Home Amines 119567-63-4
119567-63-4,MFCD00153960
Catalog No.:AA000IWD

119567-63-4 | 4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-

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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA000IWD
Chemical Name:
4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-
CAS Number:
119567-63-4
Molecular Formula:
C20H41NO2
Molecular Weight:
327.5450
MDL Number:
MFCD00153960
SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](N(C)C)CO)O
Properties
Computed Properties
 
Complexity:
266  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
16  
XLogP3:
6.3  

Literature

Title: Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels.

Journal: British journal of pharmacology 20130301

Title: Pharmacologic recruitment of regulatory T cells as a therapy for ischemic acute kidney injury.

Journal: Kidney international 20120501

Title: Harnessing regulatory T cells for therapeutic purposes.

Journal: Kidney international 20120501

Title: Sphingosine kinase 1 knockdown reduces insulin synthesis and secretion in a rat insulinoma cell line.

Journal: Archives of biochemistry and biophysics 20120201

Title: [Antitumor effect of sphingosine kinase 1 inhibitor in combination with chemotherapy on SGC7901 gastric cancer cells in vitro].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20120201

Title: Sphingosine kinase-1 pathway mediates high glucose-induced fibronectin expression in glomerular mesangial cells.

Journal: Molecular endocrinology (Baltimore, Md.) 20111201

Title: Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.

Journal: Bioorganic & medicinal chemistry 20110915

Title: Endogenous sphingosine 1-phosphate regulates spontaneous glutamate release from mossy fiber terminals via S1P(3) receptors.

Journal: Life sciences 20110718

Title: Sphingolipid long chain base phosphates can regulate apoptotic-like programmed cell death in plants.

Journal: Biochemical and biophysical research communications 20110708

Title: [Effect of sphingosine kinase 1 on the apoptosis, migration and invasion of colon cancer HT-29 cells and its molecular mechanisms].

Journal: Zhonghua zhong liu za zhi [Chinese journal of oncology] 20110301

Title: [Regulation of sphingosine kinase 1 in the TNF-α-induced expression of MUC5AC in airway epithelial cells].

Journal: Zhonghua yi xue za zhi 20110215

Title: Bortezomib and sphingosine kinase inhibitor interact synergistically to induces apoptosis in BCR/ABl+ cells sensitive and resistant to STI571 through down-regulation Mcl-1.

Journal: Biochemical and biophysical research communications 20110204

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Determination of sphingosine kinase activity in biological samples by liquid chromatography-tandem mass spectrometry.

Journal: Biomedical chromatography : BMC 20101001

Title: Sphingosine and FTY720 directly bind pro-survival 14-3-3 proteins to regulate their function.

Journal: Cellular signalling 20100901

Title: Sphingosine interaction with acidic leucine-rich nuclear phosphoprotein-32A (ANP32A) regulates PP2A activity and cyclooxygenase (COX)-2 expression in human endothelial cells.

Journal: The Journal of biological chemistry 20100827

Title: Sphingosine kinase inhibition alleviates endothelial permeability induced by thrombin and activated neutrophils.

Journal: Shock (Augusta, Ga.) 20100401

Title: Sphingosine kinase 1 regulates mucin production via ERK phosphorylation.

Journal: Pulmonary pharmacology & therapeutics 20100201

Title: The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia.

Journal: British journal of pharmacology 20100201

Title: Oxytocin stimulates in vitro angiogenesis via a Pyk-2/Src-dependent mechanism.

Journal: Experimental cell research 20091101

Title: Discovery of novel sphingosine kinase 1 inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091101

Title: Role of sphingosine-1-phosphate (S1P) and the S1P(2) receptor in allergen-induced, mast cell-dependent contraction of rat lung parenchymal strips.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20091001

Title: Development of an Alamar Blue viability assay in 384-well format for high throughput whole cell screening of Trypanosoma brucei brucei bloodstream form strain 427.

Journal: The American journal of tropical medicine and hygiene 20091001

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

Journal: Glycoconjugate journal 20090701

Title: Iodophenyl tagged sphingosine derivatives: synthesis and preliminary biological evaluation.

Journal: Bioorganic & medicinal chemistry letters 20090701

Title: Synthesis and evaluation of sphingosine analogues as inhibitors of sphingosine kinases.

Journal: Journal of medicinal chemistry 20090625

Title: The importance of negative superhelicity in inducing the formation of G-quadruplex and i-motif structures in the c-Myc promoter: implications for drug targeting and control of gene expression.

Journal: Journal of medicinal chemistry 20090514

Title: Galpha(q)-mediated plasma membrane translocation of sphingosine kinase-1 and cross-activation of S1P receptors.

Journal: Biochimica et biophysica acta 20090501

Title: N,N-Dimethylsphingosine conjugates of poly-L-glutamic acid: synthesis, characterization, and initial biological evaluation.

Journal: Bioorganic & medicinal chemistry letters 20090201

Title: Small molecule activators of SIRT1 replicate signaling pathways triggered by calorie restriction in vivo.

Journal: BMC systems biology 20090101

Title: Anti-inflammatory effects of sphingosine kinase modulation in inflammatory arthritis.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20081201

Title: A sphingosine kinase activity assay using direct infusion electrospray ionization tandem mass spectrometry.

