A pan-RAR inverse agonist
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BMS 493

Item No. 17418

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1E)-2-[5,6-dihydro-5,5-dimethyl-8-(2-phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid
CAS Number
215030-90-3
Synonyms
  • BMS 204493
Molecular Formula
C29H24O2
Formula Weight
404.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mLDMF:PBS (pH 7.2) (1:4): 0.2 mg/mLDMSO: 25 mg/mL
λmax
239, 297, 328 nm
SMILES
O=C(O)C1=CC=C(/C=C/C2=CC=C(C(C)(C)CC=C3C#CC4=CC=CC=C4)C3=C2)C=C1
InChi Code
InChI=1S/C29H24O2/c1-29(2)19-18-24(14-10-21-6-4-3-5-7-21)26-20-23(13-17-27(26)29)9-8-22-11-15-25(16-12-22)28(30)31/h3-9,11-13,15-18,20H,19H2,1-2H3,(H,30,31)/b9-8+
InChi Key
YCADIXLLWMXYKW-CMDGGOBGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $49

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    5 mg

    $120

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    10 mg

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    25 mg

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    Product Description

    BMS 493 is a pan-RAR inverse agonist that blocks RARα activity with an IC50 value of 114 nM.1,2 In all RAR types (RARα, RARβ, and RARγ), BMS493 prevents the recruitment of transcriptional coactivators to RARs while stabilizing corepressor interactions.3,4 BMS 493 has been used to elucidate the critical roles of RARs in development and immune response.1,5,6,7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chazaud, C., Chambon, P., and Dollé, P. Retinoic acid is required in the mouse embryo for left-right asymmetry determination and heart morphogenesis. Development 126(12), 2589-2596 (1999).

    2. García-Rodríguez, J., Pérez-Rodríguez, S., Ortiz, M.A., et al. Inhibition of I k B kinaseβ and I k B kinase-α by heterocyclic adamantyl arotinoids. Bioorg. Med. Chem. 22(4), 1285-1302 (2014).

    3. le Maire, A., Teyssier, C., Erb, C., et al. A unique secondary-structure switch controls constitutive gene repression by retinoic acid receptor. Nat. Struct. Mol. Biol. 17(7), 801-807 (2010).

    4. Germain, P., Gaudon, C., Pogenberg, V., et al. Differential action on coregulator interaction defines inverse retinoid agonists and neutral antagonists. Chem. Biol. 16(5), 479-489 (2009).

    5. Mollard, R., Ghyselinck, N.B., Wendling, O., et al. Stage-dependent responses of the developing lung to retinoic acid signaling. Int. J. Dev. Biol. 44(5), 457-462 (2000).

    6. Chazaud, C., Dollé, P., Rossant, J., et al. Retinoic acid signaling regulates murine bronchial tubule formation. Mech. Dev. 120(6), 691-700 (2003).

    7. Geissmann, F., Revy, P., Brousse, N., et al. Retinoids regulate survival and antigen presentation by immature dendritic cells. J. Exp. Med. 198(4), 623-634 (2003).