N,N-Dimethylsphingosine (BioDeep_00000002516)

   

human metabolite Endogenous natural product


代谢物信息卡片


(S-(R,S-(e)))-2-(dimethylamino)-4-Octadecene-1,3-diol

化学式: C20H41NO2 (327.3137)
中文名称: N,N-二甲基-D-赤型鞘氨醇(PKC抑制剂), N,N-二甲基鞘氨醇
谱图信息: 最多检出来源 Mus musculus(plant) 5.56%

分子结构信息

SMILES: CCCCCCCCCCCCC/C=C/[C@@H](O)[C@H](CO)N(C)C
InChI: InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1

描述信息

N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase. It is a natural metabolite of sphingosine in some cancer cell lines and tissues. N,N-Dimethylsphingosine inhibited U937 cell sphingosine kinase with a Ki value of 3.1 µM. N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C. N,N-Dimethylsphingosine (DMS) has recently been identified as an inducer of pain in a rat model of chronic pain. (PMID: 22267119) It has properties similar to capsaicin (PMID: 16740613). Other studies have indicated that DMS inhibits airway inflammation in asthma (PMID: 18359884) and is cardioprotective (PMID: 16831409).
N,N-Dimethylsphingosine is an inhibitor of sphingosine kinase. It is a natural metabolite of sphingosine in some cancer cell lines and tissues.1 N,N-Dimethylsphingosine inhibited U937 cell sphingosine kinase with a Ki value of 3.1 ?M.2 N,N-Dimethylsphingosine induces apoptosis, but it is not an inhibitor of protein kinase C. [HMDB]
D004791 - Enzyme Inhibitors

同义名列表

15 个代谢物同义名

(S-(R,S-(e)))-2-(dimethylamino)-4-Octadecene-1,3-diol; (2S,3R,4E)-2-(dimethylamino)octadec-4-ene-1,3-diol; (2R,3S,e)-2-(Dimethylamino)octadec-4-ene-1,3-diol; 2S-(dimethylamino)-4E-octadecene-1,3R-diol; 2-(dimethylamino)octadec-4-ene-1,3-diol; N,N-Dimethyl-D-erythro-sphingosine]; N,N-Dimethyl-D-erythro-sphingosine; D-Erythro-N,N-dimethylsphingosine; N,N-Dimethyl-erythro-sphingosine; N,N-dimethylsphing-4-enine; N,N-Dimethylsphingosine; N,N-DMS; DMS CPD; dms; N,N-dimethylsphingosine



数据库引用编号

19 个数据库交叉引用编号

分类词条

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)

