Synthesis of n-(4'pyridoxyl)sphingosine and its uptake and metabolism by isolated cells

Zuomin Zhang, Elizabeth Smith, Scott M. Surowiec, Alfred H. Merrill, Donald B. McCormick

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

N-(4'Pyridoxyl)sphingosine was synthesized and characterized as a stable compound for specialized delivery of a bioactive lipid. It was found to be facilely taken up by hepatocytes although by a mechanism more typical for lipids than the one used by natural vitamin B6. Some of theN-(4'pyridoxyl)sphingosine was metabolically acted upon inside the cell to release pyridoxal 5'phosphate and sphingosine, but formation of pyridoxal 5'phosphate from the synthetic compound was poor compared with natural vitamin forms of B6, which may partly be due to entrapment within cell membranes and to constraints at the level of cytosolic pyridoxal kinase which is responsible for phosphorylation of the vitamin. Unlike the parent long-chain base, the B6 conjugate was not particularly cytotoxic. Furthermore, the compound was neither an activator nor inhibitor of the respiratory burst of human neutrophils. These findings identify N-(4'pyridoxyl)sphingosine as an interesting tool for studies of the cellular transport, metabolism, and functions of both vitamin B6 and sphingosine.

Original languageEnglish
Pages (from-to)53-59
Number of pages7
JournalMolecular Membrane Biology
Volume10
Issue number1
DOIs
StatePublished - Jan 1 1993
Externally publishedYes

Fingerprint

Sphingosine
Vitamin B 6
Metabolism
Pyridoxal Phosphate
Vitamins
Pyridoxal Kinase
Lipids
Phosphorylation
Respiratory Burst
Cell membranes
Hepatocytes
Neutrophils
Cell Membrane
N-(4'-pyridoxyl)sphingosine

Keywords

  • N-(4'pyridoxyl)sphingosine
  • Rat liver cells

ASJC Scopus subject areas

  • Cell Biology
  • Molecular Biology
  • Biochemistry

Cite this

Synthesis of n-(4'pyridoxyl)sphingosine and its uptake and metabolism by isolated cells. / Zhang, Zuomin; Smith, Elizabeth; Surowiec, Scott M.; Merrill, Alfred H.; McCormick, Donald B.

In: Molecular Membrane Biology, Vol. 10, No. 1, 01.01.1993, p. 53-59.

Research output: Contribution to journalArticle

Zhang, Zuomin ; Smith, Elizabeth ; Surowiec, Scott M. ; Merrill, Alfred H. ; McCormick, Donald B. / Synthesis of n-(4'pyridoxyl)sphingosine and its uptake and metabolism by isolated cells. In: Molecular Membrane Biology. 1993 ; Vol. 10, No. 1. pp. 53-59.
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