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19176 Sigma

DL-Buthionine-sulfoximine

≥99.0% (TLC)

  • CAS Number 5072-26-4

  • Empirical Formula (Hill Notation) C8H18N2O3S

  • Molecular Weight 222.31

  •  Beilstein Registry Number 2367136

  •  MDL number MFCD00070309

  •  PubChem Substance ID 24851509

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Properties

Related Categories Biochemicals and Reagents, Enzyme Inhibitors, Enzyme Inhibitors by Type, Enzymes, Inhibitors, and Substrates, Organic Covalent Modifiers More...
assay   ≥99.0% (TLC)
solubility   H2O: soluble50 mg/mL, clear to almost clear, colorless
storage temp.   2-8°C

Description

Other Notes

Depletes glutathionine in isolated cells9,10

Application

DL-Buthionine-sulfoximine is suitable for use to:
• examine whether the inhibition of glutathione by BSO enhances the apoptotic effect of estrogen on antihormone-resistant human breast cancer cells1
• investigate the effect of BSO on development of bovine embryos2
• inhibit GSH in several studies3,4
• investigate the effect of GSH synthesis on oocyte maturation5
It may be used to inhibit GSH and evaluate the hepatotoxicity and nephrotoxicity of natural food colorants in the absence of GSH6

Biochem/physiol Actions

DL-Buthionine-sulfoximine inhibits the biosynthesis of Glutathione (GSH) in liver and other peripheral organs. It does not have any effect on GSH in the CNS.7 It augments the antiproliferative action of reactive oxygen species (e.g., hydrogen peroxide), and agents that indirectly cause accumulation of reactive oxygen species (e.g., 2-methoxyestradiol, which increases intracellular superoxide anion).8

Price and Availability

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
WGK Germany 
3
RTECS 
EK7713435

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. Buthionine sulfoximine sensitizes antihormone-resistant human breast cancer cells to estrogen-induced apoptosis. Lewis-Wambi JS, Kim HR, Wambi C, et al. Breast Cancer Res. 10(6), R104, (2008)

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2. Effect of thiol compounds on in vitro development and intracellular glutathione content of bovine embryos. Takahashi M, Nagai T, Hamano S, et al. Biol. Reprod. 49(2), 228-32, (1993)

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3. Effect of curcumin on normal and tumor cells: role of glutathione and bcl-2. Syng-Ai C, Kumari AL, and Khar A Mol. Cancer Ther. 3(9), 1101-8, (2004)

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4. Effects of exercise intensity on lymphocyte apoptosis induced by oxidative stress in men. Wang JS and Huang YH Eur. J. Appl. Physiol. 95(4), 290-7, (2005)

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5. Male pronuclear formation in denuded porcine oocytes after in vitro maturation in the presence of cysteamine. Yamauchi N and Nagai T Biol. Reprod. 61(3), 828-33, (1999)

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6. Evaluation of hepatotoxicity and nephrotoxicity of natural food colorants in mice depleted of glutathione by DL-buthionine sulfoximine. Kawazoe S, et al. J. Health Sci. 1st ed., 46, 56-58, (2000)

7. Depletion of brain glutathione in preweanling mice by L-buthionine sulfoximine. Slivka A, Spina MB, Calvin HI, et al. J. Neurochem. 50(5), 1391-3, (1988)

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8. Effect of 2-methoxyestradiol, buthionine sulfoximine and hydrogen peroxide on the viability of renal carcinoma cell lines (ACHN and ACVB) Hirai, Y., et al. Biol. Pharm. Bull. 29, 1064-1067, (2006)

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9. Depletion of glutathione by inhibition of biosynthesis. O.W. Griffith Meth. Enzymol. 77, 59, (1981)

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10. Microtiter plate assay for the measurement of glutathione and glutathione disulfide in large numbers of biological samples. M.A. Baker et al. Anal. Biochem. 190, 360, (1990)

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Glutathione and glutaredoxin act as a backup of human thioredoxin reductase 1 to reduce thioredoxin 1 preventing cell death by aurothioglucose. Du Y, Zhang H, Lu J, et al. J. Biol. Chem. 287(45), 38210-9, (2012)

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Hyperactivity of the Ero1α oxidase elicits endoplasmic reticulum stress but no broad antioxidant response. Hansen HG, Schmidt JD, Søltoft CL, et al. J. Biol. Chem. 287(47), 39513-23, (2012)

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Molecular modulated cysteine-selective fluorescent probe. Jung HS, Pradhan T, Han JH, et al. Biomaterials 33, 8495-8502, (2012)

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Isoliquiritigenin attenuates oxidative hepatic damage induced by carbon tetrachloride with or without buthionine sulfoximine. Zhao Z, Park SM, Guan L, et al. Chem. Biol. Interact. 225, 13-20, (2015)

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Implication of glutathione in the in vitro antiplasmodial mechanism of action of ellagic acid. Njomnang Soh P, Witkowski B, Gales A, et al. PLoS ONE 7(9), e45906, (2012)

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Dietary flavonoid genistein induces Nrf2 and phase II detoxification gene expression via ERKs and PKC pathways and protects against oxidative stress in Caco-2 cells. Zhai X, Lin M, Zhang F, et al. Mol. Nutr. Food. Res. 57(2), 249-59, (2013)

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Oxidative stress modulates mitochondrial failure and cyclophilin D function in X-linked adrenoleukodystrophy. López-Erauskin J, Galino J, Bianchi P, et al. Brain 135(Pt 12), 3584-98, (2012)

