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 (12)
Reviews
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.

Tocris products are intended for laboratory research use only, unless stated otherwise.

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 the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

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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References

References are publications that support the biological activity of the product.

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: AM 580, AM 580 supplier, Retinoic, acid, alpha, agonists, RARα, RARalpha, Receptors, AM580, Acid, 0760, Tocris Bioscience

12 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

Perri et al (2014) BCL-xL/MCL-1 inhibition and RARγ antagonism work cooperatively in human HL60 leukemia cells. Exp Cell Res 327 183 PMID: 25088254

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

Huk et al (2013) Increased dietary intake of vitamin A promotes aortic valve calcification in vivo. Arterioscler Thromb Vasc Biol 33 285 PMID: 23202364

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

Wingert and Davidson (2011) Zebrafish nephrogenesis involves dynamic spatiotemporal expression changes in renal progenitors and essential signals from retinoic acid and irx3b. Dev Dyn 240 2011 PMID: 21761484

Lee et al (2017) Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations. Cell Stem Cell 21 179 PMID: 28777944

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 tamox. resistance in breast cancer. Nat Commun 4 2175 PMID: 23868472


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Literature in this Area

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