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Optical Control of Cytokine Production Using Photoswitchable Galactosylceramides
Author(s) -
Hartrampf Nina,
Seki Toshiyuki,
Baumann Andreas,
Watson Philip,
Vepřek Nynke A.,
Hetzler Belinda E.,
HoffmannRöder Anja,
Tsuji Moriya,
Trauner Dirk
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201905279
Subject(s) - cytokine , immunotherapy , azobenzene , cancer research , chemistry , biology , immunology , immune system , organic chemistry , molecule
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.