n,ndimethyl sphinganine (d18:0)

N-Acetyl-D-galactosamine (GalNAc) is a terminal essential amino sugar derived from galactose and forms the antigens of blood group A in humans.

N-Acetyl-D-cysteine has antioxidant activities and scavenges ROS through the reaction with its thiol group.

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.

D-Glucosyl-β-1,1′-N-palmitoylsphingosine (C16 Glucosyl(β) Ceramide (d18:1/16:0)) serves as an endogenous ligand for the Macrophage-Inducible C-type Lectin (Mincle), exhibiting immunostimulatory properties [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.

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.

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.

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].

4-Methylumbelliferyl β-D-N,N'-diacetylchitobioside (4-μU-(GlcNAc)2) is a fluorogenic substrate for chitinases and chitobiosidases. 4-μU-(GlcNAc)2 is cleaved by chitinases and chitobiosidases to release the fluorescent moiety 4-μU. 4-μU fluorescence is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high pH (7.12-10.3), respectively, and an emission maximum ranging from 445 to 455 nm, increasing as pH decreases.

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-[(6S)-6-Carboxy-6-(glycylamino)hexanoyl]-D-alanyl-D-alanine functions as an inhibitor of the PAICS protein, effectively decreasing the accumulation of both SAICAR and SAICAr.

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.

n-Butyl β-D-fructofuranoside is a natural product.

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

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.

C24 dihydro Ceramide is a sphingolipid that has been found in the stratum corneum of human skin.[1] It is found in higher concentrations in female sebum compared to male sebum.[2] C24 dihydro Ceramide levels positively correlate with cytotoxicity in CCRF-CEM, MOLT-4, COG-LL-317h, and COG-LL-332h T cell acute lymphoblastic leukemia (ALL) cell lines.[4] Levels of C24 dihydro ceramide are increased by 149.49-fold in dihydroceramide desaturase 1 (DEGS1) knockdown UM-SCC-22A human head and neck squamous carcinoma cells in vitro.[4] C24 dihydro Ceramide levels are also increased in INS-1 β-cells incubated with glucose and palmitate.[5]

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.

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.

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.

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.

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.]

Sphinganine is a synthetic bioactive sphingolipid that inhibits the growth of C. glabrata and C. albicans with a minimum fungicidal concentration (MFC) value of 0.5 μg/ml for both. More commonly, sphinganine is used as an internal standard in the analysis of sphingoid compounds by chromatographic or spectrometric methods.

DL-erythro/threo Sphinganine (d16:0) is a sphingolipid that is decreased in rats following long-term, low-dose administration of dimethoate and is used as a biomarker for dimethoate exposure. It has been found in the fermentation broth of Bacterium SRCnm, which has antimicrobial and antioxidant activities. This product is a mixture of sphinganine (d16:0), L-erythro sphinganine (d16:0), D-threo sphinganine (d16:0), and L-threo sphinganine (d16:0).

1-β-D-Glucosylsphingadienine is a glucosylsphingosine, which are deacetylated lysolipid derivatives of glucosylcerebrosides . They are formed when sphingosines undergo glucosidation by UDP-glucose. Glucosylsphingosines completely reduce neurite outgrowth and induce death of LA-N-2 cells at concentrations of 10 and 50 μM, respectively. They also decrease the activity of glucocerebrosidase in LA-N-2 cells in a dose-dependent manner. Glucosylsphingosine levels are elevated in patients with Gaucher's disease, both in the spleen (in types 1, 2, and 3) and brain (type 2 and 3); thus, glucosylsphingosine has been used as a key biomarker of the disease. This product contains 1-β-D-glucosylsphingadienine isolated from plants.

C2 Adamantanyl globotriaosylceramide (AdaGb3) is a bioactive sphingolipid and water-soluble form of globotriaosylceramide that contains an adamantanyl group in place of the fatty acyl chain. It inhibits Vero toxin binding to globotriaosylceramide in an ELISA assay when used at a concentration of 10 μM. AdaGb3 decreases cell surface expression of P-glycoprotein (P-gp) and reduces efflux of rhodamine 123 in MDCK cells. It also increases apical-to-basal transport of vinblastine in human intestinal C2BBe1 cells.

C18 L-threo Ceramide is a synthetic ceramide and stereoisomer of C18 ceramide that has been used for structural characterization of natural sphingolipids. It inhibits rat brain mitochondrial ceramidase (mt-CDase) with an IC50 value of 0.21 mol% (16.8 μM).

C18 Phytoceramide (t18:0/18:0) (Cer(t18:0/18:0)) is a bioactive sphingolipid found in S. cerevisiae, wheat grains, and the stratum corneum layer of mammalian epidermis. Cer(t18:0/18:0) is composed of a phytosphingosine backbone amine-linked to a C18 fatty acid chain. Cer(t18:0/18:0) has a role in regulation of apoptosis, cell differentiation, proliferation of smooth muscle cells, and inhibition of the mitochondrial respiratory chain. It also inhibits expression of the allergic cytokines IL-4, TNF-α, and transcription factors c-Jun and NF-κB in histone-stimulated murine skin tissue. Formulations containing cer(t18:0/18:0) have been used used in cosmetics as a skin protectants as they reduce water loss to prevent epidermal dehydration and irritation.

