PDMP (hydrochloride)

PDMP is a ceramide analog first prepared in a search for inhibitors of glucosylceramide synthase.¹ PDMP has two adjacent chiral centers (C1 and C2) allowing for the formation of four possible isomers. PDMP contains all four of these stereoisomers. PDMP inhibits glucosylceramide synthase by 90% when used at a concentration of 0.8 μM in MDCK cell homogenates, however, the ability to inhibit glucosylceramide synthase has been found to reside in the D-threo (1R,2R) enantiomer.² 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.³ PDMP enhances curcumin-induced inhibition of proliferation, JNK activation, and Akt inhibition, as well as induction of apoptosis in WM-115 melanoma cells in vitro.⁴

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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. 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).

3. 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).

4. Yu, T., Li, J., Qiu, Y., et al. 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) facilitates curcumin-induced melanoma cell apoptosis by enhancing ceramide accumulation, JNK activation, and inhibiting PI3K/AKT activation. Mol. Cell. Biochem. 361(1-2), 47-54 (2012).