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B6688 Sigma-Aldrich

BMS 493

≥98% (HPLC)

Synonym: (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

  • CAS Number 215030-90-3

  • Empirical Formula (Hill Notation) C29H24O2

  • Molecular Weight 404.50

  •  MDL number MFCD17215944

  •  PubChem Substance ID 329773282

  •  NACRES NA.77

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Properties

Related Categories Apoptosis and Cell Cycle, Approved Therapeutics/Drug Candidates, B, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
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

Description

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)

Packaging

5, 25 mg in glass bottle

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.

Safety & Documentation

Safety Information

Hazard statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 2
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Apoptosis

Apoptosis, or programmed cell death (PCD), is a selective process for the removal of unnecessary, infected or transformed cells in various biological systems. As it plays a role in the homeostasis of...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Clinical, Diseases, Ligands, Neurodegenerative Diseases

Discover Bioactive Small Molecules for Cell Cycle Research

In proliferating cells, the cell cycle consists of four phases. Gap 1 (G1) is the interval between mitosis and DNA replication that is characterized by cell growth. Replication of DNA occurs during t...
Keywords: Apoptosis, Bioactive small molecules, Cancer, Cell division, Cell proliferation, DNA replication, Diseases, Genetic

Nuclear Receptors (Non-Steroids)

The receptors for several classes of non-steroidal compounds, including retinoids, thyroid hormones and vitamin D, also act as ligand-dependent transcription factors. In addition, a large number of r...
Keywords: Absorption, Apoptosis, Atomic absorption spectroscopy, Cancer, Cardiovascular, Cell proliferation, Clinical, Detoxification, Diabetes, Diseases, Gene expression, Hormones, Ligands, Lipid Metabolism, Metabolism, Metabolites, Obesity, Transcription, Transduction, Vitamins

Peer-Reviewed Papers
15

References

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