Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides

Hartrampf, Nina; Seki, Toshiyuki; Baumann, Andreas; Watson, Philip; Veprek, Nynke A.; Hetzler, Belinda E.; Hoffmann-Roder, Anja; Tsuji, Moriya und Trauner, Dirk (2020): Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides. In: Chemistry-A European Journal, Bd. 26, Nr. 20: S. 4476-4479

Abstract

alpha-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-gamma. The azobenzene derivative alpha-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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 0947-6539
• Sprache: Englisch