Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine(FDP), an acrolein biomarker

被引：13

作者：

Takamatsu, Masayuki ^{[1
]}

Fukase, Koichi ^{[2
]}

Kurbangalieva, Almira ^{[3
]}

Tanaka, Katsunori ^{[1
,3
]}

机构：

[1] RIKEN, Biofunct Synthet Chem Lab, Wako, Saitama 3510198, Japan

[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan

[3] Kazan Fed Univ, A Butlerov Inst Chem, Biofunct Chem Lab, Kazan 420008, Russia

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2014年 / 22卷 / 22期

基金：

日本学术振兴会;

关键词：

Acrolein; Biologically relevant amine; Biomarker 1,5-Diazacyclooctane; 3-Formyl-3,4-dehydropiperidine(FDP); Imino [4+4] cycloaddition; 2,6,9-Triazabicyclo[3.3.1] nonane; PROTEIN-BOUND ACROLEIN; SOLUBLE GUANYLATE-CYCLASE; OXIDATIVE STRESS; CELLS; 6-PI-AZAELECTROCYCLIZATION; OXIDASE; MARKERS; LYSINE; ADDUCT; MICE;

D O I：

10.1016/j.bmc.2014.09.045

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We demonstrated synthetically that the eight-membered heterocycles 2,6,9-triazabicyclo[3.3.1] nonanes and 1,5-diazacyclooctanes are the initial and exclusive products of the reaction, through an imino [4+4] cycloaddition, of biologically relevant amines with acrolein. The stabilities of the aminoacetals within the eight-membered heterocycles determined whether the product was subsequently transformed gradually into the 3-formyl-3,4-dehydropiperidine (FDP), which is widely used as an oxidative stress marker. The reactivity profiles discovered in this study suggested that some of the imino [4+4] cycloaddition products are reactive intermediates of FDP and contribute to the mechanisms underlying the oxidative stress response to acrolein. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：6380 / 6386

页数：7