ChemicalBook > CAS DataBase List > L-BUTHIONINE-(S,R)-SULFOXIMINE

L-BUTHIONINE-(S,R)-SULFOXIMINE

Product Name
L-BUTHIONINE-(S,R)-SULFOXIMINE
CAS No.
83730-53-4
Chemical Name
L-BUTHIONINE-(S,R)-SULFOXIMINE
Synonyms
L-BSO;nsc326231;L-Butionine sulfoximine;L-BUTHIONINE-SULFOXIMINE;L-BUTHIONINESULPHOXIMINE;D-Buthionine Sulfoximine;Buthionine - sulfoxide iMine;L-BUTHIONINE-[S,R]-SULFOXIME;L-BUTHIONINE-S,R-SULPHOXIMINE;L-BUTHIONINE-(S,R)-SULFOXIMINE
CBNumber
CB1150667
Molecular Formula
C8H18N2O3S
Formula Weight
222.31
MOL File
83730-53-4.mol
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L-BUTHIONINE-(S,R)-SULFOXIMINE Property

Melting point:
224-228 °C (dec.)
Boiling point:
382.3±52.0 °C(Predicted)
Density 
1.29
refractive index 
1.6300 (estimate)
storage temp. 
-20°C
solubility 
H2O: 50 mg/mL, clear, colorless to faintly yellow
form 
Fine Powder
color 
White
BRN 
2367136
Stability:
Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily.
CAS DataBase Reference
83730-53-4
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
EK7713440
F 
10
HS Code 
29309090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B2515
Product name
L-Buthionine-sulfoximine
Purity
≥97% (TLC)
Packaging
1g
Price
$444
Updated
2024/03/01
Sigma-Aldrich
Product number
B2515
Product name
L-Buthionine-sulfoximine
Purity
≥97% (TLC)
Packaging
5g
Price
$1560
Updated
2024/03/01
Sigma-Aldrich
Product number
5.08228
Product name
L-ButhionineSulfoximine-CAS83730-53-4-Calbiochem
Packaging
100mg
Price
$142
Updated
2024/03/01
Cayman Chemical
Product number
14484
Product name
Buthionine Sulfoximine
Purity
≥98%
Packaging
250mg
Price
$81
Updated
2024/03/01
Cayman Chemical
Product number
14484
Product name
Buthionine Sulfoximine
Purity
≥98%
Packaging
1g
Price
$286
Updated
2024/03/01
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L-BUTHIONINE-(S,R)-SULFOXIMINE Chemical Properties,Usage,Production

Description

L-Buthionine-(S,R)-sulfoximine 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. Administration of L-buthionine-(S,R)-sulfoximine leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis. Whereas elevated glutathione levels are associated with tumor cell resistance, L-buthionine-(S,R)-sulfoximine has been shown to enhance the toxicity of various chemotherapeutic agents in drug-resistant tumors.

Chemical Properties

White Crystalline Solid

Uses

inhibitor of gamma-glutamylcysteine synthetase

Uses

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. Administration of BSO leads to decreased GSH levels in virtually all tissues and is associated with tissue damage and apoptosis. 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.

Uses

L-Buthionine-(S,R)-sulfoximine is a potent and specific inhibitor of alpha-glutamylcysteine synthetase.

Definition

ChEBI: L-buthionine-(S,R)-sulfoximine is a 2-amino-4-(S-butylsulfonimidoyl)butanoic acid which has S-configuration. It is a inhibitor of gamma-glutamylcysteine synthetase and glutathione (GSH) biosynthesis and is capable of enhancing the apoptotic effects of several chemotherapeutic agents. It has a role as a ferroptosis inducer and an EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor.

Hazard

A reproductive hazard.

Biochem/physiol Actions

Blocks cellular resistance to chemotherapy by inhibiting γ-glutamylcysteine synthetase, a key enzyme in glutathione biosynthesis. Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.

storage

Store at -20°C

References

1) Lu?et al.?(2009),?Regulation of glutathione synthesis; Mol. Aspects Med.?30?42 2) Lee?et al.?(2008),?Adaptive response to GSH depletion and resistance to L-buthionine-(S,R)-sulfoximine; Mol. Cell Biochem.?12?174 3) Qiwei et al. (2016),?The effects of buthionine sulfoximine on the proliferation and apoptosis of biliary tract cancer cells induced by cisplatin and gemcitabine; Oncol. Lett.?11?474 4) Glasuer and Chandel (2014),?Targeting antioxidants for cancer therapy; Biochem. Pharmacol.?92?90

L-BUTHIONINE-(S,R)-SULFOXIMINE Preparation Products And Raw materials

Raw materials

Preparation Products

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L-BUTHIONINE-(S,R)-SULFOXIMINE Suppliers

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View Lastest Price from L-BUTHIONINE-(S,R)-SULFOXIMINE manufacturers

Career Henan Chemical Co
Product
L-BUTHIONINE-(S,R)-SULFOXIMINE 83730-53-4
Price
US $9.80/KG
Min. Order
1KG
Purity
≥98%
Supply Ability
20 tons
Release date
2020-01-10

83730-53-4, L-BUTHIONINE-(S,R)-SULFOXIMINERelated Search:

POLYETHERIMIDE Ozone Sulfamide SULFOXIDE DI-N-BUTYL SULFOXIDE L-METHIONINE SULFOXIMINE D,L-BUTHIONINE DL-ETHIONINE DL-METHIONINE SULFOXIDE L-ETHIONINE L-BUTHIONINE-(S,R)-SULFOXIMINE DL-BUTHIONINE-[S,R]-SULFOXIMINE,DL-BUTHIONINE (R,S)-SULFOXIMINE L-BUTHIONINE L-METHIONINE SULFOXIDE FMOC-L-BUTHIONINESULFOXIMINE DL-METHIONINE DL-SULFOXIMINE D-Buthionine-(S,R)-sulfoximine DL-ETHIONINE SULFOXIDE

  • L-BUTHIONINE-SULFOXIMINE
  • L-BUTHIONINE (R,S)-SULFOXIMINE
  • L-BUTHIONINE-[S,R]-SULFOXIME
  • L-BUTHIONINE-(S,R)-SULFOXIMINE
  • L-BSO
  • nsc326231
  • L-BUTHIONINESULPHOXIMINE
  • L-BUTHIONINE-S,R-SULPHOXIMINE
  • (2S)-2-Amino-4-(S-butylsulfonimidoyl)butanoic Acid
  • D-Buthionine Sulfoximine
  • Buthionine - sulfoxide iMine
  • -2-Amino-4-(butylsulfonimidoyl)
  • L-Buthionine-(S,R)-sulfoxiMine, 99% 1GR
  • (S)-2-Amino-4-(S-butylsulfonimidoyl)butyric acid
  • L-Buthionine-(S,R)-sulfoximine,99%
  • L-Butionine sulfoximine
  • Butanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-, (2S)-
  • 83730-53-4
  • Organic Covalent Modifiers
  • Glutathione biosynthesis and Glu-Cys Ligase
  • Enzymes, Inhibitors, and Substrates
  • Enzyme Inhibitors by Type
  • Enzyme Inhibitors by Enzyme
  • Enzyme Inhibitors
  • D to K
  • Biochemicals and Reagents
  • BioChemical
  • Core Bioreagents
  • D to
  • Enzyme InhibitorsEnzyme Inhibitors by Enzyme
  • Sulfur & Selenium Compounds
  • Enzyme InhibitorsResearch Essentials
  • Glutathione biosynthesis and Glu-Cys Ligase
  • Cancer Research
  • Chemopreventive Agents
  • Glutathione S-Transferase Agents