Zearalenone

Catalog No.S5676 Synonyms: F2 toxin, RAL

Zearalenone Chemical Structure

Molecular Weight(MW): 318.36

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

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Biological Activity

Description Zearalenone 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

Cell Research:

[4]

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  • 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]

+ Expand
  • Animal Models: ovariectomized ICR mice
  • Formulation: olive oil
  • 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 powder
in solvent
Synonyms F2 toxin, RAL

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Clinical Trial Information

NCT Number Recruitment Conditions Sponsor/Collaborators Start Date Phases
NCT03732625 Not yet recruiting HIV Infections Fundación Pública Andaluza para la Investigación de Málaga en Biomedicina y Salud|Merck Sharp & Dohme Corp. May 2019 Phase 4
NCT03732625 Not yet recruiting HIV Infections Fundación Pública Andaluza para la Investigación de Málaga en Biomedicina y Salud|Merck Sharp & Dohme Corp. May 2019 Phase 4
NCT03842488 Not yet recruiting HIV Infections Fundación Pública Andaluza para la Investigación de Málaga en Biomedicina y Salud|Merck Sharp & Dohme Corp. April 2019 Phase 4
NCT03842488 Not yet recruiting HIV Infections Fundación Pública Andaluza para la Investigación de Málaga en Biomedicina y Salud|Merck Sharp & Dohme Corp. April 2019 Phase 4
NCT03394196 Recruiting HIV-2 Infection University of Washington|Clinique des Maladies Infectieuses CHNU de Fann Dakar Senegal|Centre de Sante de Ziguinchor Casamance Senegal|Janssen Pharmaceutica|Merck Sharp & Dohme Corp.|National Institute of Allergy and Infectious Diseases (NIAID) July 4 2018 Not Applicable
NCT03394196 Recruiting HIV-2 Infection University of Washington|Clinique des Maladies Infectieuses CHNU de Fann Dakar Senegal|Centre de Sante de Ziguinchor Casamance Senegal|Janssen Pharmaceutica|Merck Sharp & Dohme Corp.|National Institute of Allergy and Infectious Diseases (NIAID) July 4 2018 Not Applicable

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID