Buthionine Sulfoximine

Cayman Chemical Item Number 14484

L-Buthionine-S,R-Sulfoximine; BSO; NSC 326231 (CAS 83730-53-4)

Buthionine Sulfoximine (CAS 83730-53-4)

See more

Description

Buthionine sulfoximine (BSO) is an irreversible inhibitor of γ-glutamylcysteine synthetase (Ki <100 μM), the rate-limiting enzyme for L-glutathione (GSH) synthesis, that induces oxidative stress in cells by depleting GSH.1,2 Administration of BSO leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis.3,4 Whereas elevated glutathione levels are associated with tumor cell resistance, BSO has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors.5

1 Reliene, R., and Schiestl, R.H. Glutathione depletion by buthionine sulfoximine induces DNA deletions in mice. Carcinogenesis 27(2) 240-244 (2006).

2 Griffith, O.W. Mechanism of action, metabolism, and toxicity of buthionine sulfoximine and its higher homologs, potent inhibitors of glutathione synthesis. J Biol Chem 257(22) 13704-13712 (1982).

3 Takahashi, K., Tatsunami, R., Oba, T., et al. Buthionine sulfoximine promotes methylglyoxal-induced apoptotic cell death and oxidative stress in endothelial cells. Biol Pharm Bull 33(4) 556-560 (2010).

4 Han, Y.H., Moon, H.J., You, B.R., et al. The effects of buthionine sulfoximine, diethyldithiocarbamate or 3-amino-1,2,4-triazole on propyl gallate-treated HeLa cells in relation to cell growth, reactive oxygen species and glutathione. Int J Mol Med 24(2) 261-268 (2009).

5 Lewis-Wambi, J.S., Kim, H.R., Wambi, C., et al. Buthionine sulfoximine sensitizes antihormone-resistant human breast cancer cells to estrogen-induced apoptosis. Breast Cancer Res 10(6) (2008).

Synonyms
  • L-Buthionine-S,R-Sulfoximine
  • BSO
  • NSC 326231
Formal Name 2S-​amino-​4-​(S-​butylsulfonimidoyl)-​butanoic acid
CAS Number 83730-53-4
Molecular Formula C8H18N2O3S
Formula Weight 222.3
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
Copy SMILES to clipboard
O=S(CCCC)​(CC[C@H]​(N)​C(O)​=O)​=N
InCHI Code
Copy InCHI code to clipboard
​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
InCHI Key
Copy InCHI key to clipboard
KJQFBVYMGADDTQ-CVSPRKDYSA-N

Download free InCHI Key generation software

Size Price Quantity Subtotal
250 mg $65.00 $0.00
500 mg $124.00 $0.00
1 g $234.00 $0.00
Bulk Contact
Cart Total $0.00

Please Login or Register to use this page.

Pricing updated 2014-04-23. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

Related Products

L-Glutathione, reduced

Downloads

Batch-specific Information

Get batch-specific data and documents by batch number


Separate multiple batch numbers with commas

Cayman Chemical Company regularly evaluates our shipping methods to ensure product stability is maintained and our corporate environmental impact is minimized. Products selected for review are evaluated and shipping methods are certified by our Scientists. While occasionally our method of shipping a product may change, rest assured the shipping conditions on all Cayman Chemical products have been reviewed and validated.

Upon receipt, it is important to check the storage requirements of your products and place them at the appropriate temperature. Products shipped without ice may require frozen storage for long term stability.

Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

See personalized New Product recommendations! Get personalized New Product recommendations! Register or Login for personalized New Product recommendations!

Join us! · Experimental Biology 2014 · San Diego, California · April 26-30, 2014 · Booth 323 Join us! · ASPET Symposium 2014: Scientists versus Street Chemists: The Toxicity of Designer Marijuana · San Diego, California · April 30, 2014
Other Resources
About Cayman Management Team Company Profile ChemAssistant Tools FAQs Cayman Europe Cayman Pharma CaBRI Cayman Gear Press Releases Illustrations and Charts Key Research Area Posters Article Library Analysis Tools Conference Schedule Order Terms Browser Recommendation Privacy Statement Site Map Conference Travel Grants

Cayman Chemical Company · 1180 East Ellsworth Road · Ann Arbor, Michigan 48108 · USA

Toll Free: (800) 364-9897 (USA and Canada Only) · Fax: (734) 971-3640

Copyright 2014 Cayman Chemical Company

Manufacturer, supplier, and vendor of biochemical reagents, assay kits, forensic chemistry standards, antibodies, and proteins for scientific research · Buy now! · Analytical testing services and custom synthesis also available

Lost password?