Abstract
Acrolein, a toxic unsaturated aldehyde generated as a result of oxidative stress, readily reacts with a variety of nucleophilic biomolecules. Polyamines, which produced acrolein in the presence of amine oxidase, were then found to react with acrolein to produce 1,5-diazacyclooctane, a previously unrecognized but significant downstream product of oxidative stress. Although diazacyclooctane formation effectively neutralized acrolein toxicity, the diazacyclooctane hydrogel produced through a sequential diazacyclooctane polymerization reaction was highly cytotoxic. This study suggests that diazacyclooctane formation is involved in the mechanism underlying acrolein-mediated oxidative stress.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acrolein / metabolism
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Acrolein / toxicity*
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Amine Oxidase (Copper-Containing) / antagonists & inhibitors
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Amine Oxidase (Copper-Containing) / metabolism
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Azocines / metabolism
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Azocines / toxicity*
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Cell Line, Tumor
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Cell Survival / drug effects
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Enzyme Activation / drug effects
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Enzyme Inhibitors / pharmacology
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Epithelial Cells / cytology
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Epithelial Cells / drug effects*
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Epithelial Cells / enzymology
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Guanidines / pharmacology
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HeLa Cells
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Heme Oxygenase-1 / metabolism
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Humans
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Hydrogels / chemistry*
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Oxidative Stress / drug effects
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Polymerization
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Spermidine / chemistry
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Spermidine / metabolism*
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Spermine / chemistry
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Spermine / metabolism*
Substances
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Azocines
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Enzyme Inhibitors
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Guanidines
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Hydrogels
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Spermine
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Acrolein
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HMOX1 protein, human
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Heme Oxygenase-1
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Amine Oxidase (Copper-Containing)
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pimagedine
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Spermidine