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Could CO2 be a player in a redox relay team? 二氧化碳能在氧化还原接力队中发挥作用吗?
Pub Date : 2023-07-14 DOI: 10.1016/j.rbc.2023.100006
Alexander V. Peskin

It has been established that hydrogen peroxide (H2O2) acts as a signalling messenger by triggering the reversible oxidation of redox-regulated proteins via a redox-relay provided by peroxiredoxins (Prdxs). Exceptionally high reactivity of Prdxs with H2O2 exceeding other thiols by orders of magnitude places Prdxs as sensors of H2O2 and distributers of oxidizing equivalents to specific thiol targets which can't be oxidized by H2O2 directly. By this mechanism the oxidative stress response can be achieved.

Despite its involvement in oxidative stress responses, H2O2 is continuously generated as a normal metabolite necessary for regular cell functioning. The challenge lies in understanding how the Prdx-dependent redox relay can differentiate between basal levels of H2O2 and excessive amounts that lead to oxidative stress.

Peroxymonocarbonate, an oxidant formed when H2O2 reacts with CO2/HCO3, emerges as a potent cellular oxidant. The peroxymonocarbonate formation could be catalysed and then consumed at localised sites by certain thiol proteins. This mechanism could prevent H2O2 from reacting with Prdx, thereby averting the redox-relayed activation of regulatory thiol proteins and subsequent oxidative stress response below a certain level of H2O2.

已经证实,过氧化氢(H2O2)作为信号信使,通过过氧化物酶体(Prdxs)提供的氧化还原继电器触发氧化还原调节蛋白的可逆氧化。Prdxs与H2O2的异常高的反应性超过其他硫醇几个数量级,使Prdxs成为H2O2的传感器和不能被H2O2直接氧化的特定硫醇靶标的氧化当量的分配器。通过这种机制可以实现氧化应激反应。尽管H2O2参与氧化应激反应,但它作为正常细胞功能所必需的正常代谢产物不断产生。挑战在于理解Prdx依赖性氧化还原继电器如何区分H2O2的基础水平和导致氧化应激的过量。过氧一碳酸酯是H2O2与CO2/HCO3−反应时形成的一种氧化剂,是一种强效的细胞氧化剂。过氧一碳酸酯的形成可以被某些硫醇蛋白催化,然后在局部位点被消耗。该机制可以防止H2O2与Prdx反应,从而避免调节巯基蛋白的氧化还原中继激活和随后低于一定H2O2水平的氧化应激反应。
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引用次数: 0
In vitro radical-scavenging mechanism of melatonin and its in vivo protective effect against radiation-induced lipid peroxidation 褪黑素的体外自由基清除机制及其对辐射诱导的脂质过氧化的体内保护作用
Pub Date : 2023-07-01 DOI: 10.1016/j.rbc.2023.100003
Kailash Manda , Kei Ohkubo , Yoshimi Shoji , A. K. M. Raushan Kabir Zoardar , Masato Kamibayashi , Toshihiko Ozawa , Kazunori Anzai , Ikuo Nakanishi

Melatonin (N-acetyl-5-methoxytryptamine, MLT), an evolutionarily conserved indoleamine, is known to act as an antioxidant. However, the evidence indicating the role of MLT as a powerful chain-breaking antioxidant by scavenging peroxyl radical remains controversial. The radical-scavenging rate of MLT determined in this study in methanol using galvinoxyl radical (GO) was much lower than that of an α-tocopherol model compound. The acceleration of the GO-scavenging reaction by MLT was observed in the presence of magnesium ion (Mg2+), a bio-related redox-inactive metal ion, suggesting that this reaction may proceed via a rate-determining electron transfer followed by proton transfer. The coordination of Mg2+ to the carbonyl oxygen in the one-electron reduced species of GO (GO) may stabilize the product, resulting in the acceleration of the electron-transfer process. We also demonstrated that prophylactically administrated MLT efficiently inhibited the lipid peroxide-derived protein modification, which can be detected by a sensitive marker, Nε-(hexanoyl)lysine adduct, in the plasma of X-irradiated mice. The relatively weak GO-scavenging activity of MLT suggests that the ameliorative effect of MLT against in vivo lipid peroxidation does not result from the direct scavenging of lipid peroxyl radicals by MLT. Therefore, the observed superior protective efficiency of MLT against in vivo lipid peroxidation may partly support the earlier studies, which reported the synergistic antioxidative effect of the metabolites of MLT.

