sphingosine

Sphingosines are long-chain base precursors of cellular sphingolipids used directly in the synthesis of ceramide, which in combination with sialic acid forms ganglioside. Sphingosine can exist in four stereoisomers, however only sphingosine occurs naturally. Compared to other sphingolipids throughout the body, which are predominantly composed of C-18 sphingosine, only central nervous system (CNS) gangliosides contain significant amounts of sphingosine. The concentration of sphingosine within mammalian brain gangliosides apparently increases with developmental maturation. Furthermore, the ratio of C-18 to C-20 sphingosine in the brain is thought to be related to some nervous system degeneration processes.

Sphingosine (d14:1) is a bioactive sphingolipid that has been found in B. mori (silkworm), P. clarkii (crayfish), and A. aurita (jellyfish) extracts. It increases the germination rate of N. rileyi, an entomopathogenic fungus, with an EC50 value of 10.2 nM. Sphingosine (d14:1) inhibits protein kinase C (PKC) in vitro (IC50 = 7.3 mol%) as well as superoxide generation induced by phorbol 12-myristate 13-acetate in neutrophils and reduces growth of CHO cells (IC50s = 19 and 8 μM, respectively).

Sphingosine-1-phosphate (S1P) is an agonist for S1P1-5 receptors and a ligand for GPR3, GPR6, and GPR12. As an intracellular second messenger, it mobilizes Ca2+ and acts as an extracellular ligand for G-protein coupled receptors. This important lipid mediator is generated from sphingosine or other membrane phospholipids.

L-erythro-Sphingosine is an L-isomer of sphingosine.

L-threo-Sphingosine C-18 is a protein kinase C inhibitor.

C16 Sphingosine-1-phosphate (C16 S1P) is a derivative of sphingosine-1-phosphate that binds to S1P1/EDG-1, S1P3/EDG-3, and S1P2/EDG-5 receptors with affinities of 115%, 83%, and 103%, respectively, relative to S1P in CHO cells. C16 S1P was increased in postmortem primary open angle glaucoma trabecular meshwork samples.

D-erythro-Sphingosine hydrochloride, also known as Erythrosphingosine, serves as a specific TRPM3 activator and induces retinoblastoma protein dephosphorylation.

Sphingosine (d17:1) (C17 Sphingosine) is a 17-carbon sphingolipid found in human skin that can be phosphorylated by sphingomyelin kinase.Sphingosine C-17 can be used as an internal standard to perform spectroscopic analysis of sphingolipids.

Sphingosine (d18:1), an amino alcohol, is chiefly recognized for its 18-carbon unsaturated hydrocarbon chain. Nevertheless, in mammalian tissues, both sphingosine and its variant, dihydrosphingosine, feature hydrocarbon chains ranging from 12 to 26 carbons. Sphingosine (d15:1) represents a naturally rare variant, serving as an internal standard for chromatographic or spectrometric analyses of sphingoid compounds.

Sphingosine (d16:1), an unconventional sphingolipid, is synthesized through enzymatic reactions starting with the condensation of myristoyl-CoA and serine by serine palmitoyltransferase long-chain base subunit 3 (SPTLC3), which shows a preference for myristoyl-CoA. This compound is found in minute quantities in its free form in human plasma and as a component of various plasma sphingolipids, such as sphingosine-1-phosphate, ceramides, sphingomyelins, and in brain cerebrosides, albeit at lower concentrations than the more common d18:1 sphingoid base. Sphingosine (d16:1) acts as an inhibitor of PKC in mixed micelle assays and diminishes superoxide production triggered by phorbol 12-myristate 13-acetate in isolated human neutrophils, as well as inhibiting the growth of CHO cells with IC50 values of 1 and 3.2 µM, respectively. Additionally, the concentration of sphingolipids containing sphingosine (d16:1) in the plasma is linked to the dietary consumption of saturated fatty acids and protein among ethnic Chinese populations.

N,N-dihexyl Sphingosine (d18:1/6:0/6:0) is a lipid molecule that can be used in life science related research. The CAS number of N,N-dihexyl Sphingosine (d18:1/6:0/6:0) is 2377379-53-6.

Lactosylsphingosine (d18:1) is a sphingolipid with a lactose moiety that can inhibit fMetLeuPhe-induced cell aggregation at a concentration of 1 μm.

C12-Sphingosine (Sphingosine (d12:1)) is a sphingosine congener with 12 carbon atoms, inducing serine palmitoyltransferase activity in a time- and concentration-dependent manner.

D-erythro-Sphingosine (trans-4-Sphingenine) is a protein kinase C (PKC) inhibitor. D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator

Glucosylsphingosine (Lyso-Gb1) is a naturally occurring glycosyl ceramide, a metabolite of GBA (acid β-glucosidase), involved in cellular recognition, signaling, and intercellular interactions.Glucopsychosine accumulates in certain neurodegenerative diseases (e.g., Gaucher disease), disrupts lysosomal function through activation of mammalian target of rapamycin complex 1 (mTORC1), and is a noncompetitive inhibitor of glucocerebrosidase.

K145 hydrochloride is a selective sphk2 inhibitor with substrate competitiveness and oral activity, with IC50 of 4.3 µM and Ki of 6.4 µM. K145 hydrochloride can induce apoptosis and has strong antitumor activity.

N-Desmethyltamoxifen hydrochloride is the primary metabolite of tamoxifen in humans.

ARN14974 is a benzoxazolone carboxamide. ARN14974 is a potent inhibitor of acid ceramidase with IC50 of 79 nM[1].

SKI V is a potent and noncompetitive non-lipid sphingosine kinase (SPHK; SK) inhibitor (GST-hSK,IC50 : 2 μM), and is a PI3K inhibitor(hPI3k,IC50 : 6 μM), induces apoptosis and has antitumor activity

Phorbol 12-myristate 13-acetate (PMA) is a natural phorbol ester that acts as an activator of PKC, SphK, and NF-κB, and is commonly used to induce differentiation of THP-1 cells and establish dermatitis models.

PF-543 Citrate (Sphingosine Kinase 1 Inhibitor II Citrate) is a selective and potent inhibitor of sphingosine kinase 1 (SPHK1) and is an efficient inhibitor of 1-phosphate sphingosine (S1P) formation. It possesses anticancer, antifibrotic, and anti-inflammatory activities and can be used in research on colorectal cancer.

Fumonisin B1 (Fumonisin-B1) is a mycotoxin produced by Fusarium oxysporum that is widely present in crops, contaminating them and posing a significant food safety hazard.Fumonisin B1 is structurally a sphingosine and sphingomyelin analog, and inhibits the biosynthesis of complex sphingolipids through the inhibition of ceramidic synthases.

Fumonisin B2 is a mycotoxin produced by Fusarium moniliforme in various grains. It also is a potent inhibitor of sphingosine N-acyltransferase (ceramide synthase). Which disrupts de novo sphingolipid biosynthesis.

MP-A08 is a highly selective, ATP-competitive inhibitor of sphingosine kinase (SPHK1) that targets both SphK1 and SphK2 [Ki: 6.9 ± 0.8 μM and 27 ± 3 μM, respectively].