KRN7000

• CAT Number: I000024
• CAS Number: 158021-47-7
• Molecular Formula: C50H99NO9
• Molecular Weight: 858.34
• Purity: ≥95%
• Synonyms: a-Galactosylceramide; N-[(1S,2S,3R)-1-[(α-D-Galactopyranosyloxy)methyl]-2,3-dihydroxyheptadecyl]hexacosanamide
• Solubility: Insoluble in water, methanol, ethanol or other organic solvents, very slightly soluble in tetrahydrofuran, slightly soluble in pyridine
• Storage: -20°C
• IUPAC Name: N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• InChI: 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
• InChIKey: VQFKFAKEUMHBLV-BYSUZVQFSA-N
• SMILES: CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C(CCCCCCCCCCCCCC)O)O

KRN7000 (Cat. No.:I000024), also known as a-Galactosylceramide, is mainly used in laboratory organic synthesis and in chemical and pharmaceutical R&D. KRN7000 is a synthetic glycolipid with antitumor and immunostimulatory effects. It is also a very effective NKT cell agonist and binds effectively to CD1d.

Reference

1: 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.
2: 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.
3: 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.
4: Park JJ, Lee JH, Ghosh SC, Bricard G, Venkataswamy MM, Porcelli SA, Chung SK. Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand. Bioorg Med Chem Lett. 2008 Jul 15;18(14):3906-9. doi: 10.1016/j.bmcl.2008.06.036. Epub 2008 Jun 14. PubMed PMID: 18586489; PubMed Central PMCID: PMC2754801.
5: Xia C, Yao Q, Schümann J, Rossy E, Chen W, Zhu L, Zhang W, De Libero G, Wang PG. Synthesis and biological evaluation of alpha-galactosylceramide (KRN7000) and isoglobotrihexosylceramide (iGb3). Bioorg Med Chem Lett. 2006 Apr 15;16(8):2195-9. Epub 2006 Feb 2. PubMed PMID: 16458002.
6: Ishikawa A, Motohashi S, Ishikawa E, Fuchida H, Higashino K, Otsuji M, Iizasa T, Nakayama T, Taniguchi M, Fujisawa T. A phase I study of alpha-galactosylceramide (KRN7000)-pulsed dendritic cells in patients with advanced and recurrent non-small cell lung cancer. Clin Cancer Res. 2005 Mar 1;11(5):1910-7. PubMed PMID: 15756017.
7: 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. PubMed PMID: 15246159.
8: Matsumoto G, Nagai S, Muta M, Tsuruta K, Okamoto A, Toi M. Survival benefit of KRN7000 immune therapy in combination with TNP470 in hamster liver metastasis model of pancreatic cancer. Oncol Rep. 2003 Sep-Oct;10(5):1201-6. PubMed PMID: 12883681.
9: Yan HM, Han MZ, Han JL, Li CW, Liu HZ. [Antitumor Activities of KRN7000 in NS-1 Myeloma-Bearing Mice]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2001 Dec;9(4):343-346. Chinese. PubMed PMID: 12578576.
10: Hayakawa Y, Rovero S, Forni G, Smyth MJ. Alpha-galactosylceramide (KRN7000) suppression of chemical- and oncogene-dependent carcinogenesis. Proc Natl Acad Sci U S A. 2003 Aug 5;100(16):9464-9. Epub 2003 Jul 16. PubMed PMID: 12867593; PubMed Central PMCID: PMC170941.