J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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Journal of Lipid Research, Vol. 13, 86-91, January 1972
Copyright © 1972 by Lipid Research, Inc.

Ceramide-like synthetic amides that inhibit cerebroside galactosidase

Ramesh C. Arora and Norman S. Radin

Mental Health Research Institute, University of Michigan, Ann Arbor, Michigan 48104

Amides resembling ceramide (fatty acyl sphingosine) were synthesized and tested for their effects on rat brain cerebrosidase (galactosyl ceramide ßbeta;-galactosidase). The best inhibitor was N-decanoyl dl-erythro-3-phenyl-2-aminopro-panediol, which exhibited a Ki of 0.4 mm. A Lineweaver-Burk plot indicated that the amide acted as a noncompetitive inhibitor, presumably by attachment to a site other than the substrate-active site. Preincubation did not affect the degree of inhibition, and inhibition was independent of incubation duration; these observations suggest that the inhibitor does not combine with the enzyme irreversibly. Structural variations produced decreased inhibitory activity: loss of one of the hydroxyl groups, replacement of the aromatic side chain with an aliphatic or substituted phenyl group, or isomeric inversion of the 3-hydroxyl group. It appears that the best activity is obtained with a substance most closely resembling natural ceramide. The cerebrosidases of rat spleen, kidney, and liver are also inhibited by the same amide.

Supplementary key words N-decanoyl 3-phenyl-2-amino-propane-1,3-diol and homologs • N-decanoyl 3-phenyl-2-amino-propan-3-ol and homologs • N-decanoyl 3-phenyl-2-amino-propan-1-ol and homologs • N-decanoyl 3-(p-nitro-phenyl)-2-amino-propane-1,3-diol • N-decanoyl 3-(m-nitro-phenyl)-2-amino-propane-1,3-diol • N-decanoyl 3-(p-bi-phenyl)-2-amino-propane-1,3-diol • N-decanoyl 2-aminopropanol and homologs • N-decanoyl 2-amino-butan-1-ol and homologs • N-decanoyl 1-amino-propan-2-ol and homologs • galactocerebrosidase of rat brain, liver, kidney, and spleen

Submitted on April 6, 1971
Accepted on August 30, 1971


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