L-Buthionine sulfoximine | CAS# 83730-53-4 | γ-GCS inhibitor

L-Buthionine sulfoximine
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 574070

CAS#: 83730-53-4

Description: 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

CAS# 83730-53-4

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 574070
Name: L-Buthionine sulfoximine
CAS#: 83730-53-4
Chemical Formula: C8H18N2O3S
Exact Mass: 222.10
Molecular Weight: 222.303
Elemental Analysis: C, 43.22; H, 8.16; N, 12.60; O, 21.59; S, 14.42

Price and Availability

Size	Price	Availability
250mg	USD 300	2 Weeks
500mg	USD 500	2 Weeks
1g	USD 850	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

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Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	22.2	100.00
	PBS (pH 7.2)	5.0	22.49
	Water	26.9	120.80

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.

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.

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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

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