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Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress.

Publication ,  Journal Article
Hyman, LM; Stephenson, CJ; Dickens, MG; Shimizu, KD; Franz, KJ
Published in: Dalton transactions (Cambridge, England : 2003)
January 2010

A fluorescent sensor prochelator, FlamB (fluorescein hydrizido 2-imidophenylboronic ester), has been developed that selectively probes for copper under conditions of oxidative stress. High levels of hydrogen peroxide trigger the release of a boronic ester masking group from the prochelator to unveil a metal chelator, FlamS (fluorescein hydrizido 2-imidophenol), that provides a modest fluorescence increase in response to Cu(2+) but not other metal ions. X-Ray crystal structures of FlamB, FlamS, and Cu-bound FlamS are all reported. The fluorescence turn-on results from opening of a fluorescein spirolactam ring upon Cu(2+) binding to FlamS in aqueous solution. Oxidation of the aryl boronic ester of FlamB to the metal-binding phenol of FlamS proceeds in organic solvents. However, in aqueous solution a competing mechanism occurs due to hydrolytic instability of the masked prochelator. Hydrolysis of FlamB leads to formation of fluorescein hydrazide, which interacts with copper or H(2)O(2) to produce fluorescein and a significant fluorescence increase.

Duke Scholars

Published In

Dalton transactions (Cambridge, England : 2003)

DOI

EISSN

1477-9234

ISSN

1477-9226

Publication Date

January 2010

Issue

2

Start / End Page

568 / 576

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Oxidative Stress
  • Molecular Conformation
  • Inorganic & Nuclear Chemistry
  • Fluorescent Dyes
  • Fluoresceins
  • Crystallography, X-Ray
  • Copper
  • Chelating Agents
  • 3402 Inorganic chemistry
 

Citation

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Hyman, L. M., Stephenson, C. J., Dickens, M. G., Shimizu, K. D., & Franz, K. J. (2010). Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress. Dalton Transactions (Cambridge, England : 2003), (2), 568–576. https://doi.org/10.1039/b914568k
Hyman, Lynne M., Clifton J. Stephenson, Marina G. Dickens, Ken D. Shimizu, and Katherine J. Franz. “Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress.Dalton Transactions (Cambridge, England : 2003), no. 2 (January 2010): 568–76. https://doi.org/10.1039/b914568k.
Hyman LM, Stephenson CJ, Dickens MG, Shimizu KD, Franz KJ. Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress. Dalton transactions (Cambridge, England : 2003). 2010 Jan;(2):568–76.
Hyman, Lynne M., et al. “Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress.Dalton Transactions (Cambridge, England : 2003), no. 2, Jan. 2010, pp. 568–76. Epmc, doi:10.1039/b914568k.
Hyman LM, Stephenson CJ, Dickens MG, Shimizu KD, Franz KJ. Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress. Dalton transactions (Cambridge, England : 2003). 2010 Jan;(2):568–576.
Journal cover image

Published In

Dalton transactions (Cambridge, England : 2003)

DOI

EISSN

1477-9234

ISSN

1477-9226

Publication Date

January 2010

Issue

2

Start / End Page

568 / 576

Related Subject Headings

  • Spectrophotometry, Ultraviolet
  • Oxidative Stress
  • Molecular Conformation
  • Inorganic & Nuclear Chemistry
  • Fluorescent Dyes
  • Fluoresceins
  • Crystallography, X-Ray
  • Copper
  • Chelating Agents
  • 3402 Inorganic chemistry