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Chemical Compound Review

Nbd-ceramide     N-[(E)-1,3-dihydroxyoctadec- 4-en-2-yl]-6...

Synonyms: C6-Nbd-cer, AC1O4696, 86701-10-2, C6-Nbd-ceramide
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Disease relevance of Nbd-ceramide

  • Chlamydia trachomatis acquires C6-NBD-sphingomyelin endogenously synthesized from C6-NBD-ceramide and transported to the vesicle (inclusion) in which they multiply [1].

High impact information on Nbd-ceramide

  • Morphological dynamics and membrane transport within the living Golgi apparatus of astrocytes labeled with NBD-ceramide were imaged using both electronically enhanced fluorescence video and laser confocal microscopy [2].
  • In all cases, C6-NBD-ceramide revealed a Golgi apparatus in the living cell that was identical to that obtained with conventional procedures that require fixation [3].
  • The SDYQRL-TR-containing structures, however, do not colocalize with TGN markers (e.g., NBD ceramide), and therefore the SDYQRL motif is not sufficient to target the TR to the TGN [4].
  • Approximately 40-50% of the sphingomyelin synthesized from exogenously added NBD-ceramide is specifically transported from the Golgi apparatus to the chlamydial inclusion (Hackstadt, T., M.A. Scidmore, and D.D. Rockey. 1995. Proc. Natl. Acad. Sci. USA. 92: 4877-4881) [5].
  • After 1 h at 37 degrees C, VT1B accumulated in a juxtanuclear structure that colocalized with several Golgi markers, including alpha-mannosidase II, beta-COP, and NBD-ceramide [6].

Biological context of Nbd-ceramide

  • Indeed, the surface C6-NBD-PC synthesis was reduced to 40-50% by addition of C6-NBD-ceramide or hydrolysis of cell surface SM by exogenous neutral sphingomyelinase [7].

Anatomical context of Nbd-ceramide


Associations of Nbd-ceramide with other chemical compounds


Gene context of Nbd-ceramide

  • The structure of the Golgi region, as examined by immunofluorescence microscopy with antibodies against Golgi markers (the 110-kDa protein and mannosidase II) or with fluorescent lipid NBD-ceramide, was unchanged in the mutant cells as compared to that in the wild-type cells [17].
  • S1P concentrations were quantified by bioassay based on the ability of S1P to stimulate its receptor. cITP was performed using plasma that had been prestained with NBD-ceramide [18].
  • The C6-NBD-ceramide vital staining method should be useful for studying stage-dependent Sertoli cell Golgi complex movement and spermatogonial maturation [19].

