lysosphingomyelin (d18:1)

Sphingomyelins are complex membrane lipids composed of phosphorylcholine, sphingosine, and an acylated group, such as a fatty acid. Lysosphingomyelin is a naturally-occurring lipid which is produced by the removal of the acylated group of sphingomyelin by a deacylase. Lysosphingomyelin may, in turn, serve as a substrate for autotaxin, which removes choline to produce sphingosine-1-phosphate. The receptors and signaling pathways that are activated by lyso-sphingosine are diverse and vary between cell types. Lysosphingomyelin occurs naturally in plasma, is a constituent of lipoproteins, and is increased in some diseases, including dermatitis and Niemann-Pick disease.

L-threo Lysosphingomyelin (d18:1) (L-threo-Sphingosylphosphorylcholine) is a naturally occurring bioactive sphingolipid. It acts as a potent agonist for S1P receptors, with EC50 values of 19.3, 131.8, and 313.3 nM for hS1P1, hS1P3, and hS1P2, respectively.

Lysosphingomyelin is an endogenous bioactive sphingolipid and a constituent of lipoproteins.1,2It is produced by the removal of the acyl group from sphingomyelin by a deacylase and acts as a precursor in the biosynthesis of sphingosine-1-phosphate . D-erythroLysosphingomyelin is an agonist of the S1P receptors S1P1, S1P2, and S1P3(EC50s = 167.7, 368.1, and 482.6 nM, respectively, for the human receptors).3It is also an agonist of the orphan receptor ovarian cancer G protein-coupled receptor 1 (ORG1) that induces calcium accumulation in cells overexpressing OGR1 (EC50= ~35 nM).4Levels of D-erythrolysosphingomyelin are increased in skin isolated from patients with atopic dermatitis, as well as postmortem brain from patients with Niemann-Pick disease type A, but not type B.2,5L-threolysosphingomyelin is also an S1P1-3agonist (EC50s = 19.3, 131.8, and 313.3 nM, respectively).3This product is a mixture of D-erythroand L-threolysosphingomyelin. [Matreya, LLC. Catalog No. 1321] 1.Ito, M., Kurita, T., and Kita, K.A novel enzyme that cleaves the N-acyl linkage of ceramides in various glycosphingolipids as well as sphingomyelin to produce their lyso formsJ. Biol. Chem.270(41)24370-24374(1995) 2.Nixon, G.F., Mathieson, F.A., and Hunter, I.The multi-functional role of sphingosylphosphorylcholineProg. Lipid Res.47(1)62-75(2008) 3.Im, D.-S., Clemens, J., Macdonald, T.L., et al.Characterization of the human and mouse sphingosine 1-phosphate receptor, S1P5 (Edg-8): Structure-activity relationship of sphingosine1-phosphate receptorsBiochemistry40(46)14053-14060(2001) 4.Meyer zu Heringdorf, D., Himmel, H.M., and Jakobs, K.H.Sphingosylphosphorylcholine-biological functions and mechanisms of actionBiochim. Biophys. Acta1582(1-3)178-189(2002) 5.Rodriguez-Lafrasse, C., and Vanier, M.T.Sphingosylphosphorylcholine in Niemann-Pick disease brain: Accumulation in type A but not in type BNeurochem. Res.24(2)199-205(1999)

Genipin 1-β-D-gentiobioside is a natural product for research related to life sciences. The catalog number is T4S2299 and the CAS number is 29307-60-6.

1-{1H-pyrrolo[2,3-d]pyrimidin-4-yl}piperazine dihydrochloride (1-PPZ-DHC) is a compound used as a molecular structural unit. It is an analog of the natural product piperazine and has a wide range of biological activities, including anti-inflammatory, anti-tumor and antibacterial activities. It has also been studied for the treatment of neurological disorders such as Alzheimer's and Parkinson's.

Kaempferol-3-O-β-D-glucosyl(1-2)rhamnoside is a natural peoduct isolated from Arabian jasmine

D-JNKI-1 acetate (AM-111 acetate) is a highly potent and cell-permeable peptide inhibitor of JNK.

