Edelfosine, (S)- (BioDeep_00000847281)
代谢物信息卡片
化学式: C27H58NO6P (523.4002)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCCCCCCCCCCOCC(COP(=O)([O-])OCC[N+](C)(C)C)OC
InChI: InChI=1S/C27H58NO6P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-32-25-27(31-5)26-34-35(29,30)33-24-22-28(2,3)4/h27H,6-26H2,1-5H3/t27-/m0/s1
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
亚细胞结构定位 | 关联基因列表 |
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文献列表
- C Rodríguez-Nogales, S Mura, P Couvreur, M J Blanco-Prieto. Squalenoyl-gemcitabine/edelfosine nanoassemblies: Anticancer activity in pediatric cancer cells and pharmacokinetic profile in mice.
International journal of pharmaceutics.
2020 May; 582(?):119345. doi:
10.1016/j.ijpharm.2020.119345
. [PMID: 32311470] - Yu Sun, Zhong-Liang Sun. Transferrin-conjugated polymeric nanomedicine to enhance the anticancer efficacy of edelfosine in acute myeloid leukemia.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie.
2016 Oct; 83(?):51-57. doi:
10.1016/j.biopha.2016.05.046
. [PMID: 27470549] - Mark Mahadeo, Safia Nathoo, Suriakarthiga Ganesan, Michael Driedger, Vanina Zaremberg, Elmar J Prenner. Disruption of lipid domain organization in monolayers of complex yeast lipid extracts induced by the lysophosphatidylcholine analogue edelfosine in vivo.
Chemistry and physics of lipids.
2015 Oct; 191(?):153-62. doi:
10.1016/j.chemphyslip.2015.09.004
. [PMID: 26386399] - Zuzana Berkova, Shu Wang, Xue Ao, Jillian F Wise, Frank K Braun, Abdol H Rezaeian, Lalit Sehgal, David M Goldenberg, Felipe Samaniego. CD74 interferes with the expression of fas receptor on the surface of lymphoma cells.
Journal of experimental & clinical cancer research : CR.
2014 Oct; 33(?):80. doi:
10.1186/s13046-014-0080-y
. [PMID: 25304249] - Michał Flasiński, Katarzyna Hąc-Wydro, Paweł Wydro, Patrycja Dynarowicz-Łątka. Influence of platelet-activating factor, lyso-platelet-activating factor and edelfosine on Langmuir monolayers imitating plasma membranes of cell lines differing in susceptibility to anti-cancer treatment: the effect of plasmalogen level.
Journal of the Royal Society, Interface.
2014 Jun; 11(95):20131103. doi:
10.1098/rsif.2013.1103
. [PMID: 24694892] - Consuelo Gajate, Faustino Mollinedo. Lipid rafts, endoplasmic reticulum and mitochondria in the antitumor action of the alkylphospholipid analog edelfosine.
Anti-cancer agents in medicinal chemistry.
2014 May; 14(4):509-27. doi:
10.2174/1871520614666140309222259
. [PMID: 24628241] - Pranati Samadder, Hoe-Sup Byun, Robert Bittman, Gilbert Arthur. A fluorescent alkyllysophospholipid analog exhibits selective cytotoxicity against the hormone-insensitive prostate cancer cell line PC3.
Anti-cancer agents in medicinal chemistry.
2014 May; 14(4):528-38. doi:
10.2174/1871520614666140309223603
. [PMID: 24628239] - Álvaro Cuesta-Marbán, Javier Botet, Ola Czyz, Luis M Cacharro, Consuelo Gajate, Valentín Hornillos, Javier Delgado, Hui Zhang, Francisco Amat-Guerri, A Ulises Acuña, Christopher R McMaster, José Luis Revuelta, Vanina Zaremberg, Faustino Mollinedo. Drug uptake, lipid rafts, and vesicle trafficking modulate resistance to an anticancer lysophosphatidylcholine analogue in yeast.
The Journal of biological chemistry.
2013 Mar; 288(12):8405-8418. doi:
10.1074/jbc.m112.425769
. [PMID: 23335509] - Ola Czyz, Teshager Bitew, Alvaro Cuesta-Marbán, Christopher R McMaster, Faustino Mollinedo, Vanina Zaremberg. Alteration of plasma membrane organization by an anticancer lysophosphatidylcholine analogue induces intracellular acidification and internalization of plasma membrane transporters in yeast.
The Journal of biological chemistry.
