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AMP-Deoxynojirimycin Exclusive
Cayman Chemical Item Number 10010332
Description The lipid messenger ceramide is converted to glucosylceramide by glucosylceramide synthase (GCS). In the reverse direction, non-lysosomal glucosylceramidase (GCase), also known as β-glucosidase 2 (BGD),1↗ cleaves the glucosyl moiety from glucosylceramide, liberating ceramide, which can be converted into sphingomyelin.2↗ AMP-deoxynojirimycin (AMP-dNM) is a hydrophobic derivative of dNM. It potently inhibits BGD (IC50 = 0.3 nM),3↗ less potently antagonizes GCS (IC50 = 25 nM),2↗ but only poorly inhibits other GCase isoforms. AMP-dNM has been shown to strongly suppress inflammation in a murine model of hapten-induced colitis,4↗ enhance insulin sensitivity in murine and rat models of insulin resistance,5↗ and induce sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells.1↗
Synonyms AMP-dNM,N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin,Adamantane-pentyl-dNM
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
Molecular Formula C22H39NO5
Formula Weight 397.6
Formulation A solution in ethanol
Purity ≥95%
Stability 1 year
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES OC[C@H]1N(CCCCCOCC23CC4CC(CC(C4)C3)C2)C[C@H](O)[C@@H](O)[C@@H]1O
InCHI Code 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 |