1-beta-D-Arabinofuranosylthymine (Thymine 1-β-D-arabinofuranoside) is a purine nucleoside analog. Purine nucleoside analogs have a broad spectrum of antitumor activity, targeting inert lymphoid malignancies and inducing apoptosis.1-beta-D-Arabinofuranosylthymine's anticancer mechanism is dependent on the inhibition of DNA synthesis.1-beta-D-Arabinofuranosylthymine is a purine nucleoside analog.

2H-Naphth[2′,1′:4,5]indeno[1,2-d][1,3]dioxole, pregn-4-ene-3,20-dione deriv showed high local anti-inflammatory potency and high lung selectivity when tested on Sprague Dawley rats.

(2S)-1-O-p-coumaroyl-2-O-acetyl-3-O-β-D-glucopyranosylglycerol is a useful research compound for many research applications, including the fields of chemistry and life sciences, among others.

3-(2,6-dichlorophenyl)-1-methyl-7-(methylsulfanyl)-1H,2H,3H,4H-pyrimido[4,5-d][1,3]diazin-4-one is a compound that has been extensively investigated for the treatment of a variety of disorders including tumors, Alzheimer's and Parkinson's diseases, anti-inflammatory drugs, and analgesic agents.

(25R)-3β,17α-dihydroxy-5α- spirostan-6-one3-O-α-L- rhamnopyranosyl-(1→2)-β- D-glucopyranoside is a natural product isolated from the bulbs of Lilium brownii var. viridulum.

1-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)thieno[3,2-d]pyrimidin-2-yl)phenyl)-3-(pyridin-4-yl)urea is a useful organic compound for research related to life sciences. The catalog number is T67700 and the CAS number is 1144075-47-7.

1H-benzo[d][1,2,3]triazol-1-yl 8-methoxy-6-nitrophenanthro[3,4-d][1,3]dioxole-5-carboxylate is a useful organic compound for research related to life sciences and the catalog number is T72065.

Complement factor D-IN-1 is an effective and selective small-molecule reversible factor d inhibitor (IC50s: 0.006 and 0.05 μM in FD Thioesterolytic Fluorescent Assay and a MAC Deposition Assay, respectively).

Hederagenin 28-O-{β-D-xylopyranosyl-(1→6)-β-D-glucopyranosyl ester}3-O-{α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl} is a saponin known for its antitumor and anti-inflammatory properties [1].

C12 Galactosylceramide is a bioactive sphingolipid. It inhibits IL-4 production by 53.84% in EL4 T cells when used at a concentration of 10 μM. C12 Galactosylceramide reduces the growth of human papillomavirus type 16-associated tumors in mice and reduces tumor recurrence following surgical removal or chemotherapy. It also reduces natural killer T cell activity, delays the onset of proteinuria, and improves survival in a mouse model of systemic lupus.

C22 Glucosylceramide (d18:1/22:0) is an endogenous glucosylceramide. Glucosylceramides are major constituents of skin lipid membranes where they play a role in maintaining the water permeability barrier. They are precursors in the synthesis of lactosylceramide , as well as oligoglycolipids and gangliosides. Phospholipase A2 (PLA2) type XIIA knockdown increases C22 glucosylceramide (d18:1/22:0) expression in rat brain. It is also increased in the brain, but not the liver or spinal cord, of mice fed a methionine-restricted diet. In human athletes, plasma levels of C22 glucosylceramide (d18:1/22:0) increase during exercise and return to basal levels during recovery. This product contains C22 glucosylceramide (d18:1/22:0) isolated from bovine buttermilk.

