Home Amines 77286-66-9
77286-66-9,MFCD00063527
Catalog No.:AA01DPGL

77286-66-9 | 3,5,9-Trioxa-4-phosphaheptacosan-1-aminium,4-hydroxy-7-methoxy-N,N,N-trimethyl-, inner salt, 4-oxide, (7R)-

Pack Size
Purity
Availability
Price(USD)
Quantity
  
5mg
>99%
in stock  
$1,040.00   $728.00
- +
25mg
>99%
in stock  
$2,020.00   $1,414.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA01DPGL
Chemical Name:
3,5,9-Trioxa-4-phosphaheptacosan-1-aminium,4-hydroxy-7-methoxy-N,N,N-trimethyl-, inner salt, 4-oxide, (7R)-
CAS Number:
77286-66-9
Molecular Formula:
C27H58NO6P
Molecular Weight:
523.7263
MDL Number:
MFCD00063527
SMILES:
CCCCCCCCCCCCCCCCCCOC[C@H](COP(=O)(OCC[N+](C)(C)C)[O-])OC
Properties
Computed Properties
 
Complexity:
492  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Heavy Atom Count:
35  
Hydrogen Bond Acceptor Count:
6  
Rotatable Bond Count:
27  
XLogP3:
7.6  

Literature

Title: Involvement of presynaptic voltage-dependent Kv3 channel in endothelin-1-induced inhibition of noradrenaline release from rat gastric sympathetic nerves.

Journal: European journal of pharmacology 20121105

Title: In vitro and in vivo efficacy of ether lipid edelfosine against Leishmania spp. and SbV-resistant parasites.

Journal: PLoS neglected tropical diseases 20120401

Title: Targeting SKCa channels in cancer: potential new therapeutic approaches.

Journal: Current medicinal chemistry 20120101

Title: Exogenous ether lipids predominantly target mitochondria.

Journal: PloS one 20120101

Title: Edelfosine disturbs the sphingomyelin-cholesterol model membrane system in a cholesterol-dependent way - the Langmuir monolayer study.

Journal: Colloids and surfaces. B, Biointerfaces 20111201

Title: Phosphoinositide phosphatase SHIP-1 regulates apoptosis induced by edelfosine, Fas ligation and DNA damage in mouse lymphoma cells.

Journal: The Biochemical journal 20111115

Title: New alkyl-lipid blockers of SK3 channels reduce cancer cell migration and occurrence of metastasis.

Journal: Current cancer drug targets 20111101

Title: Selenocyanates and diselenides: a new class of potent antileishmanial agents.

Journal: European journal of medicinal chemistry 20110801

Title: Impact of alkylphospholipids on the gene expression profile of HaCaT cells.

Journal: Pharmacogenetics and genomics 20110701

Title: Involvement of lipid rafts in the localization and dysfunction effect of the antitumor ether phospholipid edelfosine in mitochondria.

Journal: Cell death & disease 20110501

Title: The novel synthetic ether lipid inositol-C2-PAF inhibits phosphorylation of the tyrosine kinases Src and FAK independent of integrin activation in transformed skin cells.

Journal: Biochemical pharmacology 20110415

Title: Antitumoral alkylphospholipids induce cholesterol efflux from the plasma membrane in HepG2 cells.

Journal: The Journal of pharmacology and experimental therapeutics 20110301

Title: The SK3/K(Ca)2.3 potassium channel is a new cellular target for edelfosine.

Journal: British journal of pharmacology 20110101

Title: The relationship between the concentration of ganglioside GM1 and antitumor activity of edelfosine--the Langmuir monolayer study.

Journal: Colloids and surfaces. B, Biointerfaces 20101101

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

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Vitamin E prevents lipid raft modifications induced by an anti-cancer lysophospholipid and abolishes a Yap1-mediated stress response in yeast.

Journal: The Journal of biological chemistry 20100813

Title: Cell specific dopamine modulation of the transient potassium current in the pyloric network by the canonical D1 receptor signal transduction cascade.

Journal: Journal of neurophysiology 20100801

Title: Lipid raft-targeted therapy in multiple myeloma.

Journal: Oncogene 20100701

Title: Computational screening for membrane-directed inhibitors of mast cell activation.

Journal: European journal of medicinal chemistry 20100601

Title: Disruption of cellular cholesterol transport and homeostasis as a novel mechanism of action of membrane-targeted alkylphospholipid analogues.

Journal: British journal of pharmacology 20100501

Title: In vitro and In vivo selective antitumor activity of Edelfosine against mantle cell lymphoma and chronic lymphocytic leukemia involving lipid rafts.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20100401

Title: Effect of edelfosine on tumor and normal cells model membranes--a comparative study.

Journal: Colloids and surfaces. B, Biointerfaces 20100301

Title: Edelfosine-induced metabolic changes in cancer cells that precede the overproduction of reactive oxygen species and apoptosis.

Journal: BMC systems biology 20100101

Title: Targeting the PI3K/Akt cell survival pathway to induce cell death of HIV-1 infected macrophages with alkylphospholipid compounds.

Journal: PloS one 20100101

Title: Membrane rafts are involved in intracellular miconazole accumulation in yeast cells.

Journal: The Journal of biological chemistry 20091120

Title: Langmuir monolayer study toward combined antileishmanian therapy involving amphotericin B and edelfosine.

Journal: The journal of physical chemistry. B 20091029

Title: Study of the stress proteins secreted by Leishmania donovani after treatment with edelfosine, mitelfosine and ilmofosine, and morphological alterations analyzed by electronic microscopy.

Journal: Parasite (Paris, France) 20090901

Title: Novel anti-inflammatory action of edelfosine lacking toxicity with protective effect in experimental colitis.

Journal: The Journal of pharmacology and experimental therapeutics 20090501

Title: Lipid raft connection between extrinsic and intrinsic apoptotic pathways.

Journal: Biochemical and biophysical research communications 20090320

Title: Phospholipase C-mediated regulation of transient receptor potential vanilloid 6 channels: implications in active intestinal Ca2+ transport.

Journal: Molecular pharmacology 20090301

Title: Involvement of raft aggregates enriched in Fas/CD95 death-inducing signaling complex in the antileukemic action of edelfosine in Jurkat cells.

Journal: PloS one 20090101

Title: Testing the hypothesis that amphiphilic antineoplastic lipid analogues act through reduction of membrane curvature elastic stress.

Journal: Journal of the Royal Society, Interface 20081106

Title: Serotonin increases GABA release in rat entorhinal cortex by inhibiting interneuron TASK-3 K+ channels.

Journal: Molecular and cellular neurosciences 20081001

Title: In vivo activity of perifosine against Leishmania amazonensis.

Journal: Acta tropica 20081001

Title: Edelfosine is incorporated into rafts and alters their organization.

Journal: The journal of physical chemistry. B 20080918

Title: Localization of Fas/CD95 into the lipid rafts on down-modulation of the phosphatidylinositol 3-kinase signaling pathway.

Journal: Molecular cancer research : MCR 20080401

Title: Lipid nanoparticles for alkyl lysophospholipid edelfosine encapsulation: development and in vitro characterization.

Journal: European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20080201

Title: Alkylphospholipids inhibit capillary-like endothelial tube formation in vitro: antiangiogenic properties of a new class of antitumor agents.

Journal: Anti-cancer drugs 20080101

Title: The antitumor ether lipid edelfosine (ET-18-O-CH3) induces apoptosis in H-ras transformed human breast epithelial cells: by blocking ERK1/2 and p38 mitogen-activated protein kinases as potential targets.

Journal: Asia Pacific journal of clinical nutrition 20080101

Title: [Synthesis and cytotoxicity of novel phosphorusless analogues of edelfosine].

Journal: Bioorganicheskaia khimiia 20080101

Title: Lipid rafts and metabolic energy differentially determine uptake of anti-cancer alkylphospholipids in lymphoma versus carcinoma cells.

Journal: Biochemical pharmacology 20071115

Title: Roles of brain phosphatidylinositol-specific phospholipase C and diacylglycerol lipase in centrally administered histamine-induced adrenomedullary outflow in rats.

Journal: European journal of pharmacology 20071001

Title: Effect of alkyl-lysophospholipids on some aspects of the metabolism of Leishmania donovani.

Journal: The Journal of parasitology 20071001

Title: A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells.

Journal: Molecular cancer therapeutics 20070801

Title: Surface-active properties of the antitumour ether lipid 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine (edelfosine).

Journal: Biochimica et biophysica acta 20070701

Title: Mitochondrial-derived ROS in edelfosine-induced apoptosis in yeasts and tumor cells.

Journal: Acta pharmacologica Sinica 20070601

Title: A novel ATP-binding cassette transporter from Leishmania is involved in transport of phosphatidylcholine analogues and resistance to alkyl-phospholipids.

Journal: Molecular microbiology 20070601

Title: Clustering of monosialyl-Gb5 initiates downstream signalling events leading to invasion of MCF-7 breast cancer cells.

Journal: The Biochemical journal 20070201

Title: Edelfosine protects precultured heart fragments against the invasion of malignant cells through altered sialylation.

Journal: Oncology reports 20070201

Title: Edelfosine and perifosine induce selective apoptosis in multiple myeloma by recruitment of death receptors and downstream signaling molecules into lipid rafts.

Journal: Blood 20070115

Title: Resistance to alkyl-lysophospholipid-induced apoptosis due to downregulated sphingomyelin synthase 1 expression with consequent sphingomyelin- and cholesterol-deficiency in lipid rafts.

Journal: The Biochemical journal 20070115

Title: Phospholipase C and myosin light chain kinase inhibition define a common step in actin regulation during cytokinesis.

Journal: BMC cell biology 20070101

Title: Involvement of phosphatidylinositol-phospholipase C in immune response to Salmonella lipopolysacharide in chicken macrophage cells (HD11).

Journal: International immunopharmacology 20061205

Title: Ultrastructural analysis of edelfosine-treated trypomastigotes and amastigotes of Trypanosoma cruzi.

Journal: Parasitology research 20061201

Title: PAR-1-dependent pp60src activation is dependent on protein kinase C and increased [Ca2+]: evidence that pp60src does not regulate PAR-1-dependent Ca2+ entry in human platelets.

Journal: Journal of thrombosis and haemostasis : JTH 20061201

Title: Phospholipase C isoforms are localized at the cleavage furrow during cytokinesis.

Journal: Journal of biochemistry 20061201

Title: Beta-1, 3-glucan modulates PKC signalling in Lymnaea stagnalis defence cells: a role for PKC in H2O2 production and downstream ERK activation.

Journal: The Journal of experimental biology 20061201

Title: Aspects of the cytological activity of edelfosine, miltefosine, and ilmofosine in Leishmania donovani.

Journal: The Journal of parasitology 20061001

Title: Angiotensin II regulates neuronal excitability via phosphatidylinositol 4,5-bisphosphate-dependent modulation of Kv7 (M-type) K+ channels.

Journal: The Journal of physiology 20060815

Title: Effects of the anti-neoplastic agent ET-18-OCH3 and some analogs on the biophysical properties of model membranes.

Journal: International journal of pharmaceutics 20060802

Title: Inositol triphosphate participates in an oestradiol nongenomic signalling pathway involved in accelerated oviductal transport in cycling rats.

Journal: The Journal of endocrinology 20060301

Title: Brown recluse spider (Loxosceles reclusa) venom phospholipase D (PLD) generates lysophosphatidic acid (LPA).

Journal: The Biochemical journal 20051015

Title: Ethanol triggers neural crest apoptosis through the selective activation of a pertussis toxin-sensitive G protein and a phospholipase Cbeta-dependent Ca2+ transient.

Journal: Alcoholism, clinical and experimental research 20050701

Title: Anti-proliferative synergy of lysophospholipid analogues and ketoconazole against Trypanosoma cruzi (Kinetoplastida: Trypanosomatidae): cellular and ultrastructural analysis.

Journal: The Journal of antimicrobial chemotherapy 20050501

Title: A comparative study of the effect of the antineoplastic ether lipid 1-O-octadecyl-2-O-methyl-glycero-3-phosphocholine and some homologous compounds on PKC alpha and PKC epsilon.

Journal: Biochimica et biophysica acta 20050221

Title: Purging of peripheral blood stem cell transplants in AML: a predictive model based on minimal residual disease burden.

Journal: Experimental hematology 20050101

Title: Leishmanicidal activity of edelfosine, miltefosine and ilmofosine.

Journal: Basic & clinical pharmacology & toxicology 20050101

Title: ET-18-OCH3 inhibits the phosphorylation and activation of p70 S6 kinase in MCF-7 cells.

Journal: Anticancer research 20050101

Title: ET-18-OCH3 (edelfosine): a selective antitumour lipid targeting apoptosis through intracellular activation of Fas/CD95 death receptor.

Journal: Current medicinal chemistry 20041201

Title: Effect of the lysophospholipid analogues edelfosine, ilmofosine and miltefosine against Leishmania amazonensis.

Journal: The Journal of antimicrobial chemotherapy 20041001

Title: Endogenous production and exogenous exposure to nitric oxide augment doxorubicin cytotoxicity for breast cancer cells but not cardiac myoblasts.

Journal: Nitric oxide : biology and chemistry 20040501

Title: Apical and basolateral ATP-induced anion secretion in polarized human airway epithelia.

Journal: American journal of respiratory cell and molecular biology 20040301

Title: Cell membranes and apoptosis: role of cardiolipin, phosphatidylcholine, and anticancer lipid analogues.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20040201

Title: Functional cloning of the miltefosine transporter. A novel P-type phospholipid translocase from Leishmania involved in drug resistance.

Journal: The Journal of biological chemistry 20031212

Title: Fibroblast growth factors regulate prolactin transcription via an atypical Rac-dependent signaling pathway.

Journal: Molecular endocrinology (Baltimore, Md.) 20031001

Title: Lem3p is essential for the uptake and potency of alkylphosphocholine drugs, edelfosine and miltefosine.

Journal: The Journal of biological chemistry 20030919

Title: Activity, pharmacokinetics and tissue distribution of TLC ELL-12 (liposomal antitumor ether lipid) in rats with transplantable, s.c. methylnitrosourea-induced tumors.

Journal: Anti-cancer drugs 20030701

Title: Synaptic Drosophila UNC-13 is regulated by antagonistic G-protein pathways via a proteasome-dependent degradation mechanism.

Journal: Journal of neurobiology 20030215

Title: Anti-cancer alkyl-lysophospholipids inhibit the phosphatidylinositol 3-kinase-Akt/PKB survival pathway.

Journal: Anti-cancer drugs 20030201

Title: Antiprotozoal activities of phospholipid analogues.

Journal: Molecular and biochemical parasitology 20030201

Title: Preferential inactivation of paediatric solid tumour cells by sequential exposure to Merocyanine 540-mediated photodynamic therapy and Edelfosine: implications for the ex vivo purging of autologous haematopoietic stem cell grafts.

Journal: Journal of photochemistry and photobiology. B, Biology 20030201

Title: Sensitivity of oocyte-expressed epithelial Na+ channel to glibenclamide.

Journal: Biochimica et biophysica acta 20030131

Title: Signaling events mediating activation of brain ethanolamine plasmalogen hydrolysis by ceramide.

Journal: European journal of biochemistry 20030101

Title: Alkylphospholipids reversibly open epithelial tight junctions.

Journal: Anticancer research 20030101

Title: Crystal structure of phospholipase A2 complex with the hydrolysis products of platelet activating factor: equilibrium binding of fatty acid and lysophospholipid-ether at the active site may be mutually exclusive.

Journal: Biochemistry 20021217

Title: Anti-tumor effect of Merocyanine 540-mediated photochemotherapy combined with Edelfosine: potential implications for the ex vivo purging of hematopoietic stem cell grafts from breast cancer patients.

Journal: Journal of photochemistry and photobiology. B, Biology 20021101

Title: Induction of cyclooxygenase-2 in Ras-transformed human mammary epithelial cells undergoing apoptosis.

Journal: Annals of the New York Academy of Sciences 20021101

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Perturbations in choline metabolism cause neural tube defects in mouse embryos in vitro.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20020401

Title: Ether phospholipids affect mast cell histamine release with relative potency similar to that with leukocyte membrane Ca2+-ATPase activity.

Journal: Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20020401

Title: Sensitivities of Leishmania species to hexadecylphosphocholine (miltefosine), ET-18-OCH(3) (edelfosine) and amphotericin B.

Journal: Acta tropica 20020201

Title: Requirement of Ca(2+) and PKCdelta for Janus kinase 2 activation by angiotensin II: involvement of PYK2.

Journal: Molecular endocrinology (Baltimore, Md.) 20020201

Title: Choline transport in Leishmania major promastigotes and its inhibition by choline and phosphocholine analogs.

Journal: Molecular and biochemical parasitology 20020101

Title: The antitumor ether lipid ET-18-OCH(3) induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells.

Journal: Blood 20011215

Title: Regulation of eosinophil function by phosphatidylinositol-specific PLC and cytosolic PLA(2).

Journal: American journal of physiology. Lung cellular and molecular physiology 20011001

Title: Inhibitors of choline uptake and metabolism cause developmental abnormalities in neurulating mouse embryos.

Journal: Teratology 20010801

Title: Altered mitochondrial function and overgeneration of reactive oxygen species precede the induction of apoptosis by 1-O-octadecyl-2-methyl-rac-glycero-3-phosphocholine in p53-defective hepatocytes.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20010801

Title: Regulation of energy metabolism in macrophages during hypoxia. Roles of fructose 2,6-bisphosphate and ribose 1,5-bisphosphate.

Journal: The Journal of biological chemistry 20010727

Title: Alkyl-lysophospholipid 1-O-octadecyl-2-O-methyl- glycerophosphocholine induces invasion through episialin-mediated neutralization of E-cadherin in human mammary MCF-7 cells in vitro.

Journal: International journal of cancer 20010515

Title: Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis.

Journal: International journal of radiation oncology, biology, physics 20010201

Title: Protein kinase CbetaII activation by 1-beta-D-arabinofuranosylcytosine is antagonistic to stimulation of apoptosis and Bcl-2alpha down-regulation.

Journal: The Journal of biological chemistry 19970919

Title: Hexadecanoic and neuraminic acid incorporations in two rat colon carcinoma cell lipids: selective influence of 1-O-octadecyl 2-O-methyl-3-phosphocholine on glycerolipid and ganglioside biosynthesis.

Journal: Archives internationales de physiologie et de biochimie 19900801

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:77286-66-9 Molecular Formula|77286-66-9 MDL|77286-66-9 SMILES|77286-66-9 3,5,9-Trioxa-4-phosphaheptacosan-1-aminium,4-hydroxy-7-methoxy-N,N,N-trimethyl-, inner salt, 4-oxide, (7R)-