9 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
Cytoplasm 13 EGFR, ISG20, MAPK14, MAPK3, MAPK8, NFKB1, PIK3C3, PIK3CA, PRKX, S1PR1, SPHK1, SPHK2, TNK1
Peripheral membrane protein 2 SPHK1, TNK1
Endosome membrane 2 EGFR, SPHK1
Endoplasmic reticulum membrane 2 CD4, EGFR
Cytoplasmic vesicle, autophagosome 1 PIK3C3
Nucleus 9 EGFR, ISG20, MAPK14, MAPK3, MAPK8, NFKB1, PRKX, SPHK1, SPHK2
autophagosome 1 PIK3C3
cytosol 10 MAPK14, MAPK3, MAPK8, NFKB1, NGF, PIK3C3, PIK3CA, PRKCQ, SPHK1, SPHK2
dendrite 1 NGF
phosphatidylinositol 3-kinase complex, class III 1 PIK3C3
nucleoplasm 9 ISG20, MAPK14, MAPK3, MAPK8, NFKB1, PRKX, S1PR1, SPHK1, SPHK2
Cell membrane 5 CD4, EGFR, S1PR1, SPHK1, TNF
lamellipodium 1 PIK3CA
ruffle membrane 1 EGFR
Early endosome membrane 2 EGFR, SPHK1
Multi-pass membrane protein 1 S1PR1
Synapse 2 MAPK8, SPHK1
cell junction 1 EGFR
cell surface 2 EGFR, TNF
glutamatergic synapse 4 EGFR, MAPK14, MAPK3, PIK3C3
Golgi apparatus 1 MAPK3
Golgi membrane 1 EGFR
lysosomal membrane 2 EGF, SPHK2
mitochondrial inner membrane 1 SPHK2
neuronal cell body 1 TNF
synaptic vesicle 1 NGF
Presynapse 2 S1PR1, SPHK1
endosome 3 EGFR, PIK3C3, S1PR1
plasma membrane 11 CD4, EGF, EGFR, F2, MAPK3, PIK3CA, PRKCQ, S1PR1, SPHK1, TNF, TNK1
Membrane 6 EGF, EGFR, PIK3C3, SPHK1, SPHK2, TNK1
apical plasma membrane 1 EGFR
axon 2 MAPK8, NGF
basolateral plasma membrane 1 EGFR
caveola 1 MAPK3
extracellular exosome 2 EGF, F2
endoplasmic reticulum 1 SPHK2
extracellular space 6 EGF, EGFR, F2, IL6, NGF, TNF
perinuclear region of cytoplasm 2 EGFR, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 MAPK14, MAPK3, NFKB1, SPHK2
protein-containing complex 1 EGFR
intracellular membrane-bounded organelle 3 S1PR1, SPHK1, SPHK2
Single-pass type I membrane protein 2 CD4, EGFR
Secreted 3 F2, IL6, NGF
extracellular region 7 EGF, F2, IL6, MAPK14, NFKB1, NGF, TNF
transcription regulator complex 1 NFKB1
centriolar satellite 1 PRKCQ
nuclear membrane 1 EGFR
external side of plasma membrane 3 CD4, S1PR1, TNF
nucleolus 1 ISG20
midbody 1 PIK3C3
Cytoplasm, P-body 1 ISG20
P-body 1 ISG20
Early endosome 2 CD4, MAPK3
Membrane, clathrin-coated pit 1 SPHK1
clathrin-coated pit 1 SPHK1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Mitochondrion inner membrane 1 SPHK2
Membrane raft 4 CD4, EGFR, S1PR1, TNF
Cell junction, focal adhesion 1 MAPK3
focal adhesion 2 EGFR, MAPK3
GABA-ergic synapse 1 PIK3C3
Peroxisome 1 PIK3C3
intracellular vesicle 1 EGFR
PML body 1 ISG20
collagen-containing extracellular matrix 1 F2
axoneme 1 PIK3C3
nuclear speck 1 MAPK14
Late endosome 2 MAPK3, PIK3C3
receptor complex 1 EGFR
chromatin 1 NFKB1
phagocytic cup 1 TNF
phagocytic vesicle membrane 1 PIK3C3
cytoskeleton 1 MAPK3
Nucleus, nucleolus 1 ISG20
spindle pole 1 MAPK14
blood microparticle 1 F2
nuclear envelope 1 MAPK3
endosome lumen 1 NGF
Membrane, caveola 1 MAPK3
phagophore assembly site 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type I 1 PIK3C3
phosphatidylinositol 3-kinase complex, class III, type II 1 PIK3C3
pseudopodium 1 MAPK3
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 MAPK14, NFKB1
Golgi lumen 2 F2, NGF
endoplasmic reticulum lumen 4 CD4, F2, IL6, MAPK3
platelet alpha granule lumen 1 EGF
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 NFKB1
endocytic vesicle 1 SPHK1
immunological synapse 1 PRKCQ
presynaptic endosome 1 PIK3C3
aggresome 1 PRKCQ
clathrin-coated endocytic vesicle membrane 3 CD4, EGF, EGFR
Cajal body 1 ISG20
basal dendrite 1 MAPK8
nucleosome 1 SPHK2
