L-Buthionine-(S,R)-sulfoximine
Based on 21 publication(s) in Google Scholar
L-Buthionine-(S,R)-sulfoximine is a cell-permeable, potent, fast acting and irreversible inhibitor of g-glutamylcysteine synthetase and depletes cellular glutathione levels. The IC50 value of L-Buthionine-(S,R)-sulfoximine on melanoma, breast and ovarian tumor specimens are 1.9 μM, 8.6 μM, and 29 μM, respectively.
For research use only. We do not sell to patients.
- Purity : 99.95%
- CAS No.: 83730-53-4
- Formula: C8H18N2O3S
- Molecular Weight:222.31
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Storage:
-20°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
Publications Citing Use of MedChemExpress (MCE) L-Buthionine-(S,R)-sulfoximine
More- Nat Commun. 2022 Jul 11;13(1):4007. [Abstract]
- Redox Biol. 2026 Feb:89:103962. [Abstract]
- Theranostics. 2024 May 27;14(8):3339-3357. [Abstract]
- Acta Pharm Sin B. 2022 Apr;12(4):2074-2088. [Abstract]
- Adv Sci (Weinh). 2025 Jan;12(1):e2310308. [Abstract]
- J Control Release. 2026 Mar 10:391:114591. [Abstract]
- J Immunother Cancer. 2026 Jun 30;14(6):e014808.
- J Colloid Interface Sci. 2022 Dec 15;628(Pt B):189-203. [Abstract]
- Free Radic Biol Med. 2026 Aug 16:252:1-17. [Abstract]
- Fundam Res. 2025 Dec 16.
- Biochem Pharmacol. 2024 May:223:116194. [Abstract]
- EMBO Rep. 2025 Jun;26(12):3106-3137. [Abstract]
- Eur J Pharmacol. 2025 Aug 15:1001:177746. [Abstract]
- Expert Rev Clin Immunol. 2025 Aug;21(8):1171-1181. [Abstract]
- Vet Res. 2024 Dec 20;55(1):172. [Abstract]
- Immun Inflamm Dis. 2023 Sep;11(9):e1015. [Abstract]
- Discov Oncol. 2025 Oct 21;16(1):1934. [Abstract]
- J Obstet Gynaecol Res. 2023 Aug;49(8):2175-2184. [Abstract]
- bioRxiv. 2026 Jan 26.
- Temple University. 2025.
- Oxid Med Cell Longev. 2022 Jan 17;2022:8038857. [Abstract]
Customer Validation & Images
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In Vivo Efficacy Study
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Histological Imaging/Staining
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IF
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Bio/Physico-chemical Assay
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Cell Imaging/Staining
Biological Activity
Description
IC50 & Target
γ-glutamylcysteine synthetase[1].
In Vitro
L-Buthionine-(S,R)-sulfoximine (BSO: 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-π protein and mRNA levels are significantly reduced in both cell lines[1].
L-Buthionine-(S,R)-sulfoximine (BSO) induces oxidative stress in a cell by irreversibly inhibiting g-glutamylcysteine synthetase, an essential enzyme for the synthesis of glutathione (GSH)[2].
L-Buthionine-(S,R)-sulfoximine (BSO) induces ferroptosis in cancer cells[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:C57BL/6J pun/pun mice[2].
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Dosage:2 mM L-Buthionine-(S,R)-sulfoximine (BSO), 20 mM BSO, 2 mM BSO and 20 mM NAC, 20 mM NAC or unsupplemented water for 18 days from 0.5 to 18.5 d.p.c. The pH of supplemented water is as follows: 6.88, 20 mM BSO; 3.37, 2 mM BSO; 2.65, 2 mM BSO plus 20 mM NAC; and 2.58, 20 mM NAC. The pH of regular water used in our facility is ~4.
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Administration:Drinking water.
