Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H37NO2 |
| Molecular Weight | 299.4919 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCC\C=C\[C@H](O)[C@@H](N)CO
InChI
InChIKey=WWUZIQQURGPMPG-DNWQSSKHSA-N
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18-/m0/s1
Threo-sphingosine, (-)- is a stereoisomer of naturally occurring D-erythro-sphingosine. It is a Protein kinase C inhibitor. Threo-sphingosine, (-)- is partly active in induction of apoptosis and inhibition of MAPK activity in different kinds of solid tumor cell lines. It can be phosphorylated by cells, but the resulting L-Threo-sphingosine 1-phosphate does not bind and activate sphingosine 1-phosphate receptors, excluding their role in Threo-sphingosine, (-)-induced growth inhibition. Cell culture experiments with Diffuse large B cell lymphoma cell lines that were incubated with Threo-sphingosine, (-)- manifested significant inhibition of cell growth, while incubation of cells with similar concentrations of sphingosine 1-phosphate was ineffective. These results suggest that Threo-sphingosine, (-)- accumulation could be an alternative treatment option for Diffuse large B cell lymphoma.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chemical properties and stereoisomerism of heterogeneous long chain bases in lysosphingolipids by positive ion fast atom bombardment mass spectrometry and carbon-13 NMR spectroscopy. | 1986 Aug |
|
| A series of fluorescent N-acylsphingosines: synthesis, physical properties, and studies in cultured cells. | 1988 Jun 14 |
|
| D-erythro-sphingosine lowers 3-hydroxy-3-methylglutaryl coenzyme A reductase activity in Chinese hamster ovary cells. | 1993 Jan 15 |
|
| Role of ceramide in mitogenesis induced by exogenous sphingoid bases. | 1994 Mar 4 |
|
| Chemoenzymatic Synthesis of All Four Stereoisomers of Sphingosine from Chlorobenzene: Glycosphingolipid Precursors(1)(a). | 1998 Feb 6 |
|
| Selectivity of sphingosine-induced apoptosis. Lack of activity of DL-erythyro-dihydrosphingosine. | 1998 May 29 |
|
| Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers. | 2003 Mar 21 |
Patents
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
25695-95-8
Created by
admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
|
PRIMARY | |||
|
11130338
Created by
admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
|
PRIMARY | |||
|
AQ8E26TZ1N
Created by
admin on Sat Dec 16 01:34:35 GMT 2023 , Edited by admin on Sat Dec 16 01:34:35 GMT 2023
|
PRIMARY |
SUBSTANCE RECORD
