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 (13)
Reviews
Literature (3)

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 2.0 Max 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.

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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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

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

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

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


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Literature in this Area

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