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MedKoo Cat#: 555123 | Name: KRN7000
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

KRN-7000 is a potent synthetic α-galactosylceramide, which, in association with the antigen-presenting CD1d protein, activates NKT immune cells

Chemical Structure

KRN7000
KRN7000
CAS#158021-47-7

Theoretical Analysis

MedKoo Cat#: 555123

Name: KRN7000

CAS#: 158021-47-7

Chemical Formula: C50H99NO9

Exact Mass: 857.7320

Molecular Weight: 858.34

Elemental Analysis: C, 69.97; H, 11.63; N, 1.63; O, 16.78

Price and Availability

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1mg USD 505.00 2 Weeks
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Synonym
KRN-7000; KRN 7000; KRN7000; α-Galactosylceramide; ALPHA-GALACTOSYLCERAMIDE; ALPHA.-GALCER
IUPAC/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
InChi Key
VQFKFAKEUMHBLV-BYSUZVQFSA-N
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
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
α-Galactosylceramide is a very potent NKT cell agonist and binds effectively to CD1d.
In vitro activity:
Human Valpha24 + NKT cells, a subpopulation of natural killer cell receptor (NKR-P1A) expressing T cells with an invariant T-cell receptor (TCR; Valpha24JalphaQ) are stimulated by the glycolipid, alpha-galactosylceramide (KRN7000), in a CD1d-dependent, TCR-mediated fashion. Reference: Immunology. 2000 Feb;99(2):229-34. https://pubmed.ncbi.nlm.nih.gov/10692041/
In vivo activity:
Airway inflammation of the OA (obese asthmatic) + KRN (KRN7000) group was reduced more than that of the A + KRN group. CD69+ NKT cells were only significantly reduced in the OA + KRN group. The levels of serum IFN-γ and TNF-α increased more in the OA + KRN group than in the A + KRN group. CaM is widely expressed in the cytoplasm of the lung tissues and was sharply decreased in the OA + KRN group. KRN7000 can significantly reduce airway inflammation in obesity-associated asthma by regulating NKT cell cytokine secretion and intracellular calcium. Reference: Inflammation. 2021 Oct;44(5):1982-1992. https://pubmed.ncbi.nlm.nih.gov/34021838/
Solvent mg/mL mM
Solubility
DMSO 0.8 0.87
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 858.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nicol A, Nieda M, Koezuka Y, Porcelli S, Suzuki K, Tadokoro K, Durrant S, Juji T. Human invariant valpha24+ natural killer T cells activated by alpha-galactosylceramide (KRN7000) have cytotoxic anti-tumour activity through mechanisms distinct from T cells and natural killer cells. Immunology. 2000 Feb;99(2):229-34. doi: 10.1046/j.1365-2567.2000.00952.x. PMID: 10692041; PMCID: PMC2327139. 2. Kobayashi E, Motoki K, Uchida T, Fukushima H, Koezuka Y. KRN7000, a novel immunomodulator, and its antitumor activities. Oncol Res. 1995;7(10-11):529-34. PMID: 8866665. 3. Chen Y, Zhu Y, Su G, Yang W, Zhao Y, Lu W, Zhang J. KRN7000 Reduces Airway Inflammation via Natural Killer T Cells in Obese Asthmatic Mice. Inflammation. 2021 Oct;44(5):1982-1992. doi: 10.1007/s10753-021-01475-2. Epub 2021 May 22. PMID: 34021838. 4. Morecki S, Panigrahi S, Pizov G, Yacovlev E, Gelfand Y, Eizik O, Slavin S. Effect of KRN7000 on induced graft-vs-host disease. Exp Hematol. 2004 Jul;32(7):630-7. doi: 10.1016/j.exphem.2004.04.005. PMID: 15246159.
In vitro protocol:
1. Nicol A, Nieda M, Koezuka Y, Porcelli S, Suzuki K, Tadokoro K, Durrant S, Juji T. Human invariant valpha24+ natural killer T cells activated by alpha-galactosylceramide (KRN7000) have cytotoxic anti-tumour activity through mechanisms distinct from T cells and natural killer cells. Immunology. 2000 Feb;99(2):229-34. doi: 10.1046/j.1365-2567.2000.00952.x. PMID: 10692041; PMCID: PMC2327139. 2. Kobayashi E, Motoki K, Uchida T, Fukushima H, Koezuka Y. KRN7000, a novel immunomodulator, and its antitumor activities. Oncol Res. 1995;7(10-11):529-34. PMID: 8866665.
