N-Dodecanoyl-NBD-L-threo-dihydrosphingosineN-Dodecanoyl-NBD-L-threo-dihydrosphingosine
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N-Dodecanoyl-NBD-L-threo-dihydrosphingosine

N-C12:0-NBD-Dihydroceramide; N-C12:0-NBD-L-threo-Dihydrosphingosine

N-Dodecanoyl-NBD-L-threo-dihydrosphingosine is a synthetic dihydroceramide analog containing the 7-(4-nitrobenzo-2- oxa-1,3-diazole) (NBD) fluorescent group. NBD has been shown to have only a small influence on lipid adsorption into cells and cellular membranes in many applications. This fluorescent analog of L-threo-dihydroceramide is comparable to C12:0- L-threo-dihydroceramide in some biological functions. Safingol is a fully saturated, non-natural analog of sphingosine that has anticancer properties and is being investigated for its potential as an antitumor therapy. It has been shown to inhibit both protein kinase C (PKC) and sphingosine kinase. Safingol competitively interacts at the regulatory phorbol-binding domain of PKC, a kinase involved in tumorigenesis. Safingol has been shown to potentiate the effect of doxorubicin (DOX) in tumorbearing animals.1 It has been reported that safingol is able to increase the activity of DOX and other chemotherapeutic agents, including mitomycin C, by generating the pro-apoptotic second messenger ceramide, even in tumor cell lines that were resistant to chemotherapy due to mutations.2 However, a study has recently claimed that safingol induces cell death of an exclusively autophagic character and lacking any of the hallmarks of apoptosis.3 Safingol inhibited the reactive oxygen intermediates (ROI) released from isolated neutrophils and phorbol ester-induced edema and neutrophil influx. Safingol also demonstrates anti-inflammatory activity. Safingol, like the natural D-erythro-sphinganine, is used as a biosynthetic precursor for all complex sphingolipids althogh the metabolism of the natural and the non-natural compounds are different.4
Cat# Size Price Qty Buy
1623 100 ug £187.50

Additional Information

Property Value or Rating
Product Size 100 ug
Manufacturer Matreya, LLC
Empirical Formula C36H63N5O6
CAS# 474943-07-2
Formula Weight 661.9
Source synthetic
Purity 98+%
Analytical Methods TLC
Natural Source Synthetic
Solubility methanol, chloroform/methanol, 2:1
Physical Appearance A neat orange solid
Storage -20°C
References

1. Darges, et al. “Inhibition of leukotriene B4 (LTB4) in human neutrophils by L-threo-dihydrosphingosine” Adv. Exp. Med. Biol, Vol. 400A pp. 387-392, 1997 
2. G. Schwartz, et al. “A pilot clinical/pharmacological study of the protein kinase C-specific inhibitor safingol alone and in combination with doxorubicin” Clin. Cancer Res, Vol. 3 pp. 537-543, 1997 
3. J. Coward et al. “Safingol (L-threo-sphinganine) induces autophagy in solid tumor cells through inhibition of PKC and the PI3-kinase pathway” Autophagy Vol. 5(2) pp.184-193, 2009 
4. M. Dragusin et al. “Metabolism of the unnatural anticancer lipid safingol,L-threo-dihydrosphingosine, in cultured cells” Vol. 44 pp. 1772, 2003

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