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https://hdl.handle.net/2440/18017
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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 1477-0539 |
Statement of Responsibility: | 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 Hepatocytes Animals Mice Aldehydes Acrolein Hydralazine Culture Media Chromatography, High Pressure Liquid Molecular Structure Lipid Peroxidation Kinetics |
Description: | © Royal Society of Chemistry 2004 |
DOI: | 10.1039/B408796H |
Published version: | http://dx.doi.org/10.1039/b408796h |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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