Ceramide analogues

The lactosyl ceramide analogue (39 c) was also obtained by condensation, in acetone-methanol, of 4-0-triflyl galactosyl sphingosine (34c) with thiogalactose (8 c) generated in situ from the corresponding pseudothiourea derivative [38]. 

Vavrova, K., et al. 2003. L-serine and glycine based ceramide analogues as transdermal permeation enhancers Polar head size and hydrogen bonding. Bioorg Med Chem Lett 14 2351. 

Selzner, M., Bielawska, A., Morse, M.A., Rudiger, H.A., Sindram, D., Hannun, Y.A., Clavien, P-A. 2001. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. Cancer Res. 61, 1233-1240. 

T. and Fabrias, G. (2007) Synthesis of a novel ceramide analogue and its use in a high-throughput fluorogenic assay for ceramidases. Chemhiochem, 8, 642-648. 

He L, Byun H-S, Smit J, Wilschut J, Bittman RJ. Enantioselective synthesis of a novel trans double bond ceramide analogue via catalytic asymmetric dihydroxylation of an enyne. The role of the trans double bond of ceramide in the fusion of Semliki Forest virus with target membranes. J. Am. Chem. Soc. 1999 121 3897-3903. Broun P, Shanklin J, Whittle E, Somerville C. Catalyic plasticity of fatty acid modification enzymes underlying chemical diversity of plant lipids. Science 1998 282 1315-1317. 

Novel ceramide analogues display selective cytotoxicity in drug- 93. resistant breast tumor cell lines compared to normal breast epithelial cells. Cell. Mol. Biol. 2003 49 1017-1023. 

Hannun YA, Clavier PA. Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic 159. human colon cancer. Cancer Res. 2001 61 1233-1240. 

Macchia M, Barontini S, Bartini S, DiBussolo V, Fogli S, Giovannetti E, et al. Design, synthesis, and characterization of the antitumor activity of novel ceramide analogues. J. Med. Chem. 2001 44 3994-4000. 

Bieberich E, Silva J, Wang G, Krishnamurthy K, Condie BG. Selective apoptosis of pluripotent mouse and human stem cells by novel ceramide analogues prevents teratoma formation and enriches for neural precursors in ES cell-derived neural transplants. J. Cell Biol. 2004 167 723-734. 

Lipsky NG, Pagano RE. Sphingolipid metabolism in clntnred 162. fibroblasts microscopic and biochemical studies employing a florescent ceramide analogue. Proc. Natl. Acad. Sci. U.S.A. 1983 80 2608-2612. 

One common approach to promote apoptosis in cancer cells is the use of exogenous ceramide analogues or mimetics as therapeutic agents (Table 16.1). There have been tremendous recent improvements in the design and delivery of these ceramides. For example, varied chain pyridinium ceramides (Pyr-Cers)... 

Vos JP, Giudici ML, van der Bijl P, et al. Sphingomyelin is synthesized at the plasma membrane of oligodendrocytes and by purified myelin membranes a study with fluorescent- and radio-labelled ceramide analogues. FEES Lett. 1995 368(2) 393-396. 

J Jervis, M. Mouhs, J.-P. Jukes, H. Ghadbane, L.R. Cox, V. Cerundolo, V.S. Besra, Towards multivalent CD Id hgands synthesis and biological activity of homodimeric a-galactosyl ceramide analogues. Carbohydr. Res., 356 152-162, 2012. 

Nieuwenhuizen, W. F. van Leeuwen, S. Gotz, K Egmond, M. R. Synthesis of a novel fluorescent ceramide analogue and its use in the characterization of recombinant ceramidase from Pseudomonas aeruginosa PAOl. Chem. Phys. Lipids 2002, 114, 181-191. 

Felding-Habermann,B., Igarashi,Y, Fenderson, B.A., Park, L.S., Radin, N.S., Inokuchi, J., Strassmann, G., Handa, K., and Hakomori, S., 1990, A ceramide analogue inhibits T cell proliferative response through inhibition of glycosphingolipid synthesis and enhancement of N,N-dimethylsphingosine synthesis. Biochemistry. 29(26) 6314-6322. 

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