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73257-80-4,MFCD00236490
Catalog No.:AA005PHZ

73257-80-4 | DL-PDMP

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  • Technical Information
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  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA005PHZ
Chemical Name:
DL-PDMP
CAS Number:
73257-80-4
Molecular Formula:
C23H38N2O3
Molecular Weight:
390.5594
MDL Number:
MFCD00236490
SMILES:
CCCCCCCCCC(=O)NC(C(c1ccccc1)O)CN1CCOCC1
Properties
Computed Properties
 
Complexity:
407  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
13  
Undefined Atom Stereocenter Count:
2  
XLogP3:
4.2  

Literature

Title: A reconstructed human epidermal keratinization culture model to characterize ceramide metabolism in the stratum corneum.

Journal: Archives of dermatological research 20120901

Title: Membrane raft disruption results in neuritic retraction prior to neuronal death in cortical neurons.

Journal: Bioscience trends 20120801

Title: Cholesterol level influences opioid signaling in cell models and analgesia in mice and humans.

Journal: Journal of lipid research 20120601

Title: Involvement of ganglioside GT1b in glutamate release from neuroblastoma cells.

Journal: Neuroscience letters 20120531

Title: Increasing ceramides sensitizes genistein-induced melanoma cell apoptosis and growth inhibition.

Journal: Biochemical and biophysical research communications 20120511

Title: Dissociation of ERK signalling inhibition from the anti-amyloidogenic action of synthetic ceramide analogues.

Journal: Clinical science (London, England : 1979) 20120501

Title: Relevance of the salvage pathway to N-hexanoylsphingosine metabolic downregulation in human neurotumor cells: implications for apoptosis.

Journal: Drug metabolism letters 20120301

Title: 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) facilitates curcumin-induced melanoma cell apoptosis by enhancing ceramide accumulation, JNK activation, and inhibiting PI3K/AKT activation.

Journal: Molecular and cellular biochemistry 20120201

Title: Property-based design of a glucosylceramide synthase inhibitor that reduces glucosylceramide in the brain.

Journal: Journal of lipid research 20120201

Title: Imiglucerase in the treatment of Gaucher disease: a history and perspective.

Journal: Drug design, development and therapy 20120101

Title: GD1a modulates GM-CSF-induced cell proliferation.

Journal: Cytokine 20111201

Title: Glucosylceramide synthase inhibitor PDMP sensitizes chronic myeloid leukemia T315I mutant to Bcr-Abl inhibitor and cooperatively induces glycogen synthase kinase-3-regulated apoptosis.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20111001

Title: Combinatorial therapies improve the therapeutic efficacy of nanoliposomal ceramide for pancreatic cancer.

Journal: Cancer biology & therapy 20111001

Title: Targeting glucosylceramide synthase sensitizes imatinib-resistant chronic myeloid leukemia cells via endogenous ceramide accumulation.

Journal: Journal of cancer research and clinical oncology 20111001

Title: D,L-Threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (DL-PDMP) increases endoplasmic reticulum stress, autophagy and apoptosis accompanying ceramide accumulation via ceramide synthase 5 protein expression in A549 cells.

Journal: Biochimie 20110901

Title: Roles of ceramide synthase and ceramide clearence genes in nilotinib-induced cell death in chronic myeloid leukemia cells.

Journal: Leukemia & lymphoma 20110801

Title: Physiopathological function of hematoside (GM3 ganglioside).

Journal: Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110511

Title: The roles of bioactive sphingolipids in resveratrol-induced apoptosis in HL60: acute myeloid leukemia cells.

Journal: Journal of cancer research and clinical oncology 20110201

Title: Effect of D, L-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol and tetrandrine on the reversion of multidrug resistance in K562/A02 cells.

Journal: Hematology (Amsterdam, Netherlands) 20110101

Title: C6-ceramide synergistically potentiates the anti-tumor effects of histone deacetylase inhibitors via AKT dephosphorylation and α-tubulin hyperacetylation both in vitro and in vivo.

Journal: Cell death & disease 20110101

Title: Resveratrol triggers apoptosis through regulating ceramide metabolizing genes in human K562 chronic myeloid leukemia cells.

Journal: Nutrition and cancer 20110101

Title: Isofagomine in vivo effects in a neuronopathic Gaucher disease mouse.

Journal: PloS one 20110101

Title: Production of multiple brain-like ganglioside species is dispensable for fas-induced apoptosis of lymphoid cells.

Journal: PloS one 20110101

Title: Modulation of amyloid precursor protein processing by synthetic ceramide analogues.

