An RARβ agonist, RARα/γ antagonist
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BMS 453

Item No. 19076

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(1E)-2-(5,6-dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl], benzoic acid
CAS Number
166977-43-1
Synonyms
  • BMS 189453
Molecular Formula
C27H24O2
Formula Weight
380.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 10 mg/ml
λmax
235, 291, 327 nm
SMILES
CC1(C)C2=C(C=C(/C=C/C3=CC=C(C(O)=O)C=C3)C=C2)C(C4=CC=CC=C4)=CC1
InChi Code
InChI=1S/C27H24O2/c1-27(2)17-16-23(21-6-4-3-5-7-21)24-18-20(12-15-25(24)27)9-8-19-10-13-22(14-11-19)26(28)29/h3-16,18H,17H2,1-2H3,(H,28,29)/b9-8+
InChi Key
VUODRPPTYLBGFM-CMDGGOBGSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $41

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    5 mg

    $128

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    10 mg

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    25 mg

    $389

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    Product Description

    Nuclear retinoic acid receptors (RARs) are transcriptional regulators with roles in cell proliferation and differentiation. BMS 453 is a synthetic retinoid that acts as an agonist of RARβ and an antagonist of RARα and RARγ.1 It has been shown to inhibit the proliferation of normal breast cells via the induction of TGF-β activity, causing G1 arrest.2 BMS 453 binding to RARα and RARγ can induce a transrepression of phorbol ester-induced AP-1 activity (IC50s = ~0.1 nM in HeLa and MCSF-7 cells), which also correlates with reduced cell proliferation.1 BM 453 has been used to trigger the differentiation of mouse embryonic stem cells (mES) in a study of RARβ-induced mES cell adipogenesis.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chen, J.Y., Penco, S., Ostrowski, J., et al. RAR-specific agonist/antagonists which dissociate transactivation and AP1 transrepression inhibit anchorage-independent cell proliferation. EMBO J. 14(6), 1187-1197 (1995).

    2. Yang, L., Ostrowski, J., Reczek, P., et al. The retinoic acid receptor antagonist, BMS453, inhibits normal breast cell growth by inducing active TGFß and causing cell cycle arrest. Oncogene 20(55), 8025-8035 (2001).

    3. Monteiro, M.C., Wdziekonski, B., Villageois, P., et al. Commitment of mouse embryonic stem cells to the adipocyte lineage requires retinoic acid receptorβand active GSK3. Stem Cells Dev. 18(3), 457-463 (2009).