Synthesis and biological evaluation of ceramide analogues with substituted aromatic rings or an allylic fluoride in the sphingoid moiety

Journal of Medicinal Chemistry

Volumn 43, Issue 22, 2000, Pages 4189-4199

  Van Overmeire, I ^a   Boldin, S A ^b   Venkataraman, K ^b   Zisling, R ^b   De Jonghe, S ^a   Van Calenbergh, S ^a   De Keukeleire, D ^a   Futerman, A H ^b   Herdewijn, P ^a  

^a GHENT UNIVERSITY   (Belgium)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

2 DECANOYLAMINO 3 MORPHOLINO 1 PHENYL 1 PROPANOL; CERAMIDE DERIVATIVE; FLUORIDE; FLUORINE; FUMONISIN B1;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; HIPPOCAMPUS; NERVE CELL; NERVE FIBER GROWTH; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ALLYL COMPOUNDS; ANIMALS; AXONS; CARBOXYLIC ACIDS; CELLS, CULTURED; CERAMIDES; FUMONISINS; GLUCOSYLTRANSFERASES; GOLGI APPARATUS; HIPPOCAMPUS; LIVER; RATS; RATS, WISTAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0034597611     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm000939v     Document Type: Article

References (28)

1. The novel second messenger ceramide: Identification, mechanism of action, and cellular activity
2. Ceramide and the induction of apoptosis
3. The localization of gangliosides in neurons of the central nervous system: The use of antiganglioside antibodies
4. Effects of an inhibitor of glucosylceramide synthase on glycosphingolipid synthesis and neurite outgrowth in murine neuroblastoma cell lines
5. Preparation of the active isomer of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol, inhibitor of glucocerebroside synthetase
6. Inhibition of sphingolipid synthesis affects axonal outgrowth in cultured hippocampal neurons
7. Sphingolipid biosynthesis is necessary for dendrite growth and survival of cerebellar purkinje cells in culture
8. Distinct roles for ceramide and glucosylceramide at different stages of neuronal growth
9. Glucosylceramide synthesis is required for basic fibroblast growth factor and laminin to stimulate axonal growth
10. Effect of aromatic short-chain analogues of ceramide on axonal growth in hippocampal neurons
11. The synthesis and configurational stability of differentially protected b-hydroxy-a-amino aldehydes
12. Regio- and stereo-selectivities in some nucleophilic reactions
13. Sphingosine and phytosphingosine from D-threose, synthesis of a 4-keto-ceramide
14. 3-receptor antagonists with high oral central nervous system activity
15. Asymmetric addition reactions of lithium (trimethylsilyl)acetylide with chiral α-amino nitrones
16. New fluorinating reagents. Dialkylaminosulfur fluorides
17. Structure-activity relationships of short-chain sphingoid bases as inhibitors of sphingosine kinase
18. Synthesis of D-erythro- and D-threo-sphingosine derivatives from L-serine
19. Nucleophilic and organometallic displacement reactions of allylic compounds: Stereo- and regiochemistry
20. Purification and characterization of UDP-glucose: Ceramide glucosyltransferase from rat liver golgi membranes
21. Determination of the intracellular sites and topology of glucosylceramide synthesis in rat liver
22. A series of fluorescent N-acylsphingosines: Synthesis, physical properties, and studies in cultured cells
23. Rat hippocampal neurons in low-density culture
24. Regulatory role for sphingolipids in neuronal growth
25. A simple method for the synthesis of ceramides and radioloabeled analogues
26. 14C]Hexanoyl)-D-erythro-sphingolipids to assay sphingolipid metabolism
27. Fusogenic domains of golgi membranes are sequestered into specialized regions of the stack that can be released by mechanical fragmentation
28. A rapid method of total lipid extraction and purification