2. Apoptosis
  3. Ferroptosis
  4. L-Buthionine-(S,R)-sulfoximine

L-Buthionine-(S,R)-sulfoximine  (Synonyms: L-Buthionine sulfoximine; L-BSO)

Cat. No.: HY-106376A Pureté: 99.95%
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SDS
Instruction de manipulation Technical Support

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.

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CAS No. : 83730-53-4

Size Prix Stock Quantité
Solid + Solvent (Highly Recommended)
10 mM * 1 mL in Water
ready for reconstitution
 En stock
Solution
10 mM * 1 mL in Water En stock
Solid
50 mg En stock
100 mg En stock
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500 mg   Obtenir un devis  

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Based on 19 publication(s) in Google Scholar

Other Forms of L-Buthionine-(S,R)-sulfoximine:

L-Buthionine-(S,R)-sulfoximine Related Antibodies

Top Publications Citing Use of Products

    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.

    L-Buthionine-(S,R)-sulfoximine purchased from MedChemExpress. Usage Cited in: Acta Pharm Sin B. 2022 Apr;12(4):2074-2088.

    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.

    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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    Description

    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.

    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.

    L-Buthionine-(S,R)-sulfoximine Related Antibodies
    In Vivo

    BSO causes an elevated frequency of DNA deletions during mouse development. BSO treatment reduced GSH concentration in mouse fetuses by 55% and 70% at 2 mM and 20 mM BSO doses, respectively, compared to untreated mice. Co-treatment with 2 mM BSO and 20 mM NAC depleted GSH to a similar extent as 2 mM BSO, consistent with the function of BSO to inhibit the g-GCS enzyme indispensable for GSH synthesis. Like GSH, cysteine levels dropped following BSO treatment[2].

    MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

    Animal Model: C57BL/6J pun/pun mice[2].
    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.
    Administration: Drinking water.
    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.
    Masse moléculaire

    222.31

    Formule

    C8H18N2O3S
    CAS No.
    Appearance

    Solid

    Color

    White to off-white

    SMILES

    N[C@H](C(O)=O)CCS(CCCC)(=O)=N
    Livraison

    Room temperature in continental US; may vary elsewhere.
    Stockage

    -20°C, sealed storage, away from moisture

    *In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)

    Solvant et solubilité
    In Vitro: 

    H2O : 18.33 mg/mL (82.45 mM; Need ultrasonic)

    DMSO : < 1 mg/mL (insoluble or slightly soluble)

    Preparing
    Stock Solutions
    Concentration Solvent Mass 1 mg 5 mg 10 mg
    1 mM 4.4982 mL 22.4911 mL 44.9822 mL
    5 mM 0.8996 mL 4.4982 mL 8.9964 mL
    View the 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.

    * 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.

    • Calculateur de molarité

    • Calculateur de dilution

    Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

    Mass
    =
    Concentration
    ×
    Volume
    ×
    Molecular Weight *

    Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

    This equation is commonly abbreviated as: C1V1 = C2V2

    Concentration (start)

    C1

    ×
    Volume (start)

    V1

    =
    Concentration (final)

    C2

    ×
    Volume (final)

    V2

    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.

    • Protocol 1

      Add each solvent one by one:  PBS

      Solubility: 100 mg/mL (449.82 mM); Clear solution; Need ultrasonic

    In Vivo Dissolution Calculator
    Please enter the basic information of animal experiments:

    Dosage

    mg/kg

    Animal weight
    (per animal)

    g

    Dosing volume
    (per animal)

    μL

    Number of animals

    Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
    Calculation results:
    Working solution concentration: mg/mL
    This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
    The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
    Pureté et documentation

    Purity: 99.95%

    SDS (393 KB)

    COA (245 KB) HNMR (241 KB) RP-HPLC (247 KB) MS (228 KB)

    Instruction de manipulation (2659 KB)
    Références

    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.

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    L-Buthionine-(S,R)-sulfoximine Related Classifications

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    • Do most proteins show cross-species activity?

      Species cross-reactivity must be investigated individually for each product. Many human cytokines will produce a nice response in mouse cell lines, and many mouse proteins will show activity on human cells. Other proteins may have a lower specific activity when used in the opposite species.

    Keywords:

    L-Buthionine-(S,R)-sulfoximine83730-53-4L-Buthionine sulfoximine L-BSOFerroptosisBSOeye-spotGSHoxidativestressglutamylcysteineInhibitorinhibitorinhibit

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