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Mechanistic insight into hydroxamate transfer reaction mimicking the inhibition of zinc-containing enzymes

Title
Mechanistic insight into hydroxamate transfer reaction mimicking the inhibition of zinc-containing enzymes
Authors
Kwon, NamSuh, Jong-MinLim, Mi HeeHirao, HajimeCho, Jaeheung
DGIST Authors
Kwon, Nam; Suh, Jong-Min; Lim, Mi Hee; Hirao, Hajime; Cho, Jaeheung
Issue Date
2020-09
Citation
Chemical Science, 11(33), 9017-9021
Type
Article
Article Type
Article
Keywords
MATRIX-METALLOPROTEINASE INHIBITORSCOBALT COMPLEXESCARBONIC-ANHYDRASELIGANDSCHEMISTRYDESIGNMODELSTUMORSACIDS
ISSN
2041-6520
Abstract
A hydroxamate transfer reaction between metal complexes has been investigated by a combination of experimental and theoretical studies. A hydroxamate-bound cobalt(ii) complex bearing a tetradentate macrocyclic ligand, [Co-II(TBDAP)(CH3C(-NHO)O)](+)(1), is prepared by the reduction of a hydroximatocobalt(iii) complex with a biological reductant. Alternatively,1is accessibleviaa synthetic route for the reaction between the cobalt(ii) complex and acetohydroxamic acid in the presence of a base.1was isolated and characterized by various physicochemical methods, including UV-vis, IR, ESI-MS, and X-ray crystallography. The hydroxamate transfer reactivity of1was examined with a zinc complex, which was followed by UV-vis and ESI-MS. Kinetic and activation parameter data suggest that the hydroxamate transfer reaction occursviaa bimolecular mechanism, which is also supported by DFT calculations. Moreover,1is able to inhibit the activity against a zinc enzyme,i.e., matrix metalloproteinase-9. Our overall investigations of the hydroxamate transfer using the synthetic model system provide considerable insight into the final step involved in the inhibition of zinc-containing enzymes.
URI
http://hdl.handle.net/20.500.11750/12843
DOI
10.1039/d0sc02676j
Publisher
Royal Society of Chemistry
Files:
There are no files associated with this item.
Collection:
Department of Emerging Materials ScienceBiomimetic Materials Laboratory1. Journal Articles


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