Journal: Biochimica et biophysica acta 20100801

Title: How adhesion/growth-regulatory galectins-1 and -3 attain cell specificity: case study defining their target on neuroblastoma cells (SK-N-MC) and marked affinity regulation by affecting microdomain organization of the membrane.

Journal: IUBMB life 20100801

Title: Inhibition of glucosylceramide synthase reversibly decreases the capsaicin-induced activation and TRPV1 expression of cultured dorsal root ganglion neurons.

Journal: Pain 20100701

Title: Insulin inhibits Abeta fibrillogenesis through a decrease of the GM1 ganglioside-rich microdomain in neuronal membranes.

Journal: Journal of neurochemistry 20100501

Title: Direct quantitative determination of ceramide glycosylation in vivo: a new approach to evaluate cellular enzyme activity of glucosylceramide synthase.

Journal: Journal of lipid research 20100401

Title: Hypoxia-induced neuronal apoptosis is mediated by de novo synthesis of ceramide through activation of serine palmitoyltransferase.

Journal: Cellular signalling 20100401

Title: Myriocin-mediated up-regulation of hepatocyte apoA-I synthesis is associated with ERK inhibition.

Journal: Clinical science (London, England : 1979) 20100330

Title: [Effect of PDMP, a glucosylceramide synthase inhibitor, on reversion of daunorubicin resistance in human leukemia cell line K562/A02].

Journal: Zhongguo shi yan xue ye xue za zhi 20100201

Title: P-Glycoprotein is not a key target for the chemosensitizing effect of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol in HepG2 cells exposed to doxorubicin.

Journal: Drug metabolism letters 20100101

Title: Glucosylceramide synthase upregulates MDR1 expression in the regulation of cancer drug resistance through cSrc and beta-catenin signaling.

Journal: Molecular cancer 20100101

Title: Increased hepatic insulin action in diet-induced obese mice following inhibition of glucosylceramide synthase.

Journal: PloS one 20100101

Title: Gaucher disease: clinical profile and therapeutic developments.

Journal: Biologics : targets & therapy 20100101

Title: Use of a novel anti-proliferative compound coated on a biopolymer to mitigate platelet-derived growth factor-induced proliferation in human aortic smooth muscle cells: comparison with sirolimus.

Journal: Glycoconjugate journal 20090801

Title: VEGF recruits lactosylceramide to induce endothelial cell adhesion molecule expression and angiogenesis in vitro and in vivo.

Journal: Glycoconjugate journal 20090701

Title: Glycosphingolipid requirements for endosome-to-Golgi transport of Shiga toxin.

Journal: Traffic (Copenhagen, Denmark) 20090701

Title: Neurotrophic and neuroprotective actions of an enhancer of ganglioside biosynthesis.

Journal: International review of neurobiology 20090101

Title: L-PDMP improves glucosylceramide synthesis and behavior in rats with focal ischemia.

Journal: Neurological research 20081101

Title: Membrane type sialidase inhibits the megakaryocytic differentiation of human leukemia K562 cells.

Journal: Biochimica et biophysica acta 20080501

Title: Review of miglustat for clinical management in Gaucher disease type 1.

Journal: Therapeutics and clinical risk management 20080401

Title: Depletion of the lipid raft constituents, sphingomyelin and ganglioside, decreases serotonin binding at human 5-HT7(a) receptors in HeLa cells.

Journal: Acta physiologica (Oxford, England) 20070501

Title: [Effect of endogeneous gangliosides on integrin alpha2beta1-mediated adhesion of neuroblastoma cells to collagen].

Journal: Zhongguo dang dai er ke za zhi = Chinese journal of contemporary pediatrics 20070201

Title: A study of the xenoantigenicity of neonatal porcine islet-like cell clusters (NPCC) and the efficiency of adenovirus-mediated DAF (CD55) expression.

Journal: Xenotransplantation 20060901

Title: Synthesis and biological evaluation of novel PDMP analogues.

Journal: Bioorganic & medicinal chemistry 20060801

Title: The synthetic ceramide analog L-PDMP partially protects striatal dopamine levels but does not promote dopamine neuron survival in murine models of parkinsonism.

Journal: Brain research 20060712

Title: Lipid rafts serve as a signaling platform for nicotinic acetylcholine receptor clustering.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20060503

Title: Lactosylceramide is required in apoptosis induced by N-Smase.

Journal: Glycoconjugate journal 20060501

Title: D-threo-1-phenyl-2-decanoylamino-3-morpholino-1-propanol alters cellular cholesterol homeostasis by modulating the endosome lipid domains.

Journal: Biochemistry 20060411

Title: Role of gangliosides in the association of ErbB2 with lipid rafts in mammary epithelial HC11 cells.

