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|Title:||Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde|
|Citation:||Organic and Biomolecular Chemistry, 2004; 2(18):2578-2584|
|Publisher:||Royal Soc Chemistry|
|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.|
Chromatography, High Pressure Liquid
|Description:||© Royal Society of Chemistry 2004|
|Appears in Collections:||Aurora harvest 2|
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