Zearalenone Estrogen/progestogen Receptor agonist

Cat.No.S5676

Zearalenone (F2 toxin, RAL) is a non-steroidal estrogenic mycotoxin that acts by binding the estrogen receptor (ER).
Zearalenone Estrogen/progestogen Receptor agonist Chemical Structure

Chemical Structure

Molecular Weight: 318.36

Quality Control

Chemical Information, Storage & Stability

Molecular Weight 318.36 Formula

C18H22O5

Storage (From the date of receipt) 3 years -20°C powder
CAS No. 17924-92-4 -- Storage of Stock Solutions

Synonyms F2 toxin, RAL Smiles CC1CCCC(=O)CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1

Solubility

In vitro
Batch:

DMSO : 64 mg/mL (201.03 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

Ethanol : 64 mg/mL

Water : Insoluble

Molarity Calculator

Mass Concentration Volume Molecular Weight

In vivo
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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Mechanism of Action

Targets/IC50/Ki
ERβ [1]
165.7 nM
ERα [1]
240.4 nM
In vitro
Zearalenone is able to occupy the active site of ERs in a strikingly similar manner as E2[1]. This compound disrupts genome stability and inhibits growth of porcine granulosa cells via the estrogen receptors which may promote granulosa cell apoptosis when the DNA repair system is not enough to rescue this serious damage[3]. At low concentrations, it enhances cell proliferation, increases colony formation and fastens cell migration after wound healing. This chemical exhibits carcinogenesis-like properties[4].
In vivo
In ovariectomized female ICR mice, s.c. administration of ZEN at doses ≥2 mg/kg/day for 3 consecutive days significantly increased uterine wet weight compared with the control group[1]. This compound is an immunotoxic compound similar to estrogen and some endocrine disruptors. After oral exposure, ZEA is rapidly absorbed and initially metabolized by the intestinal tissue and hepatocytes; this initiates the biotransformation of the compound into its major biologically active reductive metabolites, α- and β-zearalenol (α- and β-ZOL). The estrogenic activity of this chemical and its metabolites is mediated by their binding affinity to estrogen receptors (ER), and they are as potent as coumestrol and genistein, two endocrine-disrupting phytestrogens[2].
References

Clinical Trial Information

(data from https://clinicaltrials.gov, updated on 2024-05-22)

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT05751031 Recruiting
HIV Infections
Fondazione Penta UK|UCL Great Ormond Street Institute of Child Health|PENTA Foundation
February 20 2023 --

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