AM 580

Name: AM 580
Brand: Tocris Bioscience
SKU: 0760

Catalog # 0760

Citations (13)

COA / SDS

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$35 to United States

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Key Product Details

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)
Molecular Weight:	351.44

View Full Technical Details for AM 580

Biological Activity

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

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

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

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

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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References

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

Wang 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. 2011 PMID: 21990348
Charton Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives. Bioorg.Med.Chem.Lett. 2009 PMID: 19058965
Dawson The retinoic acid receptor-α mediates human T-cell activation and Th2 cytokine and chemokine production. BMC Immunol. 2008 PMID: 18416830
Kagechika Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity. J.Med.Chem. 1988 PMID: 3184125

Citations for AM 580 (13)

Showing 1 - 10 of 13 citations Showing All

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Citations are publications that use Bio-Techne products. Selected citations for AM 580 include:

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(5):e0178116
PMID: 28552962
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
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
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
Johansson et al. (2013) Retinoic acid receptor alpha is associated with tamox. resistance in breast cancer. Nat Commun. 4:2175
PMID: 23868472
Huk et al. (2013) Increased dietary intake of vitamin A promotes aortic valve calcification in vivo. Arterioscler Thromb Vasc Biol. 33:285
PMID: 23202364
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
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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