褪黑激素(N-乙酰基-5-甲氧基色胺,MLT)是一种进化上保守的吲哚胺,已知具有抗氧化剂的作用。然而,有证据表明MLT作为一种强大的破链抗氧化剂通过清除过氧自由基的作用仍然存在争议。本研究中使用甲氧基自由基(GO•)在甲醇中测定的MLT的自由基清除率远低于α-生育酚模型化合物。在镁离子(Mg2+)存在的情况下,观察到MLT对GO•-清除反应的加速,镁离子是一种生物相关的氧化还原非活性金属离子,这表明该反应可能通过决定速率的电子转移和质子转移进行。在单电子还原的GO•(GO–)物种中,Mg2+与羰基氧的配位可以稳定产物,从而加速电子转移过程。我们还证明,预防性给药MLT有效地抑制了脂质过氧化物衍生的蛋白质修饰,这可以通过敏感标记物Nε-(己酰基)赖氨酸加合物在X射线照射小鼠的血浆中检测到。MLT相对较弱的GO•-清除活性表明,MLT对体内脂质过氧化的改善作用不是由MLT直接清除脂质过氧自由基引起的。因此,观察到的MLT对体内脂质过氧化的卓越保护作用可能部分支持早期的研究,这些研究报道了MLT代谢产物的协同抗氧化作用。
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引用次数: 1
Intracellular distribution of bis-allylic deuterated linoleic acid into the lipidome of human keratinocytes 双烯丙基氘化亚油酸进入人角质形成细胞脂质组的细胞内分布
Pub Date : 2023-06-16 DOI: 10.1016/j.rbc.2023.100005
Rosangela S. Santos , Márcia S.F. Franco , Felipe G. Ravagnani , Adriano B. Chaves-Filho , Sayuri Miyamoto , Mauricio S. Baptista , Mikhail S. Shchepinov , Marcos Y. Yoshinaga

Polyunsaturated fatty acids (PUFA) are particularly susceptible to free radical-induced lipid peroxidation (LPO). Specific deuteration at bis-allylic positions of PUFA (D-PUFA) has been recently proposed as a way to inhibit the LPO. Here, a high mass resolution untargeted lipidomic analysis protocol was applied to examine the changes in the lipidome of keratinocytes supplemented with bis-allylic deuterated linoleic acid (D2-LA). Incorporation of D2-LA occurs preferentially in membrane phospholipids such as phosphatidylcholine and phosphatidylethanolamine, followed by triglycerides. However, the relative contribution of D2-LA among membrane lipids is highest in cardiolipin (60%) followed by its precursor phosphatidylglycerol (50%). Cardiolipins are enriched in PUFA and exclusively located in mitochondrial membranes, thus representing major targets for lipid peroxidation. These findings indicate that D2-LA supplementation is linked to the preservation of mitochondrial function under oxidative stress. Finally, our study highlights the suitability of high mass resolution lipidomic analysis to investigate lipid metabolism at the level of individual molecular species in stable isotope tracing experiments.

多不饱和脂肪酸(PUFA)特别容易受到自由基诱导的脂质过氧化(LPO)的影响。PUFA的双烯丙基位置上的特定氘化(D-PUFA)最近被提出作为抑制LPO的一种方式。在此,应用高质量分辨率非靶向脂质组学分析方案来检测补充了双烯丙基氘化亚油酸(D2-LA)的角质形成细胞的脂质组学变化。D2-LA的掺入优先发生在膜磷脂中,如磷脂酰胆碱和磷脂酰乙醇胺,其次是甘油三酯。然而,D2-LA在膜脂质中的相对贡献在心磷脂中最高(60%),其次是其前体磷脂酰甘油(50%)。心磷脂富含PUFA,仅位于线粒体膜中,因此是脂质过氧化的主要靶点。这些发现表明,补充D2-LA与氧化应激下线粒体功能的保存有关。最后,我们的研究强调了高质量分辨率脂质组学分析在稳定同位素示踪实验中在单个分子物种水平上研究脂质代谢的适用性。
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引用次数: 0
Initiating redox reactions by ionizing radiation: A versatile, selective and quantitative tool 电离辐射引发氧化还原反应:一种多功能、选择性和定量的工具
Pub Date : 2023-05-09 DOI: 10.1016/j.rbc.2023.100004
Peter Wardman

The absorption of ionizing radiation initiates redox reactions, producing chemical species resulting from single electron loss or electron gain. Radiation chemists have developed methods to study individual redox species selectively and to monitor their reactions in real time. This has provided an enormous resource of kinetic, thermodynamic and spectroscopic information concerning the characteristics and reactions of free radicals and their redox reactions, mainly in aqueous solution. While the techniques are specialized and exploiting them is certainly more difficult than initiating redox changes by simple mixing of two chemicals or adding a reagent to a biological target, it is useful to gain an understanding of the basic mechanisms and approaches involved in exploiting radiation chemistry in the wider context of redox reactions in biochemistry, chemistry, and biology. This should enable readers both to appreciate the reliance which can be placed on the kinetic and other information resulting from such studies, as well as identify potential new applications of the technique which might be exploited in their research, by seeking partners who have access to the necessary specialized equipment or just basic irradiation facilities. This review outlines how radiation can be used to initiate selective redox reactions, mainly in water, and helps point readers to resources which should be useful in considering such reactions in a wider context.

