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Chemical Compound Review

AG-K-85834     (2S)-2-(butan-2-ylamino)-4- sulfanyl...

Synonyms: AC1Q5QTD, CTK4H0586, AR-1K6379, AR-1K6380, AC1L4O26, ...
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Disease relevance of L-Buthionine

  • Metastasis (number of foci/100 mm(3) of liver) increased in B16MF1 cells pretreated with GSH ester ( approximately 3-fold, P <.01), and decreased in B16MF1/Tet-GGT and B16MF10 cells pretreated with the GSH synthesis inhibitor L-buthionine (S,R)-sulphoximine ( approximately 5-fold and 2-fold, respectively, P <.01) [1].
  • The toxicity assay utilized cells that were previously exposed to 100 microM L-buthionine (S,R)-sulfoximine (BSO), an inhibitor of gamma-glutamyl-cysteine synthetase, for 24 h [2].
  • Enzyme induction by L-buthionine (S,R)-sulfoximine in cultured mouse hepatoma cells [3].

High impact information on L-Buthionine


Chemical compound and disease context of L-Buthionine

  • However, in the presence of the GSH synthesis inhibitor, L-buthionine (S,R)-sulfoximide (BSO), the protective effect of CA toward cadmium toxicity remained [9].

Biological context of L-Buthionine

  • Stereoselective pharmacokinetics of L-buthionine SR-sulfoximine in patients with cancer [10].
  • In part 2, the effect of glutathione (a major component of NAC hepatoprotection) was examined by measuring ACh-induced vasorelaxation in rings from rats treated with L-buthionine sulfoxamine (BSO, a glutathione synthesis inhibitor) [11].
  • In plants treated with 1 mM L-buthionine sulphoximine, a potent inhibitor of GSH/hGSH synthesis, only the oxidative stress symptoms appeared, indicating that the depletion of the GSH/hGSH pool was not sufficient to promote cell death, and that other phytotoxic mechanisms might be involved [12].
  • When pre-treated with l-buthionine S,R-sulphoximine (BSO) to deplete GSH, CYP2C9-expressing cells showed also a loss of cell viability as compared to LNCX cells, although to a lesser extent as compared to non-depleted CYP2C9-expressing cells [13].

Anatomical context of L-Buthionine

  • When the endogenous GSH content was reduced by pretreatment of the cells with L-buthionine (S,R)-sulfoximine, the cytotoxicity of the herbicides increased strongly in both cell lines [14].

Associations of L-Buthionine with other chemical compounds


Gene context of L-Buthionine

  • To elucidate the role of GSH in regulation of AP-1, NF-kappaB, and VCAM-1 expression, we employed l-buthionine (S,R)-sulfoximine (BSO), a specific gamma-glutamylcysteine synthetase (gamma-GCS) inhibitor, to block intracellular GSH synthesis [16].
  • Induction of Phase II enzymes of the [Ah] gene battery by L-buthionine (S,R)-sulfoximine (BSO) and other agents was examined in mouse hepatoma Hepa-1c1c7 cells [3].
  • L-Buthionine (R)-sulfoximine (0.2 mmol/kg) did not cause significant GSH depletion in liver or pancreas [15].


