関: GSSG、oxidized glutathione

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/04/23 19:14:19」(JST)

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Glutathione disulfide (GSSG) is a disulfide derived from two glutathione molecules.^[1]

In living cells, glutathione disulfide is reduced into two molecules of glutathione with reducing equivalents from the coenzyme NADPH. This reaction is catalyzed by the enzyme glutathione reductase.^[2] Antioxidant enzymes, such as glutathione peroxidases and peroxiredoxins, generate glutathione disulfide during the reduction of peroxides such as hydrogen peroxide (H₂O₂) and organic hydroperoxides (ROOH):^[3]

2 GSH + ROOH → GSSG + ROH + H₂O

Other enzymes, such as glutaredoxins, generate glutathione disulfide through thiol-disulfide exchange with protein disulfide bonds or other low molecular mass compounds, such as coenzyme A disulfide or dehydroascorbic acid.^[4]

2 GSH + R-S-S-R → GSSG + 2 RSH

The GSH:GSSG ratio is therefore an important bioindicator of cellular health, with a higher ratio signifying less oxidative stress in the organism. A lower ratio may even be indicative of neurodegenerative diseases, such as Parkinson's disease (PD) and Alzheimer's disease.^[5]

Neuromodulator

GSSG, along with glutathione and S-nitrosoglutathione (GSNO), have been found to bind to the glutamate recognition site of the NMDA and AMPA receptors (via their γ-glutamyl moieties), and may be endogenous neuromodulators.^[6]^[7] At millimolar concentrations, they may also modulate the redox state of the NMDA receptor complex.^[7]

References

^ Meister A, Anderson ME (1983). "Glutathione". Annual Review of Biochemistry. 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189.
^ Deneke SM, Fanburg BL (1989). "Regulation of cellular glutathione". The American Journal of Physiology. 257 (4 Pt 1): L163–73. PMID 2572174.
^ Meister A (1988). "Glutathione metabolism and its selective modification". The Journal of Biological Chemistry. 263 (33): 17205–8. PMID 3053703.
^ Holmgren A, Johansson C, Berndt C, Lönn ME, Hudemann C, Lillig CH (December 2005). "Thiol redox control via thioredoxin and glutaredoxin systems". Biochem. Soc. Trans. 33 (Pt 6): 1375–7. doi:10.1042/BST20051375. PMID 16246122.
^ Owen, Joshua B.; Butterfield, D. Allan (2010). "Measurement of oxidized/reduced glutathione ratio". In Bross, Peter; Gregersen, Niels. Protein Misfolding and Cellular Stress in Disease and Aging. Methods in Molecular Biology. 648. pp. 269–77. doi:10.1007/978-1-60761-756-3_18. ISBN 978-1-60761-755-6. PMID 20700719.
^ Steullet P, Neijt HC, Cuénod M, Do KQ (2006). "Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit: relevance to schizophrenia". Neuroscience. 137 (3): 807–19. doi:10.1016/j.neuroscience.2005.10.014. PMID 16330153.
^ ^a ^b Varga V, Jenei Z, Janáky R, Saransaari P, Oja SS (1997). "Glutathione is an endogenous ligand of rat brain N-methyl-D-aspartate (NMDA) and 2-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA) receptors". Neurochemical Research. 22 (9): 1165–71. doi:10.1023/A:1027377605054. PMID 9251108.

UpToDate Contents

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English Journal

Smart Nanoparticles Based on Hyaluronic Acid for Redox-Responsive and CD44 Receptor-Mediated Targeting of Tumor.

Park HK1, Lee SJ, Oh JS, Lee SG, Jeong YI, Lee HC.
Nanoscale research letters.Nanoscale Res Lett.2015 Dec;10(1):981. doi: 10.1186/s11671-015-0981-5. Epub 2015 Jul 11.
BACKGROUND: Since aggressive cancer cells highly express the CD44 receptor compared to normal cells, hyaluronic acid (HA) can be used for CD44 targeting molecule. Since glutathione (GSH) level is normally elevated in the intracellular compartment and in the tumor cell, the fact that disulfide bond c
PMID 26163139

Glutathione metabolism in the HaCaT cell line as a model for the detoxification of the model sensitisers 2,4-dinitrohalobenzenes in human skin.

