D4681
L-threo-Dihydrosphingosine
≥95% (TLC)
Synonym(s):
Safingol
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About This Item
Empirical Formula (Hill Notation):
C18H39NO2
CAS Number:
Molecular Weight:
301.51
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:
Product Name
L-threo-Dihydrosphingosine, ≥95% (TLC)
InChI key
OTKJDMGTUTTYMP-ROUUACIJSA-N
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
assay
≥95% (TLC)
form
powder
storage temp.
−20°C
Quality Level
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
Yidi Sun et al.
Molecular biology of the cell, 23(12), 2388-2398 (2012-04-27)
Sphingoid intermediates accumulate in response to a variety of stresses, including heat, and trigger cellular responses. However, the mechanism by which stress affects sphingolipid biosynthesis has yet to be identified. Recent studies in yeast suggest that sphingolipid biosynthesis is regulated
Juliana M Figueiredo et al.
Molecular and biochemical parasitology, 182(1-2), 62-74 (2012-01-10)
In this study, we characterized ceramide synthase (CerS) of the protozoan parasite Trypanosoma cruzi at the molecular and functional levels. TcCerS activity was detected initially in a cell-free system using the microsomal fraction of epimastigote forms of T. cruzi, [(3)H]dihydrosphingosine
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