Mono and dihydroxy coumarin derivatives: Copper chelation and reduction ability
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
PubMed
29413115
DOI
10.1016/j.jtemb.2017.11.014
PII: S0946-672X(17)30713-7
Knihovny.cz E-zdroje
- Klíčová slova
- Catecholic, Chelation, Copper, Coumarin, Reduction,
- MeSH
- chelátory chemie MeSH
- fluorescenční barviva chemie MeSH
- fluorescenční spektrometrie metody MeSH
- koncentrace vodíkových iontů MeSH
- kumariny chemie MeSH
- měď analýza MeSH
- oxidace-redukce MeSH
- stereoizomerie MeSH
- vztahy mezi strukturou a aktivitou MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- chelátory MeSH
- cuprous ion MeSH Prohlížeč
- fluorescenční barviva MeSH
- kumariny MeSH
- měď MeSH
UNLABELLED: Due to the limited array of the currently available copper chelators, research of such compounds continues to be of clinical interest. Notably, o-dihydroxycoumarins have been previously shown to be potent iron chelators under neutral conditions. Within this study, the interaction of a series of natural coumarins and their synthetic analogs with copper has been evaluated in order to obtain structure-activity relationships under different pathophysiological pH conditions. Both competitive and non-competitive methods have been employed. Analysis of cupric ion reduction has also been performed. Under mildly competitive conditions, cupric chelation was observed for o-dihydroxycoumarins, and partially for o-diacetoxycoumarin. Non-competitive studies showed that cuprous ions are not chelated at all and that the stoichiometries of the most active 6,7- and 7,8-dihydroxycoumarins to cupric ions ranged from 1:1 to 2:1 depending on pH and concentration. Interestingly, under highly competitive conditions, coumarins were not capable of chelating cupric ions, either. Reduction experiments have shown that 13 out of the 15 coumarins included in this study reduced cupric ions. However, significant differences depending on their structures were apparent in their potencies. O-dihydroxycoumarins were the most potent ones again. CONCLUSION: O-dihydroxycoumarins are moderately active cupric ion chelators with potent copper reducing properties.
Bioorganic Laboratory Department of Chemistry University of Delhi Delhi 110 007 India
Centre of Biotechnology Maharshi Dayanand University Rohtak 124 001 Haryana India
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