Synthesis and antioxidant activity evaluation of a syringic hydrazones family

被引:134
作者
Belkheiri, Nadji [2 ,3 ]
Bouguerne, Benaissa [1 ,2 ,3 ]
Bedos-Belval, Florence [2 ,3 ]
Duran, Hubert [2 ,3 ]
Bemis, Corinne [1 ]
Salvayre, Robert [1 ]
Negre-Salvayre, Anne [1 ]
Baltas, Michel [2 ,3 ]
机构
[1] CHU Rangueil, INSERM 12MR 858, IFR 31, F-31432 Toulouse 4, France
[2] Univ Toulouse, UPS, LSPCMIB, F-31062 Toulouse 9, France
[3] CNRS, LSPCMIB, F-31062 Toulouse 9, France
关键词
Syringic hydrazones; Antioxidants; Oxidative stress; Carbonyl stress; LDL oxidation; Atherosclerosis; LOW-DENSITY-LIPOPROTEIN; OXIDATION; PRODUCTS; DESIGN; LDL;
D O I
10.1016/j.ejmech.2010.03.031
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A novel series of hydrazones derived from syringaldehyde and their antioxidant properties have been explored. Several employed methods such as scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS(center dot+)) radical cation expressed as Trolox equivalent antioxidant capacity (TEAC), inhibition of superoxide anion (O-2(center dot)) generation and of human cell-mediated low-density lipoprotein oxidation (monitored by the formation of TBARS) exhibited their potent antioxidant properties. The carbonyl scavenger efficacy was also evaluated by measuring the ability to decrease the protein carbonyl content in cells challenged with oxidized LDL In this report, we discuss about the synthesis of hydrazones and their dual biological role, antioxidant and carbonyl scavenger for further application in atherosclerosis. (c) 2010 Elsevier Masson SAS. All rights reserved.
引用
收藏
页码:3019 / 3026
页数:8
相关论文
共 24 条
  • [1] Prooxidant and antioxidant properties of Trolox C, analogue of vitamin E, in oxidation of low-density lipoprotein
    Albertini, R
    Abuja, PM
    [J]. FREE RADICAL RESEARCH, 1999, 30 (03) : 181 - 188
  • [2] Is there a future for antioxidants in atherogenesis?
    Brigelius-Flohé, R
    Kluth, D
    Banning, A
    [J]. MOLECULAR NUTRITION & FOOD RESEARCH, 2005, 49 (11) : 1083 - 1089
  • [3] Development of novel antiatherogenic biaryls:: Design, synthesis, and reactivity
    Delomenede, Melanie
    Bedos-Belval, Florence
    Duran, Hubert
    Vindis, Cecile
    Baltas, Michel
    Negre-Salvayre, Anne
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (11) : 3171 - 3181
  • [4] CHEMISTRY AND BIOCHEMISTRY OF 4-HYDROXYNONENAL, MALONALDEHYDE AND RELATED ALDEHYDES
    ESTERBAUER, H
    SCHAUR, RJ
    ZOLLNER, H
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 1991, 11 (01) : 81 - 128
  • [5] Electron-transfer reaction of cinnamic acids and their methyl esters with the DPPH• radical in alcoholic solutions
    Foti, MC
    Daquino, C
    Geraci, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (07) : 2309 - 2314
  • [6] Carbonyl scavenger and antiatherogenic effects of hydrazine derivatives
    Galvani, Sylvain
    Coatrieux, Christelle
    Elbaz, Meyer
    Grazide, Marie-Helene
    Thiers, Jean-Claude
    Parini, Angelo
    Uchida, Koji
    Kamar, Nassim
    Rostaing, Lionel
    Baltas, Michel
    Salvayre, Robert
    Negre-Salvayre, Anne
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 2008, 45 (10) : 1457 - 1467
  • [7] Autoxidation of hydrazones. Some new insights
    Harej, Maja
    Dolenc, Darko
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19) : 7214 - 7221
  • [8] HEINECKE JW, 1993, J LIPID RES, V34, P2051
  • [9] Design, synthesis, and evaluation of pharmacological properties of cinnamic derivatives as antiatherogenic agents
    Lapeyre, C
    Delomenède, M
    Bedos-Belval, F
    Duran, H
    Nègre-Salvayre, A
    Baltas, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (26) : 8115 - 8124
  • [10] Lipid oxidation products in cell signaling
    Leonarduzzi, G
    Arkan, MC
    Basaga, H
    Chiarpotto, E
    Sevanian, A
    Poli, G
    [J]. FREE RADICAL BIOLOGY AND MEDICINE, 2000, 28 (09) : 1370 - 1378