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Submit ReviewAM 580
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)
Biological Activity for AM 580
AM 580 is 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.
AM 580 synthesized to Ancillary Material Grade also available.
Compound Libraries for AM 580
AM 580 is also offered as part of the Tocriscreen 2.0 Max and Tocriscreen Stem Cell Library. Find out more about compound libraries available from Tocris.
Technical Data for AM 580
| 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 for AM 580
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 35.14 | 100 | |
| ethanol | 17.57 | 50 |
Preparing Stock Solutions for AM 580
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 for AM 580
References for AM 580
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
If you know of a relevant reference for AM 580, please let us know.
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Keywords: AM 580, AM 580 supplier, Retinoic, acid, alpha, agonists, RARα, RARalpha, Receptors, AM580, Acid, Organoids, 0760, Tocris Bioscience
13 Citations for AM 580
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
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
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
DePaolo et al (2011) Co-adjuvant effects of retinoic acid and IL-15 induce inflammatory immunity to dietary antigens. Nature 471 220 PMID: 21307853
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
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
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
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
Kelley (2017) Retinoic acid receptor gamma impacts cellular adhesion, Alpha5 Beta1 integrin expression and proliferation in K562 cells. PLoS One 12 e0178116 PMID: 28552962
Ping et al (2018) Genome-wide DNA methylation analysis reveals that mouse chemical iPSCs have closer epigenetic features to mESCs than OSKM-integrated iPSCs. Cell Death Dis 9 187 PMID: 29416007
Do you know of a great paper that uses AM 580 from Tocris? Please let us know.
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Literature in this Area
Tocris offers the following scientific literature in this area to showcase our products. We invite you to request* your copy today!
*Please note that Tocris will only send literature to established scientific business / institute addresses.
Retinoid Receptors Scientific Review
Written by Alexander Moise, this review summarizes the nature of retinoid receptors, their isotype and isoform variants and modulation of retinoid signaling. Compounds available from Tocris are listed.