  1. gamma-Glutamyl transpeptidase overexpression increases metastatic growth of B16 melanoma cells in the mouse liver. Obrador, E., Carretero, J., Ortega, A., Medina, I., Rodilla, V., Pellicer, J.A., Estrela, J.M. Hepatology (2002) [Pubmed]
  2. Effects of lazaroids and a peroxynitrite scavenger in a cell model of peroxynitrite toxicity. Fici, G.J., Althaus, J.S., VonVoigtlander, P.F. Free Radic. Biol. Med. (1997) [Pubmed]
  3. Enzyme induction by L-buthionine (S,R)-sulfoximine in cultured mouse hepatoma cells. Shertzer, H.G., Vasiliou, V., Liu, R.M., Tabor, M.W., Nebert, D.W. Chem. Res. Toxicol. (1995) [Pubmed]
  4. ars1, an Arabidopsis mutant exhibiting increased tolerance to arsenate and increased phosphate uptake. Lee, D.A., Chen, A., Schroeder, J.I. Plant J. (2003) [Pubmed]
  5. Oxidative stress in glial cultures: detection by DAF-2 fluorescence used as a tool to measure peroxynitrite rather than nitric oxide. Roychowdhury, S., Luthe, A., Keilhoff, G., Wolf, G., Horn, T.F. Glia (2002) [Pubmed]
  6. Regulation of [Ah] gene battery enzymes and glutathione levels by 5,10-dihydroindeno[1,2-b]indole in mouse hepatoma cell lines. Liu, R.M., Vasiliou, V., Zhu, H., Duh, J.L., Tabor, M.W., Puga, A., Nebert, D.W., Sainsbury, M., Shertzer, H.G. Carcinogenesis (1994) [Pubmed]
  7. 1-Benzyl-1,2,3,4-tetrahydroisoquinoline, a Parkinsonism-inducing endogenous toxin, increases alpha-synuclein expression and causes nuclear damage in human dopaminergic cells. Shavali, S., Carlson, E.C., Swinscoe, J.C., Ebadi, M. J. Neurosci. Res. (2004) [Pubmed]
  8. Glutathione-independent mechanism of apoptosis inhibition by curcumin in rat thymocytes. Jaruga, E., Bielak-Zmijewska, A., Sikora, E., Skierski, J., Radziszewska, E., Piwocka, K., Bartosz, G. Biochem. Pharmacol. (1998) [Pubmed]
  9. Cyproterone acetate induces a cellular tolerance to cadmium in rat liver epithelial cells involving reduced cadmium accumulation. Takiguchi, M., Cherrington, N.J., Hartley, D.P., Klaassen, C.D., Waalkes, M.P. Toxicology (2001) [Pubmed]
  10. Stereoselective pharmacokinetics of L-buthionine SR-sulfoximine in patients with cancer. Lacreta, F.P., Brennan, J.M., Hamilton, T.C., Ozols, R.F., O'Dwyer, P.J. Drug Metab. Dispos. (1994) [Pubmed]
  11. N-acetylcysteine enhances endothelium-dependent vasorelaxation in the isolated rat mesenteric artery. Lopez, B.L., Snyder, J.W., Birenbaum, D.S., Ma, X.I. Annals of emergency medicine. (1998) [Pubmed]
  12. Cellular damage induced by cadmium and mercury in Medicago sativa. Ortega-Villasante, C., Rellán-Alvarez, R., Del Campo, F.F., Carpena-Ruiz, R.O., Hernández, L.E. J. Exp. Bot. (2005) [Pubmed]
  13. Metabolism-mediated cytotoxicity of ochratoxin A. Simarro Doorten, A.Y., Bull, S., van der Doelen, M.A., Fink-Gremmels, J. Toxicology in vitro : an international journal published in association with BIBRA. (2004) [Pubmed]
  14. Glutathione-dependent cytotoxicity of the chloroacetanilide herbicides alachlor, metolachlor, and propachlor in rat and human hepatoma-derived cultured cells. Dierickx, P.J. Cell Biol. Toxicol. (1999) [Pubmed]
  15. Analytical and preparative separation of the diastereomers of L-buthionine (SR)-sulfoximine, a potent inhibitor of glutathione biosynthesis. Campbell, E.B., Hayward, M.L., Griffith, O.W. Anal. Biochem. (1991) [Pubmed]
  16. Arsenite enhances tumor necrosis factor-alpha-induced expression of vascular cell adhesion molecule-1. Tsou, T.C., Yeh, S.C., Tsai, E.M., Tsai, F.Y., Chao, H.R., Chang, L.W. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
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