Jacquoilleot S1, Sheffield D2, Olayanju A3, Sison-Young R3, Kitteringham NR3, Naisbitt DJ3, Aleksic M2.
Toxicology letters.Toxicol Lett.2015 Aug 19;237(1):11-20. doi: 10.1016/j.toxlet.2015.05.016. Epub 2015 May 26.
Glutathione (GSH) is the most prominent antioxidant in cells and the co-factor of an important set of enzymes involved in the skin metabolic clearance system, glutathione S-transferases (GST). Here, we describe an LC-MS (liquid chromatography-mass spectroscopy) method to measure GSH and its disulfid
PMID 26022718

Sulfur amino acid metabolism in Zucker diabetic fatty rats.

Kwak HC1, Kim YM2, Oh SJ3, Kim SK4.
Biochemical pharmacology.Biochem Pharmacol.2015 Aug 1;96(3):256-66. doi: 10.1016/j.bcp.2015.05.014. Epub 2015 Jun 3.
The present study was aimed to investigate the metabolomics of sulfur amino acids in Zucker diabetic fatty (ZDF) rats, an obese type 2 diabetic animal model. Plasma levels of total cysteine, homocysteine and methionine, but not glutathione (GSH) were markedly decreased in ZDF rats. Hepatic methionin
PMID 26047850

Japanese Journal

Metabolomics changes in a rat model of obstructive jaundice: mapping to metabolism of amino acids, carbohydrates and lipids as well as oxidative stress

Journal of Clinical Biochemistry and Nutrition 57(1), 50-59, 2015
NAID 130005085269

Metabolomics changes in a rat model of obstructive jaundice: mapping to metabolism of amino acids, carbohydrates and lipids as well as oxidative stress

Journal of Clinical Biochemistry and Nutrition advpub(0), 2015
NAID 130005074644

Efficient Separation and Sensitive Detection of Biothiols by Hydrophilic Interaction Liquid Chromatography with Fluorescence Detection after Derivatization with 4-Aminosulfonyl-7-fluoro-2,1,3-benzoxadiazole

CHROMATOGRAPHY 35(3), 169-172, 2014
NAID 130005057729

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★リンクテーブル★

リンク元	「グルタチオンジスルフィド」「GSSG」
関連記事	「disulfide」

「グルタチオンジスルフィド」

Glutathione disulfide
Names
	IUPAC name (2S)-2-Amino-5-[[(2R)-3-[(2R)-2-[[(4S)-4-amino-5-hydroxy-5-oxopentanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]disulfanyl-1- (carboxymethylamino)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
Identifiers
CAS Number	27025-41-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	GSSG
ChEMBL	ChEMBL1372 ;
ChemSpider	58835 ;
ECHA InfoCard	100.043.777
IUPHAR/BPS	6835;
PubChem CID	65359; 11215652;
	InChI InChI=1S/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 Key: YPZRWBKMTBYPTK-BJDJZHNGSA-N ; InChI=1/C20H32N6O12S2/c21-9(19(35)36)1-3-13(27)25-11(17(33)23-5-15(29)30)7-39-40-8-12(18(34)24-6-16(31)32)26-14(28)4-2-10(22)20(37)38/h9-12H,1-8,21-22H2,(H,23,33)(H,24,34)(H,25,27)(H,26,28)(H,29,30)(H,31,32)(H,35,36)(H,37,38)/t9-,10-,11-,12-/m0/s1 Key: YPZRWBKMTBYPTK-BJDJZHNGBD ;
	SMILES C(CC(=O)N[C@@H](CSSC[C@@H](C(=O)NCC(=O)O)NC(=O)CC[C@@H](C(=O)O)N)C(=O)NCC(=O)O)[C@@H](C(=O)O)N ;
Properties
Chemical formula	C20H32N6O12S2
Molar mass	612.63 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: glutathione disulfide, GSSG
同: 酸化型グルタチオン、オキシグルタチオン oxiglutatione
商: ビーエスエスプラス
関: グルタチオン

[show details]

っていうか、オキシグルタチオンなんていう名称は正しくない気がする。ただのGSSGじゃん。どういう使い分けがされているの？

酸化型グルタチオン : 約 3,990 件
グルタチオンジスルフィド : 約 902 件
オキシグルタチオン : 約 1,210 件

酸化型グルタチオン。
グルタチオン(GSH)の酸化型(GSSG)である。酸化型グルタチオン、あるいはグルタチオンジスルフィドと呼ばれる。眼内に投与されたオキシグルタチオンは組織に取り込まれグルタチオン還元酵素によりグルタチオンとなり、組織のH2O2の除去などをおこなう。眼内灌流液にオキシグルタチオンを添加することで、角膜保護作用、血液房水柵破壊抑制作用、水晶体透明性維持作用、網膜機能維持作用の効果が期待できる。

