78524-76-2Relevant articles and documents
STUDIES ON PEROXIDIZED LIPIDS. II. FLUORESCENT PRODUCTS RELEVANT TO AGING PIGMENTS DERIVED FROM MALONDIALDEHYDE AND METHYLAMINE
Kikugawa, Kiyomi,Maruyama, Teppei,Machida, Yasuko,Kurechi, Tsutao
, p. 1423 - 1432 (2007/10/02)
Malondialdehyde (MDA) is a secondary product of in vitro and in vivo lipid peroxidation.Reactions of MDA, prepared by acid hydrolysis of malonaldehyde bis(dimethylacetal), with methylamine were performed at 37 deg under various pH conditions (pH 1-8).Two major fluorescent compounds, 1,4-dimethyl-1,4-dihydropyridine-3,5-dialdehyde (1) and 1-methyl-4-(dimethoxyethyl)-1,4-dihydropyridine-3,5-dialdehyde (2), and two nonfluorescent UV-absorbing by-products, β-methylaminoacrolein (3) and 2,6-dimethyl-2,6-diazabicyclo3,7-nonadiene-4,8-dialdhyde (4), were isolated.The structures of these products were elucidated by analysis of their 13C and 1H NMR spectra, mass spectra and UV absorption spectra.Compounds 1 and 2 were produced in the best yields at pH 6-8, 3 was produced at every pH, and 4 was produced at pH 2-5.The 1,4-dihydropyridine-3,5-dialdehyde fluorophore in 1 and 2 may have been formed via a Hantzsch-type reaction of MDA and methylamine.The fluorescence spectrum of 1 with a maximum at 460 nm was the same as that of a conjugated Schiff base of MDA and amino acid or those of aging or lipofuscin pigments accumulated in the cells.Keywords: malondialdehyde; 1,4-dimethyl-1,4-dihydropyridine-3,5-dialdehyde; 1-methyl-4-(dimethoxyethyl)-1,4-dihydropyridine-3,5-dialdehyde; β-methylaminoacrolein; 2,6-dimethyl-2,6-diazabicyclo3,7-nonadiene-4,8-dialdehyde; Hantzsch reaction; lipofuscin pigments