In vivo protocol:
1. Chen Y, Zhu Y, Su G, Yang W, Zhao Y, Lu W, Zhang J. KRN7000 Reduces Airway Inflammation via Natural Killer T Cells in Obese Asthmatic Mice. Inflammation. 2021 Oct;44(5):1982-1992. doi: 10.1007/s10753-021-01475-2. Epub 2021 May 22. PMID: 34021838. 2. Morecki S, Panigrahi S, Pizov G, Yacovlev E, Gelfand Y, Eizik O, Slavin S. Effect of KRN7000 on induced graft-vs-host disease. Exp Hematol. 2004 Jul;32(7):630-7. doi: 10.1016/j.exphem.2004.04.005. PMID: 15246159.
1: Altiti AS, Bachan S, Mootoo DR. The Crotylation Way to Glycosphingolipids: Synthesis of Analogues of KRN7000. Org Lett. 2016 Sep 16;18(18):4654-7. doi: 10.1021/acs.orglett.6b02284. Epub 2016 Aug 25. PubMed PMID: 27560147; PubMed Central PMCID: PMC5721664. 2: Chang YJ, Hsuan YC, Lai AC, Han YC, Hou DR. Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4'-epi-C-Glycoside of KRN7000. Org Lett. 2016 Feb 19;18(4):808-11. doi: 10.1021/acs.orglett.6b00090. Epub 2016 Feb 4. PubMed PMID: 26844691. 3: Altiti AS, Mootoo DR. Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000. Org Lett. 2014 Mar 7;16(5):1466-9. doi: 10.1021/ol5002686. Epub 2014 Feb 21. PubMed PMID: 24559301; PubMed Central PMCID: PMC3993873. 4: Tashiro T, Nakagawa R, Shigeura T, Watarai H, Taniguchi M, Mori K. RCAI-61 and related 6'-modified analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo. Bioorg Med Chem. 2013 Jun 1;21(11):3066-79. doi: 10.1016/j.bmc.2013.03.028. Epub 2013 Mar 30. PubMed PMID: 23602521. 5: Shiozaki M, Tashiro T, Koshino H, Shigeura T, Watarai H, Taniguchi M, Mori K. Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide). Carbohydr Res. 2013 Apr 5;370:46-66. doi: 10.1016/j.carres.2013.01.010. Epub 2013 Feb 4. PubMed PMID: 23454137. 6: Tashiro T, Shigeura T, Watarai H, Taniguchi M, Mori K. RCAI-84, 91, and 105-108, ureido and thioureido analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines. Bioorg Med Chem. 2012 Jul 15;20(14):4540-8. doi: 10.1016/j.bmc.2012.05.073. Epub 2012 Jun 7. PubMed PMID: 22739091. 7: Hunault J, Diswall M, Frison JC, Blot V, Rocher J, Marionneau-Lambot S, Oullier T, Douillard JY, Guillarme S, Saluzzo C, Dujardin G, Jacquemin D, Graton J, Le Questel JY, Evain M, Lebreton J, Dubreuil D, Le Pendu J, Pipelier M. 3-fluoro- and 3,3-difluoro-3,4-dideoxy-KRN7000 analogues as new potent immunostimulator agents: total synthesis and biological evaluation in human invariant natural killer T cells and mice. J Med Chem. 2012 Feb 9;55(3):1227-41. doi: 10.1021/jm201368m. Epub 2012 Feb 1. PubMed PMID: 22243602. 8: Nicol AJ, Tazbirkova A, Nieda M. Comparison of clinical and immunological effects of intravenous and intradermal administration of α-galactosylceramide (KRN7000)-pulsed dendritic cells. Clin Cancer Res. 2011 Aug 1;17(15):5140-51. doi: 10.1158/1078-0432.CCR-10-3105. Epub 2011 Jun 8. PubMed PMID: 21653690. 9: Macho Fernandez E, Chang J, Fontaine J, Bialecki E, Rodriguez F, Werkmeister E, Krieger V, Ehret C, Heurtault B, Fournel S, Frisch B, Betbeder D, Faveeuw C, Trottein F. Activation of invariant Natural Killer T lymphocytes in response to the α-galactosylceramide analogue KRN7000 encapsulated in PLGA-based nanoparticles and microparticles. Int J Pharm. 2012 Feb 14;423(1):45-54. doi: 10.1016/j.ijpharm.2011.04.068. Epub 2011 May 14. PubMed PMID: 21575695. 