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

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

Cat. No.: HY-106376C Purity: ≥98.0%
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L-Buthionine-(S,R)-sulfoximine hydrochloride is a cell-permeable, potent, fast acting, orally active 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.

L-Buthionine-(S,R)-sulfoximine hydrochloride Chemical Structure

L-Buthionine-(S,R)-sulfoximine hydrochloride Chemical Structure

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10 mM * 1 mL in DMSO
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Based on 7 publication(s) in Google Scholar

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

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

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  • Purity & Documentation

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Description

L-Buthionine-(S,R)-sulfoximine hydrochloride is a cell-permeable, potent, fast acting, orally active 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[1][2].

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 hydrochloride 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.
Molecular Weight

258.77

Formula

C8H19ClN2O3S
Appearance

Solid

Color

White to off-white

SMILES

N[C@H](C(O)=O)CCS(CCCC)(=O)=N.[H]Cl
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

-20°C, sealed storage, away from moisture

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

Solvent & Solubility
In Vitro: 

DMSO : 250 mg/mL (966.11 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

H2O : 70 mg/mL (270.51 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.8644 mL 19.3222 mL 38.6444 mL
5 mM 0.7729 mL 3.8644 mL 7.7289 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.

  • Molarity Calculator

  • Dilution Calculator

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

Mass
=
Concentration
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Volume
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Molecular Weight *

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

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

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Volume (start)

V1

=
Concentration (final)

C2

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Volume (final)

V2

In Vivo:

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
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:  10% DMSO    40% PEG300    5% Tween-80    45% Saline

    Solubility: ≥ 2.08 mg/mL (8.04 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.

    Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
  • Protocol 2

    Add each solvent one by one:  10% DMSO    90% (20% SBE-β-CD in Saline)

    Solubility: ≥ 2.08 mg/mL (8.04 mM); Clear solution

    This protocol yields a clear solution of ≥ 2.08 mg/mL (saturation unknown).

    Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (20.8 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.

    Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
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).
Purity & Documentation

Purity: ≥98.0%

COA (246 KB) HNMR (200 KB)

Handling Instructions (2659 KB)
References

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 / DMSO 1 mM 3.8644 mL 19.3222 mL 38.6444 mL 96.6109 mL
5 mM 0.7729 mL 3.8644 mL 7.7289 mL 19.3222 mL
10 mM 0.3864 mL 1.9322 mL 3.8644 mL 9.6611 mL
15 mM 0.2576 mL 1.2881 mL 2.5763 mL 6.4407 mL
20 mM 0.1932 mL 0.9661 mL 1.9322 mL 4.8305 mL
25 mM 0.1546 mL 0.7729 mL 1.5458 mL 3.8644 mL
30 mM 0.1288 mL 0.6441 mL 1.2881 mL 3.2204 mL
40 mM 0.0966 mL 0.4831 mL 0.9661 mL 2.4153 mL
50 mM 0.0773 mL 0.3864 mL 0.7729 mL 1.9322 mL
60 mM 0.0644 mL 0.3220 mL 0.6441 mL 1.6102 mL
80 mM 0.0483 mL 0.2415 mL 0.4831 mL 1.2076 mL
100 mM 0.0386 mL 0.1932 mL 0.3864 mL 0.9661 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 hydrochloride 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)-sulfoximineL-Buthionine sulfoximineL-BSOFerroptosisBSOeye-spotGSHoxidativestressglutamylcysteineInhibitorinhibitorinhibit

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