Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides

Nina Hartrampf, Toshiyuki Seki, Andreas Baumann, Philip Watson, Nynke A. Vepřek, Belinda E. Hetzler, Anja Hoffmann-Röder, Moriya Tsuji, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

α-Galactosylceramides are glycosphingolipids that show promise in cancer immunotherapy. After presentation by CD1d, they activate natural killer T cells (NKT), which results in the production of a variety of pro-inflammatory and immunomodulatory cytokines. Herein, we report the synthesis and biological evaluation of photochromic derivatives of KRN-7000, the activity of which can be modulated with light. Based on established structure–activity relationships, we designed photoswitchable analogues of this glycolipid that control the production of pro-inflammatory cytokines, such as IFN-γ. The azobenzene derivative α-GalACer-4 proved to be more potent than KRN-7000 itself when activated with 370 nm light. Photolipids of this type could improve our mechanistic understanding of cytokine production and could open new directions in photoimmunotherapy.

Original languageEnglish (US)
Pages (from-to)4476-4479
Number of pages4
JournalChemistry - A European Journal
Volume26
Issue number20
DOIs
StatePublished - Apr 6 2020

Keywords

  • azobenzenes
  • cancer immunotherapy
  • galactosyl ceramides
  • natural killer T cells
  • photopharmacology

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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  • Cite this

    Hartrampf, N., Seki, T., Baumann, A., Watson, P., Vepřek, N. A., Hetzler, B. E., Hoffmann-Röder, A., Tsuji, M., & Trauner, D. (2020). Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides. Chemistry - A European Journal, 26(20), 4476-4479. https://doi.org/10.1002/chem.201905279