N-Acetyl-phytosphingosine Reference: M1897-5 This product is a phytoceramide containing an acetyl group on the amide linkage which enables it to easily enter into cells. N-acetyl-phytosphingosine elevates Cyclooxygenase-2 expression via tyrosine kinase and protein kinase C, with subsequent extracellular signal–regulated kinase activation.1 This may be in response to N-acetyl-phytosphingosine induced apoptosis in cells.2 Phytosphingosine is a long-chain sphingoid base having important cellular functions such as signaling, cytoskeletal structure, cellular cycle, and heat stress response. It is found largely in mammals, plants, and yeast. Phytosphingosine has seen much use in cosmetics due to its effects on the skin such as reducing inflammation by inhibiting the expression of the allergic cytokines IL-4 and TNF-α and the activation of the transcription factors NF-jB and c-jun in histamine-stimulated skin tissues.3 Phytosphingosine can lead to apoptosis via two distinct pathways and has been investigated as a possible cancer therapeutic treatment. Phytoceramides (fatty acid acylated to Phytosphingosine) are distributed at the microvillous membrane of the epithelial cells of the small intestine. Crypt cells and the adjacent epithelial cells produce phytosphingoglycolipids in much greater quantities than more differentiated epithelial cells.4 The kidney and skin also contain phytosphingoglycolipids although in much lower concentrations than in the small intestine. Phytoceramides form part of the water barrier lipids of the skin. Phytoceramides have lately been studied in regards to their role in the central nervous system and have been found to have important functions in neuroprotection.5
N-Hexanoyl-D-erythro-sphingosine Reference: M1900-10 Ceramide is a fatty acid amide of sphingosine. This product is a well-defined ceramide having a hexanoyl acyl group. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine- 1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. Ceramides with short side chains have been shown to enter easily into cells where they are biologically active. Short-chain ceramide-1-phosphates can stimulate DNA synthesis while this effect can be counteracted by short-chain ceramides. Treatment of cells with C6:0-ceramide has been shown to result in a significant increase in long chain ceramide levels due to the degradation of the short-chain ceramide and subsequent utilization of the liberated sphingosine for synthesis of long-chain ceramides.4 Short-chain ceramides also decrease the plasma membrane lipid order which is an important factor in lipid raft signal transduction.
N-Acetyl-D-erythro-sphingosine Reference: M1901-10 This product contains a short-chain fatty acid and enters easily into cells where it is biologically active and has been shown to induce downregulation of Bcl-2 protein, inhibiting cell proliferation and inducing apoptosis.1 N-Acetyl-sphingosine demonstrates many of the biological activities associated with ceramides that contain long-chain fatty acids. However, it has also been found that N-acetyl-sphingosine may inhibit neutrophil superoxide release,2 stimulation of DNA synthesis, and phospholipase D activity. N-acetyl-sphingosine is different from sphingosine as seen by its inability to inhibit protein kinase C or cause calcium release. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.2 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.3 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.4 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. 2-hydroxy fatty acid ceramides are especially abundant in nervous and epidermal cells and are important for the permeability barrier function of epidermis and the lipid organization in membranes. The 2-hydroxylation is catalyzed by fatty acid 2-hydroxylase (FA2H or fatty acid alpha-hydroxylase).
N-Octanoyl-D-erythro-sphingosine Reference: M1903-10 Ceramide is a fatty acid amide of sphingosine that has many important biological functions and is the precursor for many complex glycosphingolipids. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity. In contrast to long chain ceramides short chain ceramides, such as octanoylsphingosine, can pass thru the cell membrane. This allows short chain ceramides to be used to induce apoptisis or necrosis in cancer cells.4
N-Acetyl-sphingosylphosphorylcholine (mixture of D-erythro and L-threo isomers) Reference: M1907-5 Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis. An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease and neonatal respiratory distress syndrome.1 However, the ratio of sphingomyelin to ceramide is different for different cell types.2 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.3 In contrast to ceramides, N-hexanoyl-sphingosylphosphorylcholine does not initiate vesicle formation in cells.4 Sphingosylphosphorylcholine has been shown to induce intracellular calcium release while its short chain analog, N-acetyl-sphingosylphosphoylcholine, requires a significantly higher concentration to initiate the same level of response.5
N-Hexanoyl-D-erythro-dihydrosphingosine Reference: M1910-5 This high purity and well-defined dihydroceramide is ideal as a standard and for biological studies.1 Dihydroceramide is a critical intermediate in the synthesis of many complex sphingoid bases. Inhibition of dihydroceramide synthesis by some fungal toxins that have a similar structure causes an increase in sphinganine and sphinganine-1-phosphate and a decrease in other sphingolipids leading to a number of diseases including oesophageal cancer. Dihydroceramide, synthesized by the acylation of sphinganine, is subsequently converted into ceramide via a desaturase enzyme or into phytosphingosine via the C4-hydrozylase enzyme2. N-(4-Hydroxyphenyl) retinamide has been tested as an anti-cancer agent. It inhibits the dihydroceramide desaturase enzyme in cells resulting in a high concentration of dihydroceramide and dihydro-sphingolipids and this is thought to be the cause of the anti-cancer effects.3 Dihydrosphingosine induces cell death in a number of types of malignant cells.
