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867000P

Avanti

KRN7000

Avanti Polar Lipids

Synonym(s):

α-Galactosyl Ceramide

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About This Item

Empirical Formula (Hill Notation):
C50H99NO9
CAS Number:
158021-47-7
Molecular Weight:
858.32
UNSPSC Code:
12352211
NACRES:
NA.25

form

powder

packaging

pkg of 1 × 1 mg (867000P-1mg)

manufacturer/tradename

Avanti Polar Lipids

lipid type

sphingolipids

shipped in

dry ice

storage temp.

−20°C

SMILES string

O[C@]([H])(CCCCCCCCCCCCCC)[C@](O)([H])[C@@]([H])(NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O)CO[C@@H](O1)[C@H](O)[C@@H](O)[C@H]([C@H]1CO)O

InChI

1S/C50H99NO9/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-45(54)51-42(41-59-50-49(58)48(57)47(56)44(40-52)60-50)46(55)43(53)38-36-34-32-30-28-16-14-12-10-8-6-4-2/h42-44,46-50,52-53,55-58H,3-41H2,1-2H3,(H,51,54)/t42?,43-,44-,46+,47+,48+,49-,50+/m1/s1

InChI key

VQFKFAKEUMHBLV-VDYNBUGPSA-N

General description

α-Galactosyl Ceramide (KRN7000) is a high affinity glycolipid ligand for invariant natural killer T cell (iNKT). It has  α-galactosyl ceramide core  and is a variant of agelasphin-9b ceramide core. It is a synthetic homolog of α‐GalCer from marine sponges. It comprises long fatty acyl chain (C26) and sphingosine base (C18).

Application

α-Galactosyl Ceramide (KRN7000) has been used in the in-vitro stimulation of natural killer cells. It is suitable for use as a lipid antigen in bone marrow derived cells (BMDC) and hepatocyte primary cells prior to antigen presentation assay. It is also suitable for use as a ligand invariant natural killer T cell activation.

Biochem/physiol Actions

α-Galactosyl Ceramide (KRN7000) administration results in T helper (TH0) or TH2 cytokine response. it displays potent antitumor activity in various in vivo models such as B6 melanoma, colon26 adenocarcinoma and hepatic metastases.

Packaging

5 mL Amber Glass Screw Cap Vial (867000P-1mg)

Other Notes

Not available in Japan

Legal Information

Avanti Research is a trademark of Avanti Polar Lipids, LLC

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Antitumor effect of alpha-galactosylceramide (KRN7000) on spontaneous hepatic metastases requires endogenous interleukin 12 in the liver
Fuji N, et al.
Clinical Cancer Research, 6(8), 3380-3387 (2000)
Pivotal Advance: alpha-Galactosylceramide induces protection against lipopolysaccharide-induced shock
Sireci G, et al.
Journal of Leukocyte Biology, 81(3), 607-622 (2007)
N Fuji et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 6(8), 3380-3387 (2000-08-24)
Hepatic metastasis is a major clinical problem in cancer treatment. We examined antitumor activity of alpha-galactosylceramide (KRN7000) on mice with spontaneous liver metastases of reticulum cell sarcoma M5076 tumor cells (spontaneous metastasis model). In this model, all mice that were
Synthesis and Biological Activities of 5-Thio-alpha-GalCers
Bi J, et al.
ACS Medicinal Chemistry Letters, 6(4), 476-480 (2015)
TBK-binding protein 1 regulates IL-15-induced autophagy and NKT cell survival
Zhu L, et al.
Nature Communications, 9(1), 2812-2812 (2018)
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