Copper-induced peroxidation of phosphatidylserine-containing liposomes is inhibited by nanomolar concentrations of specific antioxidants
Copper-induced peroxidation of phosphatidylserine-containing liposomes is inhibited by nanomolar concentrations of specific antioxidants
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DOI：
10.1016/j.chemphyslip.2007.08.001
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发表时间：
2007-12-01
影响因子：
3.4
通讯作者：
Pinchuk, I.
中科院分区：
文献类型：
--
作者：
Gal, S.;Lichtenberg, D.;Pinchuk, I.
铜诱导的脂质体棕榈酰亚油酰磷脂酰胆碱（PLPC）过氧化作用被微摩尔浓度的α -生育酚所抑制。在我们之前的研究中，我们发现当脂质体含有磷脂酰丝氨酸（PS）时，纳摩尔浓度的Toc足以抑制过氧化作用。为了了解这种极端抗氧化能力的来源，我们测试了另外36种抗氧化剂的抗氧化能力，以及它们的抗氧化能力对脂质体中PS存在的依赖。这些研究结果表明，只有11种抗氧化剂具有与Toc相似的抗氧化能力。其中包括三氯酚、丁基羟基甲苯（BHT）、姜黄素、去甲二氢愈创木酸（NDGA）、二乙基己烯雌酚（DES）、13种测试类黄酮中的2种（木犀草素和7,3',4'-三羟基黄酮；T-414）、α -萘酚、1,5-、1,6-和1,7-二羟基萘（hns）。没食子酸丙酯（PG）、丁香酸甲酯、迷迭香酸、白藜芦醇、其他类黄酮以及-萘酚、1,2-、1,3-、1,4-、2,3-、2,6-和2,7- dhns具有中度抗氧化或促氧化作用。对于由PLPC （250 μ M）和PS （25 μ M）制成的脂质体，在添加30-130 nM的“超活性”抗氧化剂后，铜诱导的过氧化反应（5 μ M铜）之前的“滞后”时间增加了一倍。我们提出，在含有ps的脂质体中，对铜诱导的过氧化具有极强的抗氧化能力的机制涉及在三元ps -铜-抗氧化剂复合物中补充抗氧化剂。根据37种抗氧化剂的构效关系，“超强抗氧化能力”归因于相对稳定的半醌或半醌类自由基的再循环。2007爱思唯尔爱尔兰有限公司版权所有。
Copper-induced peroxidation of liposomal palmitoyllinoleoyl-phosphatidylcholine (PLPC) is inhibited by alpha-tocopherol at micromolar concentrations. In our previous study we found that when the liposomes contain phosphatidylserine (PS), nanomolar concentrations of Toc were sufficient to inhibit peroxidation. In an attempt to gain understanding of the origin of this extreme antioxidative potency, we tested the antioxidative potency of 36 additional antioxidants and the dependence of their potency on the presence of PS in the liposomes. The results of these studies reveal that only 11 of the tested antioxidants possess similar antioxidative potency to that of Toc. These include trolox, butylated hydroxytoluene (BHT), curcumin, nordihydroguaiaretic acid (NDGA), diethylstilbestrol (DES), 2 of the 13 tested flavonoids (luteolin and 7,3',4'-trihydroxyflavone; T-414), alpha-naphthol, 1,5-, 1,6- and 1,7-dihydroxynaphthalenes (DHNs). Propyl gallate (PG), methyl syringate, rosmarinic acid, resveratrol, other flavonoids, as well as beta-naphthol, 1,2-, 1,3-, 1,4-, 2,3-, 2,6-, and 2,7-DHNs were either moderately antioxidative or pro-oxidative. For liposomes made of PLPC (250 mu M) and PS (25 mu M) the "lag" preceding copper-induced peroxidation (5 mu M copper) was doubled upon addition of 30-130 nM of the "super-active" antioxidants. We propose that the mechanism responsible for the extreme antioxidative potency against copper-induced peroxidation in PS-containing liposomes involves replenishment of the antioxidant in a ternary PS-copper-antioxidant complex. Based on structure-activity relationship of the 37 tested antioxidants, the "super-antioxidative potency" is attributed to the recycling of relatively stable semiquinone or semiquinone-like radicals. (C) 2007 Elsevier Ireland Ltd. All rights reserved.