AM 580

Catalog # Availability Size / Price Qty
0760/10
0760/50
AM 580 | CAS No. 102121-60-8 | Retinoic Acid Receptor Agonists
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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%

Product Details
Citations (13)
Reviews

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

M.Wt:
351.44
Formula:
C22H25NO3
Solubility:
Soluble to 100 mM in DMSO and to 50 mM in ethanol
Purity:
≥98%
Storage:
Store at RT
CAS No:
102121-60-8

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

  1. Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations
    JH Lee, SI Protze, Z Laksman, PH Backx, GM Keller
    Cell Stem Cell, 2017;21(2):179-194.e4.
  2. Retinoids induce integrin-independent lymphocyte adhesion through RAR-alpha nuclear receptor activity.
    Whelan J, Wang L, Chen J, Metts M, Nasser T, McGoldrick L, Bridges L
    Biochem Biophys Res Commun, 2014;454(4):537-542.
  3. Direct Reprogramming of Fibroblasts via a Chemically Induced XEN-like State
    X Li, D Liu, Y Ma, X Du, J Jing, L Wang, B Xie, D Sun, S Sun, X Jin, X Zhang, T Zhao, J Guan, Z Yi, W Lai, P Zheng, Z Huang, Y Chang, Z Chai, J Xu, H Deng
    Cell Stem Cell, 2017;0(0):.
  4. High-throughput genotoxicity assay identifies antioxidants as inducers of DNA damage response and cell death.
    Fox JT, Sakamuru S, Huang R
    Proc. Natl. Acad. Sci. U.S.A., 2012;109(14):5423-8.
  5. 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
  6. Retinobenzoic acids. 1. Structure-activity relationships of aromatic amides with retinoidal activity.
    Kagechika et al.
    J.Med.Chem., 1988;31:2182
  7. Novel non-carboxylic acid retinoids: 1,2,4-oxadiazol-5-one derivatives.
    Charton et al.
    Bioorg.Med.Chem.Lett., 2009;19:489
  8. The retinoic acid receptor-α mediates human T-cell activation and Th2 cytokine and chemokine production.
    Dawson et al.
    BMC Immunol., 2008;9:16

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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

  1. 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
  2. Human Pluripotent Stem Cell-Derived Atrial and Ventricular Cardiomyocytes Develop from Distinct Mesoderm Populations.
    Authors: Lee Et al.
    Cell Stem Cell  2017;21:179
  3. Retinoic acid receptor gamma impacts cellular adhesion, Alpha5 Beta1 integrin expression and proliferation in K562 cells.
    Authors: Kelley
    PLoS One  2017;12(5):e0178116
  4. ATRA mechanically reprograms pancreatic stellate cells to suppress matrix remodelling and inhibit cancer cell invasion
    Authors: Chronopoulos Et al.
    Nature Communications  2016;7:12630
  5. 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
  6. 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
  7. 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
  8. Macrophages engulfing apoptotic cells produce nonclassical retinoids to enhance their phagocytic capacity.
    Authors: Sarang Et al.
    J Immunol  2014;192:5730
  9. Retinoic acid receptor alpha is associated with tamox. resistance in breast cancer.
    Authors: Johansson Et al.
    Nat Commun  2013;4:2175
  10. 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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