Skip to main content
Journal cover image

The hydrolytic susceptibility of prochelator BSIH in aqueous solutions.

Publication ,  Journal Article
Wang, Q; Franz, KJ
Published in: Bioorganic & medicinal chemistry letters
September 2017

The prochelator BSIH ((E)-N'-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylidene)isonicotinohydrazide) contains a boronate group that prevents metal coordination until reaction with peroxide releases the iron chelator SIH ((E)-N'-(2-hydroxybenzylidene)isonicotinohydrazide). BSIH exists in aqueous buffer and cell culture media in equilibrium with its hydrolysis products isoniazid and (2-formylphenyl)boronic acid (FBA). The relative concentrations of these species limit the yield of intact SIH available for targeted iron chelation. While the hydrolysis fragments are nontoxic to retinal pigment epithelial cells, these results suggest that modifications to BSIH that improve its hydrolytic stability yet maintain its low inherent cytotoxicity are desirable for creating more efficient prochelators for protection against cellular oxidative damage.

Duke Scholars

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

September 2017

Volume

27

Issue

17

Start / End Page

4165 / 4170

Related Subject Headings

  • Water
  • Structure-Activity Relationship
  • Solutions
  • Retinal Pigment Epithelium
  • Oxidative Stress
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Isonicotinic Acids
  • Hydrolysis
  • Hydrogen Peroxide
 

Citation

APA
Chicago
ICMJE
MLA
NLM
Wang, Q., & Franz, K. J. (2017). The hydrolytic susceptibility of prochelator BSIH in aqueous solutions. Bioorganic & Medicinal Chemistry Letters, 27(17), 4165–4170. https://doi.org/10.1016/j.bmcl.2017.07.019
Wang, Qin, and Katherine J. Franz. “The hydrolytic susceptibility of prochelator BSIH in aqueous solutions.Bioorganic & Medicinal Chemistry Letters 27, no. 17 (September 2017): 4165–70. https://doi.org/10.1016/j.bmcl.2017.07.019.
Wang Q, Franz KJ. The hydrolytic susceptibility of prochelator BSIH in aqueous solutions. Bioorganic & medicinal chemistry letters. 2017 Sep;27(17):4165–70.
Wang, Qin, and Katherine J. Franz. “The hydrolytic susceptibility of prochelator BSIH in aqueous solutions.Bioorganic & Medicinal Chemistry Letters, vol. 27, no. 17, Sept. 2017, pp. 4165–70. Epmc, doi:10.1016/j.bmcl.2017.07.019.
Wang Q, Franz KJ. The hydrolytic susceptibility of prochelator BSIH in aqueous solutions. Bioorganic & medicinal chemistry letters. 2017 Sep;27(17):4165–4170.
Journal cover image

Published In

Bioorganic & medicinal chemistry letters

DOI

EISSN

1464-3405

ISSN

0960-894X

Publication Date

September 2017

Volume

27

Issue

17

Start / End Page

4165 / 4170

Related Subject Headings

  • Water
  • Structure-Activity Relationship
  • Solutions
  • Retinal Pigment Epithelium
  • Oxidative Stress
  • Molecular Structure
  • Medicinal & Biomolecular Chemistry
  • Isonicotinic Acids
  • Hydrolysis
  • Hydrogen Peroxide