Zearalenone

Catalog No.S5676 Synonyms: F2 toxin, RAL

For research use only.

Zearalenone (F2 toxin, RAL) is a non-steroidal estrogenic mycotoxin that acts by binding the estrogen receptor (ER).

Zearalenone Chemical Structure

CAS No. 17924-92-4

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Biological Activity

Description Zearalenone (F2 toxin, RAL) is a non-steroidal estrogenic mycotoxin that acts by binding the estrogen receptor (ER).
Targets
ERβ [1]
()
ERα [1]
()
165.7 nM 240.4 nM
In vitro

Zearalenone is able to occupy the active site of ERs in a strikingly similar manner as E2[1]. Zearalenone 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, ZEN enhances cell proliferation, increases colony formation and fastens cell migration after wound healing. Zearalenone 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]. Zearalenone 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 ZEA 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].

Protocol (from reference)

Cell Research:

[4]

  • Cell lines: HCT116 cells
  • Concentrations: 0-320 μM
  • Incubation Time: 48 h
  • Method:

    Human colon carcinoma cells (HCT116) were maintained as monolayer culture in DMEM, supplemented with 10 % fetal bovine serum (FBS), 1 % l-glutamine (200 mM), 1 % of mixture penicillin (100 IU/ml) and streptomycin (100 μg/ml), in a humidified incubator at 37°C in an atmosphere of 5 % CO2 in air. ZEN is dissolved in pure ethanol. Cell viability was assessed using the methylene blue staining assay. Approximately 20,000 cells per well were seeded in 96-well plates with increasing ZEN or AFB1 concentrations (0-320 μM) at 37°C for 48 h in a final volume of 200 μl. The medium was then removed and cells were gently washed twice with PBS (1x), fixed with 3 % PFA for 5 min at room temperature then stained for 5 min with 0.1 % methylene blue. After extensive washing in water, methylene blue was eluted from cells using 0.1 % HCl, and the absorption of the supernatants was measured at 590 nm in a fluorimiter plate reader.

  • (Only for Reference)
Animal Research:

[1]

  • Animal Models: ovariectomized ICR mice
  • Dosages: 0.5-100 mg/kg/day
  • Administration: s.c.
  • (Only for Reference)

Solubility (25°C)

In vitro

DMSO 64 mg/mL
(201.03 mM)
Ethanol 64 mg/mL
(201.03 mM)
Water Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 318.36
Formula

C18H22O5

CAS No. 17924-92-4
Storage 3 years -20°C powder
2 years -80°C in solvent
Smiles CC1CCCC(=O)CCCC=CC2=C(C(=CC(=C2)O)O)C(=O)O1

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Molarity Calculator

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Clinical Trial Information

NCT Number Recruitment Interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04687176 Recruiting Drug: Oral Arsenic Trioxide Formulation Acute Promyelocytic Leukemia The University of Hong Kong January 1 2021 Phase 2
NCT04477746 Recruiting -- Musculoskeletal Pain|Musculoskeletal Strain|Fatigue; Muscle Heart|Cognitive Impairment Lancaster University|National Health Service United Kingdom November 12 2020 --

(data from https://clinicaltrials.gov, updated on 2022-01-17)

Tech Support

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