Nucleus, Cajal body 1 ISG20
[Isoform 2]: Lysosome membrane 1 SPHK2
postsynaptic endosome 1 PIK3C3
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
T cell receptor complex 1 CD4
Autolysosome 1 PIK3C3
interleukin-6 receptor complex 1 IL6
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Shy Yang, Jin-Ping Hu, Yan Li. The involvement of blood cells in the phosphorylation of the selective sphingosine-1-phosphate receptor 1 agonist SYL-927. Die Pharmazie. 2019 02; 74(2):107-110. doi: 10.1691/ph.2019.8809. [PMID: 30782260]
  • Yan-Chang Lei, Ling-Ling Yang, Wen Li, Pan Luo, Pei-Fen Zheng. Inhibition of sphingosine kinase 1 ameliorates acute liver failure by reducing high-mobility group box 1 cytoplasmic translocation in liver cells. World journal of gastroenterology. 2015 Dec; 21(46):13055-63. doi: 10.3748/wjg.v21.i46.13055. [PMID: 26676341]
  • Caroline H Johnson, Gary J Patti, Jean-Philippe Courade, Leah P Shriver, Linh T Hoang, Marianne Manchester, Gary Siuzdak. Alterations in Spinal Cord Metabolism during Treatment of Neuropathic Pain. Journal of neuroimmune pharmacology : the official journal of the Society on NeuroImmune Pharmacology. 2015 Sep; 10(3):396-401. doi: 10.1007/s11481-015-9624-y. [PMID: 26232265]
  • Daniel Plano, Shantu Amin, Arun K Sharma. Importance of sphingosine kinase (SphK) as a target in developing cancer therapeutics and recent developments in the synthesis of novel SphK inhibitors. Journal of medicinal chemistry. 2014 Jul; 57(13):5509-24. doi: 10.1021/jm4011687. [PMID: 24471412]
  • Li-Wen Lai, Kim-Chong Yong, Yeong-Hau H Lien. Pharmacologic recruitment of regulatory T cells as a therapy for ischemic acute kidney injury. Kidney international. 2012 May; 81(10):983-992. doi: 10.1038/ki.2011.412. [PMID: 22189844]
  • Laurence Chan. Harnessing regulatory T cells for therapeutic purposes. Kidney international. 2012 May; 81(10):935-936. doi: 10.1038/ki.2012.29. [PMID: 22543901]
  • Tian Lan, Weihua Liu, Xi Xie, Suowen Xu, Kaipeng Huang, Jing Peng, Xiaoyan Shen, Peiqing Liu, Lijing Wang, Pu Xia, Heqing Huang. Sphingosine kinase-1 pathway mediates high glucose-induced fibronectin expression in glomerular mesangial cells. Molecular endocrinology (Baltimore, Md.). 2011 Dec; 25(12):2094-105. doi: 10.1210/me.2011-0095. [PMID: 21998146]
  • Keith P Alden, Sandrine Dhondt-Cordelier, Kerrie L McDonald, Theresa J Reape, Carl K-Y Ng, Paul F McCabe, Christopher J Leaver. Sphingolipid long chain base phosphates can regulate apoptotic-like programmed cell death in plants. Biochemical and biophysical research communications. 2011 Jul; 410(3):574-80. doi: 10.1016/j.bbrc.2011.06.028. [PMID: 21683064]
  • Fang-Cheng Bi, Quan-Fang Zhang, Zhe Liu, Ce Fang, Jian Li, Jian-Bin Su, Jean T Greenberg, Hong-Bin Wang, Nan Yao. A conserved cysteine motif is critical for rice ceramide kinase activity and function. PloS one. 2011 Mar; 6(3):e18079. doi: 10.1371/journal.pone.0018079. [PMID: 21483860]
  • Tian Lan, Huichang Bi, Weihua Liu, Xi Xie, Suowen Xu, Heqing Huang. Simultaneous determination of sphingosine and sphingosine 1-phosphate in biological samples by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Mar; 879(7-8):520-6. doi: 10.1016/j.jchromb.2011.01.015. [PMID: 21292568]
  • Wei-Ching Huang, Chia-Ling Chen, Yee-Shin Lin, Chiou-Feng Lin. Apoptotic sphingolipid ceramide in cancer therapy. Journal of lipids. 2011; 2011(?):565316. doi: 10.1155/2011/565316. [PMID: 21490804]
