Molecular structure of L-Buthionine-(S,R)-Sulfoximine, CAS Number: 83730-53-4
L-Buthionine-(S,R)-Sulfoximine (CAS 83730-53-4)
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Alternate Names:
(2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid; L-Buthionine Sulfoximine; NSC 326231
Application:
L-Buthionine-(S,R)-Sulfoximine is an irreversible inhibitor of γ-glutamylcysteine synthetase
CAS Number:
83730-53-4
Purity:
≥97%
Molecular Weight:
222.30
Molecular Formula:
C8H18N2O3S
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
L-Buthionine-(S,R)-Sulfoximine is a chemical widely used in biochemical research focused on elucidating the role of glutathione in cellular processes. It functions as an inhibitor of γ-glutamylcysteine synthetase, the enzyme responsible for the first step in glutathione synthesis. By modulating glutathione levels, L-Buthionine-(S,R)-Sulfoximine allows researchers to investigate the effects of oxidative stress on cells and to study the mechanisms of cellular defense against such stress. The compound also serves as useful in the study of apoptosis, particularly in understanding how the intracellular redox state can influence cell death pathways. Moreover, L-Buthionine-(S,R)-Sulfoximine is used in plant biology to explore the role of glutathione in the response of plants to environmental stressors and in the detoxification of xenobiotics.
L-Buthionine-(S,R)-Sulfoximine (CAS 83730-53-4) References
- Oxidative stress induced by L-buthionine-(S,R)-sulfoximine, a selective inhibitor of glutathione metabolism, abrogates mouse kidney mineralocorticoid receptor function. | Piwien-Pilipuk, G. and Galigniana, MD. 2000. Biochim Biophys Acta. 1495: 263-80. PMID: 10699465
- Glutathione depletion with L-buthionine-(S,R)-sulfoximine demonstrates deleterious effects in acute pancreatitis of the rat. | Alsfasser, G., et al. 2002. Dig Dis Sci. 47: 1793-9. PMID: 12184532
- A novel model of continuous depletion of glutathione in mice treated with L-buthionine (S,R)-sulfoximine. | Watanabe, T., et al. 2003. J Toxicol Sci. 28: 455-69. PMID: 14746349
- Gamma-glutamylcysteine synthetase and L-buthionine-(S,R)-sulfoximine: a new selection strategy for gene-transduced neural and hematopoietic stem/progenitor cells. | Lorico, A., et al. 2005. Hum Gene Ther. 16: 711-24. PMID: 15960602
- Adaptive response to GSH depletion and resistance to L-buthionine-(S,R)-sulfoximine: involvement of Nrf2 activation. | Lee, HR., et al. 2008. Mol Cell Biochem. 318: 23-31. PMID: 18587629
- In vivo inhibition of l-buthionine-(S,R)-sulfoximine-induced cataracts by a novel antioxidant, N-acetylcysteine amide. | Carey, JW., et al. 2011. Free Radic Biol Med. 50: 722-9. PMID: 21172425
- Glutathione Depletion by L-Buthionine-S,R-Sulfoximine Induces Apoptosis of Cardiomyocytes through Activation of PKC-δ. | Kim, YA., et al. 2013. Biomol Ther (Seoul). 21: 358-63. PMID: 24244823
- Inhibition of glutathione production by L-S,R-buthionine sulfoximine activates hepatic ascorbate synthesis - A unique anti-oxidative stress mechanism in mice. | Yu, M., et al. 2017. Biochem Biophys Res Commun. 484: 56-63. PMID: 28115164
- Circulating liver-specific microRNAs in cynomolgus monkeys. | Iguchi, T., et al. 2018. J Toxicol Pathol. 31: 3-13. PMID: 29479135
- Systemic L-buthionine-S-R-sulfoximine administration modulates glutathione homeostasis via NGF/TrkA and mTOR signaling in the cerebellum. | Garza-Lombó, C., et al. 2018. Neurochem Int. 121: 8-18. PMID: 30300680
- Systemic L-Buthionine -S-R-Sulfoximine Treatment Increases Plasma NGF and Upregulates L-cys/L-cys2 Transporter and γ-Glutamylcysteine Ligase mRNAs Through the NGF/TrkA/Akt/Nrf2 Pathway in the Striatum. | Valdovinos-Flores, C., et al. 2019. Front Cell Neurosci. 13: 325. PMID: 31396052
- Determination of L-buthionine-(S,R)-sulfoximine in plasma by high-performance liquid chromatography with o-phthalaldehyde derivatization and fluorometric detection. | Duff, R. and Murrill, E. 1987. J Chromatogr. 385: 275-82. PMID: 3558582
- L1210(A) mouse lymphoma cells depleted of glutathione with L-buthionine-S-R-sulfoximine proliferate in tissue culture. | Gaetjens, EC., et al. 1984. Biochem Biophys Res Commun. 123: 626-32. PMID: 6487304
- Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. | Fruehauf, JP., et al. 1997. Pigment Cell Res. 10: 236-49. PMID: 9263331
- Melanin content and downregulation of glutathione S-transferase contribute to the action of L-buthionine-S-sulfoximine on human melanoma. | Fruehauf, JP., et al. 1998. Chem Biol Interact. 111-112: 277-305. PMID: 9679561
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
L-Buthionine-(S,R)-Sulfoximine, 500 mg | sc-218630 | 500 mg | $222.00 | |||
L-Buthionine-(S,R)-Sulfoximine, 1 g | sc-218630A | 1 g | $414.00 | |||
L-Buthionine-(S,R)-Sulfoximine, 5 g | sc-218630B | 5 g | $1638.00 | |||
L-Buthionine-(S,R)-Sulfoximine, 10 g | sc-218630C | 10 g | $2760.00 |