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Join us! · InformexUSA 2012 · New Orleans, Louisiana · February 14-17, 2012 · Booth 2514

AMP-Deoxynojirimycin Exclusive

Cayman Chemical Item Number 10010332

Adamantane-pentyl-dNM; N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin; AMP-dNM (CAS 216758-20-2)

AMP-Deoxynojirimycin (CAS 216758-20-2)

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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 Hep-G2 cells.1

1 Bijl, N., Scheij, S., Houten, S., et al. The glucosylceramide synthase inhibitor N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin induces sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells. J Pharmacol Exp Ther 326(3) 849-855 (2008).

2 Aerts, J.M., Hollak, C., Boot, R., et al. Biochemistry of glycosphingolipid storage disorders: Implications for therapeutic intervention. Philos Trans R Soc Lond B Biol Sci 358 905-914 (2003).

3 Overkleeft, H.S., Renkema, G.H., Neele, J., et al. Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase. J Biol Chem 273(41) 26522-26527 (1998).

4 Shen, C., Bullens, D., Kasran, A., et al. Inhibition of glycolipid biosynthesis by N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin protects against the inflammatory response in hapten-induced colitis. Int Immunopharmacol 4 939-951 (2004).

5 Aerts, J.M., Ottenhoff, R., Powlson, A.S., et al. Pharmacological inhibition of glucosylceramide synthase enhances insulin sensitivity. Diabetes 56 1341-1349 (2007).

Synonyms
  • Adamantane-pentyl-dNM
  • N-(5-adamantane-1-yl-methoxy-pentyl)-Deoxynojirimycin
  • AMP-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
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OC[C@H]​1N(CCCCCOCC23CC4CC(CC(C4)​C3)​C2)​C[C@H]​(O)​[C@@H]​(O)​[C@@H]​1O

Background Reading

Bijl, N., Scheij, S., Houten, S., et al. The glucosylceramide synthase inhibitor N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin induces sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in HepG2 cells. J Pharmacol Exp Ther 326(3) 849-855 (2008).

Aerts, J.M., Hollak, C., Boot, R., et al. Biochemistry of glycosphingolipid storage disorders: Implications for therapeutic intervention. Philos Trans R Soc Lond B Biol Sci 358 905-914 (2003).

Overkleeft, H.S., Renkema, G.H., Neele, J., et al. Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase. J Biol Chem 273(41) 26522-26527 (1998).

Shen, C., Bullens, D., Kasran, A., et al. Inhibition of glycolipid biosynthesis by N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin protects against the inflammatory response in hapten-induced colitis. Int Immunopharmacol 4 939-951 (2004).

Aerts, J.M., Ottenhoff, R., Powlson, A.S., et al. Pharmacological inhibition of glucosylceramide synthase enhances insulin sensitivity. Diabetes 56 1341-1349 (2007).

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Size Price Quantity Subtotal
500 µg $34.00 $0.00
1 mg $65.00 $0.00
5 mg $272.00 $0.00
10 mg $476.00 $0.00
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Cart Total $0.00

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Pricing updated 2012-02-10. Prices are subject to change without notice.

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