  • Joanna M Woodcock, Yuefang Ma, Carl Coolen, Duyen Pham, Claire Jones, Angel F Lopez, Stuart M Pitson. Sphingosine and FTY720 directly bind pro-survival 14-3-3 proteins to regulate their function. Cellular signalling. 2010 Sep; 22(9):1291-9. doi: 10.1016/j.cellsig.2010.04.004. [PMID: 20403428]
  • Tomas Blom, Nina Bergelin, Annika Meinander, Christoffer Löf, J Peter Slotte, John E Eriksson, Kid Törnquist. An autocrine sphingosine-1-phosphate signaling loop enhances NF-kappaB-activation and survival. BMC cell biology. 2010 Jun; 11(?):45. doi: 10.1186/1471-2121-11-45. [PMID: 20573281]
  • Robert A McDonald, Susan Pyne, Nigel J Pyne, Anne Grant, Cherry L Wainwright, Roger M Wadsworth. The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia. British journal of pharmacology. 2010 Feb; 159(3):543-53. doi: 10.1111/j.1476-5381.2009.00533.x. [PMID: 20015089]
  • Xianglan Liu, Wei Wu, Qiang Li, Xuliang Huang, Bo Chen, Jing Du, Keseng Zhao, Qiaobing Huang. Effect of sphingosine 1-phosphate on morphological and functional responses in endothelia and venules after scalding injury. Burns : journal of the International Society for Burn Injuries. 2009 Dec; 35(8):1171-9. doi: 10.1016/j.burns.2009.02.012. [PMID: 19520517]
  • Antonina Kolmakova, Mohanraj Rajesh, David Zang, Roberto Pili, Subroto Chatterjee. VEGF recruits lactosylceramide to induce endothelial cell adhesion molecule expression and angiogenesis in vitro and in vivo. Glycoconjugate journal. 2009 Jul; 26(5):547-58. doi: 10.1007/s10719-008-9206-9. [PMID: 19219548]
  • Michael ter Braak, Kerstin Danneberg, Karin Lichte, Kerstin Liphardt, Nicholas T Ktistakis, Stuart M Pitson, Timothy Hla, Karl H Jakobs, Dagmar Meyer zu Heringdorf. Galpha(q)-mediated plasma membrane translocation of sphingosine kinase-1 and cross-activation of S1P receptors. Biochimica et biophysica acta. 2009 May; 1791(5):357-70. doi: 10.1016/j.bbalip.2009.01.019. [PMID: 19830907]
  • R Jason Kirby, Ying Jin, Jian Fu, Jimena Cubillos, Debi Swertfeger, Lois J Arend. Dynamic regulation of sphingosine-1-phosphate homeostasis during development of mouse metanephric kidney. American journal of physiology. Renal physiology. 2009 Mar; 296(3):F634-41. doi: 10.1152/ajprenal.90232.2008. [PMID: 19073640]
  • Arthur C M Mulders, Marie-Jeanne Mathy, Dagmar Meyer zu Heringdorf, Michael ter Braak, Najat Hajji, Dominique C Olthof, Martin C Michel, Astrid E Alewijnse, Stephan L M Peters. Activation of sphingosine kinase by muscarinic receptors enhances NO-mediated and attenuates EDHF-mediated vasorelaxation. Basic research in cardiology. 2009 Jan; 104(1):50-9. doi: 10.1007/s00395-008-0744-x. [PMID: 18777003]
  • David R Gude, Sergio E Alvarez, Steven W Paugh, Poulami Mitra, JiaDe Yu, Rachael Griffiths, Suzanne E Barbour, Sheldon Milstien, Sarah Spiegel. Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a "come-and-get-me" signal. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2008 Aug; 22(8):2629-38. doi: 10.1096/fj.08-107169. [PMID: 18362204]
  • Sarah T Pruett, Anatoliy Bushnev, Kerri Hagedorn, Madhura Adiga, Christopher A Haynes, M Cameron Sullards, Dennis C Liotta, Alfred H Merrill. Biodiversity of sphingoid bases ('sphingosines') and related amino alcohols. Journal of lipid research. 2008 Aug; 49(8):1621-39. doi: 10.1194/jlr.r800012-jlr200. [PMID: 18499644]
  • Ji-Yeong Jo, Hyo-Lim Kim, Yun-Kyung Lee, Hideaki Tomura, Yoe-Sik Bae, Fumikazu Okajima, Dong-Soon Im. N,N-Dimethyl-D-erythro-sphingosine inhibits store-operated Ca2+ entry in U937 monocytes. Journal of pharmacological sciences. 2008 Jul; 107(3):303-7. doi: 10.1254/jphs.08078fp. [PMID: 18635921]
