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Zinc complexes of chloroquine and hydroxychloroquine versus the mixtures of their components: Structures, solution equilibria/speciation and cellular zinc uptake.
J. Inorg. Biochem. 252:112478 (2024)
The zinc complexes of chloroquine (CQ; [Zn(CQH+)Cl3]) and hydroxychloroquine (HO-CQ; [Zn(HO-CQH+)Cl3]) were synthesized and characterized by X-Ray structure analysis, FT-IR, NMR, UV-Vis spectroscopy, and cryo-spray mass spectrometry in solid state as well as in aqueous and organic solvent solutions, respectively. In acetonitrile, up to two Zn2+ ions bind to CQ and HO-CQ through the tertiary amine and aromatic nitrogen atoms (KN-aminCQ = (3.8 ± 0.5) x 104 M-1 and KN-aromCQ = (9.0 ± 0.7) x 103 M-1 for CQ, and KN-aminHO-CQ = (3.3 ± 0.4) x 104 M-1 and KN-aromHO-CQ = (1.6 ± 0.2) x 103 M-1 for HO-CQ). In MOPS buffer (pH 7.4) the coordination proceeds through the partially deprotonated aromatic nitrogen, with the corresponding equilibrium constants of KN-arom(aq)CQ = (3.9 ± 1.9) x 103 M-1and KN-arom(aq)HO-CQ = (0.7 + 0.4) x 103 M-1 for CQ and HO-CQ, respectively. An apparent partition coefficient of 0.22 was found for [Zn(CQH+)Cl3]. Mouse embryonic fibroblast (MEF) cells were treated with pre-synthesized [Zn((HO-)CQH+)Cl3] complexes and corresponding ZnCl2/(HO-)CQ mixtures and zinc uptake was determined by application of the fluorescence probe and ICP-OES measurements. Administration of pre-synthesized complexes led to higher total zinc levels than those obtained upon administration of the related zinc/(hydroxy)chloroquine mixtures. The differences in the zinc uptake between these two types of formulations were discussed in terms of different speciation and character of the complexes. The obtained results suggest that intact zinc complexes may exhibit biological effects distinct from that of the related zinc/ligand mixtures.
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Publication type
Article: Journal article
Document type
Scientific Article
Keywords
Chloroquine ; Ionophore ; Solution Equilibria ; Zinc ; Zinc Uptake; Metal-based Chemotherapy; Antimalarial Activity; Tropical Diseases; In-vitro; Covid-19; Coordination; Stability; Phosphate; Sites
ISSN (print) / ISBN
0162-0134
e-ISSN
0162-0134
Quellenangaben
Volume: 252,
Article Number: 112478
Publisher
Elsevier
Publishing Place
Ste 800, 230 Park Ave, New York, Ny 10169 Usa
Non-patent literature
Publications
Reviewing status
Peer reviewed
Institute(s)
Research Unit Analytical BioGeoChemistry (BGC)
Grants
Bayerisches Staatsminis-terium fur Wissenschaft und Kunst
Ludwig-Max-imilians University Muenchen (LMU)
Ludwig-Max-imilians University Muenchen (LMU)