59662-49-6

Usage

Uses

Used in Pharmaceutical Industry:
4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID is used as a RARβ2 receptor agonist for the development of treatments for type 2 diabetes and hepatic steatosis. Its agonistic activity on the RARβ2 receptor makes it a potential drug candidate in the field of metabolic disorders.
Used in Chemical Research:
4'-N-OCTYLBIPHENYL-4-CARBOXYLIC ACID may also be utilized in chemical research as a starting material or intermediate for the synthesis of more complex molecules with specific applications in various fields, such as materials science, pharmaceuticals, or agrochemicals. Its unique structure and functional groups can be exploited to create novel compounds with desired properties.

Biological Activity

Potent, isoform-selective RAR β 2 receptor agonist (pEC 50 values are 6.9, 5.7 and 5.6 at RAR β 2, RAR β 1 and RAR α respectively) that displays 100-fold selectivity versus other retinoid receptors. Inhibits proliferation of the breast cancer cell line MCF-7.

Biochem/physiol Actions

AC-55649 is a subtype selective RAR (RARβ2) agonist. AC-55649 is a potent, orally available isoform selective Retinoic Acid Receptor β2. AC-55649 has high selectivity, 99% for RARβ2 and 31% for RARβ1. When compared to the gold standard AM-580 (Cat. No A8843), both isoform receptors were 100%. AC-55649 has a potent EC50 of 6.9 μM compared to an EC50 of 7.7 μM for AM-580.

Upstream product

• 52709-84-9 4-octyl-4'-cyanobiphenyl 
• 14047-29-1 4-carboxyphenylboronic acid 
• 252011-38-4 1-hexyl-2-(4-bromophenyl)acetylene 

Downstream Products

• 920270-45-7 3-(4'-octyl-biphenyl-4-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-propionitrile 

Relevant academic research and scientific papers

Improvement in Aqueous Solubility of Retinoic Acid Receptor (RAR) Agonists by Bending the Molecular Structure

Aqueous solubility is a key requirement for many functional molecules, e. g., drug candidates. Decrease of the partition coefficient (log P) by chemical modification, i.e., introduction of hydrophilic group(s) into molecules, is a classical strategy for improving aqueous solubility. We have been investigating alternative strategies for improving the aqueous solubility of pharmaceutical compounds by disrupting intermolecular interactions. Here, we show that introducing a bend into the molecular structure of retinoic acid receptor (RAR) agonists by changing the substitution pattern from para to meta or ortho dramatically enhances aqueous solubility by up to 890-fold. We found that meta analogs exhibit similar hydrophobicity to the parent para compound, and have lower melting points, supporting the idea that the increase of aqueous solubility was due to decreased intermolecular interactions in the solid state as a result of the structural changes.

Liposomal formulation of retinoids designed for enzyme triggered release

The design of retinoid phospholipid prodrugs is described based on molecular dynamics simulations and cytotoxicity studies of synthetic retinoid esters. The prodrugs are degradable by secretory phospholipase A2 IIA and have potential in liposomal drug delivery targeting tumors. We have synthesized four different retinoid phospholipid prodrugs and shown that they form particles in the liposome size region with average diameters of 94-118 nm. Upon subjection to phospholipase A2, the lipid prodrugs were hydrolyzed, releasing cytotoxic retinoids and lysolipids. The formulated lipid prodrugs displayed IC50 values in the range of 3-19 μM toward HT-29 and Colo205 colon cancer cells in the presence of phospholipase A 2, while no significant cell death was observed in the absence of the enzyme.

COMPOUNDS WITH ACTIVITY AT RETINOIC ACID RECEPTORS

Disclosed herein are novel compounds with activity at RARβ 2 receptors. Further disclosed are the use of such compounds for treatment of or to alleviate symptoms of cancer, neurological disorders such as memory deficits and schizophrenia, neurodegenerative disorders such as Parkinson's and Alzheimer's diseases, inflammatory disorders such as psoriasis and rheumatoid arthritis, eye disorders and depression.