  • Hyo-Lim Kim, Mijin Han, Dong-Soon Im. Differential signaling of sphingosine derivatives in U937 human monocytes depends on the degree of N-methylation. Prostaglandins & other lipid mediators. 2008 Jun; 86(1-4):68-72. doi: 10.1016/j.prostaglandins.2008.03.003. [PMID: 18467142]
  • Hyo-Lim Kim, Santosh J Sacket, Mijin Han, Dong-Soon Im. Characterization of N,N,-dimethyl-D-erythro-sphingosine-induced apoptosis and signaling in U937 cells: independence of sphingosine kinase inhibition. Prostaglandins & other lipid mediators. 2008 Jun; 86(1-4):18-25. doi: 10.1016/j.prostaglandins.2008.01.001. [PMID: 18316219]
  • Bei You, Aixia Ren, Guijun Yan, Jianxin Sun. Activation of sphingosine kinase-1 mediates inhibition of vascular smooth muscle cell apoptosis by hyperglycemia. Diabetes. 2007 May; 56(5):1445-53. doi: 10.2337/db06-1418. [PMID: 17325258]
  • Amy B Ghering, W Sean Davidson. Ceramide structural features required to stimulate ABCA1-mediated cholesterol efflux to apolipoprotein A-I. Journal of lipid research. 2006 Dec; 47(12):2781-8. doi: 10.1194/jlr.m600380-jlr200. [PMID: 16990644]
  • You-Xun Jin, Hwan-Soo Yoo, Akio Kihara, Chang-Hwan Choi, Seikwan Oh, Dong-Cheul Moon, Yasuyuki Igarashi, Yong-Moon Lee. Sphingosine kinase assay system with fluorescent detection in high performance liquid chromatography. Archives of pharmacal research. 2006 Nov; 29(11):1049-54. doi: 10.1007/bf02969290. [PMID: 17146975]
  • Yun-Kyung Lee, Young-Jin Im, Yu-Lee Kim, Dong-Soon Im. Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes. Biochemical and biophysical research communications. 2006 Sep; 348(3):1116-22. doi: 10.1016/j.bbrc.2006.07.164. [PMID: 16904073]
  • Harsimran S Saini, Rochelle P Coelho, Sravan K Goparaju, Puneet S Jolly, Michael Maceyka, Sarah Spiegel, Carmen Sato-Bigbee. Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors. Journal of neurochemistry. 2005 Dec; 95(5):1298-310. doi: 10.1111/j.1471-4159.2005.03451.x. [PMID: 16313513]
  • Andreas Billich, Frédéric Bornancin, Diana Mechtcheriakova, François Natt, Dieter Huesken, Thomas Baumruker. 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. Cellular signalling. 2005 Oct; 17(10):1203-17. doi: 10.1016/j.cellsig.2004.12.005. [PMID: 16038795]
  • Liudmila Pietrovna Vlasenko, Alirio J Melendez. A critical role for sphingosine kinase in anaphylatoxin-induced neutropenia, peritonitis, and cytokine production in vivo. Journal of immunology (Baltimore, Md. : 1950). 2005 May; 174(10):6456-61. doi: 10.4049/jimmunol.174.10.6456. [PMID: 15879148]
  • Fu-Xu Wang, Zuo-Ren Dong, Ze-Lin Liu, Ling Pan, Jian-Min Luo, Xue-Jun Zhang, Hong-Ling Hao, Xiao-Ling Li, Jing-Ci Yang, Ling-Ling Jiang. mitochondrial ceramidase overexpression up-regulates Bcl-2 protein level in K562 cells, probably through its metabolite sphingosine-1-phosphate. Zhongguo shi yan xue ye xue za zhi. 2004 Oct; 12(5):577-83. doi: . [PMID: 15498114]
  • Sven C D Van IJzendoorn, Johanna M Van Der Wouden, Gerhard Liebisch, Gerd Schmitz, Dick Hoekstra. Polarized membrane traffic and cell polarity development is dependent on dihydroceramide synthase-regulated sphinganine turnover. Molecular biology of the cell. 2004 Sep; 15(9):4115-24. doi: 10.1091/mbc.e04-04-0290. [PMID: 15229289]