α-D-Glucose-1-phosphate is an intermediate in glycogen metabolism.1,2It is a precursor in the biosynthesis of UDP-glucose, the glucose donor in glycogen biosynthesis.2α-D-Glucose-1-phosphate can be formed during glycogen breakdownviaphosphorolytic cleavage of glycogen by glycogen phosphorylase.1It can be converted to glucose-6-phosphate by phosphoglucomutase. α-D-Glucose-1-phosphate is combined with CTP by α-D-glucose-1-phosphate cytidylyltransferase to form CDP-glucose in the first step of CDP-D-tyvelose biosynthesis inS. typhi.3Bacterial sucrose phosphorylase converts sucrose and phosphate into D-fructose and α-D-glucose-1-phosphate.4 1.Berg, J.M., Tymoczko, J.L., and Stryer, L.Glycogen breakdown requires the interplay of several enzymesBiochemistry(2002) 2.Berg, J.M., Tymoczko, J.L., and Stryer, L.Glycogen is synthesized and degraded by different pathwaysBiochemistry(2002) 3.Koropatkin, N.M., and Holden, H.M.Molecular structure of ɑ-D-glucose-1-phosphate cytidylyltransferase from Salmonella typhiJ. Biol. Chem.279(42)44023-44029(2004) 4.Goedl, C., Schwarz, A., Minani, A., et al.Recombinant sucrose phosphorylase from Leuconostoc mesenteroides: Characterization, kinetic studies of transglucosylation, and application of immobilised enzyme for production of ɑ-Ｄ-glucose 1-phosphateJ. Biotechnol.129(1)77-86(2007)

Acetyl-(D-Phe2,Lys15,Arg16,Leu27)-VIP(1-7)-GRF(8-27) is a selective antagonist [1] for the vasoactive intestinal peptide 1 (VIP 1) receptor.

C26 Sphingomyelin is a sphingolipid that has been found in serum and cell or brain extracts.1,2,3C26 sphingomyelin levels are increased in the serum of patients with hemophagocytic lymphohistiocytosis, an inflammatory condition characterized by excessive immune activation.3C26 sphingomyelin has been used a component of monolayers to study the influence of sphingomyelin acyl chain length on sphingomyelin-sterol interactions.4[Matreya, LLC.] 1.Wang, J.-R., Zhang, H., Yau, L.D., et al.Improved sphingolipidomic approach based on ultra-high performance liquid chromatography and multiple mass spectrometries with application to cellular neurotoxicityAnal. Chem.86(12)5688-5696(2014) 2.Willmann, J., Mahlstedt, K., Leibfritz, D., et al.Characterization of sphingomyelins in lipid extracts using a HPLC-MS-offline-NMR methodAnal. Chem.79(11)4188-4191(2007) 3.Jenkins, R.W., Clarke, C.J., Lucas, J.T., Jr., et al.Evaluation of the role of secretory sphingomyelinase and bioactive sphingolipids as biomarkers in hemophagocytic lymphohistiocytosisAm. J. Hematol.88(11)E265-E272(2013) 4.Li, X.M., Momsen, M.M., Brockman, H.L., et al.Sterol structure and sphingomyelin acyl chain length modulate lateral packing elasticity and detergent solubility in model membranesBiophys. J.85(6)3788-3801(2003)

N-Acetyl-α-D-glucosamine 1-phosphate disodium (GlcNAc-1-P), an anomeric sugar phosphate, plays a crucial role as an intermediate in the biosynthesis of N-linked glycoproteins. Additionally, it serves as a metabolic precursor for the synthesis of bacterial cell-wall components, particularly teichoic acid and murein [1].

C17 Ceramide is a synthetic ceramide that contains a non-natural C17:0 fatty acid acylated to sphingosine. It has been used as a marker of arylsulfatase A and sphingolipid activator B activity in patients undergoing enzyme replacement therapy for the genetic disease metachromatic leukodystrophy.

C8 Galactosylceramide is a synthetic C8 short-chain derivative of known membrane microdomain-forming sphingolipids. It increases the amount delivered and toxicity of doxorubicin in cancerous but not non-cancerous cells when incorporated into the nanoliposomal membrane of nanoliposomal-doxorubicin. C8 Galactosylceramide induces proliferation and cytokine production by splenocytes in vitro at concentrations ranging from 100-1,000 ng/ml but has no effect on natural killer T cell production in vivo. It also activates NF-κB production in C6 glioma cells when used at a concentration of 10 μM.