「GSSG」

　　[★]

グルタチオンジスルフィド

関: glutathione disulfide、oxidized glutathione

「disulfide」

　　[★]

ジスルフィド、二硫化物

関: disulphide

[MeisterB-1] Meister A, Anderson ME (1983). "Glutathione". Annual Review of Biochemistry. 52: 711–60. doi:10.1146/annurev.bi.52.070183.003431. PMID 6137189.

[2] Deneke SM, Fanburg BL (1989). "Regulation of cellular glutathione". The American Journal of Physiology. 257 (4 Pt 1): L163–73. PMID 2572174.

[3] Meister A (1988). "Glutathione metabolism and its selective modification". The Journal of Biological Chemistry. 263 (33): 17205–8. PMID 3053703.

[4] Holmgren A, Johansson C, Berndt C, Lönn ME, Hudemann C, Lillig CH (December 2005). "Thiol redox control via thioredoxin and glutaredoxin systems". Biochem. Soc. Trans. 33 (Pt 6): 1375–7. doi:10.1042/BST20051375. PMID 16246122.

[5] Owen, Joshua B.; Butterfield, D. Allan (2010). "Measurement of oxidized/reduced glutathione ratio". In Bross, Peter; Gregersen, Niels. Protein Misfolding and Cellular Stress in Disease and Aging. Methods in Molecular Biology. 648. pp. 269–77. doi:10.1007/978-1-60761-756-3_18. ISBN 978-1-60761-755-6. PMID 20700719.

[SteulletNeijt2006-6] Steullet P, Neijt HC, Cuénod M, Do KQ (2006). "Synaptic plasticity impairment and hypofunction of NMDA receptors induced by glutathione deficit: relevance to schizophrenia". Neuroscience. 137 (3): 807–19. doi:10.1016/j.neuroscience.2005.10.014. PMID 16330153.

[VargaJenei1997-7] Varga V, Jenei Z, Janáky R, Saransaari P, Oja SS (1997). "Glutathione is an endogenous ligand of rat brain N-methyl-D-aspartate (NMDA) and 2-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA) receptors". Neurochemical Research. 22 (9): 1165–71. doi:10.1023/A:1027377605054. PMID 9251108.

v t e Antioxidants
Food antioxidants	6-Hydroxymelatonin Acetyl-L-carnitine (ALCAR) Alpha-lipoic acid (ALA) Ascorbic acid (vitamin C) Carotenoids (vitamin A) Curcumin Edaravone Polyphenols Glutathione Hydroxytyrosol L-carnitine Ladostigil Melatonin Mofegiline N-Acetylcysteine (NAC) N-Acetylserotonin (NAS) Oleocanthal Oleuropein Rasagiline Resveratrol Selegiline Selenium Tocopherols (vitamin E) Tocotrienols (vitamin E) Tyrosol Ubiquinone (coenzyme Q) Uric acid
Fuel antioxidants	Butylated hydroxytoluene 2,6-Di-tert-butylphenol 1,2-Diaminopropane 2,4-Dimethyl-6-tert-butylphenol Ethylenediamine
Measurements	Folin method ORAC TEAC FRAP

v t e Neurotransmitters
Amino acid-derived	Major excitatory/inhibitory systems: Glutamate system: Agmatine Aspartic acid (aspartate) Cycloserine Glutamic acid (glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC) Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine (adrenaline) NAS (normelatonin) Norepinephrine (noradrenaline) Serotonin (5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine Neuropeptides: See here instead.
Lipid-derived	Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide (AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine (O-AEA) Neurosteroids: See here instead.
Nucleobase-derived	Nucleosides: Adenosine system: Adenosine ADP AMP ATP
Vitamin-derived	Cholinergic system: Acetylcholine
Miscellaneous	Gasotransmitters: Carbon monoxide (CO) Hydrogen sulfide (H₂S) Nitric oxide (NO); Candidates: Acetaldehyde Ammonia (NH₃) Carbonyl sulfide (COS) Nitrous oxide (N₂O) Sulfur dioxide (SO₂)

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案内

glutathione disulfide