  • Riccarda Granata, Letizia Trovato, Giovanni Garbarino, Marina Taliano, Renata Ponti, Giusy Sala, Riccardo Ghidoni, Ezio Ghigo. Dual effects of IGFBP-3 on endothelial cell apoptosis and survival: involvement of the sphingolipid signaling pathways. FASEB journal : official publication of the Federation of American Societies for Experimental Biology. 2004 Sep; 18(12):1456-8. doi: 10.1096/fj.04-1618fje. [PMID: 15247143]
  • Carole A Welsch, Lukas W A Roth, Jean François Goetschy, N Rao Movva. Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine. The Journal of biological chemistry. 2004 Aug; 279(35):36720-31. doi: 10.1074/jbc.m406179200. [PMID: 15190065]
  • Hai-Feng Duan, Chu-Tse Wu, Ying Lu, Hua Wang, Hong-Jun Liu, Qun-Wei Zhang, Xiang-Xu Jia, Zhu-Zhuang Lu, Li-Sheng Wang. Sphingosine kinase activation regulates hepatocyte growth factor induced migration of endothelial cells. Experimental cell research. 2004 Aug; 298(2):593-601. doi: 10.1016/j.yexcr.2004.04.049. [PMID: 15265705]
  • Tilla S Worgall, Rebecca A Juliano, Toru Seo, Richard J Deckelbaum. Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein. Arteriosclerosis, thrombosis, and vascular biology. 2004 May; 24(5):943-8. doi: 10.1161/01.atv.0000125703.20434.4d. [PMID: 15132973]
  • Jeannene Butler, Diana Lana, Oliver Round, Kenneth LaMontagne. Functional characterization of sphingosine 1-phosphate receptor agonist in human endothelial cells. Prostaglandins & other lipid mediators. 2004 Jan; 73(1-2):29-45. doi: 10.1016/j.prostaglandins.2003.11.003. [PMID: 15165029]
  • Neera V Gopee, Raghubir P Sharma. Sphingoid bases and their phosphates: transient activation and delayed repression of protein kinase C isoforms and their possible involvement in fumonisin B1 cytotoxicity. Toxicology. 2003 May; 187(2-3):239-50. doi: 10.1016/s0300-483x(03)00048-9. [PMID: 12699912]
  • Akio Kihara, Mika Ikeda, Yuki Kariya, Eun-Young Lee, Yong-Moon Lee, Yasuyuki Igarashi. Sphingosine-1-phosphate lyase is involved in the differentiation of F9 embryonal carcinoma cells to primitive endoderm. The Journal of biological chemistry. 2003 Apr; 278(16):14578-85. doi: 10.1074/jbc.m211416200. [PMID: 12584204]
  • Norio Hanafusa, Yutaka Yatomi, Koei Yamada, Yuichi Hori, Masaomi Nangaku, Toshihiro Okuda, Toshiro Fujita, Kiyoshi Kurokawa, Masafumi Fukagawa. Sphingosine 1-phosphate stimulates rat mesangial cell proliferation from outside the cells. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2002 Apr; 17(4):580-6. doi: 10.1093/ndt/17.4.580. [PMID: 11917049]
  • O Cuvillier, T Levade. Sphingosine 1-phosphate antagonizes apoptosis of human leukemia cells by inhibiting release of cytochrome c and Smac/DIABLO from mitochondria. Blood. 2001 Nov; 98(9):2828-36. doi: 10.1182/blood.v98.9.2828. [PMID: 11675357]
  • J S Karliner, N Honbo, K Summers, M O Gray, E J Goetzl. The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes. Journal of molecular and cellular cardiology. 2001 Sep; 33(9):1713-7. doi: 10.1006/jmcc.2001.1429. [PMID: 11549349]
  • Y Osawa, M Nagaki, Y Banno, Y Nozawa, H Moriwaki, S Nakashima. Sphingosine kinase regulates hepatoma cell differentiation: roles of hepatocyte nuclear factor and retinoid receptor. Biochemical and biophysical research communications. 2001 Aug; 286(4):673-7. doi: 10.1006/bbrc.2001.5451. [PMID: 11520048]
  • L C Edsall, O Cuvillier, S Twitty, S Spiegel, S Milstien. Sphingosine kinase expression regulates apoptosis and caspase activation in PC12 cells. Journal of neurochemistry. 2001 Mar; 76(5):1573-84. doi: 10.1046/j.1471-4159.2001.00164.x. [PMID: 11238741]
