D,L-erythro-PDMP 109760-77-2

H1755

D,L-erythro-PDMP

109760-77-2

synthetic

C₂₃H₃₈N₂O₃•HCl

427

100mg

solid

98+% TLC; HPLC; identity confirmed by MS

D,L-erythro-1-Phenyl-2-decanoylamino-3-morpholino-1-propanol•HCl

ethanol, methanol, chloroform, DMSO

-20°C

D,L-erythro-PDMP inhibits the growth of cells, including cancer cells. D-threo-PDMP has been shown to inhibit cell growth by inhibiting the enzyme glucosylceramide synthase1 but erythro-PDMP inhibits growth according to a different mechanism. PDMP has four possible isomers (D-threo, L-threo, D-erythro, and L-erythro) due to its two chiral centers. This product (D,L-erythro-PDMP) is a mixture of D-erythro (1R,2R) and L-erythro (1S,2S). The D-threo isomer has been shown to be the active glucosyl ceramide synthetase inhibitor.2 Although erythro-PDMP does not inhibit glucosylceramide synthase it does cause cell growth inhibition similar to threo-PDMP.3 This has been suggested as a treatment for cancer.4 In addition to its stereochemistry, the acyl chain of PDMP has a very marked effect on the intensity of the inhibitory action of the molecule.
1. R. Vunnam, N. Radin “Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain” Chem Phys Lipids, Vol. 26(3) pp. 265-278, 1980
2. N. Radin 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” Journal of Cellular Physiology, Vol. 141(3) pp. 573–583, 1989
3. N. Radin et al. “Effect of an inhibitor of glucosylceramide synthesis on cultured rabbit skin fibroblasts” Journal of Biochemsitry, vol. 108:4 pp. 525-530, 1990
4. N. Radin, et al. “Structural and stereochemical studies of potent inhibitors of glucosylceramide synthase and tumor cell growth” Journal of Lipid Research, Vol. 36 pp. 611-621, 1995