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Result:The average number of eye-spots (mean±SEM) is 5.36±0.29 (n=46), 7.79±0.45 (n=34) and 8.78±0.61 (n=32) in untreated controls, 2 mM L-Buthionine-(S,R)-sulfoximine (BSO) and 20 mM BSO treated mice, respectively. The 2 mM BSO treatment results in ~30% more eye-spots, and the 20 mM treatment results in 40% more eye-spots compared with untreated mice.
Chemical Information
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CAS No. 83730-53-4
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Appearance Solid
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Molecular Weight 222.31
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Formula C8H18N2O3S
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Color White to off-white
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SMILES
N[C@H](C(O)=O)CCS(CCCC)(=O)=N
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Synonyms
L-Buthionine sulfoximine; L-BSO
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
-20°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Publications (21)
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Journal Impact Factor
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Most Recent
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Nat Commun
Blocking glycine utilization inhibits multiple myeloma progression by disrupting glutathione balance. [Abstract]2022 Jul 11;13(1):4007. PMID: 35817773 -
Redox Biol
Protein CoAlation is regulated by and integrated with growth factor signalling and the cellular antioxidant response. [Abstract]2026 Feb:89:103962. PMID: 41371167 -
Theranostics
Energy competition remodels the metabolic glucose landscape of psoriatic epidermal cells. [Abstract]2024 May 27;14(8):3339-3357. PMID: 38855186
L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Theranostics. 2024 May 27;14(8):3339-3357. [Abstract]
Macroscopic feature and PASI scores of the back of mice in control, IMQ, IMQ+GSH, and IMQ+BS0(2 mg/kg, s.c., 7 d) groups.
L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Theranostics. 2024 May 27;14(8):3339-3357. [Abstract]
Statistical analysis of representative H&E staining, baker score, and epidermal thickness of the back of mice in control, IMQ, IMQ+GSH, and IMQ+BSO(2 mg/kg, s.c., 7 d) groups. Scale bar, 100 μm.
L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Theranostics. 2024 May 27;14(8):3339-3357. [Abstract]
Immunofluorescence staining of BrdU, and PCNA shows proliferation of epidermal cells in mice in control, IMQ, IMQ+GSH, and IMQ+BSO(2 mg/kg, s.c., 7 d) groups. Scale bar, 100 μm.
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Acta Pharm Sin B
"Pincer movement": Reversing cisplatin resistance based on simultaneous glutathione depletion and glutathione S-transferases inhibition by redox-responsive degradable organosilica hybrid nanoparticles. [Abstract]2022 Apr;12(4):2074-2088. PMID: 35847508
L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Acta Pharm Sin B. 2022 Apr;12(4):2074-2088. [Abstract]
GSH levels of A375/DDP cells after incubation with BSO (200 mmol/L), SHMONs (120 mg/mL), and HMONs (120 mg/mL) for 6 h.
L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Acta Pharm Sin B. 2022 Apr;12(4):2074-2088. [Abstract]
CLSM images of A375/DDP cells incubated with DCFH-DA for the observation of ROS generation after incubation with BSO (200 mmol/L), SHMONs (60 mg/mL), and HMONs (60 mg/mL) for 6 h. Scale bar = 50 mm.