10: Schneiders FL, Scheper RJ, von Blomberg BM, Woltman AM, Janssen HL, van den Eertwegh AJ, Verheul HM, de Gruijl TD, van der Vliet HJ. Clinical experience with α-galactosylceramide (KRN7000) in patients with advanced cancer and chronic hepatitis B/C infection. Clin Immunol. 2011 Aug;140(2):130-41. doi: 10.1016/j.clim.2010.11.010. Epub 2010 Dec 18. Review. PubMed PMID: 21169066. 11: Veerapen N, Reddington F, Salio M, Cerundolo V, Besra GS. Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation. Bioorg Med Chem. 2011 Jan 1;19(1):221-8. doi: 10.1016/j.bmc.2010.11.032. Epub 2010 Nov 19. PubMed PMID: 21145749; PubMed Central PMCID: PMC3052434. 12: Shiozaki M, Tashiro T, Koshino H, Nakagawa R, Inoue S, Shigeura T, Watarai H, Taniguchi M, Mori K. Synthesis and biological activity of ester and ether analogues of alpha-galactosylceramide (KRN7000). Carbohydr Res. 2010 Aug 16;345(12):1663-84. doi: 10.1016/j.carres.2010.05.003. Epub 2010 May 12. PubMed PMID: 20591421. 13: Veerapen N, Reddington F, Bricard G, Porcelli SA, Besra GS. Synthesis and biological activity of alpha-L-fucosyl ceramides, analogues of the potent agonist, alpha-D-galactosyl ceramide KRN7000. Bioorg Med Chem Lett. 2010 Jun 1;20(11):3223-6. doi: 10.1016/j.bmcl.2010.04.079. Epub 2010 Apr 22. PubMed PMID: 20462758; PubMed Central PMCID: PMC2957807. 14: Park JJ, Lee JH, Seo KC, Bricard G, Venkataswamy MM, Porcelli SA, Chung SK. Syntheses and biological activities of KRN7000 analogues having aromatic residues in the acyl and backbone chains with varying stereochemistry. Bioorg Med Chem Lett. 2010 Feb 1;20(3):814-8. doi: 10.1016/j.bmcl.2009.12.103. Epub 2010 Jan 4. PubMed PMID: 20061147; PubMed Central PMCID: PMC5584937. 15: Tashiro T, Nakagawa R, Hirokawa T, Inoue S, Watarai H, Taniguchi M, Mori K. RCAI-37, 56, 59, 60, 92, 101, and 102, cyclitol and carbasugar analogs of KRN7000: their synthesis and bioactivity for mouse lymphocytes to produce Th1-biased cytokines. Bioorg Med Chem. 2009 Sep 1;17(17):6360-73. doi: 10.1016/j.bmc.2009.07.025. Epub 2009 Jul 18. PubMed PMID: 19656685. 16: Lacône V, Hunault J, Pipelier M, Blot V, Lecourt T, Rocher J, Turcot-Dubois AL, Marionneau S, Douillard JY, Clément M, Le Pendu J, Bonneville M, Micouin L, Dubreuil D. Focus on the controversial activation of human iNKT cells by 4-deoxy analogue of KRN7000. J Med Chem. 2009 Aug 13;52(15):4960-3. doi: 10.1021/jm900290r. PubMed PMID: 19580320. 17: Raju R, Castillo BF, Richardson SK, Thakur M, Severins R, Kronenberg M, Howell AR. Synthesis and evaluation of 3''- and 4''-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4122-5. doi: 10.1016/j.bmcl.2009.06.005. Epub 2009 Jun 6. PubMed PMID: 19535248; PubMed Central PMCID: PMC2710405. 18: Veerapen N, Brigl M, Garg S, Cerundolo V, Cox LR, Brenner MB, Besra GS. Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide. Bioorg Med Chem Lett. 2009 Aug 1;19(15):4288-91. doi: 10.1016/j.bmcl.2009.05.095. Epub 2009 May 27. PubMed PMID: 19502056; PubMed Central PMCID: PMC2722241. 19: Leung L, Tomassi C, Van Beneden K, Decruy T, Trappeniers M, Elewaut D, Gao Y, Elliott T, Al-Shamkhani A, Ottensmeier C, Werner JM, Williams A, Van Calenbergh S, Linclau B. The synthesis and in vivo evaluation of 2',2'-difluoro KRN7000. ChemMedChem. 2009 Mar;4(3):329-34. doi: 10.1002/cmdc.200800348. PubMed PMID: 19137519. 20: Michieletti M, Bracci A, Compostella F, De Libero G, Mori L, Fallarini S, Lombardi G, Panza L. Synthesis of alpha-galactosyl ceramide (KRN7000) and analogues thereof via a common precursor and their preliminary biological assessment. J Org Chem. 2008 Nov 21;73(22):9192-5. doi: 10.1021/jo8019994. Epub 2008 Oct 29. PubMed PMID: 18956839.