A synthetic retinoid and RXR agonist
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BMS 649

Item No. 30037

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-1,3-dioxolan-2-yl]-benzoic acid
CAS Number
146670-40-8
Synonyms
  • BMS 188649
  • SR 11237
  • UVI 2108
Molecular Formula
C24H28O4
Formula Weight
380.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Sparingly soluble: 1-10 mg/ml
SMILES
CC1(C)CCC(C)(C)C2=CC=C(C3(C4=CC=C(C(O)=O)C=C4)OCCO3)C=C21
InChi Code
InChI=1S/C24H28O4/c1-22(2)11-12-23(3,4)20-15-18(9-10-19(20)22)24(27-13-14-28-24)17-7-5-16(6-8-17)21(25)26/h5-10,15H,11-14H2,1-4H3,(H,25,26)
InChi Key
ZZUKALQMHNSWTK-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    BMS 649 is a synthetic retinoid and retinoid X receptor (RXR) agonist.1 It binds to RXRα homodimers and selectively induces transactivation in CV-1 cells expressing RXRα over CV-1 cells expressing retinoic acid receptor α (RARα), RARβ, or RARα and RXRα when used at a concentration of 0.1 µM. BMS 649 (1 µM), in combination with the RARα agonist BMS 753, induces morphological differentiation of F9 embryonal carcinoma cells.2 It prevents differentiation induced by phorbol-12-myristate-13-acetate (PMA; Item No. 10008014) of THP-1 monocytes into macrophages.3 BMS 649 (25 mg/kg) reduces body weight and bone lengths when administered to newborn rats.4 It induces malformations in Xenopus embryos.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lehmann, J.M., Jong, L., Fanjul, A., et al. Retinoids selective for retinoid X receptor response pathways. Science 258(5090), 1944-1946 (1992).

    2. Taneja, R., Roy, B., Plassat, J.L., et al. Cell-type and promoter-context dependent retinoic acid receptor (RAR) redundancies for RARβ2 and Hoxa-1 activation in F9 and P19 cells can be artefactually generated by gene knockouts. Proc. Natl. Acad. Sci. USA 93(12), 6197-6202 (1996).

    3. Zhou, L., Shen, L.-H., Hu, L.-H., et al. Retinoid X receptor agonists inhibit phorbol-12-myristate-13-acetate (PMA)-induced differentiation of monocytic THP-1 cells into macrophages. Mol. Cell. Biochem. 335(1-2), 283-239 (2010).

    4. Dupuis, H., Pest, M.A., Hadzic, E., et al. Exposure to the RXR Agonist SR11237 in Early Life Causes Disturbed Skeletal Morphogenesis in a Rat Model. Int. J. Mol. Sci. 20(20), 5198 (2019).

    5. Minucci, S., Saint-Jeannet, J.P., Toyama, R., et al. Retinoid X receptor-selective ligands produce malformations in Xenopus embryos. Proc. Natl. Acad. Sci. USA 93(5), 1803-1807 (1996).