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Purity: ≥98%
KRN 7000 is a novel, potent and selective synthetic α-
| ln Vitro |
Supernatants from activated Vα24+ NKT cell cultures treated with monocyte-derived dendritic cells (Mo-DC) pulsed with α-galactosylceramide showed antiproliferative action against melanoma cells. The main cause of this impact is the release of IL-12 and, to a lesser extent, IFN-γ. There is also the release of other cytokines, such as IL-4 and IL-10, but their antiproliferative effects are not as strong. Soluble mediators' anti-proliferative actions enable Vα24+ NKT cells, driven by α-galactosylceramide-pulsed Mo-DC, to exhibit anti-tumor activity against human melanoma [3].
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| ln Vivo |
Mice treated with α-galactosylceramide do not develop primary tumors on their own when exposed to carcinogens or oncogenes. C-glycoside analogs of α-galactosylceramide that selectively induce IFN-γ synthesis were more efficient than α-galactosylceramide in inhibiting B16 melanoma metastasis, which is consistent with a key role for IFN-γ in NKT cell-mediated tumor responses. Amides function better [1]. α-galactosylceramide is regarded as a biological response modulator and non-specific heterosexual immune stimulator [4].
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| References |
[1]. Godfrey DI, et al. Going both ways: immune regulation via CD1d-dependent NKT cells. J Clin Invest. 2004 Nov;114(10):1379-88.
[2]. Morita M, et al. Practical Total Synthesis of (2S,3S,4R)-1-O-(α-D-Galactopyranosyl)-N-hexacosanoyl-2-amino-1,3,4-octadecanetriol, the Antitumorial and Immunostimulatory α-Galactosylcer-amide, KRN7000. Biosci Biotechnol Biochem. 1996 Jan;60(2):288-92. [3]. Kikuchi A, et al. In vitro anti-tumour activity of alpha-galactosylceramide-stimulated human invariant Valpha24+NKT cells against melanoma. Br J Cancer. 2001 Sep 1;85(5):741-6. [4]. Masahiro Morita, et al. Structure-Activity Relationship of .alpha.-Galactosylceramides against B16-Bearing Mice. J. Med. Chem. 1995, 38, 12, 2176-2187. |
| Molecular Formula |
C50H99NO9
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|---|---|
| Molecular Weight |
858.32236
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| CAS # |
158021-47-7
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| SMILES |
O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@H](NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=O)[C@H](O)[C@H](O)CCCCCCCCCCCCCC
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| InChi Key |
VQFKFAKEUMHBLV-BYSUZVQFSA-N
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| InChi Code |
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-/m0/s1
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| Chemical Name |
N-((2S,3S,4R)-3,4-dihydroxy-1-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)octadecan-2-yl)hexacosanamide
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| Synonyms |
KRN-7000; KRN 7000; KRN7000; α-Galactosylceramide.
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~0.5 mg/mL (~0.58 mM)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1651 mL | 5.8253 mL | 11.6507 mL | |
| 5 mM | 0.2330 mL | 1.1651 mL | 2.3301 mL | |
| 10 mM | 0.1165 mL | 0.5825 mL | 1.1651 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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