ceramide

C-6 NBD-dihydro-Ceramide, a biologically active, fluorescent analog of short-chain ceramides, features membrane permeability.

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 PEG-Ceramide, a lipid product, possesses the capability to synthesize lipid bilayer carriers, making it applicable for drug delivery [1] [2].

Ceramide 1 A is a waxy lipid compound that is a lipid in the top skin layer. It has a special molecular structure because it contains a linoleic acid linked to a long chain omega-hydroxy acid.

C2 Ceramide (d14:1/2:0) is a bioactive sphingolipid. Dietary administration of C2 ceramide (d14:1/2:0) (100 μM) induces lipotoxic cardiomyopathy via increasing diastolic and systolic diameter as well as reducing fractional shortening and the number of normal cardiac contractile events in Drosophila.

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]

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 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]

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)

C12-Ceramide (C12 Ceramide (d18:1/12:0)), a ceramide present in the protective membranes surrounding umbilical cord blood vessels in infants born to women with pre-eclampsia, can be used to assess the level of ASM activity in the plasma of patients with Niemann-Pick disease.

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

C16 PEG-Ceramide, a polyethylene glycolylated ceramide, serves as a lipid carrier for delivery and induces autophagy. It is utilized in cancer research [1] [2].

C19 Ceramide is a naturally occurring ceramide that has been found in J. juncea extracts as well as rat brain and mouse heart.[1],[2],[3] It is elevated in adult and decreased in juvenile whole rat brain extracts by 114 and 37%, respectively, following chronic ethanol exposure.[2] C19 Ceramide is also increased in mouse hearts following administration of angiotensin II.[3]

C6 Ceramide (N-hexanoylsphingosine) is an activator of the ceramide pathway that arrests cells in the G0/G1 phase by activating ERK. It can act in a variety of cancer cell lines.

BODIPY-C12 Ceramide (B12Cer) is a fluorescently-tagged form of C12 ceramide, with excitation/emission maxima at 505/540 nm, respectively. It is a fluorescently-labeled sphingolipid and has been utilized for quantifying acid sphingomyelinase activity in the plasma of patients with Niemann-Pick disease.

A potent modulator of cell proliferation and differentiation.

C6 L-erythro Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is metabolized by ceramide glucosyltransferase to form C6 L-erythro glucosylceramide. C6 L-erythro Ceramide is cytotoxic to U937 cells (IC50 = 18 μM).

C8 D-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is cytotoxic to U937 cells (IC50 = 17 μM) and induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 ceramide . C8 D-threo Ceramide is a substrate for E. coli diacylglycerol kinase. It activates ceramide-activated protein kinase (CAPK) in U937 cells. C8 D-threo Ceramide also enhances V. cholerae cytolysin pore formation in liposome lipid membranes, as measured by calcein release, with a 50% release dose (RD50) value of ~5 μg/ml.

C16-Urea-Ceramide s a neutral ceramidase (nCDase) inhibitor. It is a bioactive ceramide.

C4 Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. [1] [2] [3] It inhibits IL-4 production by 16% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate when used at a concentration of 10 μM. [1] C4 Ceramide is cytotoxic to SK-BR-3 and MCF-7/Adr breast cancer cells (IC50s = 15.9 and 19.9 μM, respectively). [2] C4 Ceramide also increases maturation and stability of cystic fibrosis transmembrane conductance regulator (CFTR) proteins bearing the F508 deletion (F508del) mutation, enhances cAMP-activated chloride secretion, and suppresses secretion of IL-8 in primary epithelial cells isolated from patients with cystic fibrosis.[3]

Ceramide phosphoethanolamine (CPE) is an analog of sphingomyelin that contains ethanolamine rather than choline as the head group. It is the principal membrane phospholipid in invertebrates such as Drosophila, which lacks sphingomyelin. It is only produced in small amounts in mammalian cells, accounting for approximately 0.02 mol% of total phospholipids in mouse testis and brain. In Drosophila, CPE is biosynthesized by CPE synthase from ceramide and cytidine diphosphate-ethanolamine in the Golgi lumen. In mammals, it is biosynthesized by sphingomyelin synthase 2 (SMS2) in the plasma membrane and by sphingomyelin synthase-related protein (SMSr) in the endoplasmic reticulum (ER). In Drosophila, CPE has a role in glial ensheathment of axons. Disrupting CPE synthesis by depleting SMSr in vitro in mammalian cells leads to an accumulation of ER ceramides, which are then mislocalized to the mitochondria, inducing apoptosis. However, ceramide levels are not altered in transgenic mice lacking SMSr catalytic activity. CPEs (bovine) is a mixture of CPEs with variable N-acyl chain lengths.

C20 Ceramide (N-Arachidoyl-D-sphingosine) is a 20:0 ceramide found in the brain that crosses the blood-brain barrier to activate microglia and induce depressive-like behavior.

C18 Ceramide-1-phosphate (d18:1/18:0) is a long-chain molecule identified in murine skin known to promote the migration of mouse bone marrow-derived multipotent stromal cells and human umbilical vein endothelial cells (HUVECs) at concentrations of 0.5 to 5 µM. It exhibits elevated levels in CFPAC-1 pancreatic ductal adenocarcinoma cells compared to pancreatic cancer stem cells, and its myocardial concentration is heightened in Langendorff isolated perfused mouse hearts under an ex vivo ischemia model.

C18 L-erythro Ceramide (d18:1/18:0) significantly reduced extracellular Aβ levels and can be used to study Alzheimer's disease.

C6 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides., C6 L-threo Ceramide is cytotoxic to U937 cells in vitro (IC50 = 18 μM). It is metabolically inactive and, unlike C6 L-erythro ceramide , C6 L-threo ceramide cannot be converted to C6 glucosylceramide by ceramide glucosyltransferase. C6 L-threo Ceramide enhances IL-4 production induced by phorbol 12-myristate 13-acetate in EL4 T cells when used at a concentration of 10 μM.

Sphingolipid ceramide N-deacylase (SCDase) is an enzyme that catalyzes the cleavage of the N-acyl linkage between fatty acids and sphingosine bases in various glycosphingolipids, converting them into lysoglycosphingolipids [1].

C6 D-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides., C6 D-threo Ceramide is cytotoxic to U937 cells in vitro (IC50 = 18 μM). It is metabolically inactive and, unlike C6 L-erythro ceramide , C6 D-threo ceramide cannot be converted to C6 glucosylceramide by ceramide glucosyltransferase. C6 D-threo Ceramide promotes survival of isolated rat spinal neurons when used at concentrations up to 2.5 μM but induces cell death at concentrations greater than 5 μM. It enhances IL-4 production induced by phorbol 12-myristate 13-acetate in EL4 T cells when used at a concentration of 10 μM.

C2 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It stimulates cholesterol efflux in CHO cells expressing the human ABCA1 receptor when used at a concentration of 10 μM, however, this efflux is 50% less than that stimulated by C2 ceramide . C2 L-threo Ceramide inhibits IL-4 production by 17% in EL4 T cells stimulated with phorbol 12-myristate 13-acetate when used at a concentration of 10 μM. It also induces cell cycle arrest in the G0/G1 phase and a 7-fold increase in sphingosine accumulation as well as inhibits growth of HL-60 leukemia cells.

C8 Ceramide, a cell-permeable analog, is analog to naturally occur ceramides.

C14 Ceramide (d18:1/14:0) is an endogenous ceramide produced by ceramide synthetase 6, which can be used for Parkinson's research.

C18 Ceramide-d7 is a deuterated compound of C18 Ceramide.

C24 Ceramide-d7 is a deuterated compound of C24 Ceramide.

C6 urea ceramide is an inhibitor of neutral ceramidase.1 It increases total ceramide levels in wild-type mouse embryonic fibroblasts (MEFs) and in HT-29 colon cancer cells but not in MEFs lacking neutral ceramidase. It inhibits proliferation of, and induces apoptosis and autophagy in HT-29, but not non-cancerous RIE-1, cells when used at concentrations of 5 and 10 μM. C6 urea ceramide decreases total β-catenin, increases phosphorylated β-catenin, and induces colocalization of β-catenin with the 20S proteasome in HT-29 and HCT116, but not RIE-1, cells. It reduces tumor growth and increases C16, C18, C20, and C24 ceramide levels in tumor tissue in an HT-29 mouse xenograft model when administered at doses of 1.25, 2.5, and 5 mg/kg for five days. |1. García-Barros, M., Coant, N., Kawamori, T., et al. Role of neutral ceramidase in colon cancer. FASEB J. 30(12), 4159-4171 (2016).

Ceramide (Egg, Chicken) plays a major role in the anabolic and catabolic pathways of sphingolipid. Ceramide (Egg, Chicken) stimulates many cell differentiation, growth inhibition, cell senescence and apoptosis.

C22 Ceramide (d18:1/22:0) (C22 Ceramide), a long-chain ceramide containing behenic acid, is an endogenous bioactive sphingolipid.C22-Ceramide specifically inhibits MCSR and reduces C16 ceramide channel formation in isolated rat liver mitochondria and liposomes.

C16 dihydro Ceramide (d18:0/16:0) (Cer(d18:0/16:0)) is a precursor for the synthesis of ceramides, induces autophagy in the perinuclear region, and can be used to study cell membrane stability and neurological diseases.

C16 Ceramide-d7 is a deuterated compound of C16 Ceramide.

C24:1 Ceramide-d7 is a deuterated compound of C24:1 Ceramide.

C24-Ceramide, a sphingolipid utilized in the composition of lipid membranes, induces time-dependent modifications in membrane properties and promotes membrane reorganization [1] [2].