Journal: The FEBS journal 20060401

Title: PDMP sensitizes neuroblastoma to paclitaxel by inducing aberrant cell cycle progression leading to hyperploidy.

Journal: Molecular cancer therapeutics 20060301

Title: Substrate reduction therapy of glycosphingolipid storage disorders.

Journal: Journal of inherited metabolic disease 20060101

Title: Inhibition of sphingolipid synthesis impairs cellular activation, cytokine production and proliferation in human lymphocytes.

Journal: Biochemical pharmacology 20051219

Title: Human T-cell lymphotropic virus type I-transformed T-cells have a partial defect in ceramide synthesis in response to N-(4-hydroxyphenyl)retinamide.

Journal: The Biochemical journal 20051115

Title: Novel role of lactosylceramide in vascular endothelial growth factor-mediated angiogenesis in human endothelial cells.

Journal: Circulation research 20051014

Title: Glycosphingolipid accumulation inhibits cholesterol efflux via the ABCA1/apolipoprotein A-I pathway: 1-phenyl-2-decanoylamino-3-morpholino-1-propanol is a novel cholesterol efflux accelerator.

Journal: The Journal of biological chemistry 20050701

Title: A novel role of lactosylceramide in the regulation of tumor necrosis factor alpha-mediated proliferation of rat primary astrocytes. Implications for astrogliosis following neurotrauma.

Journal: The Journal of biological chemistry 20050408

Title: Sphingosine 1-phosphate acts as a signal molecule in ceramide signal transduction of TNF-alpha-induced activator protein-1 in osteoblastic cell line MC3T3-E1 cells.

Journal: Journal of oral science 20050301

Title: Inhibition of sphingolipid biosynthesis decreases phosphorylated ERK2 in LLC-PK1 cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20050101

Title: Effect of the modulation of the membrane lipid composition on the localization and function of P-glycoprotein in MDR1-MDCK cells.

Journal: In vitro cellular & developmental biology. Animal 20050101

Title: Inhibition of glucosylceramide synthase does not reverse drug resistance in cancer cells.

Journal: The Journal of biological chemistry 20040924

Title: Sialic acid acts as a receptor for equine rhinitis A virus binding and infection.

Journal: The Journal of general virology 20040901

Title: Gangliosides link the acidic sphingomyelinase-mediated induction of ceramide to 12-lipoxygenase-dependent apoptosis of neuroblastoma in response to fenretinide.

Journal: Journal of the National Cancer Institute 20040901

Title: In vivo influence of ceramide accumulation induced by treatment with a glucosylceramide synthase inhibitor on ischemic neuronal cell death.

Journal: Brain research 20040820

Title: The combinatorial extension method reveals a sphingolipid binding domain on pancreatic bile salt-dependent lipase: role in secretion.

Journal: Structure (London, England : 1993) 20040801

Title: A novel role of lactosylceramide in the regulation of lipopolysaccharide/interferon-gamma-mediated inducible nitric oxide synthase gene expression: implications for neuroinflammatory diseases.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040630

Title: Mechanism for the negative regulation of cell proliferation by ganglioside GM3 in high glucose-treated glomerular mesangial cells.

Journal: Life sciences 20040521

Title: Cytoprotective effect of glucosylceramide synthase inhibition against daunorubicin-induced apoptosis in human leukemic cell lines.

Journal: The Journal of biological chemistry 20040430

Title: Ceramide-mediated macroautophagy involves inhibition of protein kinase B and up-regulation of beclin 1.

Journal: The Journal of biological chemistry 20040430

Title: New PDMP analogues inhibit process outgrowth in an insect cell line.

Journal: Bioorganic & medicinal chemistry letters 20040322

Title: A turn in the road: How studies on the pharmacology of glucosylceramide synthase inhibitors led to the identification of a lysosomal phospholipase A2 with ceramide transacylase activity.

Journal: Glycoconjugate journal 20040101

Title: Apoptosis of human carcinoma cells in the presence of inhibitors of glycosphingolipid biosynthesis: I. Treatment of Colo-205 and SKBR3 cells with isomers of PDMP and PPMP.

Journal: Glycoconjugate journal 20040101

Title: Apoptosis of human carcinoma cells in the presence of potential anti-cancer drugs: III. Treatment of Colo-205 and SKBR3 cells with: cis -platin, Tamoxifen, Melphalan, Betulinic acid, L-PDMP, L-PPMP, and GD3 ganglioside.

