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J Biol Chem, Vol. 275, Issue 1, 177-181, January 7, 2000

N-Acylated Serinol Is a Novel Ceramide Mimic Inducing Apoptosis in Neuroblastoma Cells*

Erhard BieberichDagger , Takahisa Kawaguchi, and Robert K. Yu

From the Department of Biochemistry and Molecular Biochemistry, Medical College of Virginia Campus of Virginia Commonwealth University, Richmond, Virginia 23298-0614

A novel structural analog of ceramide was synthesized by N-acylation of serinol (2-amino-1,3-propanediol) and studied for its effects on glycolipid biosynthesis and cell differentiation of neuroblastoma cells. Incubation with N-palmitoylated serinol (C16-serinol) increased the concentration of endogenous ceramide by 50-80% and caused apoptosis in rapidly dividing low density cells but not in confluent cells. Cell death was not suppressed by simultaneous incubation with phorbol ester, known to antagonize ceramide-induced apoptosis by activation of protein kinase C (PKC). Purification of potential target proteins of C16-serinol was achieved by affinity chromatography of a protein preparation from rat brain on immobilized C16-serinol. A gel activity assay revealed that the eluate from C16-serinol-Sepharose contained three serine/threonine-specific protein kinases with molecular masses of 50, 70, and 95 kDa. The 70-kDa protein was immunostained on a Western blot using a PKCzeta -specific antibody. The purified PKCzeta could be activated directly by C16-serinol in an in vitro phosphorylation assay. Induction of apoptosis in neuroblastoma cells was suppressed by inhibition of PKCzeta with Gö 6983. Our overall results indicate that apoptosis in neuroblastoma cells induced by C16-serinol was at least partially mediated by activation of PKCzeta on condition of ongoing cell division. N-Acylated serinols may thus be useful for induction of apoptosis in mitotic cells and may be of therapeutic potential for treatment of cancer in the nervous system.

* This study was supported by United States Public Health Service Grant NS 11853 and an A. D. Williams grant.The costs of publication of this article were defrayed in part by the payment of page charges. The article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

Dagger To whom correspondence should be addressed: Dept. of Biochemistry and Molecular Biophysics, Medical College of Virginia Campus of Virginia Commonwealth University, 1101 E. Marshall St., P. O. Box 980614, Richmond, VA 23298. Tel.: 804-828-9217; Fax: 804-828-1473; E-mail: ebieberi@hsc.vcu.edu.

Copyright © 2000 by The American Society for Biochemistry and Molecular Biology, Inc.
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