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Issue 18, 2004
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Reactivity of hydrazinophthalazinedrugs with the lipid peroxidation products acrolein and crotonaldehyde

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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.

Graphical abstract: Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde

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Article information


Submitted
10 Jun 2004
Accepted
27 Jul 2004
First published
20 Aug 2004

Org. Biomol. Chem., 2004,2, 2578-2584
Article type
Paper

Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde

L. M. Kaminskas, S. M. Pyke and P. C. Burcham, Org. Biomol. Chem., 2004, 2, 2578
DOI: 10.1039/B408796H

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