AM 580

Cat. No. 0760

AM 580 C22H25NO3 [102121-60-8]

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Chemical Name: 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid

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.

Technical Data

M.Wt:
351.44
Formula:
C22H25NO3
Solubility:
Soluble to 50 mM in DMSO and to 100 mM in ethanol
Purity:
>98 %
Storage:
Store at RT
CAS No:
102121-60-8

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.

Certificate of Analysis / Product Datasheet / Safety Data Sheet

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.

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.

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

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.

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.

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.

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.

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.

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Keywords: AM 580, supplier, Retinoic, acid, alpha, agonists, RARα, RARalpha, Receptors, AM580, Tocris Bioscience, Retinoic Acid Receptor Agonist products

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