Skip to Content
Merck
All Photos(1)

Documents

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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 Code

11 - Combustible Solids

WGK

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Donkey serum

Sigma-Aldrich

D9663

Donkey serum

Glycerophospholipids in the Brain: Phospholipases A2 in Neurological Disorders (2006)
Alejandro García-Regalado et al.
Molecular cancer, 12, 44-44 (2013-05-23)
All-trans retinoic acid (ATRA) is currently being used in clinical trials for cancer treatment. The use of ATRA is limited because some cancers, such as lung cancer, show resistance to treatment. However, little is known about the molecular mechanisms that
Jiaying Zeng et al.
Acta neuropathologica, 133(6), 967-982 (2017-01-29)
Deposition of amyloid β protein (Aβ) to form neuritic plaques in the brain is the unique pathological hallmark of Alzheimer's disease (AD). Aβ is derived from amyloid β precursor protein (APP) by β- and γ-secretase cleavages and turned over by
Retinoic acid signaling is essential for airway smooth muscle homeostasis
Chen F, et al.
JCI insight, 3(16) (2018)
Henrik J Johansson et al.
Nature communications, 4, 2175-2175 (2013-07-23)
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
View All Related Papers

Articles

Nuclear Receptors (Non-Steroids)

We offer many products related to non-steroid nuclear receptors for your research needs.

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service