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Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy

The sulfonamide–zinc ion interaction, performing a key role in various biological contexts, is the focus of the present study, with the aim of elucidating ligation motifs in zinc complexes of sulfa drugs, namely sulfadiazine (SDZ) and sulfathiazole (STZ), in a perturbation-free environment. To this...

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Autores principales: Corinti, Davide, Chiavarino, Barbara, Maitre, Philippe, Crestoni, Maria Elisa, Fornarini, Simonetta
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9146759/
https://www.ncbi.nlm.nih.gov/pubmed/35630621
http://dx.doi.org/10.3390/molecules27103144
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author Corinti, Davide
Chiavarino, Barbara
Maitre, Philippe
Crestoni, Maria Elisa
Fornarini, Simonetta
author_facet Corinti, Davide
Chiavarino, Barbara
Maitre, Philippe
Crestoni, Maria Elisa
Fornarini, Simonetta
author_sort Corinti, Davide
collection PubMed
description The sulfonamide–zinc ion interaction, performing a key role in various biological contexts, is the focus of the present study, with the aim of elucidating ligation motifs in zinc complexes of sulfa drugs, namely sulfadiazine (SDZ) and sulfathiazole (STZ), in a perturbation-free environment. To this end, an approach is exploited based on mass spectrometry coupled with infrared multiple photon dissociation (IRMPD) spectroscopy backed by quantum chemical calculations. IR spectra of Zn(H(2)O+SDZ−H)(+) and Zn(H(2)O+STZ−H)(+) ions are consistent with a three-coordinate zinc complex, where ZnOH(+) binds to the uncharged sulfonamide via N(heterocycle) and O(sulfonyl) donor atoms. Alternative prototropic isomers Zn(OH(2))(SDZ−H)(+) and Zn(OH(2))(STZ−H)(+) lie 63 and 26 kJ mol(−1) higher in free energy, respectively, relative to the ground state Zn(OH)(SDZ)(+) and Zn(OH)(STZ)(+) species and do not contribute to any significant extent in the sampled population.
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spelling pubmed-91467592022-05-29 Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy Corinti, Davide Chiavarino, Barbara Maitre, Philippe Crestoni, Maria Elisa Fornarini, Simonetta Molecules Article The sulfonamide–zinc ion interaction, performing a key role in various biological contexts, is the focus of the present study, with the aim of elucidating ligation motifs in zinc complexes of sulfa drugs, namely sulfadiazine (SDZ) and sulfathiazole (STZ), in a perturbation-free environment. To this end, an approach is exploited based on mass spectrometry coupled with infrared multiple photon dissociation (IRMPD) spectroscopy backed by quantum chemical calculations. IR spectra of Zn(H(2)O+SDZ−H)(+) and Zn(H(2)O+STZ−H)(+) ions are consistent with a three-coordinate zinc complex, where ZnOH(+) binds to the uncharged sulfonamide via N(heterocycle) and O(sulfonyl) donor atoms. Alternative prototropic isomers Zn(OH(2))(SDZ−H)(+) and Zn(OH(2))(STZ−H)(+) lie 63 and 26 kJ mol(−1) higher in free energy, respectively, relative to the ground state Zn(OH)(SDZ)(+) and Zn(OH)(STZ)(+) species and do not contribute to any significant extent in the sampled population. MDPI 2022-05-14 /pmc/articles/PMC9146759/ /pubmed/35630621 http://dx.doi.org/10.3390/molecules27103144 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Corinti, Davide
Chiavarino, Barbara
Maitre, Philippe
Crestoni, Maria Elisa
Fornarini, Simonetta
Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title_full Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title_fullStr Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title_full_unstemmed Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title_short Ligation Motifs in Zinc-Bound Sulfonamide Drugs Assayed by IR Ion Spectroscopy
title_sort ligation motifs in zinc-bound sulfonamide drugs assayed by ir ion spectroscopy
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9146759/
https://www.ncbi.nlm.nih.gov/pubmed/35630621
http://dx.doi.org/10.3390/molecules27103144
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