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Key Documents

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D4681

Sigma-Aldrich

L-threo-Dihydrosphingosine

≥95% (TLC)

Sinónimos:

Safingol

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About This Item

Fórmula empírica (notación de Hill):
C18H39NO2
Número de CAS:
15639-50-6
Peso molecular:
301.51
MDL number:
MFCD00792847
UNSPSC Code:
12352211
PubChem Substance ID:
329798800
NACRES:
NA.77

Quality Level

100

assay

≥95% (TLC)

form

powder

storage temp.

−20°C

SMILES string

CCCCCCCCCCCCCCC[C@H](O)[C@@H](N)CO

InChI

1S/C18H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h17-18,20-21H,2-16,19H2,1H3/t17-,18-/m0/s1

InChI key

OTKJDMGTUTTYMP-ROUUACIJSA-N

Biochem/physiol Actions

Sphingosine kinase inhibitor; protein kinase C alpha (PKCα) -specific inhibitor; Sphingosine analog; potentiates the effect of doxorubicin (DOX) in tumor-bearing animals.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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J W Darges et al.
Advances in experimental medicine and biology, 400A, 387-392 (1997-01-01)
The sphingosine analog L-threo-dihydrosphingosine has been shown to inhibit protein kinase C (PKC) isoenzymes in mixed micelle and vesicle assays. This compound also inhibited the reactive oxygen intermediates (ROI) released from isolated neutrophils (IC50 approximately 2 microM) and phorbol ester-induced
Yi-Hsin Hsu et al.
Cancer research, 74(17), 4822-4835 (2014-06-28)
Triple-negative breast cancer (TNBC) is a highly heterogeneous and recurrent subtype of breast cancer that lacks an effective targeted therapy. To identify candidate therapeutic targets, we profiled global gene expression in TNBC and breast tumor-initiating cells with a patient survival
G K Schwartz et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 3(4), 537-543 (1997-04-01)
We performed a pilot clinical trial with safingol (L-threo-dihydrosphingosine), a protein kinase C-specific inhibitor that potentiates the effect of doxorubicin (DOX) in tumor-bearing animals. Safingol was initially administered as a 1-h infusion at escalating doses. Fourteen days later, patients received
Avraham Ashkenazi et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 26(11), 4628-4636 (2012-08-09)
Understanding the structural organization of lipids in the cell and viral membranes is essential for elucidating mechanisms of viral fusion that lead to entry of enveloped viruses into their host cells. The HIV lipidome shows a remarkable enrichment in dihydrosphingomyelin
Hyun Joon Kim et al.
Journal of lipid research, 53(8), 1701-1707 (2012-06-05)
The sphingolipids are a diverse family of lipids with important roles in membrane compartmentalization, intracellular signaling, and cell-cell recognition. The central sphingolipid metabolite is ceramide, formed by the transfer of a variable length fatty acid from coenzyme A to a
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