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Merck

B2515

L-Buthionine-sulfoximine

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

Synonym(s):

L-BSO

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About This Item

Empirical Formula (Hill Notation):
C8H18N2O3S
CAS Number:
83730-53-4
Molecular Weight:
222.31
NACRES:
NA.77
PubChem Substance ID:
24278263
UNSPSC Code:
12352202
MDL number:
MFCD00067000
Beilstein/REAXYS Number:
2367136

Product Name

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.

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000299225
0000299225
0000494037
0000492592
0000492592

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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)
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Scientific reports, 7(1), 16278-16278 (2017-11-28)
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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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