OCH
| Code | Size | Price |
|---|
| AG-CR1-3593-C250 | 250 ug | £130.00 |
Quantity:
| AG-CR1-3593-M001 | 1 mg | £260.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
-20°C
Storage:
-20°C
Documents
Further Information
Alternate Names/Synonyms:
(2S,3S,4R)-1-O-(alpha-D-Galactopyranosyl)-N-tetracosanoyl-2-amino-1,3,4-nonanetriol)
Appearance:
White to off-white solid.
CAS:
383187-82-4
EClass:
32160000
Form (Short):
liquid
Handling Advice:
After standard reconstitution, prepare aliquots and store at -20°C.Aliquot into glass vials.
InChi:
InChI=1S/C39H77NO9/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-26-28-34(43)40-31(35(44)32(42)27-25-6-4-2)30-48-39-38(47)37(46)36(45)33(29-41)49-39/h31-33,35-39,41-42,44-47H,3-30H2,1-2H3,(H,40,43)/t31-,32+,33+,35-,36-,37-,38+,39-/m0/s1
InChiKey:
MPKIDHIOYNMFES-CLTBVUQJSA-N
Long Description:
Chemical. CAS: 383187-82-4. Formula: C39H77NO9. MW: 704. Truncated analog of alpha-GalCer. iNKT cell glycolipid agonist. Immunosuppressive. Th2 polarizing. Stimulation of NKT with OCH results in release of primarily Th2 cytokine compared to stimulation with alpha-GalCer, which results in release of a mixture of Th1 and Th2 cytokines. Induces stronger interleukin-4 (IL-4) secretion and weaker interferon-gamma (IFN-gamma) secretion than alpha-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.
Molecular Formula:
C39H77NO9
Molecular Weight:
704
Package Type:
Vial
Product Description:
Truncated analog of alpha-GalCer. iNKT cell glycolipid agonist. Immunosuppressive. Th2 polarizing. Stimulation of NKT with OCH results in release of primarily Th2 cytokine compared to stimulation with alpha-GalCer, which results in release of a mixture of Th1 and Th2 cytokines. Induces stronger interleukin-4 (IL-4) secretion and weaker interferon-gamma (IFN-gamma) secretion than alpha-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.
Purity:
>95%
SMILES:
CCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@@H](COC1OC(CO)C(O)C(O)C1O)C(O)[C@H](O)CCCCC
Solubility Chemicals:
Soluble in DMSO, 100% ethanol (warm) or methanol (warm).
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells: K. Miyamoto, et al.; Nature 413, 531 (2001) | Synthetic glycolipid OCH prevents insulitis and diabetes in NOD mice: M. Mizuno, et al.; J. Autoimmun. 23, 293 (2004) | 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) | 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) | 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) | Synthesis and evaluation of sphinganine analogues of KRN7000 and OCH: R.M. Ndonye, et al.; J. Org. Chem. 70, 10260 (2005) | IFN-gamma?mediated negative feedback regulation of NKT-cell function by CD94/NKG2: T. Ota, et al.; Blood 106, 184 (2005) | Modulation of CD1d-restricted NKT cell responses by using N-acyl variants of alpha-galactosylceramides: Y. KO, et al.; PNAS 102, 3383 (2005) | alpha-Galactosylceramide therapy for autoimmune diseases: prospects and obstacles: L. Van Kaer; Nat. Rev. Immunol. 5, 31 (2005) | Glycolipids for natural killer T cells: P.B. Savage, et al.; Chem. Soc. Rev. 351, 771 (2006) | 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) | Mechanisms for glycolipid antigen-driven cytokine polarization by Valpha14i NKT cells: B.A. Sullivan, et al.; J. Immunol. 184, 141 (2010) | 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) | Structural and functional characterization of a novel non-glycosidic iNKT agonist with immunomodulatory properties: J. Kerzerho, et al.; J. Immunol. 188, 2254 (2012) | Synthesis and biological activity of hydroxylated analogues of KRN7000 (alpha-galactosylceramide): M. Shiozaki, et al.; Carbohydr. Res. 370, 46 (2013) | iNKT cell cytotoxic responses control T-lymphoma growth in vitro and in vivo: H. Bassiri, et al.; Cancer Immunol. Res. 2, 59 (2014) | 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)