电离辐射的吸收引发氧化还原反应,产生单电子损失或电子增益产生的化学物质。辐射化学家已经开发出选择性研究单个氧化还原物种并实时监测其反应的方法。这为主要在水溶液中的自由基及其氧化还原反应的特性和反应提供了大量的动力学、热力学和光谱信息。虽然这些技术是专门的,利用它们肯定比通过简单混合两种化学物质或向生物靶标添加试剂来引发氧化还原变化更困难,但在生物化学、化学和生物学中更广泛的氧化还原反应背景下,了解利用辐射化学的基本机制和方法是有用的。这应使读者既能理解对此类研究产生的动力学和其他信息的依赖,又能通过寻找能够获得必要专业设备或基本辐照设施的合作伙伴,确定该技术在研究中可能被利用的潜在新应用。这篇综述概述了如何使用辐射来引发选择性氧化还原反应,主要是在水中,并帮助读者找到在更广泛的背景下考虑此类反应时应该有用的资源。
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引用次数: 2
In Memoriam: Emeritus Professor Robin L. Willson 纪念:名誉教授罗宾·威尔逊
Pub Date : 2023-04-01 DOI: 10.1016/j.rbc.2022.100001
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引用次数: 0
Cross-linking between cysteine and lysine, tryptophan or tyrosine in peptides and proteins treated with hypochlorous acid and other reactive halogens 用次氯酸和其他活性卤素处理的多肽和蛋白质中半胱氨酸和赖氨酸、色氨酸或酪氨酸之间的交联
Pub Date : 2023-04-01 DOI: 10.1016/j.rbc.2023.100002
Nicholas J. Magon, Rufus Turner, Anthony J. Kettle, Christine C. Winterbourn

Cysteine residues are the most favored targets for oxidation by hypochlorous acid and other reactive halogen species. The end-products of cysteine oxidation are usually considered to be reversibly formed disulfides and the more highly oxidized sulfinic and sulfonic acids. However, reactive halogen species are capable of generating additional products in which cysteine is cross-linked to other amino acids. Here we have treated a range of peptides with hypochlorous acid (HOCl) and hypobromous acid (HOBr), and used mass spectrometry to demonstrate sulfenamide, sulfinamide and sulfonamide formation with lysine residues, as well as –S(O)- and –S(O2)- linkages with tyrosine, tryptophan and arginine residues. The -(SO2)- products were more prevalent with HOCl than HOBr, reflecting its higher oxidizing ability. There was also considerable variation between peptides in efficiency of cross-linking compared with other modifications. The –S(O)- and –S(O2)- forms were much more resistant than the disulfide to reduction by dithiothreitol. Using calprotectin as a representative cysteine-containing protein, we show that a range of products containing each of these cross-links is formed when the protein is treated with HOCl. Two of the identified cysteine-lysine calprotectin cross-links were also detected in bronchoalveolar lavage fluid from children with cystic fibrosis. Our results imply that cross-linked species would be formed when cysteine-containing proteins are exposed to reactive halogen species, with the nature of the specific products depending on structural features around the cysteine residue. Cross-linking could have a modulatory effect on protein function or be detrimental in causing oligomerization and aggregation.

半胱氨酸残基是次氯酸和其他活性卤素物质氧化的最有利靶点。半胱氨酸氧化的最终产物通常被认为是可逆形成的二硫化物以及氧化程度更高的亚磺酸和磺酸。然而,活性卤素物种能够产生半胱氨酸与其他氨基酸交联的额外产物。在这里,我们用次氯酸(HOCl)和次溴酸(HOBr)处理了一系列肽,并使用质谱法证明了与赖氨酸残基形成的亚磺酰胺、磺酰胺和磺酰胺,以及与酪氨酸、色氨酸和精氨酸残基结合的-S(O)和-S(O2)键。HOCl中的-(SO2)-产物比HOBr更普遍,反映出其更高的氧化能力。与其他修饰相比,肽之间的交联效率也有相当大的差异。-S(O)-和-S(O2)-形式比二硫化物更耐二硫苏糖醇还原。使用钙卫蛋白作为一种代表性的含半胱氨酸蛋白质,我们发现当用HOCl处理蛋白质时,会形成一系列含有这些交联的产物。在患有囊性纤维化的儿童的支气管肺泡灌洗液中也检测到两种已鉴定的半胱氨酸-赖氨酸钙卫蛋白交联。我们的结果表明,当含半胱氨酸的蛋白质暴露于活性卤素物种时,会形成交联物种,特定产物的性质取决于半胱氨酸残基周围的结构特征。交联可能对蛋白质功能有调节作用,或对引起低聚和聚集有害。
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Redox Biochemistry and Chemistry
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