1,4-Dihydroxy-2-carbomethoxy-3-prenylnaphthalene-1-O-beta-glucopyranoside may have DNA topoisomerases I and II inhibitory activity and cytotoxicity.

Ophiogenin 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (Ophiogenin-3-O-alpha-L-rhaMnopyranosyl-(1->2)-beta-D-glucopyranoside) is a natural product, and has good pharmacological effects on the cardiovascular system.

5-Phospho-D-ribose 1-diphosphate (PRPP) is a natural intermediate involved in the pentose phosphate pathway leading to purine, pyrimidine, and histidine metabolism. It is also an intermediate in the synthesis of plant hormones, alkaloids, and other secondary metabolites from glucose. Several phosphoribosyltransferases (PRTases) use PRPP as a substrate to add a 5-phosphoribosyl group to another substrate, as in the production of adenosine monophosphate from adenine and PRPP by adenine PRTase. N/A

Borneol 7-O-[beta-D-apiofuranosyl-(1->6)]-beta-D-glucopyranoside is a natural product from Radix ophiopogonis.

C18 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from lactosylceramide . It inhibits aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate (PMA; 10008014) when used at a concentration of 1 μM. C18 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes. It accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A. C18 globotriaosylceramide also accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease.

C20 Sphingomyelin is a naturally occurring sphingolipid. Levels of C20 sphingomyelin are upregulated in the hippocampus of rats with diabetes induced by streptozotocin and in human plasma where it is positively correlated with insulin resistance in obese humans. C20 sphingomyelin is also upregulated in the liver of a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder. The plasma concentration of C20 sphingomyelin is decreased in men with prostate cancer.

C2 Adamantanyl Galactosylceramide (d18:1/2:0) (AdaGalCer) is a bioactive sphingolipid. It reduces globotriaosylceramide 3 synthesis from exogenous lactosylceramide in microsomes. AdaGalCer stimulates recombinant glucocerebrosidase activity in a pH-dependent manner. It activates glucocerebrosidase to decrease glucosylceramide accumulation in fibroblasts and lymphoblasts isolated from patients with Gaucher and Fabry disease, respectively.

C16 globotriaosylceramide is an endogenous sphingolipid found in mammalian cell membranes that is synthesized from C16 lactosylceramide . C16 globotriaosylceramide acts as a receptor for Shiga toxin in B cell-derived Raji cells and THP-1 monocytes. It accumulates in endothelial cells, pericytes, vascular smooth muscle cells, renal epithelial cells, dorsal ganglia neuronal cells, and myocardial cells in patients with Fabry disease. C16 globotriaosylceramide is also upregulated in plasma of patients with ovarian carcinoma compared to those with benign ovarian tumors or uterine fibroids.

[D-Arg2]Dermorphin-(1-4) amide is an N-terminal truncated peptide of [D-Arg2]dermorphin noted for its hypothermic and analgesic effects. This compound also demonstrates degradation when subjected to soluble mouse liver and brain extracts [1].

C16 Galactosylceramide is a glycosphingolipid that contains a galactose moiety attached to a ceramide acylated with palmitic acid .

(D-Ala2)-GRF (1-29) amide (human) is a potent superagonist of Growth Hormone-Releasing Factor (GRF), demonstrating an exceptionally high Growth Hormone (GH)-releasing activity, approximately 50-fold greater than that of GRF (1-29) in both pigs and rats [1].

D-threo Sphinganine (d18:0) is a synthetic bioactive sphingolipid and stereoisomer of sphinganine (d18:0) and L-erythro sphinganine (d18:0) . It induces autophagy in HCT116 cells when used at a concentration of 12 μM. D-threo Sphinganine (d18:0) is metabolized via sphinganine N-acyltransferase and sphinganine kinase in vivo in rat liver.

