Abstract
A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B(1) (FB(1)) on axonal growth in hippocampal neurons. The analogues contained either a C(7) side chain or a phenyl group substituted for the C(13) residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C(16)-C(24) to C(2)-C(8). D-erythro-Ceramide 18a with a C(7) side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB(1) on axonal growth, although the mechanism remains unclear.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Axons / drug effects*
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Axons / physiology
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Carboxylic Acids / antagonists & inhibitors
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Carboxylic Acids / pharmacology
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Cells, Cultured
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Ceramides / chemical synthesis*
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Ceramides / chemistry
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Ceramides / pharmacology
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Fumonisins*
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Hippocampus / cytology
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Hippocampus / drug effects*
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Hippocampus / ultrastructure
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Mycotoxins / antagonists & inhibitors
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Mycotoxins / pharmacology
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Neurons / drug effects
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Neurons / physiology
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Neurons / ultrastructure
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Rats
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Rats, Wistar
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Structure-Activity Relationship
Substances
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2-(hexanoylamino)-5-phenylpent-4-ene-1,3-diol
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2-acetamido-4-dodecene-1,3-diol
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Carboxylic Acids
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Ceramides
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Fumonisins
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Mycotoxins
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fumonisin B1