Kinetics of iron oxidation upon polyphenol binding

Nathan R. Perron, Hsiao-Chuan Wang, Sean N. Deguire, Michael Jenkins, Mereze Lawson, Julia L. Brumaghim

Research output: Contribution to journalArticle

61 Citations (Scopus)

Abstract

Polyphenol prevention of iron-mediated DNA damage occurs primarily through iron binding. Once bound, iron in the Fe2+-polyphenol complex autooxidizes to Fe3+ in the presence of O2. To determine the correlation between the rate of Fe2+-polyphenol autooxidation and polyphenol antioxidant ability, kinetic studies at pH = 6.0 in the presence of oxygen were performed using UV-vis spectrophotometry. Initial rates of iron-polyphenol complex oxidation for epigallocatechin gallate (EGCG), methyl-3,4,5-trihydroxybenzoate (MEGA), gallic acid (GA), epicatechin (EC), and methyl-3,4-dihydroxybenzoate (MEPCA) were in the range of 0.14-6.7 min -1. Polyphenols with gallol groups have faster rates of iron oxidation than their catechol analogs, suggesting that stronger iron binding results in faster iron oxidation. Concentrations of polyphenol, Fe2+, and O2 were varied to investigate the dependence of the Fe 2+-polyphenol autooxidation on these reactants for MEGA and MEPCA. For these analogous gallate and catecholate complexes of Fe2+, iron oxidation reactions were first order in Fe2+, polyphenol, and O 2, but gallate complexes show saturation behavior at much lower Fe2+ concentrations. Thus, gallol-containing polyphenols promote iron oxidation at a significantly faster rate than analogous catechol-containing compounds, and iron oxidation rate also correlates strongly with polyphenol inhibition of DNA damage for polyphenol compounds with a single iron-binding moiety.

Original languageEnglish (US)
Pages (from-to)9982-9987
Number of pages6
JournalDalton Transactions
Volume39
Issue number41
DOIs
StatePublished - Nov 7 2010
Externally publishedYes

Fingerprint

Polyphenols
Iron
Oxidation
Kinetics
Iron Compounds
Gallic Acid
Catechin
DNA
Spectrophotometry
Antioxidants
Oxygen

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Perron, N. R., Wang, H-C., Deguire, S. N., Jenkins, M., Lawson, M., & Brumaghim, J. L. (2010). Kinetics of iron oxidation upon polyphenol binding. Dalton Transactions, 39(41), 9982-9987. https://doi.org/10.1039/c0dt00752h

Kinetics of iron oxidation upon polyphenol binding. / Perron, Nathan R.; Wang, Hsiao-Chuan; Deguire, Sean N.; Jenkins, Michael; Lawson, Mereze; Brumaghim, Julia L.

In: Dalton Transactions, Vol. 39, No. 41, 07.11.2010, p. 9982-9987.

Research output: Contribution to journalArticle

Perron, NR, Wang, H-C, Deguire, SN, Jenkins, M, Lawson, M & Brumaghim, JL 2010, 'Kinetics of iron oxidation upon polyphenol binding', Dalton Transactions, vol. 39, no. 41, pp. 9982-9987. https://doi.org/10.1039/c0dt00752h
Perron NR, Wang H-C, Deguire SN, Jenkins M, Lawson M, Brumaghim JL. Kinetics of iron oxidation upon polyphenol binding. Dalton Transactions. 2010 Nov 7;39(41):9982-9987. https://doi.org/10.1039/c0dt00752h
Perron, Nathan R. ; Wang, Hsiao-Chuan ; Deguire, Sean N. ; Jenkins, Michael ; Lawson, Mereze ; Brumaghim, Julia L. / Kinetics of iron oxidation upon polyphenol binding. In: Dalton Transactions. 2010 ; Vol. 39, No. 41. pp. 9982-9987.
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