AMP-Deoxynojirimycin

The lipid messenger ceramide is converted to glucosylceramide by glucosylceramide synthase (GCS). In the reverse direction, non-lysosomal glucosylceramidase (GCase), also known as beta-glucosidase 2 (BGD), cleaves the glucosyl moiety from glucosylceramide, liberating ceramide, which can be converted into sphingomyelin. AMP-deoxynojirimycin (AMP-dNM) is a hydrophobic derivative of dNM. It potently inhibits BGD (IC50 = 0.3 nM), less potently antagonizes GCS (IC50 = 25 nM), but only poorly inhibits other GCase isoforms. AMP-dNM has been shown to strongly suppress inflammation in a murine model of hapten-induced colitis, enhance insulin sensitivity in murine and rat models of insulin resistance, and induce sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells.Formal Name: 2R-(hydroxymethyl)-1-[5-(tricyclo[3.3.2.13,7]dec-1-ylmethoxy)pentyl]-3R,4R,5S-piperidinetriol. CAS Number: 216758-20-2. Synonyms: Adamantane-pentyl-dNM, AMP-DNJ, AMP-dNM, N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin. Molecular Formula: C22H39NO5. Formula Weight: 397.6. Purity: >95%. Formulation: (Request formulation change), A solution in ethanol. Solubility: DMF: 50 mg/ml, DMSO: 50 mg/ml, Ethanol: 30 mg/ml, Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml. SMILES: OC[C@H]1N(CCCCCOCC23CC4CC(CC(C4)C3)C2)C[C@H](O)[C@@H](O)[C@@H]1O. InChi Code: InChI=1S/C22H39NO5/c24-13-18-20(26)21(27)19(25)12-23(18)4-2-1-3-5-28-14-22-9-15-6-16(10-22)8-17(7-15)11-22/h15-21,24-27H,1-14H2/t15-,16+,17-,18-,19+,20-,21-,22?/m1/s1. InChi Key: XVYLNHVEAOOEGI-OIPNBASOSA-N.