AMP-Deoxynojirimycin CAS: 216758-20-2
MF: C22H39NO5
MW: 397.6
An inhibitor of BGD and GCS.

AMP-Deoxynojirimycin (CAS 216758-20-2)

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Synonym: AMP-dNM
Application: An inhibitor of BGD and GCS
CAS Number: 216758-20-2
Molecular Weight: 397.6
Molecular Formula: C22H39NO5
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* Refer to Certificate of Analysis for lot specific data (including water content).
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AMP-Deoxynojirimycin (AMP-dNM) is a hydrophobic derivative of dNM that potently inhibits β-glucosidase 2 (BGD, IC50 = 0.3 nM), less potently antagonizes glucosylceramide synthase (GCS, IC50 = 25 nM), and only poorly inhibits other GCase isoforms. The lipid messenger ceramide is converted to glucosylceramide by GCS. In the reverse direction, BGD cleaves the glucosyl moiety from glucosylceramide, liberating ceramide, which can be converted into sphingomyelin. AMP-dNM has been shown to induce sterol regulatory element-binding protein-regulated gene expression and cholesterol synthesis in Hep-G2 cells, strongly suppress inflammation in a murine model of hapten-induced colitis, and enhance insulin sensitivity in murine and rat models of insulin resistance.


References

1. Overkleeft, H S., et al., 1998. Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase. The Journal of biological chemistry. 273(41): 26522-7. PMID: 9756888
2. Aerts, Johannes M., et al., 2003. Biochemistry of glycosphingolipid storage disorders: implications for therapeutic intervention. Philosophical transactions of the Royal Society of London. Series B, Biological sciences. 358(1433): 905-14. PMID: 12803924
3. Shen, Chong., et al., 2004. Inhibition of glycolipid biosynthesis by N-(5-adamantane-1-yl-methoxy-pentyl)-deoxynojirimycin protects against the inflammatory response in hapten-induced colitis. International immunopharmacology. 4(7): 939-51. PMID: 15182733
4. Aerts, Johannes M., et al., 2007. Pharmacological inhibition of glucosylceramide synthase enhances insulin sensitivity. Diabetes. 56(5): 1341-9. PMID: 17287460
5. Bijl, Nora., et al., 2008. 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. The Journal of pharmacology and experimental therapeutics. 326(3): 849-55. PMID: 18550691

Formulation :
A solution in ethanol
Physical State :
Liquid
Solubility :
Soluble in ethanol (~30 mg/ml), DMSO (~50 mg/ml), DMF (~50 mg/ml), aqueous buffers (sparingly), and chloroform.
Storage :
Store at -20° C
Boiling Point :
78° C
Refractive Index :
n20D 1.57 (Predicted)
IC50 :
β-glucosidase 2: IC50 = 0.3 nM (human); UGCG: IC50 = 25 nM; αglucosidase: IC50 = 0.13 µM (rice); β-glucosidase: IC50 = 0.2 µM (human); LYAG: IC50 = 0.4 µM (human)
pK Values :
pKa: 13.72 (Predicted), pKb: 6.86 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
Transport :
UN 1170, Class 3, Packing group II
PubChem CID :
9822159
SMILES :
C1[[email protected]@H]([[email protected]]([[email protected]@H]([[email protected]](N1CCCCCOCC24CC3CC(C2)CC(C3)C4)CO)O)O)O

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Certificate of Analysis

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