SML1149

BMS-189453

≥98% (HPLC)

• Synonym(s): (E)-4-[2-(5,6-Dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid, BMS-453, BMS453
• Empirical Formula (Hill Notation): C₂₇H₂₄O₂
• CAS Number: 166977-43-1
• Molecular Weight: 380.48
• MDL number: MFCD18086870
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825683
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 10 mg/mL, clear
• storage temp.: −20°C
• SMILES string: OC(C(C=C1)=CC=C1/C=C/C(C=C2)=CC3=C2C(C)(C)CC=C3C4=CC=CC=C4)=O
• 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

Description

Biochem/physiol Actions

BMS-189453 is a potent RARβ agonist that acts as an antagonist against RARα and RARγ. BMS-189453 induces RARβ reporter gene expression at sub nanomolar levels, and is 30 fold more potent than all-trans retinoic acid for inducing TGFβ activity in normal breast cells. The compound BMS-189453 does not transactivate RARα or γ transcriptional activity, but binding to those family members induces a strong transrepression of phorbol ester-induced AP-1 activity (IC₅₀ = 0.1 nM in HeLa and MCSF-7). BMS-189453 significantly increases the efficiency of cardiac differentiation of hESCs.

BMS-189453 specifically has sufficient bioavailability in rats and monkeys. BMS-189453 only binds to α, β, and γ retinoid receptors but its activation is unknown. BMS-189453 is found to inhibit the action of collagenase-3 (MMP-13) which catalyses cartilage matrix degradation. Thus, it serves to treat rheumatoid arthritis.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable