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Chemical Compound Review

Cytolipin H     N-[(E)-1-[(2R,3R,4R,5R,6R)- 3,4-dihydroxy-6...

Synonyms: LS-52760, AC1O518P, Ganglioside GA3, Lactosylceramide, Ganglioside GL2a, ...
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Disease relevance of Cytolipin H


High impact information on Cytolipin H

  • GM3 synthase is a member of the sialyltransferase family and catalyzes the initial step in the biosynthesis of most complex gangliosides from lactosylceramide [6].
  • We recently showed that human skin fibroblasts internalize fluorescent analogues of the glycosphingolipids lactosylceramide and globoside almost exclusively by a clathrin-independent mechanism involving caveolae [7].
  • The neutral glycolipids of HL-60 cells are of the lacto-types such as lactosylceramide (LacCer) and lactoneotetraglycosylceramide (nLcOse4Cer) [8].
  • Thymus from lymphoma-bearing hamsters in advanced stages of tumor growth showed enhanced activities of four glycolipid-glycosyltransferases which lead to the step-wise synthesis of lactosylceramide to Forssman hapten [9].
  • METHODS: We used a fluorescent analogue of lactosylceramide, called N-[5-(5,7-dimethylborondipyrromethenedifluoride)-1-pentanoyl]D- lactosylsphingosine (BODIPY-LacCer), the emission of which changes from green to red wavelengths with increasing concentrations in membranes, to examine the intracellular distribution of the lipid within living cells [10].

Chemical compound and disease context of Cytolipin H


Biological context of Cytolipin H


Anatomical context of Cytolipin H


Associations of Cytolipin H with other chemical compounds


Gene context of Cytolipin H

  • They included the use of glass-immobilized, glycolipid films to load GLTP with glycolipid and separation of GLTP/glycolipid complexes from vesicles containing glycolipid (galactosylceramide or lactosylceramide) or from monosialoganglioside dispersions by employing nickel-nitrilotriacetic acid-based affinity or gel filtration strategies [30].
  • Glycolipid analysis showed a decrease in ganglioside GM3 and increase in lactosylceramide after NEU3 transfection, with these lipids apparently affecting cell apoptosis and motility [31].
  • Brief stimulation of an isolated GEM fraction by the exogenous addition of GM3, but not lactosylceramide, caused enhanced c-Src phosphorylation with a concomitant decrease of Csk level in GEM [32].
  • The 1.4 angstroms structure resembles the recently characterized apo-form of the human GLTP but the other two structures represent an intermediate conformation of the apo-GLTPs and the human lactosylceramide-bound GLTP structure [33].
  • The apparent Km value for LacCer was 9.3 microM. mST3Gal V did not exhibit any activity toward other substrates we tested in this study, including glycolipids, glycoproteins and disaccharides [34].

Analytical, diagnostic and therapeutic context of Cytolipin H


  1. Up-regulation of plasma membrane-associated ganglioside sialidase (Neu3) in human colon cancer and its involvement in apoptosis suppression. Kakugawa, Y., Wada, T., Yamaguchi, K., Yamanami, H., Ouchi, K., Sato, I., Miyagi, T. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  2. Infection of vaginal and colonic epithelial cells by the human immunodeficiency virus type 1 is neutralized by antibodies raised against conserved epitopes in the envelope glycoprotein gp120. Furuta, Y., Eriksson, K., Svennerholm, B., Fredman, P., Horal, P., Jeansson, S., Vahlne, A., Holmgren, J., Czerkinsky, C. Proc. Natl. Acad. Sci. U.S.A. (1994) [Pubmed]
  3. A novel mutation in the coding region of the prosaposin gene leads to a complete deficiency of prosaposin and saposins, and is associated with a complex sphingolipidosis dominated by lactosylceramide accumulation. Hulková, H., Cervenková, M., Ledvinová, J., Tochácková, M., Hrebícek, M., Poupetová, H., Befekadu, A., Berná, L., Paton, B.C., Harzer, K., Böör, A., Smíd, F., Elleder, M. Hum. Mol. Genet. (2001) [Pubmed]
  4. Inhibition of experimental metastasis of murine Lewis lung carcinoma by an inhibitor of glucosylceramide synthase and its possible mechanism of action. Inokuchi, J., Jimbo, M., Momosaki, K., Shimeno, H., Nagamatsu, A., Radin, N.S. Cancer Res. (1990) [Pubmed]
  5. GM3-enriched microdomain involved in cell adhesion and signal transduction through carbohydrate-carbohydrate interaction in mouse melanoma B16 cells. Iwabuchi, K., Yamamura, S., Prinetti, A., Handa, K., Hakomori, S. J. Biol. Chem. (1998) [Pubmed]
  6. Infantile-onset symptomatic epilepsy syndrome caused by a homozygous loss-of-function mutation of GM3 synthase. Simpson, M.A., Cross, H., Proukakis, C., Priestman, D.A., Neville, D.C., Reinkensmeier, G., Wang, H., Wiznitzer, M., Gurtz, K., Verganelaki, A., Pryde, A., Patton, M.A., Dwek, R.A., Butters, T.D., Platt, F.M., Crosby, A.H. Nat. Genet. (2004) [Pubmed]
  7. Rab proteins mediate Golgi transport of caveola-internalized glycosphingolipids and correct lipid trafficking in Niemann-Pick C cells. Choudhury, A., Dominguez, M., Puri, V., Sharma, D.K., Narita, K., Wheatley, C.L., Marks, D.L., Pagano, R.E. J. Clin. Invest. (2002) [Pubmed]
  8. Alterations of glycolipids of human leukemia cell line HL-60 during differentiation. Momoi, T., Yokota, J. J. Natl. Cancer Inst. (1983) [Pubmed]
  9. Alterations of glycolipid glycosyltrasnferase levels in lymphoma and lymphoid tissues of lymphoma-bearing hamsters. Ishibashi, T., Atsuta, T., Makita, A. J. Natl. Cancer Inst. (1975) [Pubmed]
  10. Broad screening test for sphingolipid-storage diseases. Chen, C.S., Patterson, M.C., Wheatley, C.L., O'Brien, J.F., Pagano, R.E. Lancet (1999) [Pubmed]
  11. Regulation of phospholipase C-gamma activity by glycosphingolipids. Shu, L., Lee, L., Shayman, J.A. J. Biol. Chem. (2002) [Pubmed]
  12. The K88 fimbrial adhesin of enterotoxigenic Escherichia coli binds to beta 1-linked galactosyl residues in glycosphingolipids. Payne, D., O'Reilly, M., Williamson, D. Infect. Immun. (1993) [Pubmed]
  13. P-selectin mediates metastatic progression through binding to sulfatides on tumor cells. Garcia, J., Callewaert, N., Borsig, L. Glycobiology (2007) [Pubmed]
  14. Tamoxifen retards glycosphingolipid metabolism in human cancer cells. Cabot, M.C., Giuliano, A.E., Volner, A., Han, T.Y. FEBS Lett. (1996) [Pubmed]
  15. Comparative study of the levels of sialyltransferases responsible for the formation of sugar chains in glycoproteins and gangliosides in rat liver and hepatomas. Miyagi, T., Koseki, M., Tsuiki, S. Jpn. J. Cancer Res. (1988) [Pubmed]
  16. Localization of urinary lactosylceramide in cytoplasmic vesicles of renal tubular cells in homozygous familial hypercholesterolemia. Chatterjee, S., Kwiterovich, P.O., Gupta, P., Erozan, Y.S., Alving, C.R., Richards, R.L. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  17. Lactosylceramide recruits PKCalpha/epsilon and phospholipase A2 to stimulate PECAM-1 expression in human monocytes and adhesion to endothelial cells. Gong, N., Wei, H., Chowdhury, S.H., Chatterjee, S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  18. Pertussis toxin has eukaryotic-like carbohydrate recognition domains. Saukkonen, K., Burnette, W.N., Mar, V.L., Masure, H.R., Tuomanen, E.I. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  19. Lactosylceramide-enriched glycosphingolipid signaling domain mediates superoxide generation from human neutrophils. Iwabuchi, K., Nagaoka, I. Blood (2002) [Pubmed]
