An inhibitor of sphingolipid biosynthesis
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DL-threo-PDMP (hydrochloride)

Item No. 10005276

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-decanamide, monohydrochloride
CAS Number
80938-69-8
Molecular Formula
C23H38N2O3 • HCl
Formula Weight
427.0
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMSO: 30 mg/mlEthanol: 50 mg/mlEthanol:PBS (pH 7.2) (1:5): 0.05 mg/ml
SMILES
CCCCCCCCCC(N([H])[C@H]([C@@H](O)C1=CC=CC=C1)CN2CCOCC2)=O.Cl
InChi Code
InChI=1S/C23H38N2O3.ClH/c1-2-3-4-5-6-7-11-14-22(26)24-21(19-25-15-17-28-18-16-25)23(27)20-12-9-8-10-13-20;/h8-10,12-13,21,23,27H,2-7,11,14-19H2,1H3,(H,24,26);1H/t21-,23-;/m0./s1
InChi Key
HVJHJOYQTSEKPK-IUQUCOCYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    100 mg

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    Product Description

    DL-threo PDMP is a mixture of ceramide analogs that contains two of the four possible stereoisomers of PDMP (Item No. 62595): D-threo-(1R,2R)-PDMP and L-threo-(1S,2S)-PDMP.1 DL-threo-PDMP inhibits glucosylceramide synthase by 33 and 48% in MDCK cell homogenates when used at concentrations of 5 and 10 µM.2 It reduces the synthesis of glucosylceramide, increases cellular ceramide, and induces cell cycle arrest in vitro.3 The ability to inhibit glucosylceramide synthase has been found to reside in the D-threo-(1R,2R) enantiomer.4 The D-threo-PDMP enantiomer is also responsible for inhibition of β-1,4-galactosyltransferase 6 and prevention of lactosylceramide synthesis, which is a promotor of neuroinflammation in mice during chronic experimental autoimmune encephalomyelitis (EAE), a model of multiple sclerosis.5 DL-threo-PDMP increases amyloid-β (1-42) (Aβ42) and Aβ39 production independent of ceramide metabolism via modulation of γ-secretase activity in HEK293 cells expressing the γ-secretase substrate SC100.6 [Matreya, LLC. Catalog No. 1719]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vunnam, R.R., and Radin, N.S. Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain. Chem. Phys. Lipids 26(3), 265-278 (1980).

    2. Inokuchi, J.i., and Radin, N.S. Preparation of the active isomer of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol, inhibitor of murine glucocerebroside synthetase. J. Lipid Res. 28(5), 565-571 (1987).

    3. Rani, C.S.S., Abe, A., Chang, Y., et al. Cell cycle arrest induced by an inhibitor of glucosylceramide synthase. Correlation with cyclin-dependent kinases. The Journal of Biological Chemisty 270(6), 2859-2867 (1995).

    4. Abe, A., Radin, N.S., Shayman, J.A., et al. Structural and stereochemical studies of potent inhibitors of glucosylceramide synthase and tumor cell growth. J. Lipid Res. 36(3), 611-621 (1995).

    5. Mayo, L., Trauger, S.A., Blain, M., et al. Regulation of astrocyte activation by glycolipids drives chronic CNS inflammation. Nat. Med. 20(10), 1147-1156 (2014).

    6. Takasugi, N., Sasaki, T., Shinohara, M., et al. Synthetic ceramide analogues increase amyloid-β 42 production by modulating γ-secretase activity. Biochem. Bioph. Res. Commun. 457(2), 194-199 (2015).