Mono and dihydroxy coumarin derivatives: Copper chelation and reduction ability
Language English Country Germany Media print-electronic
Document type Journal Article
PubMed
29413115
DOI
10.1016/j.jtemb.2017.11.014
PII: S0946-672X(17)30713-7
Knihovny.cz E-resources
- Keywords
- Catecholic, Chelation, Copper, Coumarin, Reduction,
- MeSH
- Chelating Agents chemistry MeSH
- Fluorescent Dyes chemistry MeSH
- Spectrometry, Fluorescence methods MeSH
- Hydrogen-Ion Concentration MeSH
- Coumarins chemistry MeSH
- Copper analysis MeSH
- Oxidation-Reduction MeSH
- Stereoisomerism MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Chelating Agents MeSH
- cuprous ion MeSH Browser
- Fluorescent Dyes MeSH
- Coumarins MeSH
- Copper 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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