  20. The glycosphingolipid, lactosylceramide, regulates beta1-integrin clustering and endocytosis. Sharma, D.K., Brown, J.C., Cheng, Z., Holicky, E.L., Marks, D.L., Pagano, R.E. Cancer Res. (2005) [Pubmed]
  21. Glycolipid and glycoprotein transport through the Golgi complex are similar biochemically and kinetically. Reconstitution of glycolipid transport in a cell free system. Wattenberg, B.W. J. Cell Biol. (1990) [Pubmed]
  22. Abnormal transport along the lysosomal pathway in mucolipidosis, type IV disease. Chen, C.S., Bach, G., Pagano, R.E. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  23. Targeted and nontargeted liposomes for in vivo transfer to rat liver cells of a plasmid containing the preproinsulin I gene. Soriano, P., Dijkstra, J., Legrand, A., Spanjer, H., Londos-Gagliardi, D., Roerdink, F., Scherphof, G., Nicolau, C. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  24. Identification of carbohydrate structures that are possible receptors for Neisseria gonorrhoeae. Stromberg, N., Deal, C., Nyberg, G., Normark, S., So, M., Karlsson, K.A. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  25. Cancer-associated expression of glycolipid sulfotransferase gene in human renal cell carcinoma cells. Honke, K., Tsuda, M., Hirahara, Y., Miyao, N., Tsukamoto, T., Satoh, M., Wada, Y. Cancer Res. (1998) [Pubmed]
  26. Ganglioside G(M3) overexpression induces apoptosis and reduces malignant potential in murine bladder cancer. Watanabe, R., Ohyama, C., Aoki, H., Takahashi, T., Satoh, M., Saito, S., Hoshi, S., Ishii, A., Saito, M., Arai, Y. Cancer Res. (2002) [Pubmed]
  27. Identification of the neutral glycosphingolipids of murine mast cells: expression of Forssman glycolipid by the serosal but not the bone marrow-derived subclass. Katz, H.R., Schwarting, G.A., LeBlanc, P.A., Austen, K.F., Stevens, R.L. J. Immunol. (1985) [Pubmed]
  28. Association of the Golgi UDP-galactose transporter with UDP-galactose:ceramide galactosyltransferase allows UDP-galactose import in the endoplasmic reticulum. Sprong, H., Degroote, S., Nilsson, T., Kawakita, M., Ishida, N., van der Sluijs, P., van Meer, G. Mol. Biol. Cell (2003) [Pubmed]
  29. Up-regulation of neutral glycosphingolipid synthesis upon long term inhibition of ceramide synthesis by fumonisin B1. Meivar-Levy, I., Futerman, A.H. J. Biol. Chem. (1999) [Pubmed]
  30. Point mutational analysis of the liganding site in human glycolipid transfer protein. Functionality of the complex. Malakhova, M.L., Malinina, L., Pike, H.M., Kanack, A.T., Patel, D.J., Brown, R.E. J. Biol. Chem. (2005) [Pubmed]
  31. Plasma membrane-associated sialidase is up-regulated in renal cell carcinoma and promotes interleukin-6-induced apoptosis suppression and cell motility. Ueno, S., Saito, S., Wada, T., Yamaguchi, K., Satoh, M., Arai, Y., Miyagi, T. J. Biol. Chem. (2006) [Pubmed]
  32. Glycosphingolipid-enriched signaling domain in mouse neuroblastoma Neuro2a cells. Mechanism of ganglioside-dependent neuritogenesis. Prinetti, A., Iwabuchi, K., Hakomori, S. J. Biol. Chem. (1999) [Pubmed]
  33. Structural evidence for adaptive ligand binding of glycolipid transfer protein. Airenne, T.T., Kidron, H., Nymalm, Y., Nylund, M., West, G., Mattjus, P., Salminen, T.A. J. Mol. Biol. (2006) [Pubmed]
  34. Molecular cloning and functional expression of a fifth-type alpha 2,3-sialyltransferase (mST3Gal V: GM3 synthase). Kono, M., Takashima, S., Liu, H., Inoue, M., Kojima, N., Lee, Y.C., Hamamoto, T., Tsuji, S. Biochem. Biophys. Res. Commun. (1998) [Pubmed]
  35. Reversion of the Jun-induced oncogenic phenotype by enhanced synthesis of sialosyllactosylceramide (GM3 ganglioside). Miura, Y., Kainuma, M., Jiang, H., Velasco, H., Vogt, P.K., Hakomori, S. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  36. Apoptosis induced by N-hexanoylsphingosine in CHP-100 cells associates with accumulation of endogenous ceramide and is potentiated by inhibition of glucocerebroside synthesis. Spinedi, A., Bartolomeo, S.D., Piacentini, M. Cell Death Differ. (1998) [Pubmed]
  37. Biologically active, recombinant DNA in clathrin-coated vesicles isolated from rat livers after in vivo injection of liposome-encapsulated DNA. Nandi, P.K., Legrand, A., Nicolau, C. J. Biol. Chem. (1986) [Pubmed]
  38. Purification and properties of rat liver globotriaosylceramide synthase, UDP-galactose:lactosylceramide alpha 1-4-galactosyltransferase. Taniguchi, N., Yanagisawa, K., Makita, A., Naiki, M. J. Biol. Chem. (1985) [Pubmed]
  39. Glycosphingolipid patterns of the gastrointestinal tract and feces of germ-free and conventional rats. Gustafsson, B.E., Karlsson, K.A., Larson, G., Midtvedt, T., Strömberg, N., Teneberg, S., Thurin, J. J. Biol. Chem. (1986) [Pubmed]
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