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Chemical Compound Review:

L-BSO (2S)-2-amino-4- (butylsulfonimidoyl)butanoi...

Synonyms: NCIMech_000342, CHEMBL1609891, B2515_SIGMA, NSC-326231, Lopac0_000221, ...

Hansson, J. et al., Hromas, R.A. et al., Lee, E.A. et al., Aidoo, A. et al., Hempel, S.L. et al., et al.

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Disease relevance of NCIMech_000342

Effect of D,L-buthionine-S,R-sulfoximine on cytotoxicity and DNA cross-linking induced by bifunctional DNA-reactive cytostatic drugs in human melanoma cells [1].
The cisplatin-resistant murine leukemia L1210 cell line L1210/PAM has an elevated cellular glutathione content, as compared to its sensitive parent cell line, L1210/*. Exposure to D,L-buthionine-S,R-sulfoximine reduced L1210/PAM cells' glutathione content to nearly that of L1210/* cells and abrogated the resistance to cisplatin [2].

High impact information on NCIMech_000342

Conversely, pretreatment of the tumor-bearing hosts with DL-buthionine-(S,R)-sulfoximine, an inhibitor of GSH biosynthesis, resulted in an increased sensitivity of Meth A to rhTNF [3].
Pretreatment of SMCs with N-acetyl-L-cysteine significantly suppressed the MG-induced AR expression, whereas DL-buthionine-(S,R)-sulfoximine further augmented the MG-induced increase in AR mRNA level [4].
Serum challenge of G(0) synchronized cultures of vSMCs with DL-buthionine-(S,R)-sulfoximine (0.1 mM), a depletor of cellular glutathione, increased c-Ha-ras mRNA levels during the early phase of the mitogenic response [5].
METHODS: Growth arrested and synchronized primary rat mesangial cells were treated with different concentrations of glucose in the presence or absence of N-acetylcysteine (NAC) or trolox, or after cellular reduced form of glutathione (GSH) depleted with DL-buthionine-(S,R)-sulfoximine (BSO) [6].
METHODS: RPE cells were treated with HGF for 24 hours (20 ng/mL) and then were treated with DL-buthionine-(S,R)-sulfoximine (BSO) for an additional 24 hours [7].

Biological context of NCIMech_000342

GSH and NPSH levels were depleted in V79 cells of varying cell densities using the gamma-glutamyl-cysteine-synthetase inhibitor, D,L-Buthionine-S,R-sulfoximine (BSO) [8].

Anatomical context of NCIMech_000342

The effects of D,L-buthionine-S,R-sulfoximine (BSO) on cytotoxicity and DNA cross-linking induced by bifunctional DNA-reactive cytostatic agents in a human melanoma cell line (RPMI 8322) were investigated [1].
Elevation of GSH levels in the bone marrow was inhibited with the use of D,L-buthionine-S,R-sulfoximine (BSO), and this resulted in loss of the protective effect of CTX pre-treatment [9].
Exposure of cells to DL-buthionine-(S,R)-sulfoximine (BSO), an inhibitor of GSH biosynthesis, significantly depleted GSH and lowered the proliferative response, suggesting a crucial role of de novo GSH synthesis for lymphocyte activation [10].

Associations of NCIMech_000342 with other chemical compounds

To study this question, the effect of D,L-buthionine-S,R-sulfoximine (BSO) on doxorubicin cytotoxicity and the stabilization of DNA-topoisomerase II complexes (cleavable complexes) was investigated in V79 cells [11].
The resistance of MRP4 to various CPTs tested was significantly reversed in the presence of dl-buthionine-(S,R)-sulfoximine (BSO, a gamma-glutamylcysteine synthetase inhibitor), MK571, celecoxib, or diclofenac (all MRP4 inhibitors) [12].

Gene context of NCIMech_000342

Depletion of GSH with D,L-buthionine-S,R-sulfoximine (BSO) had no effect on the sensitivity of these cells to either CdCl2 or DDP [13].
Glutathione depletion produced by DL-buthionine-(S,R)-sulfoximine (BSO), 1,3-bis(chloroethyl)1-nitrosourea (BCNU), or incubation in a sulfhydryl-free medium resulted in increased sensitivity of PGH synthase to the effects of added H2O2 [14].

