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L-Buthionine-(S,R)-sulfoximine (Synonyms: L-Butionine sulfoximine)

Cat. No.: HY-106376A Purity: >98.0%
Handling Instructions

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.

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

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

CAS No. : 83730-53-4

Size Price Stock Quantity
10 mM * 1 mL in Water USD 66 In-stock
Estimated Time of Arrival: December 31
50 mg USD 60 In-stock
Estimated Time of Arrival: December 31
100 mg   Get quote  
200 mg   Get quote  

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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].

In Vivo

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. It is showed that 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].

Solvent & Solubility
In Vitro: 

H2O : 41.67 mg/mL (187.44 mM; Need ultrasonic)

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
10 mM 0.4498 mL 2.2491 mL 4.4982 mL
*Please refer to the solubility information to select the appropriate solvent.
References
Animal Administration
[2]

Mice[2]
C57BL/6J pun/pun mice are used in the study. Pregnancy is timed by checking for vaginal plugs. Noon of the day of discovery is counted as 0.5 days post coitum (d.p.c.). Similarly, the time of birth of a litter is timed with the noon of discovery counted as 0.5 days post-partum (d.p.p.). Pregnant dams are given free access to drinking water supplemented by either 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. To determine the DNA deletion frequency, 20-day-old offspring (23 mice in the control group and 16-17 mice per exposure group) are sacrificed to visualize eye-spots (DNA deletions) in their RPE[2].

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

References
Molecular Weight

222.31

Formula

C₈H₁₈N₂O₃S

CAS No.

83730-53-4

SMILES

N[[email protected]](C(O)=O)CCS(CCCC)(=O)=N

Storage
Powder -20°C 3 years
In solvent -80°C 6 months
  -20°C 1 month
Shipping

Room temperature in continental US; may vary elsewhere

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Product Name:
L-Buthionine-(S,R)-sulfoximine
Cat. No.:
HY-106376A
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L-Buthionine-(S,R)-sulfoximine

Cat. No.: HY-106376A