700
SN - 1520-6882
SN - 2154-2686
ER -
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@article{2021_Corinti,
author = {Davide Corinti and Barbara Chiavarino and Aura Tintaru and Simonetta Fornarini and Maria Elisa Crestoni and M Spano},
title = {Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?},
journal = {Analytical Chemistry},
year = {2021},
volume = {93},
publisher = {American Chemical Society (ACS)},
month = {oct},
url = {https://doi.org/10.1021/acs.analchem.1c03892},
number = {44},
pages = {14869--14877},
doi = {10.1021/acs.analchem.1c03892}
}
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Corinti, Davide, et al. “Molecular Basis for the Remarkably Different Gas-Phase Behavior of Deprotonated Thyroid Hormones Triiodothyronine (T3) and Reverse Triiodothyronine (rT3): A Clue for Their Discrimination?.” Analytical Chemistry, vol. 93, no. 44, Oct. 2021, pp. 14869-14877. https://doi.org/10.1021/acs.analchem.1c03892.