AM 580 A retinoic acid analog and selective RARα agonist

AM 580 (CAS 102121-60-8)

AM 580 | CAS 102121-60-8 is rated 5.0 out of 5 by 1.
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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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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.


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

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)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
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

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Certificate of Analysis

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AM 580  Product Citations

See how others have used AM 580. Click on the entry to view the PubMed entry .

Citations 1 to 2 of 2 total

PMID: # 24264050  Xu, S. et al. 2014. Am. J. Physiol. Gastrointest. Liver Physiol. 306: G154-62.

PMID: # 24454758  Araoka, T. et al. 2014. PLoS ONE. 9: e84881.

Citations 1 to 2 of 2 total
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Rated 5 out of 5 by from Dawson HD; et al Dawson HD; et al. (PubMed ID: 18416830) determined that AM 580 increases cell differentiation and IL-4, IL-13, and IL-5 in vitro. -SCBT Publication Review
Date published: 2015-04-16
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