OCH (CAS: 383187-82-4)

C₃₉H₇₇NO₉

• Truncated analog of α-GalCer.
• iNKT cell glycolipid agonist.
• Immunosuppressive.
• Th2 polarizing. Stimulation of NKT with OCH results in release of primarily Th2 cytokine compared to stimulation with α-GalCer, which results in release of a mixture of Th1 and Th2 cytokines.
• Induces stronger interleukin-4 (IL-4) secretion and weaker interferon-γ (IFN-γ) secretion than α-GalCer both in vitro and in vivo.
• Inducer of interleukin-10 (IL-10) and suppressor of diabetes.
• Shown to prevent experimental autoimmune encephalomyelitis (EAE) in mice, an animal model of multiple sclerosis.
• Has beneficial effects on type I diabetes in NOD mice.
• Suppressor of collagen-induced arthritis.
• Might be useful for immunotherapy of transplant rejection.

1. A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells: K. Miyamoto, et al.; Nature 413, 531 (2001)
2. Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice: M. Mizuno, et al.; J. Autoimmun. 23, 293 (2004)
3. The clinical implication and molecular mechanism of preferential IL-4 production by modified glycolipid-stimulated NKT cells: S. Oki, et al.; J. Clin. Invest. 113, 1631 (2004)
4. Suppression of collagen-induced arthritis by natural killer T cell activation with OCH, a sphingosine-truncated analog of alpha-galactosylceramide: A. Chiba, et al.; Arthritis Rheum. 50, 305 (2004)
5. Total synthesis of an immunosuppressive glycolipid, (2S,3S,4R)-1-O- (alpha-d-galactosyl)-2- tetracosanoylamino-1,3,4-nonanetriol: K. Murata, et al.; J. Org. Chem. 70, 2398 (2005)
6. Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH: R.M. Ndonye, et al.; J. Org. Chem. 70, 10260 (2005)
7. IFN-γ–mediated negative feedback regulation of NKT-cell function by CD94/NKG2: T. Ota, et al.; Blood 106, 184 (2005)
8. Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides: Y. KO, et al.; PNAS 102, 3383 (2005)
9. α-Galactosylceramide therapy for autoimmune diseases: prospects and obstacles: L. Van Kaer; Nat. Rev. Immunol. 5, 31 (2005)
10. Glycolipids for natural killer T cells: P.B. Savage, et al.; Chem. Soc. Rev. 351, 771 (2006)
11. Prolongation of cardiac allograft survival by rapamycin and the invariant natural killer T cell glycolipid agonist OCH: S.M. Haeryfar, et al.; Transplantation 86, 460 (2008)
12. Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells: B.A. Sullivan, et al.; J. Immunol. 184, 141 (2010)
13. A molecular basis for the exquisite CD1d-restricted Antigen-specificity and functional responses of Natural Killer T cells: K.S. Wun, et al.; Immunity 34, 327 (2011)
14. Structural and functional characterization of a novel non-glycosidic iNKT agonist with immunomodulatory properties: J. Kerzerho, et al.; J. Immunol. 188, 2254 (2012)
15. Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide): M. Shiozaki, et al.; Carbohydr. Res. 370, 46 (2013)
16. iNKT cell cytotoxic responses control T-lymphoma growth in vitro and in vivo: H. Bassiri, et al.; Cancer Immunol. Res. 2, 59 (2014)
17. Impact of Th1/Th2 cytokine polarity induced by invariant NKT cells on the incidence of pregnancy loss in mice: M. Hoya, et al.;Am. J. Reprod. Immunol. ahead of print (2018)