OCH

CHF 170.00
In stock
AG-CR1-3593-C250250 µgCHF 170.00
AG-CR1-3593-M0011 mgCHF 360.00
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Product Details
Synonyms (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-tetracosanoyl-2-amino-1,3,4-nonanetriol)
Product Type Chemical
Properties
Formula

C39H77NO9

MW 704.0
CAS 383187-82-4
Purity Chemicals ≥95%
Appearance White to off-white solid.
Solubility Soluble in DMSO, 100% ethanol (warm) or methanol (warm).
Identity Determined by 1H-NMR.
InChi Key MPKIDHIOYNMFES-CLTBVUQJSA-N
Smiles CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COC1OC(CO)C(O)C(O)C1O)C(O)[C@H](O)CCCCC
Shipping and Handling
Shipping BLUE ICE
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice After standard reconstitution, prepare aliquots and store at -20°C.
Aliquot into glass vials.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
  • 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.
Product References
  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)
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