The biological significance of non‐enzymatic reaction of menadione with plasma thiols: enhancement of menadione‐induced cytotoxicity to platelets by the presence of blood plasma

Chung, Sun-Hwa; Chung, Seung-Min; Lee, Jooyoung; Kim, Se-Ryun; Park, Ki‐Sook; Chung, Jin‐Ho

doi:10.1016/s0014-5793(99)00452-4

Cited by 20 publications

(8 citation statements)

References 25 publications

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“…Contact allergic reactions have been linked to 2-hydroxy-2,4-naphthoquinone (henna) (27), a principal ingredient in many types of body dyes (Bolhaar et al 2001;Calogiuri et al 2010). Menadione (21) has been also found to react non-enzymatically with protein thiols that are present in rat plasma and generate ROS that potentiate cellular injury to platelets (Chung et al 1999).…”

Section: Nucleophilic Addition Of Quinonesmentioning

confidence: 99%

The chemical and biological activities of quinones: overview and implications in analytical detection

et al. 2011

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Quinones are a class of natural and synthetic compounds that have several beneficial effects. Quinones are electron carriers playing a role in photosynthesis. As vitamins, they represent a class of molecules preventing and treating several illnesses such as osteoporosis and cardiovascular diseases. Quinones, by their antioxidant activity, improve general health conditions. Many of the drugs clinically approved or still in clinical trials against cancer are quinone related compounds. Quinones have also toxicological effects through their presence as photoproducts from air pollutants. Quinones are fast redox cycling molecules and have the potential to bind to thiol, amine and hydroxyl groups. The aforementioned properties make the analytical detection of quinones problematic. However, recent advances of the available analytical techniques along with the possibility of using labeled compound facilitate their detection hence allowing a better understanding of their action. This review summarizes the current knowledge with respect to the oxido-reductive and electrophilic properties of quinones as well as to the analytical tools used for their analysis. It includes a general introduction about the physiological, and therapeutical functions of quinones. A number of studies are reported to cover the chemical reactivity in an attempt to understand quinones as biologically active compounds. Data ranging from normal analytical methods to study quinones derived from plant or biological matrices to the use of labeled compounds are presented. The examples illustrate how chemical, biological and analytical knowledge can be integrated to have a better understanding of the mode of action of the quinones.

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Section: Nucleophilic Addition Of Quinonesmentioning

confidence: 99%

The chemical and biological activities of quinones: overview and implications in analytical detection

et al. 2011

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“…It has been suggested that the cytotoxic effect of menadione is related to the generation of reactive oxygen species (ROS) by enzymatic reaction during its metabolism [8]. Menadione can generates ROS by non-enzymatic reaction with protein thiols in plasma [9]. Consistent with this observation, the thiol-depleting agent N-ethylmaleimide (NEM) suppresses menadione-induced ROS generation and cytotoxicity to platelet.…”

Section: Introductionmentioning

confidence: 99%

Pankiller effect of prolonged exposure to menadione on glioma cells: potentiation by vitamin C

et al. 2010

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SummaryMenadione (Vitamin K3) has anti-tumoral effects against a wide range of cancer cells. Its potential toxicity to normal cells and narrow therapeutic range limit its use as single agent but in combination with radiation or other anti-neoplastic agents can be of therapeutic use. In this paper, we first evaluated the early (within 3 h) effect of menadione on ongoing DNA replication. In normal rat cerebral cortex mini-units menadione showed an age dependent anti-proliferative effect. In tissue mini-units prepared from newborn rats, menadione inhibited ongoing DNA replication with an IC 50 of approximately 10 μM but 50 μM had no effect on mini-units from prepared adult rat tissue. The effect of short (72 h) and prolonged exposure (1–2 weeks) to menadione alone in the DBTRG.05MG human glioma cells line and in combination with vitamin C was studied. After short period of exposure data show that menadione alone or in combination with vitamin C provided similar concentration-response curves (and IC50 values). Prolonged exposure to these drugs was evaluated by their ability to kill 100% of glioma cells and prevent regrowth when cells are re-incubated in drug-free media. In this long-term assay, menadione:vitamin C at a ratio 1:100 showed higher anti-proliferative activity when compared to each drug alone and allowed to reduce each drug concentration between 2.5 to 5-fold. Similar anti-proliferative effect was demonstrated in 8 patient derived glioblastoma cell cultures. Our data should be able to encourage further advanced studies on animal models to evaluate the potential use of this combination therapy for glioma treatment.

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“…Menadione is a quinone which causes ROS generation from the mitochondrial and plastidal electron transport chains. Given its hydrophobic properties it can pass biological membranes easily to reach these organelles and releases ROS such as superoxide, hydrogen peroxide and hydroxyl radicals (Castro et al 2007; Chung et al 1999; Mauzeroll et al 2004). Detailed metabolic studies revealed a down-regulation of glycolysis and tricarboxylic acid (TCA) cycle and the redirection of carbon metabolism from glycolysis to oxidative pentose phosphate pathway (OPPP).…”

Section: Introductionmentioning

confidence: 99%

Metabolic recovery of Arabidopsis thaliana roots following cessation of oxidative stress

et al. 2011

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To cope with the various environmental stresses resulting in reactive oxygen species (ROS) production plant metabolism is known to be altered specifically under different stresses. After overcoming the stress the metabolism should be reconfigured to recover basal operation however knowledge concerning how this is achieved is cursory. To investigate the metabolic recovery of roots following oxidative stress, changes in metabolite abundance and carbon flow were analysed. Arabidopsis roots were treated by menadione to elicit oxidative stress. Roots were fed with 13C labelled glucose and the redistribution of isotope was determined in order to study carbon flow. The label redistribution through many pathways such as glycolysis, the tricarboxylic acid (TCA) cycle and amino acid metabolism were reduced under oxidative stress. After menadione removal many of the stress-related changes reverted back to basal levels. Decreases in amounts of hexose phosphates, malate, 2-oxoglutarate, glutamate and aspartate were fully recovered or even increased to above the control level. However, some metabolites such as pentose phosphates and citrate did not recover but maintained their levels or even increased further. The alteration in label redistribution largely correlated with that in metabolite abundance. Glycolytic carbon flow reverted to the control level only 18 h after menadione removal although the TCA cycle and some amino acids such as aspartate and glutamate took longer to recover. Taken together, plant root metabolism was demonstrated to be able to overcome menadione-induced oxidative stress with the differential time period required by independent pathways suggestive of the involvement of pathway specific regulatory processes.Electronic supplementary materialThe online version of this article (doi:10.1007/s11306-011-0296-1) contains supplementary material, which is available to authorized users.

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The biological significance of non‐enzymatic reaction of menadione with plasma thiols: enhancement of menadione‐induced cytotoxicity to platelets by the presence of blood plasma

Cited by 20 publications

References 25 publications

The chemical and biological activities of quinones: overview and implications in analytical detection

The chemical and biological activities of quinones: overview and implications in analytical detection

Pankiller effect of prolonged exposure to menadione on glioma cells: potentiation by vitamin C

Metabolic recovery of Arabidopsis thaliana roots following cessation of oxidative stress

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