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AM 580 (CAS 102121-60-8)

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Synonym:4-{[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbonyl]amino}benzoic acid
Application:A retinoic acid analog and selective RARα agonist
CAS Number:102121-60-8
Molecular Weight:351.44
Molecular Formula:C22H25NO3
Refer to Certificate of Analysis for lot specific data (including water content).
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 Ordering Information
Product NameCatalog #UnitPriceQtyAddFavorites
AM 580 sc-203505 5 mg $89
AM 580 sc-203505A 25 mg $368
Description
AM 580 is a selective retinoic acid analog, which is useful in vitro as a RARα agonist. Studies indicate that RARα increases the signaling of the RARα receptor to prevent intracellular and extracellular amyloid-β accumulation. In addition, this receptor increases the expression of disintegrin and metalloprotease. Since amyloid-β accumulation is a major finding in Alzheimer's disease (AD), AM 580 can be used to study this disease in vitro. AM 580 also induces the functions of IL-4, IL-5 and IL-13 and suppresses the production of IL-12 and IFNγ. Alternate studies suggest that AM 580 inhibits tumor proliferation by reducing the level of RARγ and activates RAR β.
Technical Information
Appearance:Crystalline
Physical State:Solid
Solubility:Soluble in DMSO (20 mg/ml), and ethanol (10 mg/ml).
Storage:Store at -20° C
Melting Point:229.77 °C (Predicted)
Boiling Point:460.97 °C at 760 mmHg (Predicted)
Density:1.15 g/cm3 (Predicted)
Refractive Index:n20D 1.59 (Predicted)
IC50:RARα: EC5050 = 0.3 nM; RARγ : EC5050 = 13 nM; RARα: IC50 = 41 nM (human); RARβ: EC5050 = 8.6 nM
pK Values:pKa: 4.28 (Predicted)
Safety and Reference Information
WGK Germany:3
RTECS:DH6834890
PubChem CID:2126
MDL Number:MFCD00673916
Beilstein Registry:3565084
SMILES:CC1(CCC(C2=C1C=CC(=C2)C(=O)NC3=CC=C(C=C3)C(=O)O)(C)C)C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Kagechika, H., et al., 1988. Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity. Journal of medicinal chemistry. 31(11): 2182-92. PMID: 3184125
2. Charton, Julie., et al., 2009. Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives. Bioorganic & medicinal chemistry letters. 19(2): 489-92. PMID: 19058965
3. Jarvis, C I., et al., 2010. Retinoic acid receptor-α signalling antagonizes both intracellular and extracellular amyloid-β production and prevents neuronal cell death caused by amyloid-β. The European journal of neuroscience. 32(8): 1246-55. PMID: 20950278
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