Home Metabolism inhibitor L-Buthionine-(S,R)-sulfoximine (L-BSO)

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L-Buthionine-(S,R)-sulfoximine (L-BSO) inhibitor

Cat.No.S9728

BSO is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase (γ-glutamylcysteine synthetase, γ-GCS) and depletes cellular glutathione levels. The IC50 of BSO on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.
L-Buthionine-(S,R)-sulfoximine (L-BSO) inhibitor Chemical Structure

Chemical Structure

Molecular Weight: 222.31

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Quality Control

Batch: Purity: 98.904%
98.904

Solubility

In vitro
Batch:

Water : 44 mg/mL

DMSO : Insoluble
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Ethanol : Insoluble

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Chemical Information, Storage & Stability

Molecular Weight 222.31 Formula

C8H18N2O3S

 Storage (From the date of receipt) 3 years -20°C powder
CAS No. 83730-53-4 -- Storage of Stock Solutions

Synonyms L-Buthionine sulfoximine, l-BSO SMILES CCCC[S](=N)(=O)CCC(N)C(O)=O

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Mechanism of Action

In vitro

BSO (L-Buthionine-(S,R)-sulfoximine) synergistically enhanced BCNU activity against melanoma cell lines and human tumors. This compound (50 μM) treatment for 48 hr results in a 95% decrease in ZAZ and M14 melanoma cell line GSH levels, and a 60% decrease in GST enzyme activity. GST-μ protein and mRNA levels are significantly reduced in both cell lines. GST-π expression is unaffected. This chemical enhancement of alkylator action may be related in part to down regulation of GST.
In vivo

LButhionine-S,R-sulfoximine (L-S,R-BSO) substantially inhibits GSH production at a greater degree and causes a higher toxicity to guinea pigs than mice, implying that mice may have an additional protective mechanism against oxidative stress injury. Indeed, administration of this compound to mice inhibits tissue GSH production while increasing ascorbate levels. This chemical also increases tissue ascorbate levels in mice fed a ascorbate and dehydroascorbatefree diet suggesting activation of ascorbate synthesis, which is further confirmed by increased urinary ascorbate excretion.
References

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2026-01-30)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT04073706 RECRUITING
Endometrial Cancer Stage I; Sentinel Lymph Node; Surgery
Queensland Centre for Gynaecological Cancer
 2021-01-18 PHASE3
NCT01820884 ACTIVE_NOT_RECRUITING
Endometrial Neoplasms
Ding Ma
 2012-11
NCT03744494 COMPLETED
Prostate Cancer; Quality of Life; Orchiectomy
University College Hospital, Ibadan
 2016-03-02
NCT00005835 COMPLETED
Neuroblastoma
New Approaches to Neuroblastoma Therapy Consortium
 2001-08 PHASE1
NCT01619800 TERMINATED
Chronotropic Incompetence
Vivek Reddy
 2012-03
NCT01369654 COMPLETED
Surgical Procedure, Unspecified
University of California, San Francisco
 2011-05

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