Improved Th17 Selectivity of α-Galactosylceramide via Noncovalent Interactions with Diether Moiety

ACS Medicinal Chemistry Letters
2019.0

Abstract

α-Galactosylceramide (α-GalCer) is a typical antigen for invariant natural killer T cells that are a subset of T cells and play critical roles in regulating immune responses. To selectively induce the secretion of certain cytokines via introducing hydrogen-bonding interaction with polar amino acid residues in the binding pocket of CD1d, a series of α-GalCer analogues with diether moiety in the acyl chain were designed and synthesized. The subsequent <i>in vitro</i> biological evaluation of these analogues revealed the structure-activity relationship for the selective IL-17 secretion. Analogues <b>5</b> and <b>6</b> induced the significantly increased IL-17 secretion over other cytokines, suggesting protective effects against pathogens. In contrast, analogue <b>7</b> showed the highly reduced IL-17 secretion, which may indicate potential anti-inflammatory effects.

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