ceramide 1 a

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.

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)

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.

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).

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]

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]

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.

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

C18:1 Ceramide is a naturally occurring ceramide.[1][2][3] Levels of C18:1 ceramide are elevated in overweight and insulin-resistant mice and cattle.[1][2] C18:1 Ceramide is also increased in the plasma and ovarian tissue of patients with advanced ovarian cancer. [3]

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.

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.

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.

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 L-threo Ceramide is a bioactive sphingolipid and cell-permeable analog of naturally occurring ceramides. It is cytotoxic to U937 cells (IC50 = 10 μM) and, like C8 D-threo ceramide , induces nuclear DNA fragmentation 5- to 6-fold more potently than C8 L-erythro ceramide . 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 ~30 μg/ml.

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.

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

P053 is a potent, non-competitive and selective ceramide synthase 1 (CerS1) inhibitor with an IC50 of 0.5 μM. P053 is an endogenous inhibitor of mitochondrial fatty acid oxidation in muscle and regulator of whole-body adiposity[1].

C8 PEG-Ceramide, a lipid product, possesses the capability to synthesize lipid bilayer carriers, making it applicable for drug delivery [1] [2].

α-Melanocyte-stimulating hormone (α-MSH) is a 13-amino acid peptide hormone produced by post-translational processing of proopiomelanocortin (POMC) in the pituitary gland, as well as in keratinocytes, astrocytes, monocytes, and gastrointestinal cells.1It is an agonist of melanocortin receptor 3 (MC3R) and MC4R that induces cAMP production in Hepa cells expressing the human receptors (EC50s = 0.16 and 56 nM, respectively).2α-MSH (100 pM) reducesS. aureuscolony formation andC. albicansgerm tube formationin vitro.3It inhibits endotoxin-, ceramide-, TNF-α-, or okadaic acid-induced activation of NF-κB in U937 cells.1α-MSH reduces IL-6- or TNF-α-induced ear edema in mice.4It also prevents the development of adjuvant-induced arthritis in rats and increases survival in a mouse model of septic shock. Increased plasma levels of α-MSH are positively correlated with delayed disease progression and reduced death in patients with HIV.1 1.Catania, A., Airaghi, L., Colombo, G., et al.α-melanocyte-stimulating hormone in normal human physiology and disease statesTrends Endocrinol. Metab.11(8)304-308(2000) 2.Miwa, H., Gantz, I., Konda, Y., et al.Structural determinants of the melanocortin peptides required for activation of melanocortin-3 and melanocortin-4 receptorsJ. Pharmacol. Exp. Ther.273(1)367-372(1995) 3.Cutuli, M., Cristiani, S., Lipton, J.M., et al.Antimicrobial effects of a-MSH peptidesJ. Leukoc. Biol.67(2)233-239(2000) 4.Lipton, J.M., Ceriani, G., Macaluso, A., et al.Antiiinflammatory effect of the neuropeptide a-MSH in acute, chronic, and systemic inflammationAnn. N.Y. Acad. Sci.25(741)137-148(1994)

C22 dihydro 1-Deoxyceramide (m18:0/22:0) is a very long-chain atypical ceramide containing a 1-deoxysphinganine backbone. 1-Deoxysphingolipids are formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during sphingolipid synthesis.1,2 C22 dihydro 1-Deoxyceramide (m18:0/22:0) has been found in mouse embryonic fibroblasts (MEFs) following application of 1-deoxysphinganine alkyne or 1-deoxysphinganine-d3.3 It has also been found as the most prevalent dihydro deoxyceramide species in mouse brain, spinal cord, and sciatic nerve at one, three, and six months of age.4 |1. Steiner, R., Saied, E.M., Othman, A., et al. Elucidating the chemical structure of native 1-deoxysphingosine. J. Lipid Res. 57(7), 1194-1203 (2016).|2. Alecu, I., Othman, A., Penno, A., et al. Cytotoxic 1-deoxysphingolipids are metabolized by a cytochrome P450-dependent pathway. J. Lipid Res. 58(1), 60-71 (2017).|3. Alecu, I., Tedeschi, A., Behler, N., et al. Localization of 1-deoxysphingolipids to mitochondria induces mitochondrial dysfunction. J. Lipid. Res. 58(1), 42-59 (2017).|4. Schwartz, N.U., Mileva, I., Gurevich, M., et al. Quantifying 1-deoxydihydroceramides and 1-deoxyceramides in mouse nervous system tissue. Prostaglandins Other Lipid Mediat. 141, 40-48 (2019).

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]

Sulfatides are endogenous sulfoglycolipids with various biological activities in the central and peripheral nervous systems, pancreas, and immune system. They are produced from the combination of ceramide and UDP-galactose in the endoplasmic reticulum followed by sulfation in the Golgi apparatus. The ceramide portion contains variable fatty acid chain lengths, which are tissue- and pathology-dependent. Sulfatides are primarily found in the myelin sheath of oligodendrocytes and Schwann cells, with smaller chain lengths predominant during development and longer chain lengths predominant in mature cells. They accumulate in the lysosome of patients with metachromatic leukodystrophy, a disorder characterized by arylsulfatase A deficiency. Sulfatides are also located in pancreatic β-cells and inhibit insulin release from isolated rat pancreatic islet cells, suggesting a potential role in diabetes. Sulfatides can induce inflammation in glia in vitro and certain sulfatides, such as C24:1 3'-sulfo-galactosylceramide, can induce an immune response in vitro in mouse splenocytes. Sulfatides (bovine) (sodium salt) is a mixture of isolated bovine sulfatides.