C18:1 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It has been found in mouse brain. It has been used as a standard for the quantification of C18:1 3'-sulfo galactosylceramide in dried blood spots from patients with metachromatic leukodystrophy (MLD) by UPLC-MS.

3-O-β-D-Glucopyranosyl(1→2)-[α-L-rhamnopyranosyl(1→3)]-β-D-glucopyranosyl 28-O-β-D-glucuronopyranoside is a saponin compound extracted from Polaskia chichipe Backbg. It demonstrates an 84.2% inhibitory activity on melanin biosynthesis at a concentration of 100μM in B16 melanoma cells[1].

Acacetin 7-O-β-D-glucuronopyranosyl-(1→2)[α-L-rhamnopyranosyl-(1→6)]-β-D-glucopyranoside, also known as compound 8, is a flavonoid glycoside isolated from the leaf extract of the black locust (Leguminosae)[1].

7-[α-L-Arabinopyranosyl-(1→6)-β-D-glucopyranosyloxy]cuminol, a cuminol glycoside, can be isolated from Rhodiola rosea^[1].

D-Fructose 1-phosphate disodium salt, a derivative of fructose, serves as a crucial intermediate in glucose metabolism.

D-MoDE-A (1) is a bifunctional small molecule that facilitates extracellular protein degradation via the asialoglycoprotein receptor (ASGPR).

1-O-Caffeoyl-3,4,6-trigalloyl-?-D-glucopyranose is a useful organic compound for research related to life sciences. The catalog number is T126195 and the CAS number is 1219501-93-5.

Lyso-globotriaosylceramide is a form of globotriaosylceramide that is lacking the fatty acyl group. It binds to Shiga toxin 1 (Stx1) in the presence of cholesterol and phosphatidylcholine but does not bind Stx2. It also reduces viability and aggregation of human neutrophils induced by phorbol 12-myristate 13-acetate when used at concentrations of 50 and 1 μM, respectively. Lyso-globotriaosylceramide accumulates in the brain, heart, kidney, liver, lung, and spleen in a mouse model of Fabry disease, a lysosomal storage disorder characterized by a deficiency in the enzyme α-galactosidase A. It also accumulates in the urine, kidney, and plasma of patients with Fabry disease. Lyso-globotriaosylceramide levels decrease in response to administration of the α-galactosidase inhibitor 1-deoxygalactonojirimycin in a transgenic mouse model of Fabry disease. Decreases in plasma and urine concentrations of lyso-globotriaosylceramide have been used as a biomarker for efficacy of enzyme replacement therapy (ERT) and other therapies in the treatment of Fabry disease.

Formononetin-8-C-beta-D-apiofuranosyl-(1->6)-O-beta-D-glucopyranoside is a natural product for research related to life sciences. The catalog number is TN6636 and the CAS number is 1147858-78-3.

1-(β-D-Xylofuranosyl)-N6-Isopentenyladenine is an adenosine analog. Adenosine analogs mostly act as smooth muscle vasodilators and have also been shown to inhibit cancer progression. Its popular products are adenosine phosphate, Acadesine , Clofarabine , Fludarabine phosphate and Vidarabine [1] .

C22 Galactosylceramide is a sphingolipid that has been found in the central nervous system.1,2C22 Galactosylceramide levels are increased in the spinal cord, but not the brain or liver, of mice fed a methionine-restricted diet.1C22 Galactosylceramide has been found in postmortem hippocampus from patients with Alzheimer's disease.2[Matreya, LLC.]

Myricetin 3-O-beta-D-xylopyranosyl(1-2)-beta-D-glucopyranoside is a natural product for research related to life sciences. The catalog number is TN4607 and the CAS number is 142449-93-2.

High affinity and potent ghrelin receptor inverse agonist (Ki values are 4.9 and 31 nM in COS7 and HEK293T cells, respectively). Blocks ghrelin receptor-mediated Gq- and G13-dependent signaling pathways.

D-JNKI-1 (AM-111) is a highly effective and cell-permeable peptide inhibitor.