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SML1149

Sigma-Aldrich

BMS-189453

≥98% (HPLC)

Synonyma:

(E)-4-[2-(5,6-Dihydro-5,5-dimethyl-8-phenyl-2-naphthalenyl)ethenyl]-benzoic acid, BMS-453, BMS453

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About This Item

Empirický vzorec (Hillův zápis):
C27H24O2
Číslo CAS:
166977-43-1
Molekulová hmotnost:
380.48
MDL number:
MFCD18086870
UNSPSC Code:
12352200
PubChem Substance ID:
329825683
NACRES:
NA.77

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

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Inhibition of disease progression by a novel retinoid antagonist in animal models of arthritis.
Beehler B C, et al.
The Journal of Rheumatology, 30(2), 355-363 (2003)
BMS-189453, a novel retinoid receptor antagonist, is a potent testicular toxin.
Schulze G E, et al.
Toxicological Sciences, 59(2), 297-308 (2001)
Siyu Wu et al.
Journal of cellular physiology, 236(5), 3929-3945 (2020-11-10)
Traumatic injuries of the central nervous system (CNS) are followed by the accumulation of cellular debris including proteins and lipids from myelinated fiber tracts. Insufficient phagocytic clearance of myelin debris influences the pathological process because it induces inflammation and blocks

Sortimentní položky

Discover Bioactive Small Molecules for Gene Regulation

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Náš tým vědeckých pracovníků má zkušenosti ve všech oblastech výzkumu, včetně přírodních věd, materiálových věd, chemické syntézy, chromatografie, analytiky a mnoha dalších..

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