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B2515

Sigma-Aldrich

L-Buthionine-sulfoximine

≥97% (TLC)

Synonyme(s) :

L-BSO

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About This Item

Formule empirique (notation de Hill):
C8H18N2O3S
Numéro CAS:
83730-53-4
Poids moléculaire :
222.31
Numéro Beilstein :
2367136
Numéro MDL:
MFCD00067000
Code UNSPSC :
12352202
ID de substance PubChem :
24278263
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥97% (TLC)

Forme

powder

Pf

224-226  °C

Solubilité

water: 50 mg/mL, clear to slightly hazy, colorless to faintly yellow

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne SMILES 

CCCCS(=N)(=O)CC[C@H](N)C(O)=O

InChI

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

Clé InChI

KJQFBVYMGADDTQ-CVSPRKDYSA-N

Informations sur le gène

human ... GCLC(2729) , GCLM(2730)

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Application

L-Buthionine-sulfoximine has been used:
  • as a selective activator for the induction of ferroptosis in rat apoptotic cells
  • as an inhibitor of γ-glutamylcysteine synthetase to study its effects on the viability and effectiveness of microspore embryogenesis (ME) induction in triticale and barley
  • as a glutathione synthesis blocker to study its effects on auranofin (AFN)-mediated interleukin-1β expression in murine alveolar macrophages

Used to induce experimental glutathione deficiency, to investigate roles of glutathione in cellular processes.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

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Triticale and barley microspore embryogenesis induction requires both reactive oxygen species generation and efficient system of antioxidative defence
Zur I, et al.
Plant Cell, Tissue and Organ Culture, 145(2), 347-366 (2021)
Boris Epel et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 276, 31-36 (2017-01-17)
Thiol redox status is an important physiologic parameter that affects the success or failure of cancer treatment. Rapid scan electron paramagnetic resonance (RS EPR) is a novel technique that has shown higher signal-to-noise ratio than conventional continuous-wave EPR in in
Kondareddy Cherukula et al.
Theranostics, 9(9), 2505-2525 (2019-05-28)
The delivery of therapeutics into tumors remains a challenge in nanoparticle-mediated drug delivery. However, effective therapies such as photothermal therapy (PTT) are limited by quick systemic clearance and non-specific biodistribution. Anti-tumor strategies tailored to accommodate both tumor accumulation/retention and cellular
Tatjana Bosnjak et al.
Basic & clinical pharmacology & toxicology, 125(2), 89-99 (2019-03-28)
Proton pump inhibitors (PPIs) are prodrugs used in the treatment of peptic ulcer diseases. Once activated by acidic pH, the PPIs subsequently inhibit the secretion of gastric acid by covalently forming disulphide bonds with the SH groups of the parietal
Zeyu Cao et al.
Scientific reports, 7(1), 16278-16278 (2017-11-28)
Enterovirus 71 (EV71) is a key pathogen of hand, foot and mouth disease (HFMD) in children under 6 years of age. The antiviral potency of antioxidant isochlorogenic acid C (ICAC) extracted from foods was evaluated in cellular and animal models.
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