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

L-BUTHIONINE-(S,R)-SULFOXIMINE

Bezeichnung:L-BUTHIONINE-(S,R)-SULFOXIMINE

CAS-Nr83730-53-4

Englisch Name:L-BUTHIONINE-(S,R)-SULFOXIMINE

CBNumberCB1150667

SummenformelC8H18N2O3S

Molgewicht222.31

MOL-Datei83730-53-4.mol

L-BUTHIONINE-(S,R)-SULFOXIMINE physikalisch-chemischer Eigenschaften

Schmelzpunkt	224-228 °C (dec.)
Siedepunkt	382.3±52.0 °C(Predicted)
Dichte	1.29
Brechungsindex	1.6300 (estimate)
storage temp.	-20°C
Löslichkeit	H₂O: 50 mg/mL, clear, colorless to faintly yellow
Aggregatzustand	Fine Powder
Farbe	White
BRN	2367136
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily.
CAS Datenbank	83730-53-4

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	22-24/25
WGK Germany	3
RTECS-Nr.	EK7713440
F	10
HS Code	29309090

Gefahreninformationscode (GHS)

L-BUTHIONINE-(S,R)-SULFOXIMINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
Beschreibung
L-Buthionine-(S,R)-sulfoximine is an irreversible inhibitor of γ-glutamylcysteine synthetase (K_i <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.
Chemische Eigenschaften
White Crystalline Solid
Verwenden
L-Buthionine-(S,R)-sulfoximine is a potent and specific inhibitor of alpha-glutamylcysteine synthetase.
Verwenden
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.
Verwenden
inhibitor of gamma-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.
Lager
Store at -20°C
Einzelnachweise
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 Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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