ChemicalBook--->CAS DataBase List--->161491-04-9

161491-04-9

161491-04-9 Structure

161491-04-9 Structure
IdentificationBack Directory
[Name]

Halcinonide
[CAS]

161491-04-9
[Synonyms]

(?)-L-threo-PDMP hydrochloride
()-L-threo-PDMP (hydrochloride)
(-)-L-threo-PDMP (hydrochloride)
()LthreoPDMP (hydrochloride),( ) L threo PDMP (hydrochloride)
[Molecular Formula]

C23H39ClN2O3
[MOL File]

161491-04-9.mol
[Molecular Weight]

427.03
Chemical PropertiesBack Directory
[storage temp. ]

Store at -20°C
[solubility ]

Ethanol: Soluble; Methanol: Soluble
[form ]

A solid
Hazard InformationBack Directory
[Description]

(–)-L-threo-PDMP is a ceramide analog and one of the four possible stereoisomers of PDMP . L-threo-PDMP is an enhancer of ganglioside biosynthesis. It increases glucosylceramide synthase activity by 4 and 8% when used at concentrations of 5 and 2.5 μM, respectively, in an enzyme assay. L-threo-PDMP increases the activity of ganglioside GM3, GD3, and GQ1b synthases and increases the levels of glucosylceramide, lactosylceramide, and ganglioside GM3 in B16 melanoma cells. It inhibits the growth of MCF-7, MDA-MB-468, SK-BR-3 cells with IC50 values of 4, 7, and 6 μM, respectively. L-threo-PDMP increases neurite outgrowth and synapse formation in vitro and improves retention of a long-term memory learned prior to forebrain ischemia in rats when administered following ischemia at a dose of 40 mg/kg per day. The L-threo-PDMP isomer is the glucosylceramide synthetase stimulatory component of DL-threo-PDMP , while D-threo-PDMP is the inhibitory component. [Matreya, LLC. Catalog No. 1749]
[Uses]

(?)-L-threo-PDMP hydrochloride is the hydrochloride form of (?)-L-threo-PDMP. L-threo-PDMP is a glucosylceramide synthase (GCS) inhibitor. L-threo-PDMP stimulates the proliferation of cultured aortic smooth muscle cells, and that increases the level of LacCer in B16 melanoma cells[1][2].
[storage]

Store at -20°C
[References]

[1] Mitchell SA, et al. Glycosyltransferase Inhibitors: Synthesis of D-threo-PDMP, L-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from D-or L-Serine. The Journal of Organic Chemistry. 1998, 63(24): 8837-8842.
[2] Chatterjee S, et al. Studies of the action of ceramide-like substances (D- and L-PDMP) on sphingolipid glycosyltransferases and purified lactosylceramide synthase. Glycoconj J. 1996 Jun;13(3):481-6. DOI:10.1007/BF00731481
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