C24 dihydro 1-Deoxyceramide (m18:0/24:0) is a very long-chain atypical ceramide containing a 1-deoxysphinganine backbone. 1-Deoxysphingolipids are formed when serine palmitoyltransferase condenses palmitoyl-CoA with alanine instead of serine during sphingolipid synthesis.1,2 C24 dihydro 1-Deoxyceramide (m18:0/24:0) has been found in mouse embryonic fibroblasts (MEFs) following application of 1-deoxysphinganine alkyne or 1-deoxysphinganine-d3.3 It has also been found in mouse brain, spinal cord, and sciatic nerve at one, three, and six months of age.4 |1. Steiner, R., Saied, E.M., Othman, A., et al. Elucidating the chemical structure of native 1-deoxysphingosine. J. Lipid Res. 57(7), 1194-1203 (2016).|2. Alecu, I., Othman, A., Penno, A., et al. Cytotoxic 1-deoxysphingolipids are metabolized by a cytochrome P450-dependent pathway. J. Lipid Res. 58(1), 60-71 (2017).|3. Alecu, I., Tedeschi, A., Behler, N., et al. Localization of 1-deoxysphingolipids to mitochondria induces mitochondrial dysfunction. J. Lipid. Res. 58(1), 42-59 (2017).|4. Schwartz, N.U., Mileva, I., Gurevich, M., et al. Quantifying 1-deoxydihydroceramides and 1-deoxyceramides in mouse nervous system tissue. Prostaglandins Other Lipid Mediat. 141, 40-48 (2019).

N-Acetylpsychosine, also known as α-galactosylated C2-ceramide (d18:1/2:0), exhibits immunostimulatory properties. This compound, N-Acetylpsychosine, holds potential as a valuable tool for studying the mechanisms of apoptosis and immune responses activated by dendritic cells (DCs).

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]

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].

ASM-IN-1 is a potent, orally active inhibitor of acid sphingomyelinase (ASM) with an IC50 of 1.5 µM, demonstrating antiatherosclerotic and anti-inflammatory activity. It effectively reduces lipid plaques in the aortic arch and aorta, along with decreasing plasma ceramide concentrations and oxidized LDL (Ox-LDL) levels [1].

N-Oleoyl serinol, a ceramide analog, plays a crucial role in stem cell therapy by inhibiting the development of teratomas in stem cells. It triggers apoptosis in remaining pluripotent embryoid body-derived cells (EBCs), thwarts teratoma formation, and promotes the enrichment of EBC cells that proceed to neural differentiation post-transplantation [1].

Sphingomyelin phosphodiesterase, a hydrolase, plays a crucial role in sphingomyelin metabolism by catalyzing the conversion of sphingomyelin into phosphocholine and ceramide. Furthermore, it is instrumental in cellular differentiation, immune and inflammatory responses, as well as intracellular cholesterol trafficking and metabolism [1] [2].

Nicotinamide-d4 is intended for use as an internal standard for the quantification of nicotinamide by GC- or LC-MS. Nicotinamide is an amide form of niacin, which is also known as vitamin B3, that can be biosynthesized in vivo or obtained through the diet. It is a precursor in the synthesis of the metabolic cofactor NAD+ and an inhibitor of sirtuin 1 (SIRT1; IC50 = <50 µM). Nicotinamide (10 µM) increases the activity of serine palmitoyltransferase (SPT) and the biosynthesis of ceramide, glucosylceramide, sphingomyelin, free fatty acids, and cholesterol in primary human keratinocytes. Nicotinamide (40 µM) induces apoptosis in SNU-398, SNU-739, and HepG2 hepatocellular carcinoma (HCC) cells, and it prevents the formation of neoplastic lesions in a diethylnitrosamine-induced mouse model of HCC. Unlike niacin, nicotinamide does not reduce plasma lipid levels or induce flushing.

K6PC-5 is a ceramide derivative that acts as an activator of sphingosine kinase 1 (SPHK1), inducing a swift and temporary rise in intracellular calcium levels. With its potential applications in skin diseases associated with abnormal keratinocyte function, as well as in studies on neurodegeneration and virus infection, K6PC-5 presents a promising compound for research purposes.

Glucocerebrosidase (Glucosylceramidase; GBA), a lysosomal enzyme, catalyzes the hydrolysis of the β-glucosidic linkage in glucocerebroside (GC) to yield glucose and ceramide [1].

Sphinganine (d20:0) is a natural isomer of dihydro-D-erythro-sphinganine (sphinganine (d18:0); that is a precursor of ceramide and sphingosine as well as a substrate for sphingosine kinases, which generate sphingosine-1-phosphate (d18:1) . In S. cerevisiae, the amount of sphinganine (d20:0) increases 10.8-fold in response to heat stress, indicating it is involved in heat stress adaptation. Sphinganine levels increase significantly in response to certain mycotoxins, including fumonisins as well as in some cancers. Sphinganine can block protein kinase C activation in some cases but not others.

UGT8-IN-1 is a brain-permeable and orally-active inhibitor that specifically targets the ceramide galactosyltransferase enzyme (UGT8). By inhibiting UGT8, this compound has the potential to be employed in research pertaining to lysosomal storage disorders.

Ibiglustat (GZ402671) is a potent and selective Glucosylceramide synthase inhibitor and ceramide glucosyltransferase inhibitor. Ibiglustat blocks the formation of glucosylceramide (GL-1), a key intermediate in the synthesis of GL-3. Ibiglustat is potentially useful for treating Fabry disease. Fabry disease is a rare lysosomal storage disorder, which results in abnormal tissue deposits of a particular fatty substance called globotriaosylceramide (GL-3 or Gb3) throughout the body.