  • K W Young, M D Bootman, D R Channing, P Lipp, P R Maycox, J Meakin, R A Challiss, S R Nahorski. Lysophosphatidic acid-induced Ca2+ mobilization requires intracellular sphingosine 1-phosphate production. Potential involvement of endogenous EDG-4 receptors. The Journal of biological chemistry. 2000 Dec; 275(49):38532-9. doi: 10.1074/jbc.m006631200. [PMID: 10954727]
  • H Okamoto, Y Yatomi, T Ohmori, K Satoh, Y Matsumoto, Y Ozaki. Sphingosine 1-phosphate stimulates G(i)- and Rho-mediated vascular endothelial cell spreading and migration. Thrombosis research. 2000 Aug; 99(3):259-65. doi: 10.1016/s0049-3848(00)00251-6. [PMID: 10942792]
  • C Sharma, T Smith, S Li, G J Schroepfer, D H Needleman. Inhibition of Ca2+ release channel (ryanodine receptor) activity by sphingolipid bases: mechanism of action. Chemistry and physics of lipids. 2000 Jan; 104(1):1-11. doi: 10.1016/s0009-3084(99)00106-1. [PMID: 10660207]
  • F Y Chuang, M Sassaroli, J C Unkeless. Convergence of Fc gamma receptor IIA and Fc gamma receptor IIIB signaling pathways in human neutrophils. Journal of immunology (Baltimore, Md. : 1950). 2000 Jan; 164(1):350-60. doi: 10.4049/jimmunol.164.1.350. [PMID: 10605030]
  • A Olivera, T Kohama, L Edsall, V Nava, O Cuvillier, S Poulton, S Spiegel. Sphingosine kinase expression increases intracellular sphingosine-1-phosphate and promotes cell growth and survival. The Journal of cell biology. 1999 Nov; 147(3):545-58. doi: 10.1083/jcb.147.3.545. [PMID: 10545499]
  • L Cavallini, R Venerando, G Miotto, A Alexandre. Ganglioside GM1 protection from apoptosis of rat heart fibroblasts. Archives of biochemistry and biophysics. 1999 Oct; 370(2):156-62. doi: 10.1006/abbi.1999.1378. [PMID: 10510273]
  • L C Edsall, J R Van Brocklyn, O Cuvillier, B Kleuser, S Spiegel. N,N-Dimethylsphingosine is a potent competitive inhibitor of sphingosine kinase but not of protein kinase C: modulation of cellular levels of sphingosine 1-phosphate and ceramide. Biochemistry. 1998 Sep; 37(37):12892-8. doi: 10.1021/bi980744d. [PMID: 9737868]
  • C Caldwell, V Norman, A Urbina, A Jarvis, C Quinonez, M Stemm, A S Dahms. Regulatory differences among avian ecto-ATPases. Biochemical and biophysical research communications. 1997 Sep; 238(3):728-32. doi: 10.1006/bbrc.1997.7377. [PMID: 9325157]
  • E A Sweeney, C Sakakura, T Shirahama, A Masamune, H Ohta, S Hakomori, Y Igarashi. Sphingosine and its methylated derivative N,N-dimethylsphingosine (DMS) induce apoptosis in a variety of human cancer cell lines. International journal of cancer. 1996 May; 66(3):358-66. doi: 10.1002/(sici)1097-0215(19960503)66:3<358::aid-ijc16>3.0.co;2-7. [PMID: 8621258]
  • B Lau, P M Macdonald. Determination of the pKa of membrane-bound N,N-dimethylsphingosine using deuterium NMR spectroscopy. Biochimica et biophysica acta. 1995 Jul; 1237(1):37-42. doi: 10.1016/0005-2736(95)00083-f. [PMID: 7619840]
  • K Uemura, A Hara, T Taketomi. Inhibition of neurite outgrowth in neuroblastoma cells by sphingosine. Journal of biochemistry. 1993 Oct; 114(4):610-4. doi: 10.1093/oxfordjournals.jbchem.a124225. [PMID: 8276777]
  • B Felding-Habermann, Y Igarashi, B A Fenderson, L S Park, N S Radin, J Inokuchi, G Strassmann, K Handa, S Hakomori. A ceramide analogue inhibits T cell proliferative response through inhibition of glycosphingolipid synthesis and enhancement of N,N-dimethylsphingosine synthesis. Biochemistry. 1990 Jul; 29(26):6314-22. doi: 10.1021/bi00478a028. [PMID: 2207076]
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