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Adv Sci (Weinh)
Inhibition of Glutamate-to-Glutathione Flux Promotes Tumor Antigen Presentation in Colorectal Cancer Cells. [Abstract]2025 Jan;12(1):e2310308. PMID: 39482885 -
J Control Release
2026 Mar 10:391:114591. PMID: 41478376 -
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J Colloid Interface Sci
A spark to the powder keg: Microneedle-based antitumor nanomedicine targeting reactive oxygen species accumulation for chemodynamic/photothermal/chemotherapy. [Abstract]2022 Dec 15;628(Pt B):189-203. PMID: 35994900 -
Free Radic Biol Med
GCSH promotes MASH progression by regulating cuproptosis through the glycine-GSH metabolic pathway. [Abstract]2026 Aug 16:252:1-17. PMID: 42082057 -
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Biochem Pharmacol
Jolkinolide B synergistically potentiates the antitumor activity of GPX4 inhibitors via inhibiting TrxR1 in cisplatin-resistant bladder cancer cells. [Abstract]2024 May:223:116194. PMID: 38583812 -
EMBO Rep
NRF2 supports non-small cell lung cancer growth independently of CBP/p300-enhanced glutathione synthesis. [Abstract]2025 Jun;26(12):3106-3137. PMID: 40369363 -
Eur J Pharmacol
Targeting eEF2K induces oxidative stress and sensitizes cancer cells to ferroptosis induction. [Abstract]2025 Aug 15:1001:177746. PMID: 40409701 -
Expert Rev Clin Immunol
TFDP1 activates SPC25-mediated glutamine metabolism to repress anti-tumor immunity of NK cells in lung adenocarcinoma. [Abstract]2025 Aug;21(8):1171-1181. PMID: 40552366 -
Vet Res
African swine fever virus enhances viral replication by increasing intracellular reduced glutathione levels, which suppresses stress granule formation. [Abstract]2024 Dec 20;55(1):172. PMID: 39707514 -
Immun Inflamm Dis
Effects of albiflorin on oxidative stress and inflammatory responses in rats with acute spinal cord injury. [Abstract]2023 Sep;11(9):e1015. PMID: 37773716 -
Discov Oncol
D-mannose suppresses HIF-1α mediated metabolic reprogramming in clear cell renal cell carcinoma. [Abstract]2025 Oct 21;16(1):1934. PMID: 41118022 -
J Obstet Gynaecol Res
ELK1/KIFC1 axis promotes breast cancer cell proliferation by regulating glutathione metabolism. [Abstract]2023 Aug;49(8):2175-2184. PMID: 37339943 -
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Oxid Med Cell Longev
Clinical Relevance and Tumor Growth Suppression of Mitochondrial ROS Regulators along NADH:Ubiquinone Oxidoreductase Subunit B3 in Thyroid Cancer. [Abstract]2022 Jan 17;2022:8038857. PMID: 35087620
Solvent & Solubility
In Vitro:
H2O : 18.33 mg/mL (82.45 mM; Need ultrasonic)
DMSO : < 1 mg/mL (insoluble or slightly soluble)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
In Vivo:
For the following dissolution methods, please prepare the working solution directly:
It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: PBS
Solubility: 100 mg/mL (449.82 mM); Clear solution; Need ultrasonic
Purity & Documentation
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Data Sheet (281 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[1]. Fruehauf JP, et al. 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. [Content Brief]
[2]. Reliene R, et al. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis. 2006 Feb;27(2):240-4. [Content Brief]
[3]. Satoru Nishizawa, et al. Low tumor glutathione level as a sensitivity marker for glutamate-cysteine ligase inhibitors. Oncol Lett. 2018 Jun;15(6):8735-8743. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| H2O | 1 mM | 4.4982 mL | 22.4911 mL | 44.9822 mL | 112.4556 mL |
| 5 mM | 0.8996 mL | 4.4982 mL | 8.9964 mL | 22.4911 mL | |
| 10 mM | 0.4498 mL | 2.2491 mL | 4.4982 mL | 11.2456 mL | |
| 15 mM | 0.2999 mL | 1.4994 mL | 2.9988 mL | 7.4970 mL | |
| 20 mM | 0.2249 mL | 1.1246 mL | 2.2491 mL | 5.6228 mL | |
| 25 mM | 0.1799 mL | 0.8996 mL | 1.7993 mL | 4.4982 mL | |
| 30 mM | 0.1499 mL | 0.7497 mL | 1.4994 mL | 3.7485 mL | |
| 40 mM | 0.1125 mL | 0.5623 mL | 1.1246 mL | 2.8114 mL | |
| 50 mM | 0.0900 mL | 0.4498 mL | 0.8996 mL | 2.2491 mL | |
| 60 mM | 0.0750 mL | 0.3749 mL | 0.7497 mL | 1.8743 mL | |
| 80 mM | 0.0562 mL | 0.2811 mL | 0.5623 mL | 1.4057 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
L-Buthionine-(S,R)-sulfoximine Related Classifications
HY-106376A Related Classifications
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