A selective RARα agonist
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

AM580

Item No. 15261

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbonyl]amino]-benzoic acid
CAS Number
102121-60-8
Synonyms
  • CD336
  • NSC 608001
  • Ro 40-6055
Molecular Formula
C22H25NO3
Formula Weight
351.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
λmax
287 nm
SMILES
OC(C1=CC=C(NC(C2=CC(C(C)(C)CCC3(C)C)=C3C=C2)=O)C=C1)=O
InChi Code
InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-15(7-10-17(18)21)19(24)23-16-8-5-14(6-9-16)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChi Key
SZWKGOZKRMMLAJ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $36

    Add

    5 mg

    $103

    Add

    10 mg

    $132

    Add

    25 mg

    $294

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    AM580 is a retinoic acid receptor agonist that is selective for RARα (Kd = 8 nM; AC50 = 0.36 nM) compared to RARβ (Kd = 131 nM; AC50 = 24.6 nM) and RARγ (Kd = 450 nM; AC50 = 27.9 nM).1 It demonstrates greater specific binding to RARα compared to retinoic acid (Item No. 11017), which exhibits little selectivity across RARα, β, or γ.1,2,3 AM580 has been used in combination with the GSK3β inhibitor CHIR99021 (Item No. 13122) to efficiently induce differentiation of human induced pluripotent stem cells into immediate mesoderm.4 It can also inhibit the proliferation of various tumor cells, inhibiting survival signaling pathways and inducing apoptosis.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bernard, B.A., Bernardon, J.-M., Delescluse, C., et al. Identification of synthetic retinoids with selectivity for human nuclear retinoic acid receptor γ. Biochem. Biophys. Res. Commun. 186(2), 977-983 (1992).

    2. Kim, M.J., Ciletti, N., Michel, S., et al. The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J. Invest. Dermatol. 114(2), 349-353 (2000).

    3. Rochette-Egly, C., and Germain, P. Dynamic and combinatorial control of gene expression by nuclear retinoic acid receptors (RARs). Nucl. Recept. Signal 7, e005 (2009).

    4. Araoka, T., Mae, S., Kurose, Y., et al. Efficient and rapid induction of human iPSCs/ESCs into nephrogenic intermediate mesoderm using small molecule-based differentiation methods. PLoS One 9(1), e84881 (2014).

    5. Lu, Y., Bertran, S., Samuels, T.A., et al. Mechanism of inhibition of MMTV-neu and MMTV-wnt1 induced mammary oncogenesis by RARα agonist AM580. Oncogene 29(25), 3665-3676 (2010).

    6. Cheng, Y.H., Utsunomiya, H., Pavone, M.E., et al. Retinoic acid inhibits endometrial cancer cell growth via multiple genomic mechanisms. J. Mol. Endocrinol. 46(2), 139-153 (2011).