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Carnosic acid prevents 6-hydroxydopamine-induced cell death in SH-SY5Y cells via mediation of glutathione synthesis. Chen JH, Ou HP, Lin CY, Lin FJ, et al. Chem. Res. Toxicol. 25, 1893-1901, (2012)

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Grape powder supplementation prevents oxidative stress-induced anxiety-like behavior, memory impairment, and high blood pressure in rats. Allam F, Dao AT, Chugh G, et al. J. Nutr. 143(6), 835-42, (2013)

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Susceptibility of human head and neck cancer cells to combined inhibition of glutathione and thioredoxin metabolism. Sobhakumari A, Love-Homan L, Fletcher EV, et al. PLoS ONE 7(10), e48175, (2012)

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Neurotoxicity of "ecstasy" and its metabolites in human dopaminergic differentiated SH-SY5Y cells. Ferreira PS, Nogueira TB, Costa VM, et al. Toxicol. Lett. 216(2-3), 159-70, (2013)

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Chimeric mice with a humanized liver as an animal model of troglitazone-induced liver injury. Kakuni M, Morita M, Matsuo K, et al. Toxicol. Lett. 214(1), 9-18, (2012)

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Inhibition of glutathione synthesis eliminates the adaptive response of ascitic hepatoma 22 cells to nedaplatin that targets thioredoxin reductase. Wang Y, Lu H, Wang D, et al. Toxicol. Appl. Pharmacol. 265(3), 342-50, (2012)

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Role of drug-independent stress factors in liver injury associated with diclofenac intake. Ramm S and Mally A Toxicology 312, 83-96, (2013)

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miR395 is a general component of the sulfate assimilation regulatory network in Arabidopsis. Matthewman CA, Kawashima CG, Húska D, et al. FEBS Lett. 586(19), 3242-8, (2012)

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BYPASS1: synthesis of the mobile root-derived signal requires active root growth and arrests early leaf development. Van Norman JM, Murphy C, and Sieburth LE BMC Plant Biol. 11, 28, (2011)

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Glutathione depletion and carbon ion radiation potentiate clustered DNA lesions, cell death and prevent chromosomal changes in cancer cells progeny. Hanot M, Boivin A, Malésys C, et al. PLoS ONE 7(11), e44367, (2012)

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Role of GSH/GSSG redox couple in osteogenic activity and osteoclastogenic markers of human osteoblast-like SaOS-2 cells. Romagnoli C, Marcucci G, Favilli F, et al. FEBS J. 280(3), 867-79, (2013)

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R- and S-equol have equivalent cytoprotective effects in Friedreich's ataxia. Richardson TE and Simpkins JW BMC Pharmacol. Toxicol. 13, 12, (2012)

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Upregulation of Nrf2 expression by human cytomegalovirus infection protects host cells from oxidative stress. Lee J, Koh K, Kim YE, et al. J. Gen. Virol. 94(Pt 7), 1658-68, (2013)

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Depletion of cellular glutathione modulates LIF-induced JAK1-STAT3 signaling in cardiac myocytes. Kurdi M, Sivakumaran V, Duhé RJ, et al. Int. J. Biochem. Cell Biol. 44(12), 2106-15, (2012)

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Redox regulation of MMP-3/TIMP-1 ratio in intestinal myofibroblasts: effect of N-acetylcysteine and curcumin. Fontani F, Marcucci T, Picariello L, et al. Exp. Cell Res. 323(1), 77-86, (2014)

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Novel phosphorylation and ubiquitination sites regulate reactive oxygen species-dependent degradation of anti-apoptotic c-FLIP protein. Wilkie-Grantham RP, Matsuzawa S, and Reed JC J. Biol. Chem. 288(18), 12777-90, (2013)

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Acute glutathione depletion induces hepatic methylglyoxal accumulation by impairing its detoxification to D-lactate. Masterjohn C, Mah E, Park Y, et al. Exp. Biol. Med. (Maywood.) 238(4), 360-9, (2013)

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Human adipose tissue-derived multilineage progenitor cells exposed to oxidative stress induce neurite outgrowth in PC12 cells through p38 MAPK signaling. Moriyama M, Moriyama H, Ueda A, et al. BMC Cell Biol. 13, 21, (2012)

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Inhibition of glutathione synthesis distinctly alters mitochondrial and cytosolic redox poise. Kolossov VL, Hanafin WP, Beaudoin JN, et al. Exp. Biol. Med. (Maywood.) 239(4), 394-403, (2014)

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8-Hydroxycalamenene isolated from the rhizomes of Reynoutria elliptica exerts neuroprotective effects both in vitro and in vivo. Jo H, Lee HJ, Kim CY, et al. Food Chem. Toxicol. 51, 231-41, (2013)

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Buthionine sulfoximine and 1,25-dihydroxyvitamin D induce apoptosis in breast cancer cells via induction of reactive oxygen species. Bohl LP, Liaudat AC, Picotto G, et al. Cancer Invest. 30(8), 560-70, (2012)

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Comparative evaluation of small-molecule chemosensitizers in reversal of cisplatin resistance in ovarian cancer cells. Yellepeddi VK, Vangara KK, Kumar A, et al. Anticancer Res. 32(9), 3651-8, (2012)

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Cellular accumulation of Cys326-OGG1 protein complexes under conditions of oxidative stress. Kaur MP, Guggenheim EJ, Pulisciano C, et al. Biochem. Biophys. Res. Commun. 447(1), 12-8, (2014)

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Multidrug resistance associated protein 1 together with glutathione plays a protective role against 4-hydroxy-2-nonenal-induced oxidative stress in bovine aortic endothelial cells. Takahashi K, Tatsunami R, Sato K, et al. Biol. Pharm. Bull. 35(8), 1269-74, (2012)

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