2013 Mar; 288(12):8419-8432. doi:
10.1074/jbc.m112.425744
. [PMID: 23344949] - Wim J van Blitterswijk, Marcel Verheij. Anticancer mechanisms and clinical application of alkylphospholipids.
Biochimica et biophysica acta.
2013 Mar; 1831(3):663-74. doi:
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Proceedings of the National Academy of Sciences of the United States of America.
2013 Jan; 110(5):E358-67. doi:
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Nanomedicine (London, England).
2012 May; 7(5):679-90. doi:
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Cell death & disease.
2011 May; 2(?):e158. doi:
10.1038/cddis.2011.41
. [PMID: 21593790] - Pablo Ríos-Marco, José M Jiménez-López, Carmen Marco, Josefa L Segovia, María P Carrasco. Antitumoral alkylphospholipids induce cholesterol efflux from the plasma membrane in HepG2 cells.
The Journal of pharmacology and experimental therapeutics.
2011 Mar; 336(3):866-73. doi:
10.1124/jpet.110.172890
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British journal of pharmacology.
2011 Jan; 162(2):464-79. doi:
10.1111/j.1476-5381.2010.01044.x
. [PMID: 20955368] - Teshager Bitew, Christopher E Sveen, Belinda Heyne, Vanina Zaremberg. Vitamin E prevents lipid raft modifications induced by an anti-cancer lysophospholipid and abolishes a Yap1-mediated stress response in yeast.
The Journal of biological chemistry.
2010 Aug; 285(33):25731-42. doi:
10.1074/jbc.m110.122200
. [PMID: 20538604] - María P Carrasco, José M Jiménez-López, Pablo Ríos-Marco, Josefa L Segovia, Carmen Marco. Disruption of cellular cholesterol transport and homeostasis as a novel mechanism of action of membrane-targeted alkylphospholipid analogues.
British journal of pharmacology.
2010 May; 160(2):355-66. doi:
10.1111/j.1476-5381.2010.00689.x
. [PMID: 20423345] - A Estella-Hermoso de Mendoza, M A Campanero, F Mollinedo, M J Blanco-Príeto. Comparative study of A HPLC-MS assay versus an UHPLC-MS/MS for anti-tumoral alkyl lysophospholipid edelfosine determination in both biological samples and in lipid nanoparticulate systems.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2009 Dec; 877(31):4035-41. doi:
10.1016/j.jchromb.2009.10.020
. [PMID: 19896423] - Marie Bénéteau, Mathieu Pizon, Benjamin Chaigne-Delalande, Sophie Daburon, Patrick Moreau, Francesca De Giorgi, François Ichas, Amélie Rebillard, Marie-Thérèse Dimanche-Boitrel, Jean-Luc Taupin, Jean-François Moreau, Patrick Legembre. Localization of Fas/CD95 into the lipid rafts on down-modulation of the phosphatidylinositol 3-kinase signaling pathway.
Molecular cancer research : MCR.
2008 Apr; 6(4):604-13. doi:
10.1158/1541-7786.mcr-07-0331
. [PMID: 18403639] - T Nieto-Miguel, C Gajate, F González-Camacho, F Mollinedo. Proapoptotic role of Hsp90 by its interaction with c-Jun N-terminal kinase in lipid rafts in edelfosine-mediated antileukemic therapy.
Oncogene.
2008 Mar; 27(12):1779-87. doi:
10.1038/sj.onc.1210816
. [PMID: 17891170] - Takahiro Shimizu, Naoko Yamaguchi, Shoshiro Okada, Lianyi Lu, Tsuyoshi Sasaki, Kunihiko Yokotani. Roles of brain phosphatidylinositol-specific phospholipase C and diacylglycerol lipase in centrally administered histamine-induced adrenomedullary outflow in rats.
European journal of pharmacology.
2007 Oct; 571(2-3):138-44. doi:
10.1016/j.ejphar.2007.05.061
. [PMID: 17628524] - Arnold H van der Luit, Stefan R Vink, Jeffrey B Klarenbeek, Daniel Perrissoud, Eric Solary, Marcel Verheij, Wim J van Blitterswijk. A new class of anticancer alkylphospholipids uses lipid rafts as membrane gateways to induce apoptosis in lymphoma cells.
Molecular cancer therapeutics.
2007 Aug; 6(8):2337-45. doi:
10.1158/1535-7163.mct-07-0202
. [PMID: 17699729] - Esther Castanys-Muñoz, Nele Alder-Baerens, Thomas Pomorski, Francisco Gamarro, Santiago Castanys. A novel ATP-binding cassette transporter from Leishmania is involved in transport of phosphatidylcholine analogues and resistance to alkyl-phospholipids.