Journal: Analytical biochemistry 20080901

Title: N-(4-Hydroxyphenyl)retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing.

Journal: Molecular cancer therapeutics 20080901

Title: Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a 'come-and-get-me' signal.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080801

Title: Brain-derived neurotrophic factor enhances the excitability of rat sensory neurons through activation of the p75 neurotrophin receptor and the sphingomyelin pathway.

Journal: The Journal of physiology 20080701

Title: N,N-Dimethyl-D-erythro-sphingosine inhibits store-operated Ca2+ entry in U937 monocytes.

Journal: Journal of pharmacological sciences 20080701

Title: Characterization of N,N,-dimethyl-D-erythro-sphingosine-induced apoptosis and signaling in U937 cells: independence of sphingosine kinase inhibition.

Journal: Prostaglandins & other lipid mediators 20080601

Title: Inhalation of sphingosine kinase inhibitor attenuates airway inflammation in asthmatic mouse model.

Journal: American journal of physiology. Lung cellular and molecular physiology 20080601

Title: Differential signaling of sphingosine derivatives in U937 human monocytes depends on the degree of N-methylation.

Journal: Prostaglandins & other lipid mediators 20080601

Title: Effects of phosphorylation of immunomodulatory agent FTY720 (fingolimod) on antiproliferative activity against breast and colon cancer cells.

Journal: Biological & pharmaceutical bulletin 20080601

Title: The role of sphingosine kinase in a murine model of allergic asthma.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20080315

Title: Sphingolipid metabolites selectively elicit increases in nuclear calcium concentration in cell suspension cultures and in isolated nuclei of tobacco.

Journal: Cell calcium 20080101

Title: Trophic action of sphingosine 1-phosphate in denervated rat soleus muscle.

Journal: American journal of physiology. Cell physiology 20080101

Title: N, N-dimethyl-D-erythro-sphingosine increases intracellular Ca2+ concentration via Na+-Ca2+-exchanger in HCT116 human colon cancer cells.

Journal: Archives of pharmacal research 20080101

Title: Sphingolipids and the sphingosine kinase inhibitor, SKI II, induce BCL-2-independent apoptosis in human prostatic adenocarcinoma cells.

Journal: The Prostate 20071101

Title: Suppression of osteoclastogenesis by N,N-dimethyl-D-erythro-sphingosine: a sphingosine kinase inhibition-independent action.

Journal: Molecular pharmacology 20070801

Title: MAO-A-induced mitogenic signaling is mediated by reactive oxygen species, MMP-2, and the sphingolipid pathway.

Journal: Free radical biology & medicine 20070701

Title: The role of sphingosine 1-phosphate in the TNF-alpha induction of IL-8 gene expression in lung epithelial cells.

Journal: Gene 20070415

Title: Multiple actions of dimethylsphingosine in 1321N1 astrocytes.

Journal: Molecules and cells 20070227

Title: N,N-dimethylsphingosine-coumarin: synthesis, chemical characterization, and biological evaluation.

Journal: Bioconjugate chemistry 20070101

Title: Dimethylsphingosine and FTY720 inhibit the SK1 form but activate the SK2 form of sphingosine kinase from rat heart.

Journal: Journal of biochemical and molecular toxicology 20070101

Title: Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases.

Journal: Investigative ophthalmology & visual science 20061101

Title: Sphingosine kinase assay system with fluorescent detection in high performance liquid chromatography.

Journal: Archives of pharmacal research 20061101

Title: Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes.

Journal: Biochemical and biophysical research communications 20060929

Title: Low dose N, N-dimethylsphingosine is cardioprotective and activates cytosolic sphingosine kinase by a PKCepsilon dependent mechanism.

Journal: Cardiovascular research 20060901

Title: Intracellular sphingosine 1-phosphate mediates the increased excitability produced by nerve growth factor in rat sensory neurons.

Journal: The Journal of physiology 20060815

Title: Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line.

Journal: Archives of pharmacal research 20060801

Title: Dimethylsphingosine regulates intracellular pH and Ca(2+) in human monocytes.

Journal: Journal of pharmacological sciences 20060401

Title: Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors.

Journal: Journal of neurochemistry 20051201

Title: Basal and induced sphingosine kinase 1 activity in A549 carcinoma cells: function in cell survival and IL-1beta and TNF-alpha induced production of inflammatory mediators.

Journal: Cellular signalling 20051001

Title: Sphingosine kinase regulates the sensitivity of Dictyostelium discoideum cells to the anticancer drug cisplatin.

Journal: Eukaryotic cell 20050101

Title: The intracellular action of sphingosine 1-phosphate in GPVI-mediated Ca2+ mobilization in platelets.

Journal: Thrombosis research 20050101

Title: Sphingosine 1-phosphate protects bovine oocytes from heat shock during maturation.

Journal: Biology of reproduction 20041201

Title: Enhancement of radiosensitivity by combined ceramide and dimethylsphingosine treatment in lung cancer cells.

