Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stressElectronic supplementary information (ESI) available. See DOI: 10.1039/c4ob00761a

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 unr...

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Main Authors: Tsutsui, Ayumi, Imamaki, Rie, Kitazume, Shinobu, Hanashima, Shinya, Yamaguchi, Yoshiki, Kaneda, Masato, Oishi, Shinya, Fujii, Nobutaka, Kurbangalieva, Almira, Taniguchi, Naoyuki, Tanaka, Katsunori
Format: Article
Language:English
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Summary: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. Polyamines were found to react with acrolein to produce 1,5-diazacyclooctane.
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00761a