Issue 28, 2014

Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stress

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.

Graphical abstract: Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stress

Supplementary files

Article information

Article type
Paper
Submitted
11 Apr 2014
Accepted
16 May 2014
First published
16 May 2014

Org. Biomol. Chem., 2014,12, 5151-5157

Author version available

Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stress

A. Tsutsui, R. Imamaki, S. Kitazume, S. Hanashima, Y. Yamaguchi, M. Kaneda, S. Oishi, N. Fujii, A. Kurbangalieva, N. Taniguchi and K. Tanaka, Org. Biomol. Chem., 2014, 12, 5151 DOI: 10.1039/C4OB00761A

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