Journal: Experimental & molecular medicine 20041031

Title: Anaphylatoxin signaling in human neutrophils. A key role for sphingosine kinase.

Journal: The Journal of biological chemistry 20041022

Title: Sphingosine kinase activation mediates ischemic preconditioning in murine heart.

Journal: Circulation 20041005

Title: mitochondrial ceramidase overexpression up-regulates Bcl-2 protein level in K562 cells, probably through its metabolite sphingosine-1-phosphate.

Journal: Zhongguo shi yan xue ye xue za zhi 20041001

Title: Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine.

Journal: The Journal of biological chemistry 20040827

Title: Sphingosine kinase activation regulates hepatocyte growth factor induced migration of endothelial cells.

Journal: Experimental cell research 20040815

Title: Sphingosine kinase activity is required for sphingosine-mediated phospholipase D activation in C2C12 myoblasts.

Journal: The Biochemical journal 20040801

Title: The immune modulator FTY720 targets sphingosine-kinase-dependent migration of human monocytes in response to amyloid beta-protein and its precursor.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040801

Title: Overexpression of sphingosine-1-phosphate lyase or inhibition of sphingosine kinase in Dictyostelium discoideum results in a selective increase in sensitivity to platinum-based chemotherapy drugs.

Journal: Eukaryotic cell 20040601

Title: Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040501

Title: Heparan sulfate proteoglycans are involved in opiate receptor-mediated cell migration.

Journal: Biochemistry 20040113

Title: Leukocyte motility in response to neuropeptides is heparan sulfate proteoglycan dependent.

Journal: Peptides 20030501

Title: Beta 1,4-galactosyltransferase (beta 4GalT)-IV is specific for GlcNAc 6-O-sulfate. Beta 4GalT-IV acts on keratan sulfate-related glycans and a precursor glycan of 6-sulfosialyl-Lewis X.

Journal: The Journal of biological chemistry 20030314

Title: Dimethylsphingosine increases cytosolic calcium and intracellular pH in human T lymphocytes.

Journal: Biochemical pharmacology 20030201

Title: Sphingosine kinase: a point of convergence in the action of diverse neutrophil priming agents.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20021201

Title: D-erythro-N,N-dimethylsphingosine inhibits bFGF-induced proliferation of cerebral, aortic and coronary smooth muscle cells.

Journal: Atherosclerosis 20021001

Title: Expression of sphingosine kinase gene in the interactions between human gastric carcinoma cell and vascular endothelial cell.

Journal: World journal of gastroenterology 20020815

Title: Sphingosine kinase inhibitors in the apoptosis of leukaemia cells.

Journal: Leukemia research 20020401

Title: Sphingosine 1-phosphate stimulates rat mesangial cell proliferation from outside the cells.

Journal: Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020401

Title: Effective cytotoxicity against human leukemias and chemotherapy-resistant leukemia cell lines by N-N-dimethylsphingosine.

Journal: Leukemia research 20020301

Title: Signalling pathways involved in the direct effects of IGFBP-5 on breast epithelial cell attachment and survival.

Journal: Journal of cellular biochemistry 20020101

Title: Depolarisation induces rapid and transient formation of intracellular sphingosine-1-phosphate.

Journal: FEBS letters 20011207

Title: Prolactin induces calcium influx and release from intracellular pools in human T lymphocytes by activation of tyrosine kinases.

Journal: Cellular signalling 20011101

Title: Sphingosine 1-phosphate antagonizes apoptosis of human leukemia cells by inhibiting release of cytochrome c and Smac/DIABLO from mitochondria.

Journal: Blood 20011101

Title: 1Alpha,25-dihydroxyvitamin D3 protects human keratinocytes from apoptosis by the formation of sphingosine-1-phosphate.

Journal: The Journal of investigative dermatology 20011101

Title: The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.

Journal: Journal of molecular and cellular cardiology 20010901

Title: Sphingosine kinase regulates hepatoma cell differentiation: roles of hepatocyte nuclear factor and retinoid receptor.

Journal: Biochemical and biophysical research communications 20010831

Title: TNF-alpha-induced sphingosine 1-phosphate inhibits apoptosis through a phosphatidylinositol 3-kinase/Akt pathway in human hepatocytes.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20010701

Title: Role of the sphingosine-1-phosphate receptor EDG-1 in PDGF-induced cell motility.

Journal: Science (New York, N.Y.) 20010302

Title: Sphingosine kinase expression regulates apoptosis and caspase activation in PC12 cells.

Journal: Journal of neurochemistry 20010301

Title: Activation of Gadd34 by diverse apoptotic signals and suppression of its growth inhibitory effects by apoptotic inhibitors.

Journal: International journal of cancer 20010220

Title: Differential regulation of protein tyrosine kinase on free radical production, granule enzyme release, and cytokine synthesis by activated murine peritoneal macrophages.

Journal: Biochemical pharmacology 20010101

Title: Involvement of sphingosine in mitochondria-dependent Fas-induced apoptosis of type II Jurkat T cells.

Journal: The Journal of biological chemistry 20000526

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SDS
Tags:119567-63-4 Molecular Formula|119567-63-4 MDL|119567-63-4 SMILES|119567-63-4 4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-