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C1159

Sigma-Aldrich

L-Cycloserine

Synonym(s):

(S)-4-Amino-3-isoxazolidone

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About This Item

Empirical Formula (Hill Notation):
C3H6N2O2
CAS Number:
339-72-0
Molecular Weight:
102.09
Beilstein/REAXYS Number:
80799
EC Number:
206-427-0
MDL number:
MFCD00064324
UNSPSC Code:
12352202
eCl@ss:
32160406
PubChem Substance ID:
24278296
NACRES:
NA.77

assay

≥95% (TLC)

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

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Geraldine Rath et al.
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.
David M Pereira et al.
Marine drugs, 12(1), 54-68 (2013-12-26)
We describe the effect of a chemically characterized lipophilic extract obtained from Marthasterias glacialis L. against human breast cancer (MCF-7) and human neuroblastoma (SH-SY5Y) cell lines. Evaluation of DNA synthesis revealed that both cell lines were markedly affected in a
Peirong Hu et al.
Journal of neuroscience research, 94(11), 1152-1168 (2016-09-18)
Currently, presymtomatic hematopoietic stem and progenitor cell transplantation (HSPCT) is the only therapeutic modality that alleviates Krabbe's disease (KD)-induced central nervous system damage. However, all HSPCT-treated patients exhibit severe deterioration in peripheral nervous system function characterized by major motor and
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
Karim Bennaceur et al.
Glycobiology, 19(6), 576-582 (2009-02-26)
Tumor escape is linked to multiple mechanisms, notably the liberation, by tumor cells, of soluble factors that inhibit the function of dendritic cells (DC). We have shown that melanoma gangliosides impair DC differentiation and induce their apoptosis. The present study
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