Molecular microbiology.
2007 Jun; 64(5):1141-53. doi:
10.1111/j.1365-2958.2007.05653.x
. [PMID: 17542911] - Arnold H Van der Luit, Marianne Budde, Shuraila Zerp, Wendy Caan, Jeffrey B Klarenbeek, Marcel Verheij, Wim J Van Blitterswijk. Resistance to alkyl-lysophospholipid-induced apoptosis due to downregulated sphingomyelin synthase 1 expression with consequent sphingomyelin- and cholesterol-deficiency in lipid rafts.
The Biochemical journal.
2007 Jan; 401(2):541-9. doi:
10.1042/bj20061178
. [PMID: 17049047] - R M Santa-Rita, H S Barbosa, S L de Castro. Ultrastructural analysis of edelfosine-treated trypomastigotes and amastigotes of Trypanosoma cruzi.
Parasitology research.
2006 Dec; 100(1):187-90. doi:
10.1007/s00436-006-0250-8
. [PMID: 16855821] - M T Harper, S O Sage. 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 of thrombosis and haemostasis : JTH.
2006 Dec; 4(12):2695-703. doi:
10.1111/j.1538-7836.2006.02207.x
. [PMID: 16965542] - Yoko Naito, Masashi Okada, Hitoshi Yagisawa. Phospholipase C isoforms are localized at the cleavage furrow during cytokinesis.
Journal of biochemistry.
2006 Dec; 140(6):785-91. doi:
10.1093/jb/mvj209
. [PMID: 17041247] - Alejandro Torrecillas, J Daniel Aroca-Aguilar, Francisco J Aranda, Consuelo Gajate, Faustino Mollinedo, Senena Corbalán-García, Ana de Godos, Juan C Gómez-Fernández. Effects of the anti-neoplastic agent ET-18-OCH3 and some analogs on the biophysical properties of model membranes.
International journal of pharmaceutics.
2006 Aug; 318(1-2):28-40. doi:
10.1016/j.ijpharm.2006.03.008
. [PMID: 16624506] - Teresa Nieto-Miguel, Consuelo Gajate, Faustino Mollinedo. Differential targets and subcellular localization of antitumor alkyl-lysophospholipid in leukemic versus solid tumor cells.
The Journal of biological chemistry.
2006 May; 281(21):14833-40. doi:
10.1074/jbc.m511251200
. [PMID: 16540473] - Vanina Zaremberg, Consuelo Gajate, Luis M Cacharro, Faustino Mollinedo, Christopher R McMaster. Cytotoxicity of an anti-cancer lysophospholipid through selective modification of lipid raft composition.
The Journal of biological chemistry.
2005 Nov; 280(45):38047-58. doi:
10.1074/jbc.m502849200
. [PMID: 16155007] - Sangderk Lee, Kevin R Lynch. Brown recluse spider (Loxosceles reclusa) venom phospholipase D (PLD) generates lysophosphatidic acid (LPA).
The Biochemical journal.
2005 Oct; 391(Pt 2):317-23. doi:
10.1042/bj20050043
. [PMID: 15926888] - Ricardo M Santa-Rita, Renee Lira, Helene Santos Barbosa, Julio A Urbina, Solange L de Castro. Anti-proliferative synergy of lysophospholipid analogues and ketoconazole against Trypanosoma cruzi (Kinetoplastida: Trypanosomatidae): cellular and ultrastructural analysis.
The Journal of antimicrobial chemotherapy.
2005 May; 55(5):780-4. doi:
10.1093/jac/dki087
. [PMID: 15790672] - Ernesto Quesada, Javier Delgado, Consuelo Gajate, Faustino Mollinedo, A Ulises Acuña, Francisco Amat-Guerri. Fluorescent phenylpolyene analogues of the ether phospholipid edelfosine for the selective labeling of cancer cells.
Journal of medicinal chemistry.
2004 Oct; 47(22):5333-5. doi:
10.1021/jm049808a
. [PMID: 15481970] - Ricardo M Santa-Rita, Andréa Henriques-Pons, Helene S Barbosa, Solange L de Castro. Effect of the lysophospholipid analogues edelfosine, ilmofosine and miltefosine against Leishmania amazonensis.
The Journal of antimicrobial chemotherapy.
2004 Oct; 54(4):704-10. doi:
10.1093/jac/dkh380
. [PMID: 15329361] - F Javier Pérez-Victoria, Francisco Gamarro, Marc Ouellette, Santiago Castanys. Functional cloning of the miltefosine transporter. A novel P-type phospholipid translocase from Leishmania involved in drug resistance.
The Journal of biological chemistry.
2003 Dec; 278(50):49965-71. doi:
10.1074/jbc.m308352200
. [PMID: 14514670] - Twila A Jackson, David M Koterwas, Melissa A Morgan, Andrew P Bradford. Fibroblast growth factors regulate prolactin transcription via an atypical Rac-dependent signaling pathway.
Molecular endocrinology (Baltimore, Md.).
2003 Oct; 17(10):1921-30. doi:
10.1210/me.2003-0167
. [PMID: 12843210] - Pamela K Hanson, Lynn Malone, Jennifer L Birchmore, J Wylie Nichols. Lem3p is essential for the uptake and potency of alkylphosphocholine drugs, edelfosine and miltefosine.
The Journal of biological chemistry.
2003 Sep; 278(38):36041-50. doi:
10.1074/jbc.m305263200
. [PMID: 12842877] - Pranati Samadder, Christina Richards, Robert Bittman, Rajinder Pal Bhullar, Gilbert Arthur. The antitumor ether lipid 1-Q-octadecyl-2-O-methyl-rac-glycerophosphocholine (ET-18-OCH3) inhibits the association between Ras and Raf-1.
Anticancer research.
2003 May; 23(3B):2291-5. doi:
. [PMID: 12894505]
- Rupinder Bhamra, Lois E Bolcsak, Patricia Roberts, Rachel Stevens, Christopher Cavanaugh, Christine E Swenson. Toxicity and disposition of TLC ELL-12 (liposomal antitumor ether lipid) in Sprague-Dawley rats.
Anti-cancer drugs.
2003 Mar; 14(3):183-91. doi:
10.1097/00001813-200303000-00001
. [PMID: 12634612] - Bharathi Aravamudan, Kendal Broadie. Synaptic Drosophila UNC-13 is regulated by antagonistic G-protein pathways via a proteasome-dependent degradation mechanism.
Journal of neurobiology.
2003 Feb; 54(3):417-38. doi:
10.1002/neu.10142
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Anticancer research.
2003 Jan; 23(1A):27-32. doi:
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. [PMID: 12680191] - C Gajate, F Mollinedo. The antitumor ether lipid ET-18-OCH(3) induces apoptosis through translocation and capping of Fas/CD95 into membrane rafts in human leukemic cells.
Blood.
2001 Dec; 98(13):3860-3. doi:
10.1182/blood.v98.13.3860
. [PMID: 11739199] - G A Ruiter, M Verheij, S F Zerp, W J van Blitterswijk. Alkyl-lysophospholipids as anticancer agents and enhancers of radiation-induced apoptosis.
International journal of radiation oncology, biology, physics.
2001 Feb; 49(2):415-9. doi:
10.1016/s0360-3016(00)01476-0
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British journal of haematology.
2000 Dec; 111(4):1145-52. doi:
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Cancer research.
1999 Oct; 59(19):4808-15. doi:
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British journal of pharmacology.
1999 Jul; 127(6):1502-10. doi:
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Experimental hematology.
1999 Mar; 27(3):470-8. doi:
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Journal of cell science.
1999 Feb; 112 ( Pt 3)(?):415-22. doi:
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Cell death and differentiation.
1999 Feb; 6(2):155-65. doi:
10.1038/sj.cdd.4400465
. [PMID: 10200562] - I H McKillop, C M Schmidt, P A Cahill, J V Sitzmann. Altered Gq/G11 guanine nucleotide regulatory protein expression in a rat model of hepatocellular carcinoma: role in mitogenesis.
Hepatology (Baltimore, Md.).
1999 Feb; 29(2):371-8. doi:
10.1002/hep.510290201
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Immunopharmacology.
1998 Aug; 40(2):163-71. doi:
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Molecular pharmacology.
1998 Apr; 53(4):602-12. doi:
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Biochimica et biophysica acta.
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Cancer chemotherapy and pharmacology.
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Immunopharmacology.
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Lipids.
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British journal of pharmacology.
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Lipids.
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The Journal of clinical investigation.
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Cancer research.
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European journal of biochemistry.
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Anticancer research.
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Leukemia research.
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Archives of physiology and biochemistry.
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Lipids.
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International journal of immunopharmacology.
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Biochemical Society transactions.
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