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Type: Journal article
Title: Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde
Author: Kaminskas, L.
Pyke, S.
Burcham, P.
Citation: Organic and Biomolecular Chemistry, 2004; 2(18):2578-2584
Publisher: Royal Soc Chemistry
Issue Date: 2004
ISSN: 1477-0520
Statement of
Lisa M. Kaminskas, Simon M. Pyke and Philip C. Burcham
Abstract: The nucleophilic drug hydralazine strongly inhibits cell toxicity mediated by acrolein, a short chain 2-alkenal formed during lipid peroxidation. We here report the chemistry of acrolein-trapping by hydralazine, and show that together with its structural analogue dihydralazine, it also readily traps crotonaldehyde. Isolable reaction products included (1E)-acrylaldehyde phthalazin-1-ylhydrazone (E-APH), (1Z)-acrylaldehyde phthalazin-1-ylhydrazone (Z-APH), (1E,2E)-but-2-enal phthalazin-1-ylhydrazone (E-BPH) and (1Z,2E)-but-2-enal phthalazin-1-ylhydrazone (Z-BPH). Concentration-dependent formation of (1E)-acrylaldehyde phthalazin-1-ylhydrazone was observed in the culture media of cells co-exposed to hydralazine and the acrolein precursor allyl alcohol. These aldehyde-sequestering properties of hydrazinophthalazine drugs may contribute to the protection they provide against 2-alkenal-mediated toxicity.
Keywords: Cells, Cultured
Culture Media
Chromatography, High Pressure Liquid
Molecular Structure
Lipid Peroxidation
Description: © Royal Society of Chemistry 2004
DOI: 10.1039/B408796H
Appears in Collections:Aurora harvest 2
Chemistry publications

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