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(+)-D-threo-PDMP (hydrochloride)

Item № 10178
CAS № 139889-62-6
Purity ≥98%
product image
                (CAS 139889-62-6)
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL
     10 mg $379.00 0.00

Pricing updated 2019-07-18. Prices are subject to change without notice.

Description

(+)-D-threo-PDMP is a ceramide analog and is one of the four possible stereoisomers of PDMP (Item No. 62595).1 (+)-D-threo-PDMP is an inhibitor of glucosylceramide synthase.2,3 It inhibits glucosylceramide synthase by 50% when used at a concentration of 5 μM in an enzyme assay.3 (+)-D-threo-PDMP is the active component of racemic DL-threo-PDMP (Item No. 10005276). In vitro, (+)-D-threo-PDMP inhibits the synthesis of glucosylceramide synthase and lactosylceramide in B16 melanoma cells when used at a concentration of 25 µM and inhibits cell binding to laminin and collagen when used at concentrations of 10 and 25 µM.4 It also inhibits β-1,4-galactosyltransferase 6 (B4GALT6) and prevents lactosylceramide synthesis, which is a promotor of neuroinflammation in mice during chronic experimental autoimmune encephalomyelitis (EAE), a model of multiple sclerosis.5 (+)-D-threo-PDMP inhibits ganglioside biosynthesis, reduces long-term potentiation (LTP) in mouse hippocampal CA1 neurons, and impairs learning in the four-pellet taking test in mice.6

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Technical Information
Formal Name
N-[(1R,2R)-2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-decanamide, monohydrochloride
CAS Number
139889-62-6
Molecular Formula
C23H38N2O3 • HCl
Formula Weight
427.0
Purity
≥98%
Formulation
A solid
SMILES
CCCCCCCCCC(N[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-;/m1./s1
InChI Key
HVJHJOYQTSEKPK-BLDCTAJRSA-N

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
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Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

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References & Product Citations
Product Description References

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

2. Abe, A., Inokuchi, J.-i., Jimbo, M., et al. Improved inhibitors of glucosylceramide synthase J. Biochem. 111, 191-196 (1992).

3. 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 Journal of Lipid Research 28, 565-571 (1987).

4. Inokuchi, J.-I., Momosaki, K., Shimeno, H., et al. Effects of D-threo-PDMP, an inhibitor of glucosylceramide synthetase, on expression of cell surface glycolipid antigen and binding to adhesive proteins by B16 melanoma cells. J. Cell. Physiol. 141(3), 573-583 (1989).

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

6. Fujiwara, H., Ikarashi, K., Yamazaki, Y., et al. Impairment of hippocampal long-term potentiation and failure of learning in mice treated with D-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol. Biomed Res. 33(5), 265-271 (2012).

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