
The hydrolytic susceptibility of prochelator BSIH in aqueous solutions.
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
DOI
EISSN
ISSN
Publication Date
Volume
Issue
Start / End Page
Related Subject Headings
- Water
- Structure-Activity Relationship
- Solutions
- Retinal Pigment Epithelium
- Oxidative Stress
- Molecular Structure
- Medicinal & Biomolecular Chemistry
- Isonicotinic Acids
- Hydrolysis
- Hydrogen Peroxide
Citation

Published In
DOI
EISSN
ISSN
Publication Date
Volume
Issue
Start / End Page
Related Subject Headings
- Water
- Structure-Activity Relationship
- Solutions
- Retinal Pigment Epithelium
- Oxidative Stress
- Molecular Structure
- Medicinal & Biomolecular Chemistry
- Isonicotinic Acids
- Hydrolysis
- Hydrogen Peroxide