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Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation.

Publication ,  Journal Article
Kielar, F; Helsel, ME; Wang, Q; Franz, KJ
Published in: Metallomics : integrated biometal science
August 2012

A prochelator named BHAPI (N'-(1-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyloxy)phenyl)ethylidene)isonicotinohydrazide) based on the structure of experimental metal chelator HAPI (N'-[1-(2-hydroxyphenyl)ethyliden]isonicotinoylhydrazide) has been synthesized. The prochelator, which shows limited affinity for metal ions, is converted efficiently upon reaction with hydrogen peroxide into its chelator form, which binds di- and trivalent metal ions, including Zn(2+), Cu(2+) and Fe(3+). This work shows that the prochelator has a protective effect on cells under oxidative stress induced by either hydrogen peroxide or the cytotoxic herbicide paraquat. The effect of BHAPI and HAPI on cellular iron status was assessed by monitoring the mRNA level of the transferrin receptor. Whereas the chelator HAPI induces iron deficiency in cultured retinal pigment epithelial cells, the prochelator does not, providing evidence that the differential metal-binding capacity of these compounds observed in vitro is replicated in the cellular context.

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Published In

Metallomics : integrated biometal science

DOI

EISSN

1756-591X

ISSN

1756-5901

Publication Date

August 2012

Volume

4

Issue

9

Start / End Page

899 / 909

Related Subject Headings

  • Time Factors
  • Stress, Physiological
  • Spectrophotometry, Ultraviolet
  • Semicarbazones
  • Retinal Pigment Epithelium
  • Receptors, Transferrin
  • Reactive Oxygen Species
  • RNA, Messenger
  • Paraquat
  • Oxidative Stress
 

Citation

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Kielar, F., Helsel, M. E., Wang, Q., & Franz, K. J. (2012). Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation. Metallomics : Integrated Biometal Science, 4(9), 899–909. https://doi.org/10.1039/c2mt20069d
Kielar, Filip, Marian E. Helsel, Qin Wang, and Katherine J. Franz. “Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation.Metallomics : Integrated Biometal Science 4, no. 9 (August 2012): 899–909. https://doi.org/10.1039/c2mt20069d.
Kielar F, Helsel ME, Wang Q, Franz KJ. Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation. Metallomics : integrated biometal science. 2012 Aug;4(9):899–909.
Kielar, Filip, et al. “Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation.Metallomics : Integrated Biometal Science, vol. 4, no. 9, Aug. 2012, pp. 899–909. Epmc, doi:10.1039/c2mt20069d.
Kielar F, Helsel ME, Wang Q, Franz KJ. Prochelator BHAPI protects cells against paraquat-induced damage by ROS-triggered iron chelation. Metallomics : integrated biometal science. 2012 Aug;4(9):899–909.
Journal cover image

Published In

Metallomics : integrated biometal science

DOI

EISSN

1756-591X

ISSN

1756-5901

Publication Date

August 2012

Volume

4

Issue

9

Start / End Page

899 / 909

Related Subject Headings

  • Time Factors
  • Stress, Physiological
  • Spectrophotometry, Ultraviolet
  • Semicarbazones
  • Retinal Pigment Epithelium
  • Receptors, Transferrin
  • Reactive Oxygen Species
  • RNA, Messenger
  • Paraquat
  • Oxidative Stress