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Issue 18, 2004
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Reactivity of hydrazinophthalazine drugs 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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Publication details

The article was received on 10 Jun 2004, accepted on 27 Jul 2004 and first published on 20 Aug 2004


Article type: Paper
DOI: 10.1039/B408796H
Citation: Org. Biomol. Chem., 2004,2, 2578-2584
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    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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