Phenylarsonic acid-DMPS redox reaction and conjugation investigated by NMR spectroscopy and X-ray diffraction.
Arsenic
GSH
Kinetics
Molecular structure
Toxicology
Unithiol
Journal
Environmental toxicology and pharmacology
ISSN: 1872-7077
Titre abrégé: Environ Toxicol Pharmacol
Pays: Netherlands
ID NLM: 9612020
Informations de publication
Date de publication:
May 2022
May 2022
Historique:
received:
23
12
2021
revised:
25
02
2022
accepted:
01
03
2022
pubmed:
7
3
2022
medline:
14
5
2022
entrez:
6
3
2022
Statut:
ppublish
Résumé
The reaction between 2,3-dimercaptopropane-1-sulfonate (DMPS, unithiol) and four phenylarsonic(V) acids, i.e. phenylarsonic acid (PAA), 4-hydroxy-3-nitrophenylarsonic acid (HNPAA), 2-aminophenylarsonic acid (o-APAA) and 4-aminophenylarsonic acid (p-APAA), is investigated in aqueous solution. The pentavalent arsenic compounds are reduced by DMPS to their trivalent analogs and instantly chelated by the vicinal dithiol, forming covalent As-S bonds within a five-membered chelate ring. The different types and positions of polar substituents at the aromatic ring of the arsonic acids influence the reaction rates in the same way as observed for reaction with glutathione (GSH), as well as the syn/anti molar ratio of the diastereomeric products, which was analyzed using time- and temperature-dependent nuclear magnetic resonance (NMR) spectroscopy. Addition of DMPS to the conjugate formed by a phenylarsonic(V) acid and the biologically relevant tripeptide GSH showed the immediate replacement of GSH by chelating DMPS, underlining the importance of dithiols as detoxifying agent.
Identifiants
pubmed: 35248761
pii: S1382-6689(22)00030-8
doi: 10.1016/j.etap.2022.103837
pii:
doi:
Substances chimiques
Arsenicals
0
Chelating Agents
0
Unithiol
4076-02-2
Glutathione
GAN16C9B8O
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
103837Informations de copyright
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