Journal: Glycoconjugate journal 20040101

Title: Reduction of glycosphingolipid levels in lipid rafts affects the expression state and function of glycosylphosphatidylinositol-anchored proteins but does not impair signal transduction via the T cell receptor.

Journal: The Journal of biological chemistry 20031219

Title: The significance of N-linked glycosylation in pig endogenous retrovirus infectivity.

Journal: Biochemical and biophysical research communications 20031017

Title: Ceramide accumulation precedes caspase-3 activation during apoptosis of A549 human lung adenocarcinoma cells.

Journal: American journal of physiology. Lung cellular and molecular physiology 20030601

Title: Gangliosides regulate tumor cell adhesion to collagen.

Journal: Clinical & experimental metastasis 20030101

Title: Increased biosynthesis of glycosphingolipids in congenital disorder of glycosylation Ia (CDG-Ia) fibroblasts.

Journal: Pediatric research 20021101

Title: Increasing endogenous ceramide using inhibitors of sphingolipid metabolism maximizes ionizing radiation-induced mitochondrial injury and apoptotic cell killing.

Journal: International journal of cancer 20021020

Title: Glycosphingolipid lysosomal storage diseases: therapy and pathogenesis.

Journal: Neuropathology and applied neurobiology 20021001

Title: Ceramide induces activation of the mitochondrial/caspases pathway in Jurkat and SCC61 cells sensitive to gamma-radiation but activation of this sequence is defective in radioresistant SQ20B cells.

Journal: International journal of radiation biology 20020901

Title: Modulation of the expression of membrane-bound CD54 (mCD54) and soluble form of CD54 (sCD54) in endothelial cells by glucosyl transferase inhibitor: possible role of ceramide for the shedding of mCD54.

Journal: Biochemical and biophysical research communications 20020809

Title: Influence of ceramide metabolism on P-glycoprotein function in immature acute myeloid leukemia KG1a cells.

Journal: Molecular pharmacology 20020801

Title: Increase in ceramide level alters the lysosomal targeting of cathepsin D prior to onset of apoptosis in HT-29 colon cancer cells.

Journal: Biological chemistry 20020601

Title: The lysosomal transport of prosaposin requires the conditional interaction of its highly conserved d domain with sphingomyelin.

Journal: The Journal of biological chemistry 20020510

Title: Possible implication of Golgi-nucleating function for the centrosome.

Journal: Biochemical and biophysical research communications 20020301

Title: P-glycoprotein modulates ceramide-mediated sensitivity of human breast cancer cells to tubulin-binding anticancer drugs.

Journal: Molecular cancer therapeutics 20020101

Title: Ceramide attenuates high glucose-induced cardiac contractile abnormalities in cultured adult rat ventricular myocytes.

Journal: Cellular and molecular biology (Noisy-le-Grand, France) 20020101

Title: Sialosyl Le(a)-carrying gangliosides present on the surface of colon carcinoma cells are not directly involved in adhesion to E-selectin.

Journal: European journal of cell biology 20011201

Title: Differential chemosensitizing effect of two glucosylceramide synthase inhibitors in hepatoma cells.

Journal: Biochemical and biophysical research communications 20011019

Title: Ceramide mediates tumor-induced dendritic cell apoptosis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20011001

Title: Agents for the treatment of glycosphingolipid storage disorders.

Journal: Current drug metabolism 20010901

Title: Glucosylceramide synthesis inhibitors block pharmacologically induced dispersal of the Golgi and anterograde membrane flow from the endoplasmic reticulum: implication of sphingolipid metabolism in maintenance of the Golgi architecture and anterograde membrane flow.

Journal: Bioscience, biotechnology, and biochemistry 20010601

Title: Activation of the endothelial nitric-oxide synthase by tumor necrosis factor-alpha. A novel feedback mechanism regulating cell death.

Journal: The Journal of biological chemistry 20010302

Title: Ceramide dissociates 3'-phosphoinositide production from pleckstrin homology domain translocation.

Journal: The Biochemical journal 20010301

Title: Lactosylceramide mediates shear-induced endothelial superoxide production and intercellular adhesion molecule-1 expression.

Journal: Journal of vascular research 20010101

Title: Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.

Journal: Cardiovascular research 19990801

Title: Differential effects of glycolipid biosynthesis inhibitors on ceramide-induced cell death in neuroblastoma cells.

Journal: Journal of neurochemistry 19990301

Title: Rationales for cancer chemotherapy with PDMP, a specific inhibitor of glucosylceramide synthase.

Journal: Molecular and chemical neuropathology 19940101

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Tags:73257-80-4 Molecular Formula|73257-80-4 MDL|73257-80-4 SMILES|73257-80-4 DL-PDMP