C1159
L-Cycloserine
Synonym(s):
(S)-4-Amino-3-isoxazolidone
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About This Item
Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
Molecular Weight:
102.09
Beilstein:
80799
EC Number:
MDL number:
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
NACRES:
NA.77
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Assay
≥95% (TLC)
Quality Level
form
powder
mp
146 °C
solubility
H2O: 50 mg/mg protein
storage temp.
−20°C
SMILES string
N[C@H]1CONC1=O
InChI
1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m0/s1
InChI key
DYDCUQKUCUHJBH-REOHCLBHSA-N
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Biochem/physiol Actions
Blocks sphingosine biosynthesis by inhibition of ketosphinganine synthetase. Cytotoxicity toward neuroblastoma and medulloblastoma cells mediated by suppression of ganglioside synthesis.
L-cycloserine is a potent inhibitor of serine palmitoyltransferase, the first step of sphingolipid synthesis.
Storage Class Code
11 - Combustible Solids
WGK
WGK 2
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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J Cinatl et al.
Anticancer research, 19(6B), 5349-5354 (2000-03-04)
Human neuroblastoma and medulloblastoma express abnormal ganglioside patterns especially GD2 and GM2 which are important for tumour growth. We tested the effects of L-cycloserine (L-CS), a potent inhibitor of synthesis of glycosphingolipids, on the growth, viability and expression of GD2
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The international journal of biochemistry & cell biology, 41(5), 1165-1172 (2008-11-26)
Doxorubicin and camptothecin are two cytotoxic chemotherapeutic agents triggering apoptosis in various cancer cells, including thyroid carcinoma cells. Recent studies revealed a critical role of ceramide in chemotherapy and suggested that anti-cancer drugs may kill tumor cells through sphingomyelinase activation.
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