Бигеловин

Description

Bigelovin is a sesquiterpene lactone of the pseudoguayanol group, isolated from plants of the genus Inula, in particular Inula helianthus-aquatica. According to modern data, the substance acts as a selective agonist of the retinoid X receptor alpha (RXRα) and as a modulator of intracellular signaling: it suppresses NF-κB activity, reducing the adhesion of monocytes to the endothelium, and in tumor cells it triggers apoptosis and autophagy through inhibition of the mTOR pathway, mediated by the generation of reactive oxygen species (ROS).

Basic Attributes

• CAS No.: 3668-14-2
• Chemical formula: C17H20O5
• Molecular Weight: 304.3377
• Exact weight: 304.34
• DSSTox ID: DTXSID80190130
• PSA specifications: 69.7
• XLogP3: 2

Physico-chemical characteristics

• Melting point: 180–182 °C (data obtained using solvents acetone, dichloromethane)

Scope of application

Research reagent for studying cell cycle signaling pathways, apoptosis and autophagy, particularly in hepatocellular carcinoma models. It is used as a tool in the pharmacology of natural compounds - a selective ligand of RXRα, an inhibitor of NF-κB-mediated adhesion of immune cells to the endothelium, an object of preclinical studies of antitumor and anti-inflammatory activity.

Mechanism of action

Binding to RXRα modifies the transcriptional activity of receptor complexes that influence cell differentiation and proliferation. In parallel, the substance increases the intracellular level of reactive oxygen species, which suppresses mTOR kinase and triggers a cascade of apoptosis and autophagy in liver tumor cells. Reduced NF-κB activity reduces the expression of cell adhesion molecules on the endothelium, attenuating the inflammatory response.

Synonyms of substance

• Bigelovine
• Azuleno[6,5-b]furan-2,5-dione,4-(acetyloxy)-3,3a,4,4a,7a,8,9,9a-octahydro-4a,8-dimethyl-3-methylene-,(3aR,4S,4aR,7aR,8R,9aS)-
• Ambrosa-2,11(13)-dien-12-oic acid,6α,8α-dihydroxy-4-oxo-,12,8-lactone,acetate
• Additional CAS No.: 48191-72-6

Storage and transportation conditions

Data on density, refractive index, solubility and hazard classification are not provided in the original source. Store in a place protected from light and moisture at low temperatures, in sealed containers; prepare solutions for analysis immediately before use in acetone or dichloromethane - solvents for which compatibility with the substance has been confirmed. When working, use standard laboratory protective equipment.

Related compounds

Bigelovin belongs to a large family of sesquiterpene lactones of the pseudoguayanol group, isolated from plants of the genus Inula and related genera Ambrosia and Helenium. A common feature of compounds of this structural class is the alpha-methylene lactone group, which is responsible for chemical reactivity towards the thiol groups of target proteins - it is this fragment that underlies the antitumor and anti-inflammatory activity of the entire group.

Delivery form

The reagent is supplied in milligram packages as a standard for pharmacological and biochemical studies, batches are accompanied by a certificate of analysis indicating the purity determined by HPLC.