Buthionine sulfoximine

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Structural formula
Structural formula buthionine sulfoximine
Structural formula without stereochemistry
General
Surname Buthionine sulfoximine
other names
  • BSO
  • ( R ) -2-amino-4- (butylsulfonimidoyl) butyric acid
  • ( S ) -2-amino-4- (butylsulfonimidoyl) butyric acid
  • ( RS ) -2-amino-4- (butylsulfonimidoyl) butyric acid
Molecular formula C 8 H 18 N 2 O 3 S
Brief description

white, crystalline solid

External identifiers / databases
CAS number
  • 5072-26-4 ( racemate )
  • 83730-53-4 [( S ) -form]
EC number 628-045-7
ECHA InfoCard 100.156.351
PubChem 21157
ChemSpider 19896
DrugBank DB12870
Wikidata Q5002519
properties
Molar mass 222.30 g mol −1
Physical state

firmly

density

1.23 g cm −3

Melting point

224–226 ° C {pure enantiomer: ( R ) -form or ( S ) -form}

solubility

soluble in water (50 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 264-280-362 + 364-261-302 + 352-332 + 313-305 + 351 + 338-337 + 313-309 + 311-304 + 340
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Buthioninsulfoximin (BSO) is a synthetically produced chemical compound that belongs to the amino acids and sulfoximines . BSO acts as an inhibitor of the glutamate cysteine ​​ligase and therefore leads to a decrease in the glutathione level . The compound is used in research to generate oxidative stress and can also be used as a radiosensitizer or to support chemotherapy to lower the resistance of tumors to the treatment.

Individual evidence

  1. ↑ a b c d data sheet L-Buthionine-sulfoximine, ≥97% (TLC) from Sigma-Aldrich , accessed on September 21, 2015 ( PDF ).
  2. ^ Carl L. Yaws: The Yaws Handbook of Physical Properties for Hydrocarbons and Chemicals Physical Properties for More Than 54,000 Organic and Inorganic Chemical Compounds, Coverage for C1 to C100 Organics and Ac to Zr Inorganics . Gulf Professional Publishing, 2015, ISBN 978-0-12-801146-1 , pp. 221 ( limited preview in Google Book search).
  3. ↑ a b caymanchem: MSDS , accessed September 21, 2015.
  4. ↑ Graciela Piwien-Pilipuk, Mario D. Galigniana: Oxidative stress induced by L-buthionine- (S, R) -sulfoximine, a selective inhibitor of glutathione metabolism, abrogates mouse kidney mineralocorticoid receptor function. In: Biochimica et Biophysica Acta (BBA) - Molecular Cell Research. 1495, 2000, p. 263, doi : 10.1016 / S0167-4889 (99) 00166-4 .
  5. ↑ Hans-Joachim Schmoll, Klaus Höffken, Kurt Possinger: Compendium Internal Oncology Part 1: Basics · Guidelines · Antineoplastic substances · Toxicities · Prophylactic and supportive therapy · Addresses . Springer-Verlag, 2013, ISBN 978-3-642-79214-4 , pp. 333 ( limited preview in Google Book search).
  6. ^ Siegfried Seeber, Jochen Schütte: Therapy Concepts Oncology . Springer-Verlag, 2013, ISBN 978-3-662-10494-1 , pp. 40 ( limited preview in Google Book search).
  7. ^ Entry at the National Cancer Institute .