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NBD-labeled derivatives of the immunomodulatory drug FTY720 as tools for metabolism and mode of action studies.

Ettmayer, Peter and Baumruker, Thomas and Guerini, Danilo and Mechtcheriakova, Diana and Nussbaumer, Peter and Streiff, Markus and Billich, Andreas (2006) NBD-labeled derivatives of the immunomodulatory drug FTY720 as tools for metabolism and mode of action studies. Bioorganic & Medicinal Chemistry Letters, 16 (1). pp. 84-87. ISSN 0960-894X

Abstract

Fluorescently labeled chiral analogs of the immunomodulatory drug FTY720 and its corresponding phosphates with variable aliphatic spacers between the aromatic ring and the NBD label have been synthesized. Determining the influence of the spacer on the in vitro phosphorylation rate by SPHK1 and 2 resulted in the identification of NBD-(R)-AAL 1c,d which are phosphorylated with an efficiency comparable to that of the unlabeled FTY720 analog (R)-AAL. Furthermore, the NBD-(R)-AAL phosphates 10c,d were proven to be a functional S1P receptor agonist.

Item Type: Article
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Additional Information: author can archive post-print (ie final draft post-refereeing); Publisher's version/PDF cannot be used
Keywords: Immunomodulation; Fluorescence; Sphingolipids; Kinase; Receptors
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Date Deposited: 14 Dec 2009 13:59
Last Modified: 31 Jan 2013 01:15
URI: https://oak.novartis.com/id/eprint/489

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