AM 580

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Cat.No. 0760 - AM 580 | C22H25NO3 | CAS No. 102121-60-8
Description: Retinoic acid analog; RARα agonist
Chemical Name: 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid
Purity: ≥98% (HPLC)
Datasheet
Citations (8)
Literature

Biological Activity

An analog of retinoic acid that acts as a selective RARα agonist (EC50 values are 0.3, 8.6 and 13 nM for RARα, RARβ and RARγ respectively). Significantly induces IL-4, IL-5 and IL-13 and inhibits IL-12 and IFNγ synthesis, and induces cell differentiation with over 7 times the activity of retinoic acid in vitro.

Compound Libraries

AM 580 is also offered as part of the Tocriscreen Plus and Tocriscreen Stem Cell Toolbox. Find out more about compound libraries available from Tocris.

Technical Data

M. Wt 351.44
Formula C22H25NO3
Storage Store at RT
Purity ≥98% (HPLC)
CAS Number 102121-60-8
PubChem ID 2126
InChI Key SZWKGOZKRMMLAJ-UHFFFAOYSA-N
Smiles CC1(C)CCC(C)(C)C2=CC(=CC=C12)C(=O)NC1=CC=C(C=C1)C(O)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 17.57 50
ethanol 35.14 100

Preparing Stock Solutions

The following data is based on the product molecular weight 351.44. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.85 mL 14.23 mL 28.45 mL
5 mM 0.57 mL 2.85 mL 5.69 mL
10 mM 0.28 mL 1.42 mL 2.85 mL
50 mM 0.06 mL 0.28 mL 0.57 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Charton et al (2009) Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives. Bioorg.Med.Chem.Lett. 19 489 PMID: 19058965

Dawson et al (2008) The retinoic acid receptor-α mediates human T-cell activation and Th2 cytokine and chemokine production. BMC Immunol. 9 16 PMID: 18416830

Kagechika et al (1988) Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity. J.Med.Chem. 31 2182 PMID: 3184125

Wang et al (2011) Rapid and efficient reprogramming of somatic cells to induced pluripotent stem cells by retinoic acid receptor gamma and liver receptor homolog 1. Proc.Natl.Acad.Sci.U.S.A. 108 18283 PMID: 21990348


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Keywords: Retinoic acid alpha agonists RARα RARalpha Receptors AM580 Retinoic Acid Receptors

8 Citations for AM 580

Citations are publications that use Tocris products. Selected citations for AM 580 include:

DePaolo et al (2011) Co-adjuvant effects of retinoic acid and IL-15 induce inflammatory immunity to dietary antigens. Nature 471 220 PMID: 21307853

Kang et al (2011) Complementary roles of retinoic acid and TGF-β1 in coordinated expression of mucosal integrins by T cells. Dev Biol 4 66 PMID: 20664575

Kelley (2017) Retinoic acid receptor gamma impacts cellular adhesion, Alpha5 Beta1 integrin expression and proliferation in K562 cells. PLoS One 12 e0178116 PMID: 28552962

Chronopoulos et al (2016) ATRA mechanically reprograms pancreatic stellate cells to suppress matrix remodelling and inhibit cancer cell invasion Nature Communications 7 12630 PMID: 27600527

Centritto et al (2015) Cellular and molecular determinants of all-trans retinoic acid sensitivity in breast cancer: Luminal phenotype and RARα expression. Cell Death Dis 7 950 PMID: 25888236

Brigger et al (2015) Activation of RARα induces autophagy in SKBR3 breast cancer cells and depletion of key autophagy genes enhances ATRA toxicity. Mucosal Immunol 6 e1861 PMID: 26313912

Sarang et al (2014) Macrophages engulfing apoptotic cells produce nonclassical retinoids to enhance their phagocytic capacity. J Immunol 192 5730 PMID: 24850721

Johansson et al (2013) Retinoic acid receptor alpha is associated with tamoxifen resistance in breast cancer. Nat Commun 4 2175 PMID: 23868472


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Pathways for AM 580

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