MedKoo Cat#: 574070 | Name: L-Buthionine sulfoximine
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

L-Buthionine sulfoximine is an irreversible γ-glutamylcysteine synthetase (γ-GCS) inhibitor that depletes glutathione levels by inhibiting synthesis. L-Buthionine sulfoximine also induces ferroptosis in vitro.

Chemical Structure

L-Buthionine sulfoximine
L-Buthionine sulfoximine
CAS#83730-53-4 (L)

Theoretical Analysis

MedKoo Cat#: 574070

Name: L-Buthionine sulfoximine

CAS#: 83730-53-4 (L)

Chemical Formula: C8H18N2O3S

Exact Mass: 222.1038

Molecular Weight: 222.30

Elemental Analysis: C, 43.22; H, 8.16; N, 12.60; O, 21.59; S, 14.42

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Synonym
L-Buthionine sulfoximine
IUPAC/Chemical Name
(2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic acid
InChi Key
KJQFBVYMGADDTQ-CVSPRKDYSA-N
InChi Code
InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)/t7-,14?/m0/s1
SMILES Code
O=C(O)[C@@H](N)CCS(=N)(CCCC)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels.
In vitro activity:
BSO (L-Buthionine-(S,R)-sulfoximine) was demonstrated to suppress glutathione levels and induce lipid peroxidation, thereby inhibiting cell viability. The viability-reducing effects of BSO were attenuated by ferroptosis inhibition and enhanced by iron, indicating that BSO induced ferroptosis in cancer cells. Reference: Oncol Lett. 2018 Jun;15(6):8735-8743. https://pubmed.ncbi.nlm.nih.gov/29928324/
In vivo activity:
Indeed, administration of L-S,R-BSO (L-Buthionine sulfoximine) to mice inhibited tissue GSH production while increasing ascorbate levels. L-S,R-BSO also increased tissue ascorbate levels in mice fed a ascorbate and dehydroascorbate-free diet suggesting activation of ascorbate synthesis, which was further confirmed by increased urinary ascorbate excretion. Other reagents inhibiting GSH production also increased tissue ascorbate levels. Reference: Biochem Biophys Res Commun. 2017 Feb 26;484(1):56-63. https://pubmed.ncbi.nlm.nih.gov/28115164/
Solvent mg/mL mM
Solubility
DMSO 22.2 100.00
PBS (pH 7.2) 5.0 22.49
Water 26.9 120.80
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 222.30 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nishizawa S, Araki H, Ishikawa Y, Kitazawa S, Hata A, Soga T, Hara T. Low tumor glutathione level as a sensitivity marker for glutamate-cysteine ligase inhibitors. Oncol Lett. 2018 Jun;15(6):8735-8743. doi: 10.3892/ol.2018.8447. Epub 2018 Apr 10. PMID: 29928324; PMCID: PMC6004701. 2. Fruehauf JP, Zonis S, al-Bassam M, Kyshtoobayeva A, Dasgupta C, Milovanovic T, Parker RJ, Buzaid AC. Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. Pigment Cell Res. 1997 Aug;10(4):236-49. doi: 10.1111/j.1600-0749.1997.tb00490.x. PMID: 9263331. 3. Yu M, Liu Y, Duan Y, Chen Y, Han J, Sun L, Yang X. Inhibition of glutathione production by L-S,R-buthionine sulfoximine activates hepatic ascorbate synthesis - A unique anti-oxidative stress mechanism in mice. Biochem Biophys Res Commun. 2017 Feb 26;484(1):56-63. doi: 10.1016/j.bbrc.2017.01.072. Epub 2017 Jan 20. PMID: 28115164. 4. Reliene R, Schiestl RH. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. doi: 10.1093/carcin/bgi222. Epub 2005 Sep 14. PMID: 16162646.
In vitro protocol:
1. Nishizawa S, Araki H, Ishikawa Y, Kitazawa S, Hata A, Soga T, Hara T. Low tumor glutathione level as a sensitivity marker for glutamate-cysteine ligase inhibitors. Oncol Lett. 2018 Jun;15(6):8735-8743. doi: 10.3892/ol.2018.8447. Epub 2018 Apr 10. PMID: 29928324; PMCID: PMC6004701. 2. Fruehauf JP, Zonis S, al-Bassam M, Kyshtoobayeva A, Dasgupta C, Milovanovic T, Parker RJ, Buzaid AC. Selective and synergistic activity of L-S,R-buthionine sulfoximine on malignant melanoma is accompanied by decreased expression of glutathione-S-transferase. Pigment Cell Res. 1997 Aug;10(4):236-49. doi: 10.1111/j.1600-0749.1997.tb00490.x. PMID: 9263331.
In vivo protocol:
1. Yu M, Liu Y, Duan Y, Chen Y, Han J, Sun L, Yang X. Inhibition of glutathione production by L-S,R-buthionine sulfoximine activates hepatic ascorbate synthesis - A unique anti-oxidative stress mechanism in mice. Biochem Biophys Res Commun. 2017 Feb 26;484(1):56-63. doi: 10.1016/j.bbrc.2017.01.072. Epub 2017 Jan 20. PMID: 28115164. 2. Reliene R, Schiestl RH. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. doi: 10.1093/carcin/bgi222. Epub 2005 Sep 14. PMID: 16162646.
Griffith & Meister (1979) Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine) J.Biol.Chem. 254 7558 PMID: 38242 Griffith et al (1982) Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologs, potent inhibitors of glutathione synthesis. J.Biol.Chem. 257 13704 PMID: 6128339 Yang et al (2014) Regulation of ferroptotic cancer cell death by GPX4. Cell. 156 317 PMID: 24439385