Analytical, diagnostic and therapeutic context of Nbd-ceramide


  1. Chlamydia trachomatis interrupts an exocytic pathway to acquire endogenously synthesized sphingomyelin in transit from the Golgi apparatus to the plasma membrane. Hackstadt, T., Rockey, D.D., Heinzen, R.A., Scidmore, M.A. EMBO J. (1996) [Pubmed]
  2. Tubulovesicular processes emerge from trans-Golgi cisternae, extend along microtubules, and interlink adjacent trans-golgi elements into a reticulum. Cooper, M.S., Cornell-Bell, A.H., Chernjavsky, A., Dani, J.W., Smith, S.J. Cell (1990) [Pubmed]
  3. A vital stain for the Golgi apparatus. Lipsky, N.G., Pagano, R.E. Science (1985) [Pubmed]
  4. Transferrin receptor containing the SDYQRL motif of TGN38 causes a reorganization of the recycling compartment but is not targeted to the TGN. Johnson, A.O., Ghosh, R.N., Dunn, K.W., Garippa, R., Park, J., Mayor, S., Maxfield, F.R., McGraw, T.E. J. Cell Biol. (1996) [Pubmed]
  5. Sphingolipids and glycoproteins are differentially trafficked to the Chlamydia trachomatis inclusion. Scidmore, M.A., Fischer, E.R., Hackstadt, T. J. Cell Biol. (1996) [Pubmed]
  6. Dynamic measurement of the pH of the Golgi complex in living cells using retrograde transport of the verotoxin receptor. Kim, J.H., Lingwood, C.A., Williams, D.B., Furuya, W., Manolson, M.F., Grinstein, S. J. Cell Biol. (1996) [Pubmed]
  7. Conversion of diacylglycerol to phosphatidylcholine on the basolateral surface of epithelial (Madin-Darby canine kidney) cells. Evidence for the reverse action of a sphingomyelin synthase. van Helvoort, A., van't Hof, W., Ritsema, T., Sandra, A., van Meer, G. J. Biol. Chem. (1994) [Pubmed]
  8. Intracellular translocation of fluorescent sphingolipids in cultured fibroblasts: endogenously synthesized sphingomyelin and glucocerebroside analogues pass through the Golgi apparatus en route to the plasma membrane. Lipsky, N.G., Pagano, R.E. J. Cell Biol. (1985) [Pubmed]
  9. Sorting of sphingolipids in epithelial (Madin-Darby canine kidney) cells. van Meer, G., Stelzer, E.H., Wijnaendts-van-Resandt, R.W., Simons, K. J. Cell Biol. (1987) [Pubmed]
  10. Molecular trapping of a fluorescent ceramide analogue at the Golgi apparatus of fixed cells: interaction with endogenous lipids provides a trans-Golgi marker for both light and electron microscopy. Pagano, R.E., Sepanski, M.A., Martin, O.C. J. Cell Biol. (1989) [Pubmed]
  11. Sphingolipid metabolism in cultured fibroblasts: microscopic and biochemical studies employing a fluorescent ceramide analogue. Lipsky, N.G., Pagano, R.E. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  12. Retinoic acid disrupts the Golgi apparatus and increases the cytosolic routing of specific protein toxins. Wu, Y.N., Gadina, M., Tao-Cheng, J.H., Youle, R.J. J. Cell Biol. (1994) [Pubmed]
  13. Cholesterol deprivation affects the fluorescence properties of a ceramide analog at the Golgi apparatus of living cells. Martin, O.C., Comly, M.E., Blanchette-Mackie, E.J., Pentchev, P.G., Pagano, R.E. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  14. Serial quantitative image analysis and confocal microscopy of hepatic uptake, intracellular distribution and biliary secretion of a fluorescent bile acid analog in rat hepatocyte doublets. Kitamura, T., Gatmaitan, Z., Arias, I.M. Hepatology (1990) [Pubmed]
  15. Identification of components of the endoplasmic reticulum and Golgi complex by murine autoreactive monoclonal antibodies. Kooy, J., Underwood, J.R., Gleeson, P.A. Immunology (1991) [Pubmed]
  16. Mepanipyrim, a new fungicide, inhibits intracellular transport of very low density lipoprotein in rat hepatocytes. Terada, M., Mizuhashi, F., Murata, K., Tomita, T. Toxicol. Appl. Pharmacol. (1999) [Pubmed]
  17. Isolation and characterization of a brefeldin A-resistant mutant of monkey kidney Vero cells. Chen, C.H., Kuwazuru, Y., Yoshida, T., Nambiar, M., Wu, H.C. Exp. Cell Res. (1992) [Pubmed]
  18. Correlation of high density lipoprotein (HDL)-associated sphingosine 1-phosphate with serum levels of HDL-cholesterol and apolipoproteins. Zhang, B., Tomura, H., Kuwabara, A., Kimura, T., Miura, S., Noda, K., Okajima, F., Saku, K. Atherosclerosis (2005) [Pubmed]
  19. Visualization of Golgi complexes and spermatogonial cohorts of viable, intact seminiferous tubules. Johnson, K.J., Boekelheide, K. J. Histochem. Cytochem. (1993) [Pubmed]
  20. PtK1 cells contain a nondiffusible, dominant factor that makes the Golgi apparatus resistant to brefeldin A. Ktistakis, N.T., Roth, M.G., Bloom, G.S. J. Cell Biol. (1991) [Pubmed]
  21. Calcium sequestration in the Golgi apparatus of cultured mammalian cells revealed by laser scanning confocal microscopy and ion microscopy. Chandra, S., Kable, E.P., Morrison, G.H., Webb, W.W. J. Cell. Sci. (1991) [Pubmed]
  22. Penetration of Toxoplasma gondii into host cells induces changes in the distribution of the mitochondria and the endoplasmic reticulum. de Melo, E.J., de Carvalho, T.U., de Souza, W. Cell Struct. Funct. (1992) [Pubmed]
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