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. Author manuscript; available in PMC: 2011 Apr 1.
Published in final edited form as: Semin Immunol. 2009 Nov 27;22(2):68–78. doi: 10.1016/j.smim.2009.10.003

Fig 2.

Fig 2

Four examples of sphingosine chain analogues of KRN7000 with iNKT cell activating properties. OCH is a Th2-cytokine biasing iNKT cell activator, which has a markedly truncated C9 phytosphingosine and a slightly shortened N-acyl chain (C24:0) compared to KRN7000. C13 is an example of a truncated sphingosine derivative in which incorporation of an aromatic ring led to increased iNKT cell activating potency. Triazole 8 has a 24 carbon alkyl chain linked to the sphingoid base by triazole ring, which is a highly stable rigid linking unit that mimics the topological and electronic features of an amide bond. RCAI-18 demonstrates how a trans-2,4-dialkylated azetidine ring can be incorporated in the ceramide portion to restrict flexibility while retaining the ability to stimulate iNKT cell responses. See text for references.