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B6688

Sigma-Aldrich

BMS 493

≥98% (HPLC), powder, pan-RAR inverse agonist

Synonym(s):

(E)-4-[2-[5,6-Dihydro-5,5-dimethyl-8-(2-phenylethynyl)naphthalen-2-yl]ethen-1-yl]benzoic acid, 4-[(1E)-2-[5,6-Dihydro-5,5-dimethyl-8-(phenylethynyl)-2-naphthalenyl]ethenyl]-benzoic acid, BMS204, 493

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About This Item

Empirical Formula (Hill Notation):
C29H24O2
CAS Number:
215030-90-3
Molecular Weight:
404.50
MDL number:
MFCD17215944
UNSPSC Code:
12352200
PubChem Substance ID:
329773282
NACRES:
NA.77

product name

BMS 493, ≥98% (HPLC)

assay

≥98% (HPLC)

form

powder

color

light yellow to yellow

solubility

DMSO: ≥20 mg/mL

originator

Bristol-Myers Squibb

storage temp.

2-8°C

SMILES string

CC1(C)CC=C(C#Cc2ccccc2)c3cc(\C=C\c4ccc(cc4)C(O)=O)ccc13

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

General description

BMS 493 inhibits the formation of neuritic processes and plasmenyethanolamine -phospholipase A2 (PLA2) activity.

Application

BMS 493 has been used:
  • as an inhibitor for the dietary and pharmacologic manipulation of retinoic acid (RA) activity in vivo and in vitro
  • for human induced pluripotent stem cells (iPSCs) culture and ventricular cardiomyocytes (VCMs) differentiation
  • to inhibit retinoic acid (RA) signaling in explants
  • as a retinoic acid receptor (RAR) inhibitor for the induction of synaptonemal complex protein 3 (SCP3) and ATP-dependent RNA helicase (DDX4) in primordial germ cells (PGCs)

Biochem/physiol Actions

BMS 493 is an inverse pan-RAR agonist. Retinoic acid receptors (RARs) are ligand-dependent transcription factors that control a number of physiological processes. RARs exert their functions by regulating gene networks controlling cell growth, differentiation, survival, and death.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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About one-third of oestrogen receptor alpha-positive breast cancer patients treated with tamoxifen relapse. Here we identify the nuclear receptor retinoic acid receptor alpha as a marker of tamoxifen resistance. Using quantitative mass spectrometry-based proteomics, we show that retinoic acid receptor
Bone morphogenetic protein and retinoic acid synergistically specify female germ-cell fate in mice
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The Embo Journal, 36(21), 3100-3119 (2017)
Structural and electrophysiological dysfunctions due to increased endoplasmic reticulum stress in a long-term pacing model using human induced pluripotent stem cell-derived ventricular cardiomyocytes
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Excitable dynamics and Yap-dependent mechanical cues drive the segmentation clock
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Spatial Fold Change of FGF Signaling Encodes Positional Information for Segmental Determination in Zebrafish
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