ChemicalBook Product Catalog Biochemical Engineering Polypeptide BEAUVERICIN

BEAUVERICIN

Product NameBEAUVERICIN
CAS26048-05-5
MFC45H57N3O9
MW783.95
EINECS618-347-7
MOL File26048-05-5.mol

Chemical Properties

Melting point	93-94℃
Boiling point	975.6±65.0 °C(Predicted)
Density	1.126±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	Soluble in DMSO (30 mg/ml)
form	Solid
pka	-1.02±0.70(Predicted)
color	White
Stability	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey	GYSCAQFHASJXRS-ABKJGVMTSA-N
SMILES	C(C1C=CC=CC=1)C1C(OC(C(N(C(C(OC(C(C)C)C(=O)N(C)C(CC2C=CC=CC=2)C(=O)OC(C(C)C)C(=O)N1C)=O)CC1C=CC=CC=1)C)=O)C(C)C)=O

Safety Information

WGK Germany	3
HS Code	29419090

MSDS

Provider	Language
SigmaAldrich	English

Usage And Synthesis

Description

Beauvericin (CAS 26048-05-5) induces apoptosis in A549 cancer cells.1 Disrupts mitochondrial volume regulation.2 Antifungal activity acting via inhibition of both multidrug efflux and TORC1 kinase.3 Crosses the blood-brain barrier in mice.4 Inhibits HIV-1 integrase.5

Chemical Properties

White powder

Uses

Toxic depsipeptide with antibiotic and insecticidal effects.Beauvericin is a toxic depsipeptide with antibiotic and insecticidal effects.

Uses

Beauvericin is a cyclic depsipeptide isolated from several fungal genera, notably Beauveria and Fusarium, first reported in 1969. Beauvericin exhibits broad antifungal, antibacterial, antiprotozoan and insecticidal activities. At the molecular level, beauvericin exhibits ionophoric properties, and inhibits acyl-CoA:cholesterol acyltransferase activity. Beauvericin induces apoptosis by elevating intracellular calcium levels.

Definition

ChEBI: A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.

in vivo

Beauvericin (5 mg/kg; i.p.; after the first dosing cycle, observe for two days and continue the second dosing cycle) reduces tumor volume and increases necrosis in allogeneic transplant model mice^[3]. Beauvericin (3, 5, 7 mg/kg; i.p.; once a week for three weeks) can significantly inhibit the growth of H22 allogeneic transplant model mice and increase the levels of TNF-α and IL-2 in mice^[5].

Animal Model:	BALB/c mice injected subcutaneously with mouse CT-26 colon cancer cells on the right side^[3]
Dosage:	5 mg/kg
Administration:	ntraperitoneal injection (i.p.)；The drug was administered on the third day after the injection of colon cancer cells and continued once a day for five days, then stopped for two days of observation, and continued on the tenth day after the injection of colon cancer cells, and continued once a day for four days.
Result:	Reduced the average tumor volume by 52.8 % and the average tumor weight by 60 %.

Animal Model:	Human cervical cancer KB-3-1 xenograft mouse model^[3]
Dosage:	5 mg/kg
Administration:	Intraperitoneal injection (i.p.)； The drug was administered once a day starting on the fifth day after cervical cancer injection for five days, followed by two days of observation. The drug was administered once a day starting on the twelfth day after cervical cancer cell injection for four days.
Result:	Reduced the average tumor volume by 31.3 % and the average tumor weight by 31.2 %.

IC 50

ACAT

References

[1] CHIEN-LIN LU. Beauvericin-induced cell apoptosis through the mitogen-activated protein kinase pathway in human nonsmall cell lung cancer A549 cells.[J]. Journal of Toxicological Sciences, 2016, 41 3: 429-437. DOI:10.2131/jts.41.429
[2] ANTON A. TONSHIN . The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis[J]. Toxicology, 2010, 276 1: Pages 49-57. DOI:10.1016/j.tox.2010.07.001
[3] TANVI SHEKHAR-GUTURJA. Dual action antifungal small molecule modulates multidrug efflux and TOR signaling[J]. Nature chemical biology, 2016, 12 10: 867-875. DOI:10.1038/nchembio.2165
[4] LIEN TAEVERNIER . Blood-brain barrier transport kinetics of the cyclic depsipeptide mycotoxins beauvericin and enniatins[J]. Toxicology letters, 2016, 258: Pages 175-184. DOI:10.1016/j.toxlet.2016.06.1741
[5] CHA-GYUN SHIN. Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase[J]. Journal of Antibiotics, 2009, 62 12: 687-690. DOI:10.1038/ja.2009.102

BEAUVERICIN

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