References

Effect of D,L-buthionine-S,R-sulfoximine on cytotoxicity and DNA cross-linking induced by bifunctional DNA-reactive cytostatic drugs in human melanoma cells. Hansson, J., Edgren, M., Ehrsson, H., Ringborg, U., Nilsson, B. Cancer Res. (1988) [Pubmed]
Glutathione depletion reverses cisplatin resistance in murine L1210 leukemia cells. Hromas, R.A., Andrews, P.A., Murphy, M.P., Burns, C.P. Cancer Lett. (1987) [Pubmed]
The role of oxidant injury in tumor cell sensitivity to recombinant human tumor necrosis factor in vivo. Implications for mechanisms of action. Zimmerman, R.J., Marafino, B.J., Chan, A., Landre, P., Winkelhake, J.L. J. Immunol. (1989) [Pubmed]
Substrate-induced up-regulation of aldose reductase by methylglyoxal, a reactive oxoaldehyde elevated in diabetes. Chang, K.C., Paek, K.S., Kim, H.J., Lee, Y.S., Yabe-Nishimura, C., Seo, H.G. Mol. Pharmacol. (2002) [Pubmed]
Activation of c-Ha-ras by benzo(a)pyrene in vascular smooth muscle cells involves redox stress and aryl hydrocarbon receptor. Kerzee, J.K., Ramos, K.S. Mol. Pharmacol. (2000) [Pubmed]
Reactive oxygen species mediate high glucose-induced plasminogen activator inhibitor-1 up-regulation in mesangial cells and in diabetic kidney. Lee, E.A., Seo, J.Y., Jiang, Z., Yu, M.R., Kwon, M.K., Ha, H., Lee, H.B. Kidney Int. (2005) [Pubmed]
Hepatocyte growth factor protects RPE cells from apoptosis induced by glutathione depletion. Jin, M., Yaung, J., Kannan, R., He, S., Ryan, S.J., Hinton, D.R. Invest. Ophthalmol. Vis. Sci. (2005) [Pubmed]
Effects of D,L-buthionine-S,R-sulfoximine on cellular thiol levels and the oxygen effect in Chinese hamster V79 cells. Astor, M.B., Hall, E.J., Biaglow, J.E., Hartog, B. Int. J. Radiat. Oncol. Biol. Phys. (1984) [Pubmed]
Inhibition of the protective effect of cyclophosphamide by pre-treatment with buthionine sulfoximine. Carmichael, J., Friedman, N., Tochner, Z., Adams, D.J., Wolf, C.R., Mitchell, J.B., Russo, A. Int. J. Radiat. Oncol. Biol. Phys. (1986) [Pubmed]
Comparative study of intracellular glutathione content in rat lymphocyte cultures treated with 2-mercaptoethanol and interleukin-2. Aidoo, A., Lyn-Cook, L.E., Morris, S.M., Kodell, R.L., Casciano, D.A. Cell Biol. Toxicol. (1991) [Pubmed]
Interaction of buthionine sulfoximine and the stabilization of DNA-topoisomerase II complexes by doxorubicin. Bonner, J.A., Christianson, T.J., Lawrence, T.S. Int. J. Radiat. Oncol. Biol. Phys. (1992) [Pubmed]
Human multidrug resistance associated protein 4 confers resistance to camptothecins. Tian, Q., Zhang, J., Tan, T.M., Chan, E., Duan, W., Chan, S.Y., Boelsterli, U.A., Ho, P.C., Yang, H., Bian, J.S., Huang, M., Zhu, Y.Z., Xiong, W., Li, X., Zhou, S. Pharm. Res. (2005) [Pubmed]
Metallothionein-mediated cisplatin resistance in human ovarian carcinoma cells. Andrews, P.A., Murphy, M.P., Howell, S.B. Cancer Chemother. Pharmacol. (1987) [Pubmed]
Effect of glutathione on endothelial prostacyclin synthesis after anoxia. Hempel, S.L., Wessels, D.A., Spector, A.A. Am. J. Physiol. (1993) [Pubmed]

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