Fe(III)-coordination properties of neuromelanin components: 5,6-dihydroxyindole and 5,6-dihydroxyindole-2-carboxylic acid.

Journal Article (Journal Article)

The Fe(III)-coordination chemistry of neuromelanin building-block compounds, 5,6-dihydroxyindole (DHI), 5,6-dihydroxyindole-2-carboxylic acid (DHICA), and 5,6-dihydroxy-N-methyl-indole (Me-DHI), and the neurotransmitter dopamine were explored in aqueous solution by anaerobic pH-dependent spectrophotometric titrations. The Fe(III)-binding constants and pH-dependent speciation parallel those of catechol in that mono, bis, and tris FeLx species are present at concentrations dependent on the pH. The bis FeL2 dihydroxyindole species are favorable for L = DHI and DHICA under neutral to mildly acidic conditions. DHI and DHICA are stronger Fe(III) chelates than catechol, dopamine, and Me-DHI at pH values from 3 to 10. Oxidation studies reveal that iron accelerates the air oxidation of DHI and DHICA.

Full Text

Duke Authors

Cited Authors

  • Charkoudian, LK; Franz, KJ

Published Date

  • May 2006

Published In

Volume / Issue

  • 45 / 9

Start / End Page

  • 3657 - 3664

PubMed ID

  • 16634598

Electronic International Standard Serial Number (EISSN)

  • 1520-510X

International Standard Serial Number (ISSN)

  • 0020-1669

Digital Object Identifier (DOI)

  • 10.1021/ic060014r


  • eng