N-Octadecanoyl-sphingosylphosphorylcholine (mixture of D-erythro and L-threo... Reference: M1911-5 Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis. An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease and neonatal respiratory distress syndrome.1 However, the ratio of sphingomyelin to ceramide is different for different cell types.2 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.3 In contrast to ceramides, N-hexanoyl-sphingosylphosphorylcholine does not initiate vesicle formation in cells.4 N-hexanoyl-sphingosylphosphorylcholine has been used to enhance the uptake of anti-tumor drugs by cancer cells, thereby increasing the cytotoxicity towards those cancer cells.5
N-Hexanoyl-NBD-sphingosylphosphorylcholine (mixture of D-erythro and L-threo... Reference: M1912-1 This product is a fluorescent sphingomyelin with an absorption of 467nm and an emission of 535nm. NBD has been shown to have only a small influence on lipid adsorption into cells and cellular membranes. Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis.1 An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease2 and neonatal respiratory distress syndrome.3 However, the ratio of sphingomyelin to ceramide is different for different cell types.4 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.5
N-Hexanoyl-NBD-sphingosylphosphorylcholine (mixture of D-erythro and L-threo... Reference: M1912-100 This product is a fluorescent sphingomyelin with an absorption of 467nm and an emission of 535nm. NBD has been shown to have only a small influence on lipid adsorption into cells and cellular membranes. Sphingomyelin is found in mammalian cell membranes, especially in the membranes of the myelin sheath. It is the most abundant sphingolipid in mammals and is thought to be found mostly in the exoplasmic leaflet of the membrane although there is also evidence of a sphingomyelin pool in the inner leaflet of the membrane. It is involved in signal transduction and apoptosis.1 An improper ratio of sphingomyelin to ceramide has been shown to be a factor in Niemann-Pick disease2 and neonatal respiratory distress syndrome.3 However, the ratio of sphingomyelin to ceramide is different for different cell types.4 Sphingomyelin is an important amphiphilic component when plasma lipoprotein pools expand in response to large lipid loads or metabolic abnormalities.5
lyso-Dihydrosphingomyelin Reference: M1913-1 This product is the saturated form of the more plentiful sphingomyelin, a lipid that is found in mammalian cell membranes, especially in the membranes of the myelin sheath, and is the most abundant sphingolipid in mammals. Dihydrosphingomyelin has been identified as a minor lipid component in many mammalian tissues but has recently been reported to be present in significant amounts in bovine brain and bovine milk.1 It is also found in much greater amounts in human lens membranes (half of all the phospholipids) where it has a critical role in ocular function and perhaps in age-related nuclear cataracts.2 However, dihydrosphingomyelin has been reported to occur only in small amounts in the lens membranes of other mammals. Dihydrosphingomyelin demonstrates good mixing properties with both sterols and sphingomyelin indicating that it could function as a membrane organizer and this may be the reason it is present in large amounts in human lens membranes where cholesterol is also enriched.3 The enzyme sphingomyelinase is active towards dihydrosphingomyelin and readily converts it to dihydroceramide. Recent evidence has been presented that indicates that dihydrosphingomyelin impairs HIV-1 infection by rigidifying liquid-ordered membrane domains, a finding that could have great potential in providing a therapeutic treatment for this debilitating disease.4
N-Hexadecanoyl-D-erythro-sphingosine Reference: M1915-10 This product is a well-defined ceramide and is ideal as a standard for mass spectrometry, biological systems,1 and studying physical properties of lipids.2 Hexadecanoyl ceramide comprises a significant amount of natural ceramides, often being the second most abundant species after C18:0-ceramide. Ceramides function as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1- phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.3 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.4 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.5 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity.
N-Tetracosanoyl-D-erythro-sphingosine Reference: M1916-5 This product is a high purity ceramide that is ideal as a standard and for biological systems. It is a ceramide containing the long chain lignoceric acid and is common in some mammalian tissues such as the brain. Ceramide is a fatty acid amide of sphingosine. Ceramide functions as a precursor in the synthesis of sphingomyelin, glycosphingolipids, and of free sphingosine and fatty acids. The sphingosine can be phosphorylated to form sphingosine-1-phosphate. Two of ceramide’s metabolites, sphingosine-1-phosphate and glucosylceramide, produce cell proliferation and other cellular functions.1 Ceramide exerts numerous biological effects, including induction of cell maturation, cell cycle arrest, terminal cell differentiation, cell senescence, and cell death.2 Because of these effects ceramide has been investigated for its use in cancer treatment and many potential approaches to cancer therapy have been presented.3 Other effects include producing reactive oxygen in mitochondria (followed by apoptosis) and stimulating phosphorylation of certain proteins (especially mitogen activated protein). It also stimulates some protein phosphatases (especially protein phosphatase 2A) making it an important controller of protein activity.