AM 580
Chemical Name: 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]benzoic acid
Purity: ≥98%
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.
Technical Data
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.
Background References
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Rapid and efficient reprogramming of somatic cells to induced pluripotent stem cells by retinoic acid receptor gamma and liver receptor homolog 1.
Wang et al.
Proc.Natl.Acad.Sci.U.S.A., 2011;108:18283 -
Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
Kagechika et al.
J.Med.Chem., 1988;31:2182 -
Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.
Charton et al.
Bioorg.Med.Chem.Lett., 2009;19:489 -
The retinoic acid receptor-α mediates human T-cell activation and Th2 cytokine and chemokine production.
Dawson et al.
BMC Immunol., 2008;9:16
Product Datasheets
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Citations for AM 580
The citations listed below are publications that use Tocris products. Selected citations for AM 580 include:
13 Citations: Showing 1 - 10
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Genome-wide DNA methylation analysis reveals that mouse chemical iPSCs have closer epigenetic features to mESCs than OSKM-integrated iPSCs.
Authors: Ping Et al.
Cell Death Dis 2018;9:187
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Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations.
Authors: Lee Et al.
Cell Stem Cell 2017;21:179
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Retinoic acid receptor gamma impacts cellular adhesion, Alpha5 Beta1 integrin expression and proliferation in K562 cells.
Authors: Kelley
PLoS One 2017;12(5):e0178116
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ATRA mechanically reprograms pancreatic stellate cells to suppress matrix remodelling and inhibit cancer cell invasion
Authors: Chronopoulos Et al.
Nature Communications 2016;7:12630
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Cellular and molecular determinants of all-trans retinoic acid sensitivity in breast cancer: Luminal phenotype and RARα expression.
Authors: Centritto Et al.
Cell Death Dis 2015;7:950
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Activation of RARα induces autophagy in SKBR3 breast cancer cells and depletion of key autophagy genes enhances ATRA toxicity.
Authors: Brigger Et al.
Mucosal Immunol 2015;6:e1861
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BCL-xL/MCL-1 inhibition and RARγ antagonism work cooperatively in human HL60 leukemia cells.
Authors: Perri Et al.
Exp Cell Res 2014;327:183
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Macrophages engulfing apoptotic cells produce nonclassical retinoids to enhance their phagocytic capacity.
Authors: Sarang Et al.
J Immunol 2014;192:5730
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Retinoic acid receptor alpha is associated with tamox. resistance in breast cancer.
Authors: Johansson Et al.
Nat Commun 2013;4:2175
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Increased dietary intake of vitamin A promotes aortic valve calcification in vivo.
Authors: Huk Et al.
Arterioscler Thromb Vasc Biol 2013;33:285
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Complementary roles of retinoic acid and TGF-β1 in coordinated expression of mucosal integrins by T cells.
Authors: Kang Et al.
Dev Biol 2011;4:66
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Co-adjuvant effects of retinoic acid and IL-15 induce inflammatory immunity to dietary antigens.
Authors: DePaolo Et al.
Nature 2011;471:220
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Zebrafish nephrogenesis involves dynamic spatiotemporal expression changes in renal progenitors and essential signals from retinoic acid and irx3b.
Authors: Wingert and Davidson
Dev Dyn 2011;240:2011
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