Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells

T. Walter; L. Collenburg; L. Japtok; B. Kleuser; S. Schneider-Schaulies; N. Müller; J. Becam; A. Schubert-Unkmeir; J. N. Kong; E. Bieberich; J. Seibel

doi:10.1039/C6CC02879A

Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells†

T. Walter,

‡^a L. Collenburg,‡^b L. Japtok,^c B. Kleuser,^c S. Schneider-Schaulies,^b N. Müller,^b J. Becam,^d A. Schubert-Unkmeir,^d J. N. Kong,^e E. Bieberich^e and J. Seibel*^a

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* Corresponding authors

^a Institute for Organic Chemistry, Julius-Maximilians University Würzburg, Am Hubland C1, Würzburg, Germany
E-mail: seibel@chemie.uni-wuerzburg.de

^b Institute of Virology and Immunobiology, Versbacher Str. 7, Würzburg, Germany

^c Institute of Nutritional Science, University of Potsdam, Arthur-Scheunert Allee 114-116, Nuthetal, Potsdam, Germany

^d Institute of Hygiene and Microbiology, Josef-Schneider-Straße 2/E1, Würzburg, Germany

^e Department of Neuroscience and Regenerative Medicine, Medical College of Georgia, Augusta University, 1120 15th Street, Augusta, USA

Abstract

The synthesis and biological evaluation of azido-N-oleoyl serinol is reported. It mimicks biofunctional lipid ceramides and has shown to be capable of click reactions for cell membrane imaging in Jurkat and human brain microvascular endothelial cells.

Chemical Communications

Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells†

Abstract

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Incorporation and visualization of azido-functionalized N-oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells

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