C17 Globotriaosylceramide is a sphingolipid that has been used as an internal standard for the quantification of globotriaosylceramides in plasma and urine from patients with Fabry disease by GC-MS.

C18 dihydro Ceramide is a bioactive sphingolipid and precursor in the de novo synthesis of C18 ceramide that lacks the 4,5-trans double bond. [1] Increased C18 dihydroceramide lipid levels lead to increased triacylglycerol storage and autophagosome accumulation as well as upregulation of the fibrosis markers α-SMA and FGF2 in Chang and LX-2 liver cells. C18 dihydro Ceramide is elevated in the plasma of pre-diabetics up to 9 years prior to the onset of type 2 diabetes. [2] It is also elevated in the skin of patients with lesional atopic dermatitis.[3]

C2 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. It has been used as an internal standard in the quantification of lysosulfatides in mouse brain tissue and plasma.

C18 D-threoCeramide (d18:1/18:0) is a synthetic ceramide and stereoisomer of C18 ceramide .1It inhibits rat brain mitochondrial ceramidase (mt-CDase) with an IC50value of 16.6 μM.2[Matreya, LLC. Catalog No. 1855] 1.Koolath, S., Murai, Y., Suga, Y., et al.Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthaseChirality32(3)308-313(2019) 2.Usta, J., El Bawab, S., Roddy, P., et al.Structural requirements of ceramide and sphingosine based inhibitors of mitochondrial ceramidaseBiochemistry40(32)9657-9668(2001)

N'-Nitro-D-arginine (N'-Nitro-D-arginine) is a Building Block.

C17 Lactosylceramide is a naturally occurring sphingolipid that has been found in human brain metastases of lung adenocarcinomas but not in healthy brain tissue.

C18 3'-sulfo Galactosylceramide is a member of the sulfatide class of glycolipids. Levels of short-chain sulfatides, including C18 3'-sulfo galactosylceramide, decrease with age in mice and humans. It is increased in brain from mice with an arylsulfatase A deficiency (ASA-KO), particularly in lipid raft fractions. Plasma levels of C18 3'-sulfo galactosylceramide positively correlate with disability progression in patients with relapsing-remitting multiple sclerosis using the Expanded Disability Status Scale. It is also increased in plasma from patients with metachromatic leukodystrophy (MLD).

18:0 DAP can be utilized in the formulation of lipid nanoparticles (LNPs) that encapsulate mRNA within their core [1].

18:0 EPC chloride, a synthetic cationic phospholipid, significantly enhances eugenol's inactivation effect on Escherichia coli [1] when used at critical synergistic concentrations ranging from 2.34 to 2.93 μM.

EOS is a ceramide found in the outer layer of the epidermis in mammals. It is comprised of an ω-hydroxy very long-chain ceramide (C28-36) esterified to the essential fatty acid linoleic acid . The consecutive regio- and stereospecific oxygenation of the linoleate portion of EOS by 12(R)-lipoxygenase (12(R)-LO) and eLOX3 is essential for the maintenance of the epidermal barrier to prevent water loss. Following oxygenation, the oxidized linoleate is hydrolyzed, leaving the ω-hydroxy end of the very long-chain fatty acid to covalently bind the protein layer, forming the corneocyte lipid envelope and sealing the gap between the extracellular lipid lamellae and the cornified cell envelope of the corneocyte.

C16 Lactosylceramide is an endogenous bioactive sphingolipid. It forms membrane microdomains with Lyn kinase and the αi subunits of inhibitory G protein-coupled receptors (GPCRs), suggesting a role in cell signaling. Plasma levels of C16 lactosylceramide are elevated in insulin-resistant cattle. C16 Lactosylceramide is also upregulated in a mouse model of Niemann-Pick type C1 disease, a neurodegenerative cholesterol-sphingolipid lysosomal storage disorder.

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)

N,N-dimethyl Sphinganine (d18:0) is a sphingolipid that increases during development ofL. donovanipromastigotes.1 1.Silva, A.M., Cordeiro-da-Silva, A., and Coombs, G.H.Metabolic variation during development in culture of Leishmania donovani promastigotesPLoS Negl. Trop. Dis.5(12)e1451(2011)

(±)-2'-Hydroxy Ceramide (d18:0/18:0) is a sphingomyelin derivative isolated from mammalian platelets upon ADP stimulation [1].

N-Acetyl-D-mannosamine (ManNAc) is a drug potentially for the treatment of hereditary inclusion body myopathy.

N-Acetyl-D-mannosamine is a monosaccharide used as a precursor in the chemical or enzymatic synthesis of neuraminic acid found in glycolipids and glycoproteins.N-Acetyl-D-mannosamine is a specific substrate for the synthesis of n -acetylneuraminic acid, an essential precursor for bacterial podoplanar polysialic acid (PA).N-Acetyl-D-mannosamine is used in the synthesis of sialic acid. mannosamine is used in the synthesis of sialic acid. It is also an intermediate in the synthesis of many carbohydrate-derived bioactive compound families and drug candidates.N-Acetyl-D-mannosamine is used in the study of cognitive disorders and aging.

N-(4-Chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-2,2-dimethyl propanamide belongs to Heterocyclic Compounds - Purine; Intermediates and Building Blocks - Nucleoside base, Electrophile; Scaffold and Template.