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SML3666

Sigma-Aldrich

AMP-Deoxynojirimycin

≥97% (HPLC)

Synonym(s):

AMP-dNJ, AMP-dNM, (2R,3R,4R,5S)-2-(Hydroxymethyl)-1-[5-(tricyclo[3.3.1.13,7]dec-1-ylmethoxy)pentyl]-3,4,5-piperidinetriol, AMP-DNJ, AMP-DNM, Adamantane-pentyl-DNM, Adamantane-pentyl-dNM, MZ-21, N-(5′-Adamantane-1′-yl-methoxy)pentyl-1-deoxynojirimycin; (2R,3R,4R,5S)-1-[5-(1-Adamantylmethoxy)pentyl]-2-(hydroxymethyl)piperidine-3,4,5-triol, N-(5-Adamantane-1-yl-methoxy)pentyl-1-deoxynojirimycin; N-(5-Adamantane-1-yl-methoxy)pentyl)-DNM

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About This Item

Empirical Formula (Hill Notation):
C22H39NO5
CAS Number:
216758-20-2
Molecular Weight:
397.55
UNSPSC Code:
51111800
UNSPSC Code:
12352200
NACRES:
NA.21

Quality Level

100

Assay

≥97% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

-10 to -25°C

SMILES string

O[C@@H]1[C@H](N(C[C@@H]([C@H]1O)O)CCCCCOCC2(C3)C[C@@H](C4)C[C@H]3C[C@@H]4C2)CO

Biochem/physiol Actions

AMP-deoxynojirimycin (AMP-DNM) is an orally available iminosugar that acts as a reversible, potent and selective inhibitor against the non-lysosomal glucosylceramidase GBA2 (IC50 = 1.7 nM) over the glucosylceramide synthase (GCS, UGCG), ER alpha-glucosidases, the lysosomal glucocerebrosidase GBA (IC50 = 0.16 μM) and alpha-glucosidase GAA (IC50 = 0.87 μM). AMP-DNM selectively inhibits cellular GBA2 in cultures (GBA2/GBA IC50 = 0.3 nM/100 nM; human melanoma cells) and exhibits in vivo therapeutic efficacy in murine models of obesity (100 mg/kg/day p.o.) and colitis (10-50 mg/kg/day via i.p. or 1.25-6.25g/kg chow).

Caution

Hygroscopic

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

新产品

Certificates of Analysis (COA)

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Generation of specific deoxynojirimycin-type inhibitors of the non-lysosomal glucosylceramidase
The Journal of biological chemistry, 273(41), 26522-26527 (1998)
Species-specific differences in nonlysosomal glucosylceramidase GBA2 function underlie locomotor dysfunction arising from loss-of-function mutations
The Journal of Biological Chemistry, 294(11), 3853-3871 (2019)
Reduction of glycosphingolipid biosynthesis stimulates biliary lipid secretion in mice
Hepatology, 49(2), 637-645 (2009)
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), 939-951 (2004)
Cytosolic glucosylceramide regulates endolysosomal function in Niemann-Pick type C disease
Neurobiology of Disease, 127, 242-252 (2019)
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