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Merck

B2515

L-Buthionine-sulfoximine

synthetic (organic), ≥97% (TLC), γ-glutamylcysteine synthetase inhibitor, powder

Sinónimos:

L-BSO

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About This Item

Fórmula empírica (notación de Hill):
C8H18N2O3S
Número CAS:
83730-53-4
Peso molecular:
222.31
NACRES:
NA.77
PubChem Substance ID:
24278263
UNSPSC Code:
12352202
MDL number:
MFCD00067000
Beilstein/REAXYS Number:
2367136

Nombre del producto

L-Buthionine-sulfoximine, ≥97% (TLC)

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

SMILES string

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

InChI key

KJQFBVYMGADDTQ-CVSPRKDYSA-N

biological source

synthetic (organic)

assay

≥97% (TLC)

form

powder

mp

224-226  °C

solubility

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

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

Gene Information

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.

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000299225
0000299225
0000494037
0000492592
0000492592

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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
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)
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.
S Busker et al.
Science advances, 6(12), eaax7945-eaax7945 (2020-03-29)
Because of its key role in cancer development and progression, STAT3 has become an attractive target for developing new cancer therapeutics. While several STAT3 inhibitors have progressed to advanced stages of development, their underlying biology and mechanisms of action are
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